UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
SCHEDULE 14A
Proxy Statement Pursuant to Section 14(a) of the
Securities Exchange Act of 1934
Filed by the Registrant   ☒                 Filed by a Party other than the Registrant   ☐
Check the appropriate box:

Preliminary Proxy Statement

Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

Definitive Proxy Statement

Definitive Additional Materials

Soliciting Material Pursuant to § 240.14a-12
Macatawa Bank Corporation
(Name of Registrant as Specified In Its Charter)
(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)
Payment of Filing Fee (Check the appropriate box):

No fee required.

Fee paid previously with preliminary materials.

Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

Macatawa Bank
Corporation
Wintrust Financial
Corporation
PROXY STATEMENT OF MACATAWA BANK CORPORATION
PROSPECTUS OF WINTRUST FINANCIAL CORPORATION
Merger Proposed — Your Vote Is Important
DEAR MACATAWA SHAREHOLDERS:
You are cordially invited to attend a special meeting of shareholders of Macatawa Bank Corporation (“Macatawa”), which will be held on July 31, 2024, at 8:00 a.m. local time, at Macatawa’s corporate offices, which are located at 10753 Macatawa Drive, Holland, Michigan 49424.
At the meeting, you will be asked to approve the merger agreement, dated April 15, 2024, by and between Macatawa, Leo Subsidiary LLC (“Merger Sub”) and Wintrust Financial Corporation (“Wintrust”), which provides for Wintrust’s acquisition of Macatawa through the merger of Macatawa with and into Merger Sub, a wholly-owned subsidiary of Wintrust. Macatawa is the parent company of Macatawa Bank. The merger consideration paid by Wintrust to Macatawa shareholders is expected to be $14.85 per share of outstanding Macatawa common stock, or an aggregate of approximately $510.3 million (the “Merger Consideration”), based on 34,361,562 shares of Macatawa common stock outstanding as of April 12, 2024, the last trading day before public announcement of the execution of the merger agreement, subject to adjustment as provided in the merger agreement. The Merger Consideration will be paid in shares of Wintrust common stock, no par value per share, other than cash to be paid in lieu of fractional shares.
For each share of Macatawa common stock owned, you will receive a number of shares of Wintrust common stock to be calculated using an exchange ratio determined in accordance with the merger agreement and as further described in this proxy statement/prospectus (the “Per Share Merger Consideration”). The Per Share Merger Consideration that you will be entitled to receive for each share of Macatawa common stock will be determined based on the average of the volume-weighted average price of Wintrust common stock as reported under the heading “Bloomberg VWAP” on the Bloomberg page for Wintrust for each trading day during the ten trading day period ending on the second trading day prior to completion of the merger, which we refer to herein as the “reference price”, subject to a minimum and maximum reference price equal to $89.03 and $113.03, respectively. Assuming that the reference price were calculated as of June 17, 2024, the last practicable date prior to the date of this proxy statement/prospectus, you would be entitled to receive 0.1590 shares of Wintrust common stock for each share of Macatawa common stock. If the reference price is less than or equal to the minimum of $89.03, each share of Macatawa common stock would instead be entitled to 0.1668 shares of Wintrust common stock, and if the reference price is greater than or equal to the maximum of $113.03, each share of Macatawa common stock would be entitled to 0.1314 shares of Wintrust common stock. If the reference price is greater than or equal to $89.03 and not more than $113.03, the exchange ratio will be variable and calculated by dividing (i) the amount obtained by dividing the Merger Consideration by the reference price by (ii) the number of outstanding shares of Macatawa common stock. Therefore, at the time of the special meeting, you will not know the precise value of the Merger Consideration you may receive on the date the merger is completed.
Wintrust common stock is traded on the Nasdaq Global Select Market (“Nasdaq”), under the symbol “WTFC.” The closing price of Wintrust common stock on June 17, 2024 was $93.42 per share.
The merger cannot be completed unless the holders of at least a majority of the outstanding shares of Macatawa common stock entitled to vote approve the merger agreement. Your board of directors has unanimously adopted the merger agreement and recommends that you vote “FOR” the approval of the merger agreement at the special meeting. Your board of directors also unanimously recommends that you vote “FOR” approval of the non-binding, advisory Macatawa merger-related compensation proposal (as defined below) and “FOR” the approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement.

Additional information regarding the merger, the merger agreement, Macatawa and Wintrust is set forth in the attached proxy statement/prospectus. This document also serves as the prospectus for the shares of Wintrust common stock to be issued by Wintrust in connection with the merger. We urge you to read this entire document carefully, including the section entitled “Risk Factors” beginning on page 15.
Sincerely,
[MISSING IMAGE: sg_richardpostma-bw.jpg]
Richard L. Postma
Chairman
Macatawa Bank Corporation
Neither the Securities and Exchange Commission (“SEC”) nor any state securities regulatory body has approved or disapproved of the securities to be issued under this proxy statement/prospectus or determined if this proxy statement/prospectus is accurate or adequate. Any representation to the contrary is a criminal offense.
The securities to be issued in connection with the merger are not savings or deposit accounts or other obligations of any bank or nonbank subsidiary of any of the parties, and they are not insured by the Federal Deposit Insurance Corporation (“FDIC”) or any other governmental agency.
This proxy statement/prospectus is dated June 17, 2024, and is first being mailed to Macatawa shareholders on or about June 18, 2024.

 
REFERENCES TO ADDITIONAL INFORMATION
As permitted by the rules of the SEC this proxy statement/prospectus incorporates important business and financial information about Wintrust from other documents that are not included in or delivered with this proxy statement/prospectus. These documents are available to you without charge upon your written or oral request. You can obtain documents incorporated by reference in this proxy statement/prospectus through the SEC’s website at www.sec.gov or by requesting them in writing or by telephone at the following address and telephone number:
Wintrust Financial Corporation
9700 W. Higgins Road, Suite 800
Rosemont, Illinois 60018
Attention: Kathleen M. Boege
Executive Vice President, General Counsel and Corporate Secretary
(847) 939-9000
In order to ensure timely delivery of these documents, you should make your request by July 26, 2024 to receive them before the special meeting. See “Where You Can Find More Information” beginning on page 84.
VOTING BY MAIL
Macatawa shareholders of record may submit their proxies by mail, by signing and dating each proxy card you receive, indicating your voting preference on each proposal and returning each proxy card in the prepaid envelope which accompanied that proxy card. The proxy card also includes instructions on how to submit your proxy via the internet or over the telephone.
 

 
MACATAWA BANK CORPORATION
10753 Macatawa Drive
Holland, Michigan 49424
Notice of Special Meeting of Shareholders
Date: July 31, 2024
Time: 8:00 a.m., local time
Place: 10753 Macatawa Drive, Holland, Michigan 49424
TO MACATAWA BANK CORPORATION SHAREHOLDERS:
NOTICE IS HEREBY GIVEN that Macatawa will hold a special meeting of shareholders on July 31, 2024 at 8:00 a.m., local time, at Macatawa’s corporate offices, which are located at 10753 Macatawa Drive, Holland, Michigan 49424. The purpose of the meeting is to consider and vote on the following matters:

a proposal to adopt the Agreement and Plan of Merger, dated as of April 15, 2024 (the “merger agreement”), by and among Wintrust Financial Corporation, Leo Subsidiary LLC and Macatawa Bank Corporation. A copy of such merger agreement is included as Annex A to the proxy statement/prospectus accompanying this notice;

a proposal to cast a non-binding, advisory vote to approve the compensation that may be paid or become payable to Macatawa’s named executive officers that is based on or otherwise related to the merger (the “Macatawa merger-related compensation proposal”);

the approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby and appoint the shareholders’ representative and the alternate shareholders’ representative under the merger agreement; and

to transact any other business that properly comes before the special meeting, or any adjournments or postponements thereof.
Holders of record of Macatawa common stock at the close of business on June 11, 2024 are entitled to receive this notice and to vote at the special meeting and any adjournments or postponements thereof. Adoption of the merger agreement requires the affirmative vote at the special meeting of holders of at least a majority of the outstanding shares of Macatawa common stock entitled to vote. Approval of the non-binding, advisory Macatawa merger-related compensation proposal and the proposal to adjourn the special meeting, if necessary, each require the affirmative vote of holders of at least a majority of the shares of Macatawa common stock entitled to vote, present in person or by proxy, if a quorum is present. In the absence of a quorum, the holders of at least a majority of the shares of Macatawa common stock present, in person or by proxy, may adjourn the special meeting.
The board of directors of Macatawa unanimously recommends that you voteFORadoption of the merger agreement, “FOR” approval of the Macatawa merger-related compensation proposal andFORapproval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby.
Your vote is important. To ensure that your shares are voted at the special meeting, please promptly complete, sign and return the proxy card in accordance with the instructions included thereon whether or not you plan to attend the meeting in person. Shareholders who attend the special meeting may revoke their proxies and vote in person, if they so desire.
 

 
Holland, Michigan
June 17, 2024
By Order of the Board of Directors
[MISSING IMAGE: sg_jonswets-bw.jpg]
Jon W. Swets
Chief Executive Officer
 

 
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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETING
Q:
What am I being asked to vote on? What is the proposed transaction?
A:
You are being asked to vote on the adoption of the merger agreement that provides for Wintrust’s acquisition of Macatawa through the merger of Macatawa with and into Merger Sub, a wholly-owned subsidiary of Wintrust. Upon completion of the merger, all shares of Macatawa common stock will be cancelled and you will become a shareholder of Wintrust.
Q:
What will Macatawa shareholders be entitled to receive in the merger?
A:
If the merger is completed, the shares of Macatawa common stock that you own immediately before the completion of the merger (including, for the avoidance of doubt, shares of Macatawa common stock received by holders of unvested shares of Macatawa restricted stock, which will automatically vest immediately prior to the effective time) will be converted into the right to receive shares of Wintrust common stock (subject to possible adjustment). The Merger Consideration paid by Wintrust to Macatawa shareholders is expected to be $14.85 per share of outstanding Macatawa common stock, or an aggregate of approximately $510.3 million, based on 34,361,562 shares of Macatawa common stock issued and outstanding as of April 12, 2024, the last trading day before public announcement of the execution of the merger agreement, subject to adjustment for fluctuations in the trading price of Wintrust common stock as described below. All of the Merger Consideration will be paid to holders of Macatawa common stock in shares of Wintrust common stock, no par value per share, calculated based on the Per Share Merger Consideration described in the merger agreement, other than cash to be paid in lieu of any fractional shares.
For each of your shares of Macatawa common stock, you will receive the Per Share Merger Consideration calculated as set forth in the merger agreement in the form of Wintrust common stock. The Per Share Merger Consideration that you will be entitled to receive for each share of Macatawa common stock will be determined based on the average of the volume-weighted average price of Wintrust common stock as reported under the heading “Bloomberg VWAP” on the Bloomberg page for Wintrust for each trading day during the ten trading day period ending on the second trading day prior to completion of the merger, which we refer to as the reference price, subject to a minimum and maximum reference price equal to $89.03 and $113.03, respectively. Assuming that the reference price were calculated as of June 17, 2024, the last practicable date prior to the date of this proxy statement/prospectus, you would be entitled to receive 0.1590 shares of Wintrust common stock for each share of Macatawa common stock. If the reference price is less than the minimum of $89.03, each share of Macatawa common stock will be entitled to 0.1668 shares of Wintrust common stock, and if the reference price is greater than the maximum of $113.03, each share of Macatawa common stock will be entitled to 0.1314 shares of Wintrust common stock. If the reference price is greater than or equal to $89.03 and not more than $113.03, the Per Share Merger Consideration will be variable and calculated by dividing (i) the amount obtained by dividing the aggregate Merger Consideration by the reference price by (ii) the number of outstanding shares of Macatawa common stock. For a description of how the Per Share Merger Consideration will be calculated, see “Description of the Merger Agreement —  Consideration to be received in the merger” on page 54 and “— Upset condition” on page 55.
Q:
Why do Macatawa and Wintrust want to engage in the merger?
A:
Macatawa believes that the merger will provide Macatawa shareholders with substantial benefits and that it presents the best option to maximize shareholder value, and Wintrust believes that the merger will further its strategic growth plans by allowing it to expand its presence in west Michigan. As a larger company, Wintrust expects to (i) be able to provide greater capital and resources and efficiencies from integrating the operations of Macatawa into Wintrust’s existing operations and (ii) allow Macatawa Bank to compete more effectively and to offer a broader array of products and services to better serve its banking customers. To review the reasons for the merger in more detail, see “The Merger — Wintrust’s reasons for the merger” on page 45 and “The Merger — Macatawa’s reasons for the merger and recommendation of the board of directors” on page 43.
 
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Q:
What does the Macatawa board of directors recommend?
A:
Macatawa’s board of directors unanimously recommends that you vote “FOR” adoption of the merger agreement, “FOR” approval of the non-binding, advisory Macatawa merger-related compensation proposal and “FOR” the approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby. To review the background and reasons for the merger in greater detail, see “The Merger” beginning on page 26.
Q:
What vote is required to adopt the merger agreement?
A:
Holders of at least a majority of the outstanding shares of Macatawa common stock entitled to vote must vote in favor of the merger. Abstentions and broker non-votes have the effect of votes against the adoption of the merger agreement. On April 15, 2024, certain of Macatawa’s directors and executive officers who own shares of Macatawa common stock agreed to vote their shares at the special meeting in favor of the merger and any other matter necessary for consummation of the transactions contemplated by the merger agreement. These shareholders and their affiliates owned approximately 8.7% of Macatawa common stock outstanding as of March 31, 2024 and the voting agreement covers approximately 6.9% of Macatawa’s outstanding shares of common stock as of March 31, 2024. Wintrust’s shareholders will not be voting on the merger agreement. For additional detail, see “The Merger — Interests of directors and executive officers in the merger” on page 49 and “The Merger — Voting agreement” on page 53.
Q:
What vote is required to approve the non-binding, advisory Macatawa merger-related compensation proposal and the proposal to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby?
A:
To approve the Macatawa merger-related compensation proposal and the proposal to adjourn the special meeting, if necessary or appropriate to solicit additional proxies, the affirmative vote of at least a majority of the shares of Macatawa common stock entitled to vote, present in person or by proxy, is required if a quorum is present at the special meeting. In the absence of a quorum, holders of at least a majority of the shares of Macatawa common stock present in person or by proxy at the special meeting may adjourn the special meeting. Abstentions have the effect of votes against the proposals, and broker non-votes will not be considered entitled to vote and will have no effect on the proposals.
Q:
What happens if the non-binding, advisory Macatawa merger-related compensation proposal is not approved?
A:
Because the vote on the Macatawa merger-related compensation proposal is advisory only, it will not be binding on either Macatawa or Wintrust. Accordingly, if the merger agreement is adopted and the merger is completed, the merger-related compensation will be payable to the applicable Macatawa executive officers, subject only to the conditions applicable thereto, regardless of the outcome of the non-binding, advisory vote of Macatawa’s shareholders.
Q:
Why is my vote important?
A:
Macatawa’s shareholders are being asked to adopt the merger agreement and thereby approve the merger. If you do not submit your proxy or vote in person at the special meeting, it will be more difficult for Macatawa to obtain the necessary quorum to hold the special meeting. In addition, your failure to submit your proxy or attend the special meeting will have the same effect as a vote against the proposal to adopt the merger agreement and make it more difficult to obtain the necessary approval.
Q:
What do I need to do now? How do I vote?
A:
You may vote at the special meeting if you own shares of Macatawa common stock of record at the close of business on the record date for the special meeting, June 11, 2024 (the “record date”). After you have carefully read and considered the information contained in this proxy statement/prospectus,
 
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please complete your proxy card in accordance with the instructions set forth thereon as soon as possible, which includes the option to (1) return a properly completed proxy card in the enclosed prepaid return envelope, (2) submit via the internet or (3) complete your proxy via telephone. This will enable your shares to be represented at the special meeting. You may also vote in person at the special meeting. If you do not submit a properly executed proxy card and do not vote at the special meeting, this will have the same effect as a vote against the adoption of the merger agreement.
Q:
How will my proxy be voted?
A:
If you complete your proxy card in accordance with the instructions set forth thereon, your proxy will be voted in accordance with your instructions. If you sign, date and send in your proxy card, but you do not indicate how you want to vote, your proxy will be voted “FOR” adoption of the merger agreement and the other proposals in the notice.
Q:
Can I revoke my proxy and change my vote?
A:
You may change your vote or revoke your proxy at any time before it is voted by filing with the secretary of Macatawa a duly executed revocation of proxy or submitting a new proxy card with a later date. You may also revoke a prior proxy by voting in person at the special meeting.
Q:
If my shares are held in “street name” by a broker, bank or other nominee, will my broker, bank or other nominee vote my shares for me?
A:
If your shares are held in “street name” in a stock brokerage account or by a broker, bank or other nominee, you must provide the record holder of your shares with instructions on how to vote your shares. Please follow the voting instructions provided by your broker, bank or other nominee. Please note that you may not vote shares held in street name by returning a proxy card or voting instruction form directly to Macatawa. Your broker, bank or other nominee is obligated to provide you with a voting instruction form for you to use.
Applicable stock exchange rules permit brokers to vote their customers’ stock held in street name on routine matters when the brokers have not received voting instructions from their customers. Those rules do not, however, allow brokers to vote their customers’ stock held in street name on non-routine matters unless they have received voting instructions from their customers. In such cases, the uninstructed shares for which the broker is unable to vote are called broker non-votes. The merger proposal, the merger-related compensation proposal and the adjournment proposal are non-routine matters on which brokers are not allowed to vote unless they have received voting instructions from their customers. You must provide voting instructions to your broker for your shares to be voted.
Q:
What if I oppose the merger? Do I have dissenters’ rights?
A:
Under Section 762 of the Business Corporation Act of the State of Michigan (“MBCA”), Macatawa shareholders are not entitled to dissenters’ rights in connection with the merger.
Q:
What are the tax consequences of the merger to me?
A:
Each of ArentFox Schiff LLP and Warner Norcross + Judd LLP have delivered opinions, dated June 13, 2024, to the effect that the merger qualifies as a “reorganization” pursuant to Section 368(a) of the Internal Revenue Code of 1986, as amended (which we refer to as the “Internal Revenue Code”). In addition, the completion of the merger is conditioned on receipt of a tax opinion from each of ArentFox Schiff LLP and Warner Norcross + Judd LLP, dated as of the closing date, to the same effect as the opinions described in the preceding sentence. However, neither Macatawa nor Wintrust has requested or received a ruling from the Internal Revenue Service that the merger will qualify as a reorganization. Macatawa shareholders generally will not recognize gain or loss if they exchange their Macatawa shares for Wintrust common stock, except in the event that Macatawa shareholders receive cash instead of a fractional share of Wintrust common stock. The tax consequence of the merger to each Macatawa shareholder will depend on such Macatawa shareholder’s own situation. You should consult
 
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with your tax advisor for the specific tax consequences of the merger to you. See “Material U.S. federal income tax consequences of the merger” on page 46.
Q:
When and where is the special meeting?
A:
The Macatawa special meeting will take place on July 31, 2024, at 8:00 a.m. local time, at Macatawa’s corporate offices, which are located at 10753 Macatawa Drive, Holland, Michigan 49424.
Q:
Who may attend the meeting?
A:
Macatawa shareholders on the record date may attend the special meeting. If you are a shareholder of record, you may need to present proof of identification in order to be admitted into the meeting.
Q:
Who will tabulate and certify the vote?
A:
Representatives of Broadridge Financial Solutions will tabulate the votes cast at the special meeting, and one or more Macatawa employees will act as the Inspectors of Election.
Q:
What happens if I sell my shares of Macatawa common stock after the Macatawa record date but before the special meeting?
A:
The record date (the close of business on June 11, 2024) is earlier than the date of the special meeting and earlier than the date that the merger is expected to be completed. If you sell or otherwise transfer your shares of Macatawa common stock after the record date but before the date of the special meeting, you will retain your right to vote at the special meeting. However, you will not have the right to receive the Merger Consideration in respect of such transferred shares to be received by Macatawa shareholders in the merger. In order to receive the merger consideration, you must hold your shares through completion of the merger.
Q:
Where can I find the voting results of the special meeting?
A:
The preliminary voting results will be announced at the special meeting. In addition, within four business days following certification of the final voting results, Macatawa intends to file the final voting results with the SEC on a Current Report on Form 8-K.
Q:
Should I send in my stock certificates now?
A:
No. After the merger is completed, the exchange agent for the merger will send you a letter of transmittal with instructions informing you how to send in your stock certificates (which, for purposes of this proxy statement/prospectus, shall be deemed to include certificates or book-entry account statements) to the exchange agent. You should use the letter of transmittal to exchange your Macatawa stock certificates for the Merger Consideration. Do not send in your stock certificates with your proxy card.
Q:
When is the merger expected to be completed?
A:
We will try to complete the merger as soon as reasonably possible. Before that happens, the merger agreement must be adopted by Macatawa’s shareholders and we must obtain the necessary regulatory approvals. Assuming shareholders vote to approve the merger and adopt the merger agreement and we obtain the other necessary approvals and satisfaction or waiver of the other conditions to the closing described in the merger agreement, we expect to complete the merger in the second half of 2024. See “Description of the Merger Agreement — Conditions to completion of the merger” on page 61.
Q:
Is completion of the merger subject to any conditions besides shareholder approval?
A:
Yes. The transaction must receive the required regulatory approvals, and there are other closing conditions that must be satisfied. See “Description of the Merger Agreement — Conditions to completion of the merger” on page 61.
 
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Q:
Are there risks I should consider in deciding to vote on the adoption of the merger agreement?
A:
Yes, in evaluating the merger agreement, you should read this proxy statement/prospectus carefully, including the factors discussed in the section titled “Risk Factors” beginning on page 15.
Q:
Who can answer my other questions?
A:
If you have more questions about the merger or how to submit your proxy, or if you need additional copies of this proxy statement/prospectus or the enclosed proxy card, you should contact Jon W. Swets, Macatawa’s Chief Executive Officer at (616) 494-7645.
 
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SUMMARY
This summary highlights selected information in this proxy statement/prospectus and may not contain all of the information that is important to you. To understand the merger more fully, you should read this entire proxy statement/prospectus carefully, including the annexes and the documents referred to or incorporated in this proxy statement/prospectus. A copy of the merger agreement is attached as Annex A to this proxy statement/prospectus and is incorporated herein by reference. See “Where You Can Find More Information” beginning on page 84.
Information about Wintrust and Macatawa (See page 26)
Wintrust Financial Corporation
9700 W. Higgins Road, Suite 800
Rosemont, Illinois 60018
(847) 939-9000
Wintrust Financial Corporation, an Illinois corporation, which we refer to as “Wintrust”, was incorporated in 1992 and is a financial holding company based in Rosemont, Illinois. Wintrust provides community-oriented, personal and commercial banking services to customers located primarily in the Chicago metropolitan area, southern Wisconsin and northwest Indiana through its 15 wholly-owned banking subsidiaries, as well as the origination and purchase of residential mortgages for sale into the secondary market through Wintrust Mortgage, a division of Barrington Bank and Trust Company, N.A. Wintrust provides specialty finance services, including financing for the payment of commercial insurance premiums and life insurance premiums on a national basis through FIRST Insurance Funding, a division of its wholly-owned subsidiary Lake Forest Bank & Trust Company, N.A., which we refer to as Lake Forest Bank, and Wintrust Life Finance, a division of Lake Forest Bank, and in Canada through its premium finance company, First Insurance Funding of Canada, lease financing and other direct leasing opportunities through its wholly-owned subsidiary, Wintrust Asset Finance, and short-term accounts receivable financing and outsourced administrative services through its wholly-owned subsidiary, Tricom, Inc. of Milwaukee. Wintrust also provides a full range of wealth management services primarily to customers in the Chicago metropolitan area, southern Wisconsin and northwest Indiana through four separate subsidiaries, The Chicago Trust Company, N.A., Wintrust Investments, LLC, Great Lakes Advisors, LLC and Chicago Deferred Exchange Company, LLC.
As of March 31, 2024, Wintrust had total assets of approximately $57.6 billion, total loans, excluding loans held-for-sale, of approximately $43.2 billion, total deposits of approximately $46.4 billion, and total shareholders’ equity of approximately $5.4 billion.
Wintrust common stock, no par value per share, which we refer to as “Wintrust common stock”, is traded on Nasdaq under the ticker symbol “WTFC.” Wintrust’s principal executive office is located at 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018, telephone number: (847) 939-9000.
Leo Subsidiary LLC
c/o Wintrust Financial Corporation
9700 W. Higgins Road, Suite 800
Rosemont, Illinois 60018
(847) 939-9000
Leo Subsidiary LLC, a Michigan limited liability company, which we refer to as “Merger Sub”, is a wholly-owned subsidiary of Wintrust and was formed solely for the purpose of consummating the merger. Merger Sub has not carried on any activities to date, except for activities incidental to its formation and activities undertaken in connection with the merger.
Macatawa Bank Corporation
10753 Macatawa Drive
Holland, Michigan 49424
(616) 494-1448
 
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Headquartered in Holland, Michigan, Macatawa offers a full range of banking, retail and commercial lending, wealth management and ecommerce services to individuals, businesses and governmental entities from a network of 26 full-service branches located throughout communities in Kent County, Ottawa County, and northern Allegan County, Michigan. As of March 31, 2024, Macatawa had consolidated total assets of approximately $2.6 billion, deposits of approximately $2.3 billion and shareholders’ equity of approximately $293.0 million. Macatawa’s common stock, no par value per share, which we refer to as “Macatawa common stock”, is traded on Nasdaq under the ticker symbol “MCBC.” Macatawa’s principal executive office is located at 10753 Macatawa Drive, Holland, Michigan 49424, telephone number: (616) 494-1448.
The merger and the merger agreement (See information beginning on pages 26 and 54)
Wintrust’s acquisition of Macatawa is governed by the Agreement and Plan of Merger, dated as of April 15, 2024, by and among Wintrust, Merger Sub and Macatawa, which we refer to as the “merger agreement”. The merger agreement provides that, if all of the conditions set forth in the merger agreement are satisfied or waived, Macatawa will be merged with and into Merger Sub and will cease to exist, which we refer to as the “merger”. After the consummation of the merger, Merger Sub will continue as the surviving company and remain a wholly-owned subsidiary of Wintrust. Promptly after completion of the merger, it is expected that Merger Sub will be merged with and into, or dissolved by, Wintrust. The merger agreement is included as Annex A to this proxy statement/prospectus and is incorporated herein by reference. We urge you to read the merger agreement carefully and fully because it is the legal document that governs the merger.
What Macatawa shareholders will receive (See page 54)
If the merger is completed, the shares of Macatawa common stock that you own immediately before the completion of the merger (including, for the avoidance of doubt, shares of Macatawa common stock received by holders of unvested shares of Macatawa restricted stock, which will automatically vest immediately prior to the effective time ) will be converted into the right to receive shares of Wintrust common stock. The Merger Consideration paid by Wintrust to Macatawa shareholders is expected to be $14.85 per share of outstanding Macatawa common stock, or an aggregate of approximately $510.3 million, based on 34,361,562 shares of Macatawa common stock issued and outstanding as of April 12, 2024, the last trading day before public announcement of the execution of the merger agreement, subject to adjustment for fluctuations in the trading price of Wintrust common stock as described below. All of the Merger Consideration will be paid to holders of Macatawa common stock in shares of Wintrust common stock, no par value per share, calculated based on the Per Share Merger Consideration described in the merger agreement, other than cash to be paid in lieu of any fractional shares.
For each of your shares of Macatawa common stock, you will receive the Per Share Merger Consideration calculated as set forth in the merger agreement in the form of shares of Wintrust common stock. The Per Share Merger Consideration that you will be entitled to receive for each share of Macatawa common stock will be determined based on the average of the volume-weighted average price of Wintrust common stock as reported under the heading “Bloomberg VWAP” on the Bloomberg page for Wintrust for each trading day during the ten trading day period ending on the second trading day prior to completion of the merger, which we refer to as the reference price, subject to a minimum and maximum reference price equal to $89.03 and $113.03, respectively. Assuming that the reference price were calculated as of June 17, 2024, the last practicable date prior to the date of this proxy statement/prospectus, you would be entitled to receive 0.1590 shares of Wintrust common stock for each share of Macatawa common stock. If the reference price is less than or equal to the minimum of $89.03, each share of Macatawa common stock will be entitled to 0.1668 shares of Wintrust common stock, and if the reference price is greater than or equal to the maximum of $113.03, each share of Macatawa common stock will be entitled to 0.1314 shares of Wintrust common stock. If the reference price is greater than or equal to $89.03 and not more than $113.03, the Per Share Merger Consideration will be variable and calculated by dividing (i) the amount obtained by dividing the aggregate Merger Consideration by the reference price by (ii) the number of outstanding shares of Macatawa common stock. For a description of how the Per Share Merger Consideration will be calculated, see “Description of the Merger Agreement — Consideration to be received in the merger” on page 54 and “— Upset condition” on page 55.
 
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Exchange of certificates (See page 56)
Once the merger is complete, Equiniti Trust Company, LLC, which we refer to as the “exchange agent”, will mail you materials and instructions for exchanging your Macatawa stock certificates (which, for purposes of this proxy statement/prospectus, shall be deemed to include certificates or book-entry account statements) for shares of Wintrust common stock to be issued by book-entry transfer. You should not send in your Macatawa stock certificates with your completed proxy card. Instead, you should wait until you receive the transmittal materials and instructions from the exchange agent.
Material U.S. federal income tax consequences of the merger (See page 46)
Macatawa shareholders generally will not recognize gain or loss if they exchange their Macatawa shares for Wintrust common stock, except in the event that Macatawa shareholders receive cash instead of a fractional share of Wintrust common stock. The tax consequences of the merger to each Macatawa shareholder will depend on such Macatawa shareholder’s own situation. Macatawa shareholders should consult with their own tax advisors for a full understanding of the tax consequences of the merger to them. Each of ArentFox Schiff LLP and Warner Norcross + Judd LLP have delivered tax opinions, dated June 13, 2024, to the effect that the merger qualifies as a reorganization under Section 368(a) of the Internal Revenue Code. In addition, the completion of the merger is conditioned on receipt of a tax opinion from each of ArentFox Schiff LLP and Warner Norcross + Judd LLP to the same effect as the opinions described in the preceding sentence. The opinions will not bind the Internal Revenue Service, which could take a different view.
Reasons for the merger (See page 43)
Macatawa’s board of directors has unanimously (i) determined that the merger is in the best interests of Macatawa and its shareholders and (ii) adopted the merger agreement. The Macatawa board of directors unanimously recommends that its shareholders vote “FOR” the adoption of the merger agreement.
In its deliberations and in making its determination, Macatawa’s board of directors considered numerous factors, including the following:

a review of the risks and prospects of Macatawa remaining independent, including the challenges of the current financial and regulatory climate and the significant costs associated with increasing regulatory and technological burdens;

the business, financial condition, safety and soundness, size, operating model, brand, acquisition history and experience, regulatory standing, culture and earnings prospects of Wintrust;

the nature and value of the Merger Consideration;

the social and economic impact of the merger on Macatawa and its employees, customers, suppliers and communities which it serves and the fact that many members of senior management, officers and employees will be retained as employees post-transaction; and

the fact that Macatawa Bank will remain a separately chartered bank subsidiary of Wintrust with a separate, legally constituted board of directors.
Wintrust’s board of directors concluded that the merger is in the best interests of Wintrust and its shareholders. In deciding to approve the merger, Wintrust’s board of directors considered a number of factors, including:

management’s view that the acquisition provides an attractive opportunity for Wintrust to expand into west Michigan;

Macatawa’s community banking orientation and its compatibility with Wintrust and its subsidiaries;

a review of the demographic, economic and financial characteristics of the markets in which Macatawa operates, including existing and potential competition and history of the market areas with respect to financial institutions;

management’s review of Macatawa’s business, operations, earnings and financial condition, including capital levels and asset quality of Macatawa Bank;
 
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efficiencies expected to come from integrating certain of Macatawa’s operations into Wintrust’s existing operations; and

the likelihood that the merger will be approved by the relevant bank regulatory authorities without undue burden and in a timely manner.
Board recommendation to Macatawa’s shareholders (See page 43)
Macatawa’s board of directors believes that the merger of Macatawa with Wintrust is in the best interests of Macatawa and its shareholders. Macatawa’s board of directors unanimously recommends that you voteFORadoption of the merger agreement.
Opinion of Macatawa’s financial advisor (See page 34 and Annex C)
Macatawa retained Morgan Stanley & Co. LLC (“Morgan Stanley”) to provide it with financial advisory services in connection with a potential sale of Macatawa. Macatawa selected Morgan Stanley to act as its financial advisor based on Morgan Stanley’s qualifications, expertise and reputation, and its knowledge of the business and affairs of Macatawa. On April 15, 2024, at a meeting of the board of directors of Macatawa, Morgan Stanley rendered its oral opinion, subsequently confirmed by delivery of a written opinion dated April 15, 2024, to the effect that, as of the date of such opinion, and based upon and subject to the various assumptions made, procedures followed, matters considered, and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth in its written opinion, the Per Share Merger Consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement was fair from a financial point of view to the holders of shares of Macatawa common stock.
The full text of the written opinion of Morgan Stanley, dated April 15, 2024, is attached as Annex C and incorporated by reference into this proxy statement/prospectus. The opinion sets forth, among other things, the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of the review undertaken by Morgan Stanley in rendering its opinion. Morgan Stanley’s opinion was directed to the board of directors of Macatawa, in its capacity as such, and addresses only the fairness from a financial point of view to holders of shares of Macatawa common stock of the Per Share Merger Consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement as of the date of the opinion. Morgan Stanley’s opinion does not address any other aspect of the transactions contemplated by the merger agreement and does not constitute a recommendation to shareholders of Macatawa as to how to vote at any shareholders’ meetings held with respect to the proposed transaction or any other matter or whether to take any other action with respect to the proposed transaction. The summary of Morgan Stanley’s opinion set forth in this proxy statement/prospectus is qualified in its entirety by reference to the full text of the opinion.
For a description of the opinion of Morgan Stanley, see “The Merger — Opinion of Macatawa’s Financial Advisor” beginning on page 34.
Interests of officers and directors of Macatawa and its subsidiary in the merger may be different from, or in addition to, yours (See page 49)
When you consider the Macatawa board of directors’ recommendation to vote in favor of the adoption of the merger agreement, you should be aware that some of Macatawa’s directors and officers may have interests in the merger that are different from, or in addition to, your interests as a shareholder. Macatawa’s board of directors was aware of these interests and took them into account in approving the merger. For example, Macatawa entered into certain change of control agreements with certain of its executive officers that provide for severance benefits in the event of termination without cause or good reason within six months before or 24 months after a change in control of Macatawa. It is also expected that certain executive officers of Macatawa will receive restricted stock units from Wintrust upon the consummation of the merger.
Wintrust has also agreed to pay for directors’ and officers’ liability insurance covering the directors and officers of Macatawa and Macatawa Bank immediately prior to the consummation of the merger, subject to limits on availability and cost, for up to six years.
 
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As of March 31, 2024, Macatawa’s directors and executive officers owned, in the aggregate, 2,980,439 shares of Macatawa’s common stock, representing approximately 8.7% of Macatawa’s outstanding shares of common stock.
Macatawa shareholders will not have dissenters’ rights in connection with the merger (See page 53)
Macatawa shareholders do not have dissenters’ rights in connection with the merger.
The merger and the performance of the surviving company are subject to a number of risks (See page 15)
There are a number of risks relating to the merger and to the businesses of Wintrust, Macatawa and Merger Sub following the merger. See the “Risk Factors” beginning on page 15 of this proxy statement/prospectus for a discussion of these and other risks and see also the documents that Wintrust and Macatawa have filed with the SEC and which have been incorporated by reference into this proxy statement/prospectus.
Macatawa shareholder approval will be required to complete the merger and to adjourn the special meeting, if necessary (See page 23)
To adopt the merger agreement at least a majority of the outstanding shares of Macatawa common stock entitled to vote must be voted in favor of such proposal at the special meeting. The proposal to adjourn the special meeting, if necessary, requires the affirmative vote of holders of at least a majority of the shares of Macatawa entitled to vote, present in person or by proxy, if a quorum is present. In the absence of a quorum, the holders of at least a majority of the shares of Macatawa present in person or by proxy may adjourn the special meeting. The Macatawa merger-related compensation proposal is a non-binding advisory vote and will not be binding on Macatawa or Wintrust.
To satisfy the quorum requirements set forth in Macatawa’s bylaws, shareholders holding at least a majority of the outstanding shares of Macatawa entitled to vote on the matter at the special meeting must be present in person or by proxy for consideration of such matter at the special meeting. Shareholders may vote their shares in person at the special meeting or in accordance with the voting instructions included on your proxy card, which permits submission of your proxy (1) by returning a properly completed proxy in the enclosed prepaid envelope, (2) via the internet or (3) over the telephone.
On April 15, 2024, certain of the directors and executive officers of Macatawa who own shares of Macatawa common stock agreed to vote all of their shares of Macatawa common stock in favor of the merger agreement pursuant to a voting agreement. The voting agreement covers approximately 6.9% of Macatawa’s outstanding shares of common stock as of March 31, 2024. The voting agreement terminates if, among other things, the merger agreement is terminated in accordance with its terms. A copy of the voting agreement is attached to this proxy statement/prospectus as Annex B.
Macatawa special meeting (See page 23)
Macatawa’s special meeting of shareholders will be held at Macatawa’s corporate offices, which are located at 10753 Macatawa Drive, Holland, Michigan 49424 on July 31, 2024 at 8:00 a.m., local time. Macatawa’s board of directors is soliciting proxies for use at the special meeting. At the special meeting, Macatawa shareholders will be asked to vote on proposals to adopt the merger agreement, to approve the Macatawa merger-related compensation proposal and to adjourn the special meeting, if necessary.
Record date for the special meeting; revocability of proxies (See page 23)
You may vote at the special meeting if you own shares of Macatawa common stock of record at the close of business on June 11, 2024. You will have one vote for each share of Macatawa common stock you owned on that date. You may change your vote or revoke your proxy at any time before it is voted by filing with the secretary of Macatawa a duly executed revocation of proxy or submitting a new proxy card with a later date. You may also revoke any previously submitted proxy by voting in person at the special meeting.
 
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Completion of the merger is subject to regulatory approvals (See page 61)
Subject to the terms of the merger agreement, Wintrust and Macatawa have agreed in the merger agreement to use commercially reasonable efforts to obtain, as promptly as practical, consents, approvals and authorizations of all third parties and governmental entities necessary or desirable for the consummation of the merger. This includes approval from the Board of Governors of the Federal Reserve System (the “Federal Reserve Board”). The initial submission of the applications to the Federal Reserve Board occurred on April 30, 2024. Wintrust and Macatawa believe that the merger does not raise significant regulatory concerns and that all requisite regulatory approvals will be obtained. However, there can be no assurance that the regulatory approvals will be obtained and that the approvals will not impose additional conditions or requirements on the merger. For more information, see “The Merger — Regulatory approvals” beginning on page 48.
Conditions to the merger (See page 61)
Conditions to Each Party’s Obligation to Effect the Merger.   The respective obligations of each party to effect the merger are subject to fulfillment of certain conditions, including:

adoption of the merger agreement at the Macatawa special meeting by the holders of at least a majority of the outstanding shares of Macatawa common stock entitled to vote;

receipt of all regulatory approvals required in connection with the merger, the expiration of all applicable notice periods and waiting periods, and all such regulatory approvals must be in effect (the “Requisite Regulatory Approval”);

no provision of any applicable law making illegal or otherwise prohibiting the consummation of the merger, temporary restraining order, preliminary or permanent injunction or other order issued by a court of competent jurisdiction preventing the consummation of the merger;

neither party shall be subject to any order of a court or agency of competent jurisdiction that enjoins or prohibits the consummation of the merger;

the registration statement having been declared effective under the Securities Act of 1933, as amended (the “Securities Act”), no stop order suspending the effectiveness of the registration statement can have been issued by the SEC and no proceedings for that purpose can have been commenced or threatened by the SEC; and

approval of the listing of the shares of Wintrust common stock issuable pursuant to the merger agreement on Nasdaq.
Conditions to Wintrust’s Obligation to Effect the Merger.   Wintrust’s obligations are subject to fulfillment of certain conditions, including:

accuracy of representations and warranties of Macatawa in the merger agreement as of the closing date, except as otherwise set forth in the merger agreement;

performance by Macatawa in all material respects of its covenants under the merger agreement;

receipt of a certificate from Macatawa’s chief executive officer or chief financial officer certifying the satisfaction of conditions including the accuracy of representations and warranties of Macatawa, performance by Macatawa of all covenants and obligations, and no material adverse effects of Macatawa;

no Macatawa material adverse effect shall have occurred and Macatawa shall not have been subject to any regulatory agreement, in each case since the date the merger agreement was signed; and

receipt of a tax opinion of ArentFox Schiff LLP (“ArentFox”), acting as counsel to Wintrust.
Conditions to Macatawa’s Obligation to Effect the Merger.   Macatawa’s obligations are subject to fulfillment of certain conditions, including:

accuracy of representations and warranties of Wintrust and Merger Sub in the merger agreement as of the closing date, except as otherwise set forth in the merger agreement;
 
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performance by Wintrust and Merger Sub in all material respects of all of the covenants and obligations under the merger agreement;

receipt of a certificate from Wintrust’s chief executive officer, chief financial officer, or general counsel certifying the satisfaction of conditions including the accuracy of representations and warranties of Wintrust, performance by Wintrust and Merger Sub of all covenants and obligations, and no material adverse effects of Wintrust;

no Wintrust material adverse effect shall have occurred; and

receipt of a tax opinion of Warner Norcross + Judd LLP (“Warner Norcross”), acting as counsel to Macatawa.
Upset Condition.   If the Upset Condition (as defined below) exists as of the last day of the Pricing Period (as defined below), Macatawa will have the right to:
(a)
proceed with the merger on the basis of the Per Share Merger Consideration as described above (the “Base Per Share Merger Consideration”); or
(b)
request Wintrust to adjust the aggregate share amount used to calculate the Per Share Merger Consideration, to an aggregate share amount computed by (i) multiplying the aggregate share amount by (ii) a fraction (A) that has as its numerator the Floor Purchaser Price (as defined below) and (B) that has as its denominator the Average Purchaser Closing Price (as defined below) (such amount resulting from such computation, the “Adjusted Per Share Merger Consideration”).
If Macatawa exercises its right to make such a request described in the foregoing clause (b), Wintrust shall either accept or decline the Adjusted Per Share Merger Consideration. If Wintrust declines the Adjusted Per Share Merger Consideration or fails to deliver written notice of its decision to accept or decline the Adjusted Per Share Merger Consideration in the time period specified in the merger agreement, Macatawa may elect to proceed with the merger on the basis of the Base Per Share Merger Consideration by delivering written notice of such election within the time period specified in the merger agreement, otherwise, the merger agreement will automatically terminate.
An “Upset Condition” occurs if both of the following conditions exist as of the last day of the Pricing Period:
(a)
the Average Purchaser Closing Price is less than $80.82 (the “Floor Purchaser Price”); and
(b)
the number determined by dividing the Average Purchaser Closing Price by $101.03 is less than the number obtained by subtracting (i) 20% from (ii) the quotient obtained by dividing the Final Index Price by the Initial Index Price.
The “Average Purchaser Closing Price” is the average volume weighted trading price per share of Wintrust common stock on which shares of Wintrust common stock were actually traded in transactions reported on Nasdaq during the 20 trading days immediately preceding the first date on which all Requisite Regulatory Approvals (and waivers, if applicable) necessary for the consummation of the merger have been received (disregarding any waiting period) (the “Pricing Period”).
The “Initial Index Price” means the $94.81 closing price of the KBW Nasdaq Regional Banking Index (KRX) on April 12, 2024. The “Final Index Price” means the closing price of the KBW Nasdaq Regional Banking Index (KRX) on the last day of the Pricing Period.
How the merger agreement may be terminated by Wintrust and Macatawa (See page 62)
By written agreement, Wintrust and Macatawa may mutually agree to terminate the merger agreement and abandon the merger at any time. Subject to conditions and circumstances described in the merger agreement, Wintrust or Macatawa, as the case may be, may also terminate the merger agreement as follows:

by either party if the merger is not completed by April 15, 2025;

in certain circumstances, by either party in the event that a material breach or failure to perform any representation, warranty or covenant results in a failure of a closing condition and is not cured within a specified period of time;
 
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in certain circumstances by either party if the merger agreement and the transactions contemplated therein are not approved by Macatawa’s shareholders;

by Wintrust, before receipt of Macatawa’s shareholder approval if the Macatawa board of directors effected a Company Adverse Recommendation Change (as defined in the merger agreement), the Macatawa board of directors failed to reject a Company Takeover Proposal (as defined below), Macatawa enters into a Company Acquisition Agreement (as defined in the merger agreement), or the Macatawa board of directors fails to publicly reaffirm its recommendation of the merger within three business days of a written request by Wintrust, in each case as further described in “Description of the Merger Agreement — No solicitation of or discussions relating to a Company Takeover Proposal” beginning on page 58;

by Macatawa prior to receipt of Macatawa’s shareholder approval in order to enter into a Company Acquisition Agreement in respect of a Company Superior Proposal (as defined below), provided that Macatawa pays Wintrust the Termination Fee (as defined below) as further described in “Description of the Merger Agreement — Termination fee” beginning on page 62;

in certain circumstances, by either party, if any governmental entity has issued an order or taken any other action permanently enjoining, restraining or otherwise prohibiting consummation of the merger;

by Wintrust, if Macatawa Bank is examined for compliance with the Community Reinvestment Act (“CRA”) and receives written notification of a rating lower than “Satisfactory”; and

in certain circumstances, in the event an Upset Condition has occurred and the Adjusted Per Share Merger Consideration is not accepted by Wintrust and Macatawa does not elect to proceed with the merger under the terms of the merger agreement.
Termination fees and expenses may be payable under some circumstances (See page 62)
If the merger agreement is terminated under certain circumstances, Macatawa will be obligated to pay Wintrust a termination fee of $20,400,000. See “Description of the Merger Agreement — Termination fee” for additional information.
Accounting treatment of the merger
The merger will be accounted for as a purchase transaction in accordance with accounting principles generally accepted in the United States.
Certain differences in Wintrust shareholder rights and Macatawa shareholder rights (See page 67)
The rights of Macatawa shareholders will change as a result of the merger due to differences in Wintrust’s and Macatawa’s governing documents. The rights of Macatawa shareholders are governed by Michigan law and by Macatawa’s articles of incorporation and amended and restated bylaws. Upon the completion of the merger, Macatawa shareholders immediately prior to the effective time will become Wintrust shareholders and their rights as Wintrust shareholders will therefore be governed by Illinois law and Wintrust’s amended and restated articles of incorporation and amended and restated bylaws.
See “Comparison of Rights of Wintrust Shareholders and Macatawa Shareholders” beginning on page 67 for a description of the material differences in shareholders’ rights under each of Wintrust and Macatawa’s governing documents.
Comparative Market Price Data
The following table sets forth the closing sales prices per share of Wintrust common stock and Macatawa common stock, respectively, on Nasdaq on April 12, 2024, the last trading day prior to the public announcement of the merger, and on June 17, 2024, the last practicable trading day prior to the mailing of this proxy statement/prospectus. The table also shows the estimated implied value of the merger consideration proposed for each share of Macatawa common stock as of the same two dates. The implied value for the merger consideration was calculated by multiplying the closing sales price of a share of Wintrust
 
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common stock on the relevant date by the Per Share Merger Consideration of 0.1590 shares of Wintrust common stock for each share of Macatawa common stock.
Wintrust Common
Stock
Macatawa Common
Stock
Implied Per Share
Value of Merger
Consideration
April 12, 2024
$ 97.00 $ 9.59 $ 14.85
June 17, 2024
$ 93.42 $ 13.73 $ 14.85
 
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RISK FACTORS
In addition to the other information contained in or incorporated by reference into this proxy statement/prospectus, including the matters addressed under the caption “Special Notes Concerning Forward-Looking Statements” on page 19, you should consider the following risk factors carefully in deciding whether to vote for the adoption of the merger agreement. Additional risks and uncertainties not presently known to Wintrust and Macatawa or that are not currently believed by Wintrust or Macatawa to be important to you, if they materialize, also may adversely affect the merger and Wintrust and Macatawa.
In addition, Wintrust and Macatawa’s respective businesses are subject to numerous risks and uncertainties, including the risks and uncertainties described, in their respective Annual Report on Form 10-K for the year ended December 31, 2023, as may be amended from time to time, which are both incorporated by reference into this proxy statement/prospectus.
Risks relating to the merger
Because the market price of Wintrust common stock may fluctuate, you cannot be certain of the precise value of the stock portion of the merger consideration you may receive in the merger.
At the time the merger is completed, each issued and outstanding share of Macatawa common stock (including each unvested share of restricted stock awarded under the Company Stock Plan (as defined in the merger agreement) and excluding shares of Macatawa common stock owned by Macatawa, Wintrust or Merger Sub or any of their subsidiaries) will be converted into the right to receive consideration in the form of Wintrust common stock, subject to adjustment. The exchange ratio for the Wintrust common stock, as calculated in accordance with the formula set forth in the merger agreement, may fluctuate depending on the market price of Wintrust common stock during the reference period.
There will be a time lapse between each of the date on which Macatawa shareholders vote to approve the merger and adopt the merger agreement at the special meeting, the date on which the exchange ratio is determined and the date on which Macatawa shareholders entitled to receive shares of Wintrust common stock actually receive such shares. The market value of Wintrust common stock may fluctuate during these periods. Consequently, at the time Macatawa shareholders must decide whether to approve the merger and the merger agreement, they will not know the actual market value of the shares of Wintrust common stock they will receive when the merger is completed. The actual value of the shares of Wintrust common stock received by the Macatawa shareholders will depend on the market value of shares of Wintrust common stock on that date. This market value may be less than the value used to determine the exchange ratio, as that determination will be made with respect to a period occurring prior to the consummation of the merger. In certain circumstances an Upset Condition may be deemed to occur and Macatawa will be permitted to request Wintrust to adjust the Merger Consideration.
Wintrust may be unable to successfully integrate Macatawa and Macatawa Bank’s operations and may not realize the anticipated benefits of acquiring Macatawa.
Wintrust and Macatawa entered into the merger agreement with the expectation that Wintrust would be able to successfully integrate Macatawa and Macatawa Bank’s operations and that the merger would result in various benefits, including, among other things, enhanced revenues and revenue synergies, an expanded market reach and operating efficiencies. Achieving the anticipated benefits of the merger is subject to a number of uncertainties, including whether Wintrust integrates and operates Macatawa in an efficient and effective manner, and general competitive factors in the marketplace. The process of integrating operations could cause an interruption of, or loss of momentum in, the activities of one or more of the surviving company’s businesses or the loss of key personnel. The diversion of management’s attention and any delays or difficulties encountered in connection with the merger and the integration of the companies’ operations could have an adverse effect on the business, financial condition, operating results and prospects of the surviving company after the merger. Failure to achieve these anticipated benefits could result in increased costs, decreases in the amount of expected revenues and diversion of management’s time and energy and could have an adverse effect on the surviving company’s business, financial condition, operating results and prospects.
 
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Among the factors considered by the boards of directors of Wintrust and Macatawa in connection with their respective approvals of the merger agreement were the benefits that could result from the merger. We cannot give any assurance that these benefits will be realized within the time periods contemplated or that they will be realized at all.
Macatawa will be subject to business uncertainties while the merger is pending, which could adversely affect its business.
Uncertainty about the effect of the merger on employees and customers may have an adverse effect on Macatawa, and, consequently, the surviving company. Although Macatawa intends to take steps to reduce any adverse effects, these uncertainties may impair Macatawa’s ability to attract, retain and motivate key personnel until the merger is consummated and for a period of time thereafter, and could cause customers and others that deal with Macatawa to seek to change their existing business relationships with Macatawa. Employee retention at Macatawa may be particularly challenging during the pendency of the merger, as employees may experience uncertainty about their roles with the surviving company following the merger.
Termination of the merger agreement could negatively impact Macatawa.
If the merger is not completed for any reason, including as a result of Macatawa’s shareholders declining to approve the merger, the ongoing business of Macatawa may be adversely impacted and, without realizing any of the anticipated benefits of completing the merger, Macatawa would be subject to a number of risks, including the following:

Macatawa may experience negative reactions from its customers, vendors and employees;

Macatawa will have incurred substantial expenses and will be required to pay certain costs relating to the merger, whether or not the merger is completed;

Macatawa could owe a termination fee of $20,400,000 to Wintrust under certain circumstances;

potential litigation related to any failure to complete the merger or related to any enforcement proceeding commenced against Wintrust or Macatawa to perform their respective obligations pursuant to the merger agreement;

the merger agreement places certain restrictions on the conduct of Macatawa’s business prior to the completion of the merger. Such restrictions, the waiver of which is subject to the consent of Wintrust (not to be unreasonably withheld, delayed or conditioned), may prevent Macatawa from making certain acquisitions or taking certain other specified actions during the pendency of the merger (see “Description of the Merger Agreement — Conduct of business pending the merger and certain covenants” beginning on page 56 of this proxy statement/prospectus for a description of the restrictive covenants applicable to Macatawa); and

matters relating to the merger (including integration planning) will require substantial commitments of time and resources by Macatawa management, which would otherwise have been devoted to other opportunities that may have been beneficial to Macatawa as an independent company.
Regulatory approvals may not be received, may take longer than expected or may impose conditions that are not presently anticipated or cannot be met.
Before the transactions contemplated in the merger agreement can be completed, various approvals must be obtained from the bank regulatory authorities. In deciding whether to grant these approvals, the relevant governmental entities will consider a variety of factors, including the regulatory standing of each of the parties and the effect of the merger on competition. An adverse development in either party’s regulatory standing or other factors could result in an inability to obtain one or more of the required regulatory approvals or delay receipt of required approvals.
The terms of the approvals that are granted may impose conditions, limitations, obligations or costs, or place restrictions on the conduct of the surviving company’s business or require changes to the terms of the transactions contemplated by the merger agreement. There can be no assurance that regulators will not impose any such conditions, limitations, obligations or restrictions and that such conditions, limitations,
 
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obligations or restrictions will not have the effect of delaying the completion of any of the transactions contemplated by the merger agreement, imposing additional material costs on or materially limiting the revenues of the surviving company following the merger or otherwise reduce the anticipated benefits of the merger if the merger were consummated successfully within the expected timeframe. Nor can there be any assurance that any such conditions, terms, obligations or restrictions will not result in the delay or abandonment of the merger. Additionally, the completion of the merger is conditioned on the absence of certain orders or injunctions issued by any court of competent jurisdiction or other legal restraints that would prohibit or make illegal the consummation of any of the transactions contemplated by the merger agreement.
Wintrust and Macatawa believe that the proposed transactions should not raise significant regulatory concerns and that the parties will be able to obtain all Requisite Regulatory Approvals in a timely manner. Wintrust will use commercially reasonable efforts to obtain the necessary regulatory approvals, and Macatawa will use commercially reasonable efforts to assist in obtaining all such approvals.
Some of the directors and executive officers of Macatawa and Macatawa Bank have interests and arrangements that could have affected their respective decision to support or approve the merger.
The interests of some of the directors and executive officers of Macatawa and its subsidiary in the merger are different from, and may be in addition to, those of Macatawa shareholders generally and could have affected their decision to support or approve the merger. These interests include, but may not be limited to, (1) Wintrust’s agreement to provide officers and directors of Macatawa with continuing indemnification rights and directors and officers insurance coverage, subject to limits on availability and cost, for up to six years following the merger, (2) certain change of control agreements between Macatawa and certain of Macatawa’s executive officers that provide such executive with severance benefits in certain circumstances and (3) it is expected that certain Macatawa executive officers will receive restricted stock units upon the consummation of the merger.
Certain of the directors and executive officers of Macatawa who own shares of Macatawa common stock have entered into a voting agreement that requires them to vote all of their shares of Macatawa common stock at the special meeting in favor of the merger agreement. The voting agreement covers approximately 6.9% of Macatawa’s outstanding shares of common stock as of March 31, 2024.
In addition, subject to the terms and conditions of the merger agreement, Wintrust will appoint one individual serving on Macatawa’s board of directors to serve on Wintrust’s board of directors, as further described in the section entitled “Description of the Merger Agreement — Governance matters” beginning on page 63 of this proxy statement/prospectus.
As a result, the directors of Macatawa may be more likely to recommend to Macatawa’s shareholders the adoption of the merger agreement than if they did not have these interests.
Macatawa shareholders are not entitled to dissenters’ rights in connection with the merger.
Dissenters’ rights are statutory rights that enable shareholders to dissent from certain extraordinary transactions, such as certain mergers, and to demand that the corporation pay the fair value for their shares as determined by a court in a judicial proceeding instead of receiving the consideration offered to shareholders in connection with the applicable transaction. Under the MBCA, holders of shares of Macatawa common stock will not have such rights in connection with the merger.
Risks relating to the businesses of Wintrust and the surviving company
Macatawa’s shareholders will not control Wintrust’s future operations.
Currently, Macatawa’s shareholders own 100% of Macatawa and have the power to approve or reject any matters requiring shareholder approval under Michigan law and Macatawa’s articles of incorporation and bylaws. After the merger, Macatawa shareholders are expected to become owners of less than 9% of the outstanding shares of Wintrust common stock. Even if all former Macatawa shareholders voted together,
 
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the former Macatawa shareholders most likely would not have a significant impact on the approval or rejection of future Wintrust proposals submitted to a shareholder vote.
The market price of Wintrust common stock after the merger may be affected by factors different from those currently affecting the price of Macatawa common stock.
Upon completion of the merger, holders of Macatawa common stock will become holders of Wintrust common stock. The results of operations of Wintrust will be affected by some factors that are different from those currently affecting the results of operations of Macatawa. For example, Wintrust operates in Canada and certain states of the United States, including Wisconsin and Indiana, where Macatawa does not have significant operations. Accordingly, the results of operations of Wintrust will be affected by business and other developments in those areas to a larger extent than those of Macatawa.
 
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SPECIAL NOTES CONCERNING FORWARD-LOOKING STATEMENTS
This document contains, and the documents into which it may be incorporated by reference may contain, forward-looking statements within the meaning of federal securities laws. Forward-looking information are often, but not always, identified through the use of words such as “intend,” “plan,” “project,” “expect,” “anticipate,” “believe,” “estimate,” “contemplate,” “possible,” “point,” “will,” “may,” “should,” “would,” “could” and similar expressions and variations or negatives of these words, but not all forward-looking statements include such words. Forward-looking statements and information are not historical facts, are premised on many factors and assumptions, and represent only management’s expectations, estimates and projections regarding future events. Similarly, these statements are not guarantees of future performance and involve certain risks and uncertainties that are difficult to predict, and which may include, but are not limited to, those listed below and the risks described in Part I, Item 1A “Risk Factors” of (i) Wintrust’s Annual Report on Form 10-K for the year ended December 31, 2023 and (ii) Macatawa’s Annual Report on Form 10-K for the year ended December 31, 2023, as amended by the Annual Report on Form 10-K/A filed with the SEC on April 29, 2024, as well as other risks and uncertainties set forth from time to time in Wintrust and Macatawa’s other filings with the SEC. Wintrust and Macatawa intend such forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995, and is including this statement for purposes of invoking these safe harbor provisions. Such forward-looking statements may be deemed to include, among other things, statements relating to Wintrust and Macatawa’s future financial performance, the performance of its loan portfolio, the expected amount of future credit reserves and charge-offs, delinquency trends, growth plans, regulatory developments, securities that Wintrust may offer from time to time, and management’s long-term performance goals, as well as statements relating to the anticipated effects on financial condition and results of operations from expected developments or events, Wintrust and Macatawa’s business and growth strategies, including future acquisitions of banks, specialty finance or wealth management businesses, internal growth and plans to form additional de novo banks or branch offices. Actual results could differ materially from those addressed in the forward-looking statements as a result of numerous factors, including, but not limited to, the following:

the risks and other factors described above under the heading “Risk Factors”;

economic conditions and events that affect the economy, housing prices, the job market and other factors that may adversely affect Wintrust’s liquidity and the performance of its loan portfolios, including an actual or threatened U.S. government debt default or rating downgrade, particularly in the markets in which it operates;

negative effects suffered by us or our customers resulting from changes in U.S. trade policies;

the extent of defaults and losses on Wintrust’s loan portfolio, which may require further increases in its allowance for credit losses;

estimates of fair value of certain of Wintrust’s assets and liabilities, which could change in value significantly from period to period;

the financial success and economic viability of the borrowers of our commercial loans;

commercial real estate market conditions in the Chicago metropolitan area and southern Wisconsin;

the extent of commercial and consumer delinquencies and declines in real estate values, which may require further increases in Wintrust’s allowance for credit losses;

inaccurate assumptions in our analytical and forecasting models used to manage our loan portfolio;

changes in the level and volatility of interest rates, the capital markets and other market indices that may affect, among other things, Wintrust’s liquidity and the value of its assets and liabilities;

the interest rate environment, including a prolonged period of low interest rates or rising interest rates, either broadly or for some types of instruments, which may affect Wintrust’s net interest income and net interest margin, and which could materially adversely affect Wintrust’s profitability;

competitive pressures in the financial services business which may affect the pricing of Wintrust’s loan and deposit products as well as its services (including wealth management services), which may result in loss of market share and reduced income from deposits, loans, advisory fees and income from other products;
 
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failure to identify and complete favorable acquisitions in the future or unexpected losses, difficulties or developments related to Wintrust’s recent or future acquisitions;

unexpected difficulties and losses related to FDIC-assisted acquisitions;

harm to Wintrust’s reputation;

any negative perception of Wintrust’s financial strength;

ability of Wintrust to raise additional capital on acceptable terms when needed;

disruption in capital markets, which may lower fair values for Wintrust’s investment portfolio;

ability of Wintrust to use technology to provide products and services that will satisfy customer demands and create efficiencies in operations and to manage risks associated therewith;

failure or breaches of our security systems or infrastructure, or those of third parties;

security breaches, including denial of service attacks, hacking, social engineering attacks, malware intrusion and similar events or data corruption attempts and identity theft;

adverse effects on our information technology systems, or those of third parties, resulting from failures, human error or cyberattacks (including ransomware);

adverse effects of failures by our vendors to provide agreed upon services in the manner and at the cost agreed, particularly our information technology vendors;

increased costs as a result of protecting our customers from the impact of stolen debit card information;

accuracy and completeness of information Wintrust receives about customers and counterparties to make credit decisions;

ability of Wintrust to attract and retain senior management experienced in the banking and financial services industries, and ability of Wintrust to effectively manage the transition of the chief executive officer role;

environmental liability risk associated with lending activities;

the impact of any claims or legal actions to which Wintrust is subject, including any effect on our reputation;

losses incurred in connection with repurchases and indemnification payments related to mortgages and increases in reserves associated therewith;

the loss of customers as a result of technological changes allowing consumers to complete their financial transactions without the use of a bank;

the soundness of other financial institutions and the impact of recent failures of financial institutions, including broader financial institution liquidity risk and concerns;

the expenses and delayed returns inherent in opening new branches and de novo banks;

liabilities, potential customer loss or reputational harm related to closings of existing branches;

examinations and challenges by tax authorities, and any unanticipated impact of the Tax Cuts and Jobs Act;

changes in accounting standards, rules and interpretations, and the impact on Wintrust’s financial statements;

the ability of Wintrust to receive dividends from its subsidiaries;

the impact of Wintrust’s transition from LIBOR to an alternative benchmark rate for current and future transactions;

a decrease in Wintrust’s capital ratios, including as a result of declines in the value of its loan portfolios, or otherwise;
 
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legislative or regulatory changes, particularly changes in regulation of financial services companies and/or the products and services offered by financial services companies;

changes in laws, regulations, rules, standards and contractual obligations regarding data privacy and cybersecurity;

a lowering of our credit rating;

changes in U.S. monetary policy and changes to the Federal Reserve’s balance sheet, including changes in response to persistent inflation or otherwise;

regulatory restrictions upon our ability to market our products to consumers and limitations on our ability to profitably operate our mortgage business;

increased costs of compliance, heightened regulatory capital requirements and other risks associated with changes in regulation and the regulatory environment;

the impact of heightened capital requirements;

increases in Wintrust’s FDIC insurance premiums, or the collection of special assessments by the FDIC;

delinquencies or fraud with respect to Wintrust’s premium finance business;

credit downgrades among commercial and life insurance providers that could negatively affect the value of collateral securing Wintrust’s premium finance loans;

Wintrust’s ability to comply with covenants under its credit facility;

fluctuations in the stock market, which may have an adverse impact on Wintrust’s wealth management business and brokerage operation;

widespread outages of operational, communication, or other systems, whether internal or provided by third parties, natural or other disasters (including acts of terrorism, armed hostilities and pandemics), and the effects of climate change could have an adverse effect on Wintrust’s financial condition and results of operations, lead to material disruption of the company’s operations or the ability or willingness of clients to access Wintrust’s products and services; and

the severity, magnitude and duration of the COVID-19 pandemic, including the continued emergence of variant strains, and the direct and indirect impact of such pandemic, as well as responses to the pandemic by the government, businesses and consumers, on the economy, our financial results, operations and personnel, commercial activity and demand across our business and our customers’ businesses.
Therefore, there can be no assurances that future actual results will correspond to any forward-looking statements. The reader is cautioned not to place undue reliance on any forward-looking statement made herein. Forward-looking statements speak only as of the date they are made or as of such date that may be referenced within the statement, and Wintrust and Macatawa undertake no obligation to update any forward-looking statement to reflect the impact of circumstances or events that arise after the date the forward-looking statement was made, except as required by law. Persons are advised, however, to consult further disclosures management makes on related subjects in its reports filed with the SEC and in future press releases.
 
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THE MACATAWA PROPOSALS
Approval of the Merger Agreement
At the special meeting, Macatawa shareholders will be asked to approve the merger agreement. Holders of Macatawa common stock should read this proxy statement/prospectus in its entirety, including the Annexes, for more detailed information concerning the merger agreement and the merger. A copy of the merger agreement is attached to this proxy statement/prospectus as Annex A.
After careful consideration, the Macatawa board of directors adopted the merger agreement, authorized and approved the merger and the transactions contemplated by the merger agreement and determined the merger agreement and the merger to be advisable and in the best interests of Macatawa and its shareholders. The Macatawa board of directors unanimously recommends that the Macatawa shareholders vote “FOR” the proposal to approve the merger agreement.
Macatawa Merger-Related Compensation Proposal
Section 14A of the Exchange Act and Rule 14a-21(c) under the Exchange Act require that Macatawa seek a non-binding, advisory vote from its shareholders to approve the “golden parachute” compensation that its named executive officers will receive in connection with the merger discussed in “The Merger — Interests of directors and executive officers in the merger” beginning on page 49. As required by these provisions, Macatawa is asking its shareholders to vote on the adoption of the following resolution:
“RESOLVED, that the compensation that may be paid or become payable to Macatawa’s named executive officers in connection with the merger, as disclosed in the table under the heading entitled “Quantification of Potential Payments and Benefits to Macatawa’s Named Executive Officers in Connection with the Merger” pursuant to Item 402(t) of Regulation S-K, including the associated narrative discussion, and the agreements or understandings pursuant to which such compensation may be paid or become payable, are hereby APPROVED.”
The vote with respect to this proposal is an advisory vote and will not be binding on Macatawa or Wintrust. Therefore, regardless of whether Macatawa shareholders approve this proposal, if the merger agreement is approved by the shareholders and the merger is completed, the “golden parachute” compensation will be paid to such named executive officers to the extent payable in accordance with the terms of their respective compensation contracts and arrangements. Approval of this proposal is not a condition to the closing of the merger. The Macatawa board of directors unanimously recommends that the Macatawa shareholders vote “FOR” the non-binding, advisory Macatawa merger-related compensation proposal.
Adjournment Proposal
The Macatawa special meeting may be adjourned to another time or place if there are insufficient votes represented at the Macatawa special meeting to constitute a quorum necessary to conduct business at the Macatawa special meeting or if there are insufficient votes necessary to obtain the approval of the merger agreement.
Macatawa requests that its shareholders authorize the holder of any proxy solicited by the Macatawa board of directors on a discretionary basis to vote in favor of adjourning the Macatawa special meeting to another time or place, if determined necessary or appropriate by Macatawa, to solicit additional proxies (including the solicitation of proxies from Macatawa shareholders who have previously voted). Approval of this proposal is not a condition to the closing of the merger. The Macatawa board of directors unanimously recommends that the Macatawa shareholders vote “FOR” approval of the adjournment proposal.
 
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INFORMATION ABOUT THE SPECIAL MEETING OF MACATAWA SHAREHOLDERS
The Macatawa board of directors is using this proxy statement/prospectus to solicit proxies from the holders of Macatawa common stock for use at the special meeting of Macatawa’s shareholders.
Date, time and place of the special meeting
The special meeting will be held at Macatawa’s corporate offices, which are located at 10753 Macatawa Drive, Holland, Michigan 49424 on July 31, 2024 at 8:00 a.m., local time.
Purpose of the special meeting
At the special meeting, the Macatawa board of directors will ask you to vote upon the following:

a proposal to adopt the merger agreement and thereby approve the merger;

a proposal to cast a non-binding, advisory vote to approve the compensation that may be paid or become payable to Macatawa’s named executive officers that is based on or otherwise related to the merger (the “Macatawa merger-related compensation proposal”);

a proposal to approve an adjournment of the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby; and

any other business that properly comes before the special meeting and any adjournment or postponement thereof.
Record date and voting rights for the special meeting
Macatawa has set the close of business on June 11, 2024, as the record date for determining the holders of its common stock entitled to notice of and to vote at the special meeting. Only Macatawa shareholders at the close of business on the record date are entitled to notice of and to vote at the special meeting. As of the record date, there were 34,361,562 shares of Macatawa common stock outstanding and entitled to vote at the special meeting.
Quorum
The presence in person or by proxy of at least a majority of the outstanding shares of Macatawa entitled to vote on the matter at the special meeting is required for a quorum to be present for consideration of such matter at the special meeting. Abstentions will count toward the establishment of a quorum, but broker non-votes will not count toward the establishment of a quorum because no routine matters will be brought before the meeting.
Vote required
Approval of the merger agreement proposal requires the affirmative vote of at least a majority of the outstanding shares of Macatawa common stock entitled to vote. Approval of the non-binding, advisory Macatawa merger-related compensation proposal and the proposal to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby, each require the affirmative vote of at least a majority of the shares of Macatawa entitled to vote, present in person or by proxy, if a quorum is present. In the absence of a quorum, holders of at least a majority of the shares of Macatawa present in person or by proxy at the special meeting may adjourn the special meeting.
The failure of a Macatawa shareholder to vote or to instruct his or her broker, bank or nominee to vote if his or her shares are held in “street name”, which we refer to as a broker non-vote, will have the same effect as voting against the proposal to adopt the merger agreement and will have no effect on the non-binding, advisory Macatawa merger-related compensation proposal or the meeting adjournment proposal. For purposes of the shareholder vote, an abstention, which occurs when a shareholder attends a meeting, either in person or by proxy, but indicates on his or her proxy card that he or she is abstaining from
 
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voting, will have the same effect as voting against (i) the proposal to adopt the merger agreement, (ii) the Macatawa merger-related compensation proposal and (iii) the proposal to adjourn the special meeting.
Shares held by Macatawa directors and executive officers; voting agreement
Macatawa’s directors and executive officers own approximately 8.7% of the outstanding shares of Macatawa common stock as of March 31, 2024. Directors and executive officers holding approximately 6.9% of Macatawa’s outstanding shares of common stock as of March 31, 2024 have committed pursuant to the voting agreement to vote their shares in favor of the merger and any other matter necessary for consummation of the transactions contemplated by the merger agreement. Wintrust does not own any shares of Macatawa common stock. See “The Merger — Voting agreement” on page 53 for a description of the provisions of the voting agreement.
How to vote
You may vote in person at the special meeting or by proxy. To ensure your representation at the special meeting, we recommend you vote by proxy even if you plan to attend the special meeting. You can always change your vote at the meeting.
Voting instructions are included on your proxy card, which explains that you may complete your proxy (1) by returning a properly completed proxy card in the enclosed prepaid envelope, (2) via the internet or (3) over the telephone. If you properly complete and timely submit your proxy, your shares will be voted as you have directed. You may vote for, against, or abstain with respect to the approval of the merger and the other proposals. If you are the record holder of your shares and submit your proxy without specifying a voting instruction, your shares will be voted as the Macatawa board of directors recommends and will be voted “FOR” adoption of the merger agreement, “FOR” the non-binding, advisory Macatawa merger-related compensation proposal and “FOR” the adjournment of the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to adopt the merger agreement and the transactions contemplated thereby.
Revocability of proxies
You may revoke your proxy at any time before it is voted by (1) delivering written notice to Macatawa’s secretary, (2) submitting a new proxy with a later date or (3) voting in person at the special meeting.
Attendance at the special meeting will not, in and of itself, constitute a revocation of a proxy. All written notices of revocation and other communication with respect to the revocation of proxies should be addressed to: Macatawa Bank Corporation, 10753 Macatawa Drive, Holland, Michigan 49424; Attention: Jon W. Swets, Chief Executive Officer.
Proxy solicitation
In addition to this mailing, proxies may be solicited by directors, officers or employees of Macatawa in person or by telephone or electronic transmission. None of such directors, officers or employees will be directly compensated for such services. Macatawa will pay the costs associated with the solicitation of proxies for the special meeting.
Other business; adjournments
Macatawa is not currently aware of any other business to be acted upon at the Macatawa special meeting. If, however, other matters are properly brought before the special meeting, or any adjournment or postponement thereof, your proxies include discretionary authority on the part of the individuals appointed to vote your shares to act on those matters according to their best judgment.
Adjournments may be made for the purpose of, among other things, soliciting additional proxies. Any adjournment may be made from time to time by the affirmative vote of the holders of at least a majority of the shares of Macatawa present in person or by proxy at the special meeting, if less than a quorum is present, or by the affirmative vote of the holders of at least a majority of the shares of Macatawa present in person or by proxy at the special meeting and entitled to vote, if a quorum is present, without further
 
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notice other than by announcement at the special meeting. In addition, Macatawa’s bylaws allow the chairman of its board of directors to adjourn the meeting if a quorum is not present, if disorder arises or if he determines that no further matters may properly come before the meeting.
 
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THE MERGER
This section of the proxy statement/prospectus describes material aspects of the merger. While Wintrust and Macatawa believe that the description covers the material terms of the merger and the related transactions, this summary may not contain all of the information that is important to you. You should carefully read this entire proxy statement/prospectus, the attached Annexes, and the other documents to which this proxy statement/prospectus refers for a more complete understanding of the merger. The merger agreement attached hereto as Annex A, not this summary, is the legal document which governs the merger.
General
The Macatawa board of directors is using this proxy statement/prospectus to solicit proxies from the holders of Macatawa common stock for use at the Macatawa special meeting, at which Macatawa shareholders will be asked to vote on the adoption of the merger agreement and thereby approve the merger. When the merger is consummated, Macatawa will merge with and into Merger Sub and will cease to exist. Merger Sub will survive the merger and remain a wholly-owned subsidiary of Wintrust. At the effective time of the merger, holders of Macatawa common stock will exchange their shares of Macatawa common stock for shares of Wintrust common stock, subject to adjustment. Each share of Macatawa common stock will be exchanged for the Per Share Merger Consideration, which cannot be determined until immediately prior to completion of the merger. See “Description of the Merger Agreement — Consideration to be received in the merger” on page 54 and “— Upset condition” on page 55 for a detailed description of the method for determining the Per Share Merger Consideration.
Only whole shares of Wintrust common stock will be issued in the merger. As a result, cash will be paid instead of any fractional shares based on the reference price of Wintrust’s common stock.
The companies
Wintrust
Wintrust Financial Corporation, an Illinois corporation, which we refer to as Wintrust, was incorporated in 1992 and is a financial holding company based in Rosemont, Illinois. Wintrust provides community-oriented, personal and commercial banking services to customers located primarily in the Chicago metropolitan area, southern Wisconsin and northwest Indiana through its fifteen wholly-owned banking subsidiaries, as well as the origination and purchase of residential mortgages for sale into the secondary market through Wintrust Mortgage, a division of Barrington Bank and Trust Company, N.A. Wintrust provides specialty finance services, including financing for the payment of commercial insurance premiums and life insurance premiums on a national basis through FIRST Insurance Funding, a division of its wholly-owned subsidiary Lake Forest Bank & Trust Company, N.A., which we refer to as Lake Forest Bank, and Wintrust Life Finance, a division of Lake Forest Bank, and in Canada through its premium finance company, First Insurance Funding of Canada, lease financing and other direct leasing opportunities through its wholly-owned subsidiary, Wintrust Asset Finance, and short-term accounts receivable financing and outsourced administrative services through its wholly-owned subsidiary, Tricom, Inc. of Milwaukee. Wintrust also provides a full range of wealth management services primarily to customers in the Chicago metropolitan area, southern Wisconsin and northwest Indiana through four separate subsidiaries, The Chicago Trust Company, N.A., Wintrust Investments, LLC, Great Lakes Advisors, LLC and Chicago Deferred Exchange Company, LLC.
As of March 31, 2024, Wintrust had total assets of approximately $57.6 billion, total loans, excluding loans held-for-sale, of approximately $43.2 billion, total deposits of approximately $46.4 billion, and total shareholders’ equity of approximately $5.4 billion.
Wintrust common stock is traded on Nasdaq under the ticker symbol “WTFC.”
Financial and other information relating to Wintrust, including information relating to Wintrust’s current directors and executive officers, is set forth in Wintrust’s 2023 Annual Report on Form 10-K filed with the SEC on February 28, 2024, Wintrust’s Proxy Statement for its 2024 Annual Meeting of Shareholders filed with the SEC on April 4, 2024 and Wintrust’s Quarterly Reports on Form 10-Q and Current Reports
 
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on Form 8-K filed during 2024, which are incorporated by reference to this proxy statement/prospectus. Copies of these documents may be obtained from Wintrust as indicated under “Where You Can Find More Information” on page 84.
Leo Subsidiary, LLC
Merger Sub is a Michigan limited liability company and is a wholly-owned subsidiary of Wintrust. It was formed solely for the purpose of consummating the merger and has not carried on any activities to date, except for activities incidental to its formation and activities undertaken in connection with the merger.
Macatawa Bank Corporation
Macatawa, a Michigan corporation, was incorporated in 1997, and is a registered bank holding company. It wholly owns Macatawa Bank, a Michigan state-chartered bank with depository accounts insured by the FDIC. Macatawa Bank operates 26 branch offices and a lending and operational service facility, providing a full range of commercial and consumer banking and trust services in Kent County, Ottawa County, and northern Allegan County, Michigan. As of March 31, 2024, Macatawa had consolidated total assets of approximately $2.6 billion, deposits of approximately $2.3 billion and shareholders’ equity of approximately $293.0 million.
Macatawa common stock is traded on Nasdaq under the ticker symbol “MCBC.”
Financial and other information relating to Macatawa, including information relating to Macatawa’s current directors and executive officers, is set forth in Macatawa’s 2023 Annual Report on Form 10-K filed with the SEC on February 15, 2024, as amended by the Annual Report on Form 10-K/A filed with the SEC on April 29, 2024, Macatawa’s Proxy Statement for its 2023 Annual Meeting of Shareholders filed with the SEC on March 17, 2023 and Macatawa’s Quarterly Reports on Form 10-Q and Current Reports on Form 8-K filed during 2024, which are incorporated by reference to this proxy statement/prospectus. Copies of these documents may be obtained from Macatawa as indicated under “Where You Can Find More Information” on page 84.
Macatawa’s proposals
At the Macatawa special meeting, holders of shares of Macatawa common stock will be asked to vote on the adoption of the merger agreement and thereby approve the merger. The merger will not be completed unless Macatawa’s shareholders adopt the merger agreement and thereby approve the merger. Additional information on the proposals to be put forth at the Macatawa special meeting can be found under the heading “The Macatawa Proposals” beginning on page 22.
Background of the merger
Macatawa’s board of directors (the “Macatawa Board”) regularly evaluates and assesses Macatawa’s performance, strategy and opportunities to strengthen its business and achieve profitable growth and value for its shareholders through various strategic initiatives, alternatives and transactions, giving consideration to the context of developments in the banking industry, including the regulatory environment, conditions in the geographic areas in which Macatawa operates, competitive considerations, technological and compliance burdens, and other factors. The Macatawa Board regularly reviews Macatawa’s performance, risks, opportunities, stock valuation and strategy and discusses such matters at board meetings.
On September 20, 2023, the Macatawa Board held a special meeting. At the invitation of the Macatawa Board, representatives of Morgan Stanley discussed with the Macatawa Board potential strategic alternatives available to Macatawa and Macatawa’s positioning in light of the current economic environment, the state of the banking industry, and the current mergers and acquisitions (“M&A”) environment. Based on conditions in the M&A market and the strength and attractiveness of Macatawa to potential purchasers based on its capital levels, liquidity position and cost of deposits, the Macatawa Board determined that a unique window of opportunity may exist with respect to exploring the potential sale or merger of Macatawa with another company and delivering enhanced shareholder value. A representative of Macatawa’s legal counsel, Warner Norcross, reviewed the fiduciary and legal obligations applicable to directors when considering a sale or
 
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merger of a company and provided an overview of the process involved with selling or merging a company. Detailed discussion occurred, including relating to the rising costs of internal and external audit, regulatory compliance, technology and other systems and controls; expected continuing net interest margin compression for Macatawa and the industry, generally; the risk of change in climate with institutional investors; the potential for growth and a path forward, including succession planning; and the importance of finding a partner with a strong operational and cultural alignment and a commitment to the communities Macatawa serves. The Macatawa Board unanimously agreed to continue the discussion at the October 19, 2023 meeting of the Macatawa Board. Following this meeting and as discussed below, representatives of Morgan Stanley consulted with Macatawa from time to time before being formally engaged by Macatawa. As described below, on December 14, 2023, Macatawa entered into an engagement letter with Morgan Stanley to act as Macatawa’s exclusive financial advisor in connection with a potential strategic transaction.
On October 19, 2023, the Macatawa Board held a regular meeting. Representatives of Warner Norcross attended the meeting. The Macatawa Board continued discussing strategic alternatives, focusing on what actions and investments of capital would be necessary to keep Macatawa competitive in the banking industry on a stand-alone basis and considering the possible sale or merger of Macatawa with another party. At this meeting, the Macatawa Board unanimously determined to engage a financial advisor to help it evaluate a potential strategic transaction and, if the Macatawa Board determined to pursue a strategic transaction, to advise the Macatawa Board. The Macatawa Board directed management to engage Morgan Stanley as Macatawa’s exclusive financial advisor in connection with a potential strategic transaction based on Morgan Stanley’s qualifications, experience and expertise and authorized the Chairman of the Macatawa Board, Richard Postma, to negotiate, with Warner Norcross’ assistance, an engagement letter with Morgan Stanley.
On November 16, 2023, the Macatawa Board held a regular board meeting. Representatives of Warner Norcross attended the meeting and provided the Macatawa Board with an update on the status of the negotiation of Morgan Stanley’s engagement letter.
On December 14, 2023, the Macatawa Board held a special meeting. Representatives of Morgan Stanley and Warner Norcross attended the meeting. Representatives of Morgan Stanley reviewed with the Macatawa Board certain preliminary financial information and capital analyses relating to Macatawa and a pool of five potential merger partners identified by representatives of Morgan Stanley together with Macatawa management and provided a hypothetical transaction process timeline for a possible sale of Macatawa. The Macatawa Board discussed (i) the financial information presented by Morgan Stanley, (ii) a pool of seven potential merger partners, including two additional potential merger partners discussed at the meeting to whom outreach might be made with respect to their interest in a potential transaction with Macatawa, (iii) Macatawa’s business plan and preliminary financial projections prepared by Macatawa management, and (iv) the importance of finding a partner with a strong operational and cultural alignment and a commitment to the communities Macatawa serves. Following this discussion, the Macatawa Board unanimously resolved to continue exploring a potential sale or merger of Macatawa. The Macatawa Board unanimously authorized representatives of Morgan Stanley to contact the seven identified potential merger partners, including Potential Merger Partner A, Potential Merger Partner B, Potential Merger Partner C, Potential Merger Partner D, Potential Merger Partner E, Potential Merger Partner F and Wintrust (each a “Potential Merger Partner” and collectively the “Potential Merger Partners”), to determine their interest in a potential strategic transaction with Macatawa in early January. The Potential Merger Partners, including Wintrust, were selected by the Macatawa Board based on, among other things, likelihood of interest in partnering with Macatawa, financial condition and performance and capacity to pay, demonstrated ability to complete a merger transaction and strategic and cultural fit with Macatawa and the west Michigan community. The Macatawa Board also established a Special Committee (the “Committee”) consisting of directors Richard Postma, Charles Geenen, Robert Herr, Thomas Rosenbach, and Jon Swets (as a non-voting member). Mr. Swets acted as a non-voting member so that each voting member of the Committee was an independent director. The established purpose of the Committee was to act on behalf of the Macatawa Board, to provide oversight and guidance as to Macatawa’s evaluation of strategic alternatives and to provide the Macatawa Board with its recommendation with respect to any potential strategic transaction. Lastly, the Macatawa Board unanimously approved an engagement letter and indemnity agreement with Morgan Stanley engaging Morgan Stanley to act as Macatawa’s exclusive financial advisor in connection with a possible sale of Macatawa. The engagement letter and indemnity agreement were executed following the meeting.
 
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During November and December 2023, management of Macatawa, with assistance from representatives of Morgan Stanley and Warner Norcross, prepared a confidential information memorandum with detailed information about Macatawa to be made available to the Potential Merger Partners and prepared a virtual data room for the Potential Merger Partners to conduct due diligence.
On December 21, 2023, the Macatawa Board held a regular board meeting. Representatives of Warner Norcross attended the meeting. A representative of Warner Norcross updated the Macatawa Board on the strategic process, including preparation of the confidential information memorandum and the virtual data room.
On January 3, 2024, at the direction of Macatawa, representatives of Morgan Stanley contacted each Potential Merger Partner, including Wintrust, to determine their level of interest in a possible strategic transaction with Macatawa. Potential Merger Partners B, C, D, E and F and Wintrust indicated an interest, and customary non-disclosure agreements (which included customary standstill provisions) were negotiated and executed with those six Potential Merger Partners on or about January 4 or 5, 2024. Potential Merger Partner A did not indicate an interest in a possible strategic transaction with Macatawa.
On or about January 8, 2024, the virtual data room was opened and access was granted to Potential Merger Partners B, C, D, E and F and Wintrust and Potential Merger Partners B, C, D, E and F and Wintrust received the final confidential information memorandum which included the finalized Macatawa Management Projections (as defined below) upon which Morgan Stanley was instructed to rely for purposes of its financial analysis in connection with any potential transaction.
Between January 3, 2024 and January 18, 2024, representatives of Morgan Stanley spoke with Mr. Postma regarding Potential Merger Partner G, who representatives of Morgan Stanley understood was interested in a potential bank acquisition. Mr. Postma authorized representatives of Warner Norcross and Morgan Stanley to negotiate a non-disclosure agreement with Potential Merger Partner G.
On January 18, 2024, the Macatawa Board held a regular meeting. Representatives of Warner Norcross attended the meeting. A representative of Warner Norcross provided an update on the strategic process, including that non-disclosure agreements were executed with Potential Merger Partners B, C, D, E and F and Wintrust, and that those Potential Merger Partners had been granted access to the virtual data room and were in the process of conducting diligence. Warner Norcross provided an update to the Macatawa Board that Warner Norcross had completed an initial reverse due diligence on all Potential Merger Partners based on public documents and that Warner Norcross had not identified any material issues or concerns. Mr. Postma informed the Macatawa Board that an additional Potential Merger Partner, Potential Merger Partner G, was expected to execute a non-disclosure agreement, following which it would be provided access to the virtual data room.
On January 19, 2024, Potential Merger Partner G executed a non-disclosure agreement (which included a customary standstill provision) and was granted access to the virtual data room.
During the weeks of January 15, 2024, January 22, 2024, and January 29, 2024, representatives of Morgan Stanley had ongoing conversations with all of the Potential Merger Partners who had executed non-disclosure agreements regarding a potential strategic transaction and the competitive nature of the process. Each Potential Merger Partner performed off-site due diligence through the virtual data room, and some submitted detailed requests related to the due diligence process.
On February 5 and 6, 2024, preliminary, non-binding indications of interest to purchase Macatawa were received from Potential Merger Partners B, C, D, E and F and Wintrust. The indicated range of purchase price per share submitted by the Potential Merger Partners was $11.65 to $14.49. Potential Merger Partner G did not submit a non-binding indication of interest and was removed from the process and its access to the virtual data room was revoked.
On February 9, 2024, the Committee held a meeting to review and consider, the preliminary, non-binding indications of interest received from Potential Merger Partners B, C, D, E and F and Wintrust and other matters related to a potential sale of Macatawa. Representatives of Morgan Stanley led a review and discussion of the financial terms of the preliminary, non-binding indications of interest submitted by Potential Merger Partners B, C, D, E and F and Wintrust, which included, among other data points, the indicated
 
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purchase price per share and total transaction value, the implied exchange ratio, form of consideration and certain financial information relating to the Potential Merger Partners and their anticipated timing for completion of due diligence and negotiation of a definitive merger agreement if advanced to Phase 2 of the strategic process. Representatives of Warner Norcross then reviewed with the Committee the fiduciary and legal obligations applicable to directors when considering a sale or merger of a company and reviewed Article XII of Macatawa’s articles of incorporation, which requires the Macatawa Board to determine that a sale or merger of the company would comply with all applicable laws and would be in the best interests of Macatawa and its shareholders and to consider several factors when considering a potential merger partner.
Discussion occurred, and the Committee concluded that Potential Merger Partner F and Wintrust had separated themselves from Potential Merger Partners B, C, D and E both from a financial point of view (representing the two proposals with the highest value per share) and because both Potential Merger Partner F and Wintrust had strong operating and cultural alignment with Macatawa. The Committee discussed the advantages and disadvantages of advancing multiple Potential Merger Partners to Phase 2 of the strategic process versus only one. After this discussion, the Committee unanimously decided to select Potential Merger Partner F and Wintrust to advance to Phase 2 of the strategic process, that doing so was in the best interests of Macatawa and its shareholders and recommended that the Macatawa Board approve the same.
Representatives of Morgan Stanley and Warner Norcross reviewed the Phase 2 process, including that additional due diligence would be conducted by Potential Merger Partner F and Wintrust, that Macatawa would conduct more detailed reverse due diligence on Potential Merger Partner F and Wintrust, and that Potential Merger Partner F and Wintrust would each be asked to provide a markup of the draft definitive merger agreement prepared by Warner Norcross. At the end of the Phase 2 process, Potential Merger Partner F and Wintrust would be asked to submit their best and final proposal to purchase Macatawa.
On February 15, 2024, the Macatawa Board held a regular meeting. Representatives of Warner Norcross attended the meeting. The Macatawa Board reviewed the financial terms of the preliminary, non-binding indications of interest submitted by Potential Merger Partners B, C, D, E and F and Wintrust on February 5 and 6, 2024 and discussed in more detail the financial terms of the indications of interest submitted by Potential Merger Partner F and Wintrust, the two Potential Merger Partners that the Committee recommended to advance to Phase 2 of the strategic process. This review included, among other data points, the indicated purchase price per share and total transaction value, the implied exchange ratio, form of consideration, certain financial information relating to Potential Merger Partner F and Wintrust and their anticipated timing for completion of due diligence and negotiation of a definitive merger agreement if advanced to Phase 2 of the strategic process, the differences between the indications of interest and their respective strategic rationales for wanting to purchase Macatawa. Representatives of Warner Norcross then reviewed with the Macatawa Board the fiduciary and legal obligations applicable to directors when considering a sale or merger of a company and reviewed Article XII of Macatawa’s articles of incorporation. Following an extensive discussion, the Macatawa Board unanimously ratified and approved the recommendation of the Committee and selected Potential Merger Partner F and Wintrust to advance to Phase 2 of the strategic process and determined that doing so was in the best interests of Macatawa and its shareholders.
Following the meeting, Potential Merger Partners B, C, D and E were informed they were no longer part of the process and their access to the virtual data room was revoked.
On or about February 15, 2024, a draft merger agreement was uploaded to the virtual data room, along with a draft company disclosure letter. On February 21, 2024, at the direction of Macatawa, representatives of Morgan Stanley sent instructions to Potential Merger Partner F and Wintrust for submitting a best and final proposal to purchase Macatawa and markup of the draft merger agreement by 12:00 p.m. eastern time on March 20, 2024.
During the weeks of February 19, February 26, March 4, and March 11, Potential Merger Partner F and Wintrust conducted detailed due diligence on Macatawa and the virtual data room was continually updated based on the inquiries and requests from Potential Merger Partner F and Wintrust.
On February 28, 2024, certain members of senior management of Macatawa met with certain members of senior management of Potential Merger Partner F in Grand Rapids, Michigan at the offices of Warner
 
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Norcross for in-person meetings and due diligence sessions. Representatives of Morgan Stanley and Warner Norcross also attended the meetings. Among others, topics included an overview of Macatawa’s business and markets, financial performance and condition, asset quality, risk management, trust and wealth management and an overview of Potential Merger Partner F’s business and markets. That evening, Mr. Postma and Jon Swets, the President and CEO of Macatawa, had a dinner meeting with the Chairman and certain members of senior management of Potential Merger Partner F and discussed various due diligence topics and the strategic rationale for a merger between the two parties. On February 29, 2024, Mr. Postma and the President and CEO of Potential Merger Partner F had a breakfast meeting and discussed various due diligence topics and the strategic rationale for a merger between the two parties. Several follow up due diligence video conference calls regarding key functional areas occurred with Potential Merger Partner F and Macatawa during the weeks of March 4, 2024 and March 11, 2024.
On March 7, 2024, certain members of senior management of Macatawa met with certain members of senior management of Wintrust in Grand Rapids, Michigan at the offices of Warner Norcross for in-person meetings and due diligence sessions. Representatives of Morgan Stanley and Warner Norcross also attended the meetings. Among others, topics included an overview of Macatawa’s business and markets, credit, trust and wealth management, commercial banking, retail banking and an overview of Wintrust’s business and markets. Messrs. Postma and Swets had a lunch meeting with certain members of senior management of Wintrust and discussed various due diligence topics and the strategic rationale for a merger between the two parties.
Reverse due diligence video conference calls occurred with Potential Merger Partner F on March 13, 2024, and with Potential Merger Partner F and Wintrust on March 19, 2024. Topics included future earnings potential, interest rate risk, and legal and regulatory matters, including any ongoing or threatened litigation of a material nature and any potential impediments to obtain regulatory approval of a merger.
On March 20, 2024, final proposals to purchase Macatawa and comments to the draft merger agreement were received from Potential Merger Partner F and Wintrust. Prior to submission, representatives of Morgan Stanley again emphasized to Potential Merger Partner F and Wintrust that they each should submit their best and final proposal.
On March 26, 2024, the Committee held a special meeting to review and consider, in detail, the final proposals and comments to the draft merger agreement received from Potential Merger Partner F and Wintrust and other matters related to a potential sale of Macatawa. Representatives of Morgan Stanley and Warner Norcross attended the meeting. Among other things, the following occurred at the meeting:

Representatives of Morgan Stanley provided the Committee with an update on the Phase 2 due diligence process, including the management meetings that occurred with Potential Merger Partner F and Wintrust, the follow up due diligence video conference calls regarding key functional areas with Potential Merger Partner F, the reverse due diligence video conference calls with both parties, the virtual data room review by both parties, and the follow up diligence requests made by both parties. Mr. Swets updated the Committee on the functional areas and topics covered in the management meetings with Potential Merger Partner F and Wintrust.

Mr. Swets and representatives of Warner Norcross then elaborated on the status and results of Macatawa’s reverse due diligence on Potential Merger Partner F and Wintrust, indicating that the reverse diligence was focused on future earnings potential, interest rate risk, and legal and regulatory matters, including any ongoing or threatened litigation of a material nature and any potential impediments to obtaining regulatory approval of a merger.

Representatives of Morgan Stanley provided an overview of the financial terms of both proposals, including the indicated purchase price per share and total transaction value, the implied exchange ratio (including the impact of the collar proposed by Wintrust as discussed further below) and form of consideration. Wintrust’s proposal indicated a purchase price per share of $14.85 (based on Wintrust’s closing stock price of $98.12 per share on March 19, 2024) payable in all stock and an implied aggregate transaction value of approximately $510.3 million (subject to the collar proposed by Wintrust as discussed further below). The indicated purchase price per share of $14.85 in Wintrust’s
 
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proposal was higher than the indicated purchase price of $13.83 per share in Potential Merger Partner F’s proposal (assuming the closing price of Potential Merger Partner F’s common stock on March 19, 2024).

Representatives of Morgan Stanley also reviewed with the Committee additional background information about each of Potential Merger Partner F and Wintrust, which included, among other things, capitalization data, asset quality, performance data and ratios, branch data and geographic location, trading data, a management team overview, research analyst recommendations, and M&A history.

Representatives of Morgan Stanley then compared the exchange ratio construct proposed by Potential Merger Partner F (fixed exchange ratio) and Wintrust (floating exchange ratio within a symmetrical $12 collar and fixed exchange ratio outside the collar at the high and low ends of the collar). For Wintrust, representatives of Morgan Stanley noted that the aggregate transaction value of approximately $510.3 million would be fixed within the $12 collar, providing price certainty within the collar, and the aggregate transaction value outside of the collar would be variable. For Potential Merger Partner F, it was noted that its proposed aggregate transaction value would be variable.

Representatives of Morgan Stanley noted that, under Wintrust’s proposal, Macatawa Bank would maintain its separate bank charter, with a separate, legally constituted board of directors consisting of certain existing directors and new directors generally residing and doing business locally in the west Michigan community and would continue to operate under the Macatawa Bank name in Michigan. It was also noted that Wintrust indicated it would be willing to appoint one individual serving on Macatawa’s board of directors to serve on Wintrust’s board of directors. For Potential Merger Partner F, it was noted that Potential Merger Partner F intended to preserve as much of the Macatawa identity as possible, including the Macatawa brand name in Michigan, and that Macatawa Bank would be merged out of existence. It was also noted that Potential Merger Partner F would be willing to appoint one individual serving on Macatawa’s board of directors to serve on Potential Merger Partner F’s board of directors.

Representatives of Warner Norcross provided a summary and comparison of the markups of the draft merger agreement submitted by Potential Merger Partner F and Wintrust. Warner Norcross reminded the Committee of the fiduciary and legal obligations applicable to directors when considering a sale or merger of a company.

Mr. Postma and representatives of Warner Norcross led a discussion of Article XII of Macatawa’s articles of incorporation, which requires the Macatawa Board to determine that a sale or merger of the company would comply with all applicable laws and would be in the best interests of Macatawa and its shareholders and to consider several factors when considering a potential merger partner including:

the adequacy and fairness of the consideration to be received by Macatawa shareholders;

the potential social and economic impact on Macatawa and its employees and customers;

the potential social and economic impact on the communities Macatawa serves;

the business and financial condition and earnings prospects of the proposed acquiror; and

the competence, experience and integrity of the proposed acquiror and its management.

Representatives of Warner Norcross advised that a merger with either Potential Merger Partner F or Wintrust would comply with all applicable laws.
The Committee discussed the final proposals, the information discussed by representatives of Morgan Stanley, the presentation by representatives of Warner Norcross and the factors under Article XII of Macatawa’s articles of incorporation. The Committee determined that the Wintrust proposal constituted the superior proposal from a financial point of view. The Committee discussed the advantages and disadvantages related to the exchange ratio constructs proposed by Potential Merger Partner F and Wintrust, including that the floating exchange ratio within a symmetrical $12 collar proposed by Wintrust would provide price certainty to Macatawa shareholders within the collar despite market price fluctuations of Wintrust common stock within the collar. The Committee also discussed that Wintrust’s proposal would permit Macatawa Bank to maintain its separate bank charter, with a separate, legally constituted board of
 
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directors consisting of certain existing directors and new directors generally residing and doing business locally in the west Michigan community and would continue to operate under the Macatawa Bank name in Michigan.
Following discussion, the Committee unanimously selected Wintrust as the preferred merger partner, based on its superior proposal from a financial point of view and strong operational and cultural alignment, concluded that doing so was in the best interests of Macatawa and its shareholders, determined that a merger with Wintrust would comply with all applicable laws, authorized management of Macatawa and its advisors to negotiate a definitive merger agreement with Wintrust and recommended the Macatawa Board ratify and approve the same.
On March 28, 2024, the Macatawa Board held a special meeting to review and consider, in detail, the final proposals received from Potential Merger Partner F and Wintrust and other matters related to a potential sale of Macatawa. Representatives of Morgan Stanley and Warner Norcross attended the meeting. Among other things, the following occurred at the meeting:

Representatives of Morgan Stanley reviewed the same information with the Macatawa Board as was discussed with the Committee on March 26, 2024. Representatives of Warner Norcross provided substantially the same presentation to the Macatawa Board as provided to the Committee on March 26, 2024. It was noted that Wintrust’s indicated purchase price per share of $14.85 was higher than the purchase price per share indicated in Potential Merger Partner F’s final proposal.

Mr. Swets, Craig Hankinson, the Chief Operating Officer of Macatawa, and Jill Walcott, the Chief Retail Officer of Macatawa, updated the Macatawa Board on the functional areas and topics covered during the in-person management meetings with Potential Merger Partner F and Wintrust.

Each member of the Committee (including Mr. Swets), Mr. Hankinson, and Ms. Walcott provided his or her personal evaluation of the relative impact of the two proposals on Macatawa and its shareholders, customers, employees and the communities served by it.

Mr. Postma and representatives of Warner Norcross led a discussion of Article XII of Macatawa’s articles of incorporation, which requires the Macatawa Board to determine that a merger of the company would comply with all applicable laws and would be in the best interests of Macatawa and its shareholders and to consider several factors described above when considering a potential merger partner.

Representatives of Warner Norcross advised that a merger with Potential Merger Partner F or Wintrust would comply with all applicable laws.
The Macatawa Board discussed the final proposals, the information reviewed by representatives of by Morgan Stanley, the presentation by representatives of Warner Norcross and the factors under Article XII of Macatawa’s articles of incorporation. The Macatawa Board determined that the Wintrust proposal constituted the superior proposal from a financial point of view. The Macatawa Board discussed the relative advantages and disadvantages related to the exchange ratio constructs proposed by Potential Merger Partner F and Wintrust, including that the floating exchange ratio within a symmetrical $12 collar proposed by Wintrust would provide price certainty to Macatawa shareholders within that collar despite market price fluctuations of Wintrust common stock within the collar. The Macatawa Board also discussed that Wintrust’s proposal would permit Macatawa Bank to maintain its separate bank charter, with a separate, legally constituted board of directors consisting of certain existing directors and new directors generally residing and doing business locally in the west Michigan community and would continue to operate under the Macatawa Bank name in Michigan.
The Macatawa Board unanimously ratified and approved the recommendation of the Committee, selected Wintrust as the preferred merger partner based on its superior proposal and strong operational and cultural alignment, concluded that doing so was in the best interests of Macatawa and its shareholders, determined that a merger with Wintrust would comply with all applicable laws and authorized management of Macatawa and its advisors to negotiate a definitive merger agreement with Wintrust.
During the time period beginning on March 29, 2024 and ending on April 15, 2024, representatives of Warner Norcross and Wintrust’s legal counsel, ArentFox, with the participation of management from each
 
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party and the assistance from representatives of Morgan Stanley, proceeded to negotiate a definitive merger agreement. Multiple drafts of the merger agreement and other ancillary documents were exchanged between Warner Norcross and ArentFox and several negotiating sessions occurred.
On April 15, 2024, the Macatawa Board held a special meeting. Representatives of Morgan Stanley and Warner Norcross attended the meeting. Among other things, the following occurred at the meeting:

Warner Norcross advised that a proposed definitive merger agreement with Wintrust had been successfully negotiated and would be presented for adoption by Macatawa Board at the meeting. Warner Norcross provided a comprehensive review of the merger agreement and referred to an executive summary of the definitive merger agreement that was provided to the Macatawa Board in advance of the meeting.

Warner Norcross reviewed the proposed definitive voting and support agreement between certain executive officers and directors of Macatawa, Wintrust and Macatawa, which would be presented for adoption by the Macatawa Board at the meeting.

Representatives of Morgan Stanley reviewed with the Macatawa Board Morgan Stanley’s financial analyses with respect to the Per Share Merger Consideration to be received by the holders of Macatawa common stock and rendered an oral opinion to the Macatawa Board, which was subsequently confirmed by the delivery of a written opinion dated April 15, 2024, that as of the date of such opinion, and based on and subject to the various assumptions made, procedures followed, matters considered and qualifications and limitations on the review undertaken by Morgan Stanley set forth therein, that the Per Share Merger Consideration was fair from a financial point of view to holders of Macatawa common stock. See the section entitled “— Opinion of Macatawa’s Financial Advisor” beginning on page 34 for more information.
The Macatawa Board discussed the merger agreement, voting and support agreement and Morgan Stanley’s financial analyses and opinion. At the conclusion of the meeting, the Macatawa Board unanimously:

Based on the evaluation and consideration of all reports and information available to the Macatawa Board as of the date of the meeting and all factors that the Macatawa Board deemed relevant, determined that the merger, the definitive merger agreement and the Per Share Merger Consideration are fair to Macatawa and its shareholders and that entering into the definitive merger agreement and completing the merger and the other transactions contemplated by the definitive merger agreement is in the best interests of Macatawa and its shareholders. See the section entitled “— Macatawa’s Reasons for the Merger and Recommendation of the Macatawa Board of Directors” beginning on page 43 for more information;

Authorized and approved the merger and all other transactions contemplated by the definitive merger agreement;

Adopted the definitive merger agreement;

Adopted the voting and support agreement;

Authorized the Chairman of the Macatawa Board to execute and deliver the definitive merger agreement and voting and support agreement; and

Recommended that Macatawa shareholders vote for approval of the definitive merger agreement.
On April 15, 2024, after the U.S. financial markets closed, Macatawa and Wintrust executed and delivered the definitive merger agreement and the respective disclosure letters, certain directors and executive officers of Macatawa executed and delivered the voting and support agreement and the parties issued a joint press release announcing execution of the definitive merger agreement and the terms of the merger.
Opinion of Macatawa’s Financial Advisor
Macatawa retained Morgan Stanley to provide it with financial advisory services in connection with a potential sale of Macatawa. Macatawa selected Morgan Stanley to act as its financial advisor based on Morgan Stanley’s qualifications, expertise and reputation and its knowledge of the business and affairs of
 
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Macatawa. On April 15, 2024, at a meeting of the board of directors of Macatawa, Morgan Stanley rendered its oral opinion, subsequently confirmed by delivery of a written opinion dated April 15, 2024, to the effect that, as of the date of such opinion, and based upon and subject to the various assumptions made, procedures followed, matters considered, and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth therein, the Per Share Merger Consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement was fair from a financial point of view to the holders of shares of Macatawa common stock.
The full text of the written opinion of Morgan Stanley, dated April 15, 2024, is attached as Annex C and incorporated by reference into this proxy statement/prospectus. The opinion sets forth, among other things, the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of the review undertaken by Morgan Stanley in rendering its opinion. Morgan Stanley’s opinion was directed to the Macatawa Board, in its capacity as such, and addresses only the fairness from a financial point of view to the holders of shares of Macatawa common stock of the Per Share Merger Consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement as of the date of the opinion. Morgan Stanley’s opinion does not address any other aspect of the transactions contemplated by the merger agreement and does not constitute a recommendation to shareholders of Macatawa as to how to vote at any shareholders’ meetings held with respect to the proposed transaction or any other matter or whether to take any other action with respect to the proposed transaction. The summary of Morgan Stanley’s opinion set forth in this proxy statement/prospectus is qualified in its entirety by reference to the full text of the opinion.
Morgan Stanley noted that the Per Share Merger Consideration will range from 0.1314 shares of Wintrust common stock to 0.1668 shares of Wintrust common stock.
For purposes of rendering its opinion, Morgan Stanley:

Reviewed certain publicly available financial statements and other business and financial information of Macatawa and Wintrust, respectively;

Reviewed certain internal financial statements and other financial and operating data concerning Macatawa;

Reviewed certain financial projections prepared by the management of Macatawa;

Discussed the past and current operations and financial condition and the prospects of Macatawa with senior executives of Macatawa;

Discussed the past and current operations and financial condition and the prospects of Wintrust with senior executives of Wintrust;

Reviewed the reported prices and trading activity for Macatawa common stock and Wintrust common stock;

Compared the financial performance of Macatawa and Wintrust and the prices and trading activity of Macatawa common stock and Wintrust common stock with that of certain other publicly-traded companies comparable with Macatawa and Wintrust, respectively, and their securities;

Reviewed the financial terms, to the extent publicly available, of certain comparable acquisition transactions;

Participated in certain discussions and negotiations among representatives of Macatawa and Wintrust and their financial and legal advisors;

Reviewed the merger agreement; and

Performed such other analyses, reviewed such other information and considered such other factors as Morgan Stanley deemed appropriate.
In arriving at its opinion, Morgan Stanley assumed and relied upon, without independent verification, the accuracy and completeness of the information that was publicly available or supplied or otherwise made available to it by Macatawa and Wintrust, and formed a substantial basis for its opinion.
 
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With respect to the financial projections, Morgan Stanley assumed that they had been reasonably prepared on bases reflecting the best currently available estimates and judgements of the management of Macatawa of the future financial performance of Macatawa.
In addition, Morgan Stanley assumed that the proposed transaction will be consummated in accordance with the terms set forth in the merger agreement without any waiver, amendment, or delay of any terms or conditions, including, among other things, that the proposed transaction would be treated as a tax-free reorganization, pursuant to the Internal Revenue Code, as amended and that the definitive merger agreement would not differ in any material respect from the draft thereof furnished to Morgan Stanley. Morgan Stanley assumed that in connection with the receipt of all the necessary governmental, regulatory or other approvals and consents required for the proposed transaction, no delays, limitations, conditions or restrictions will be imposed that would have a material adverse effect on the contemplated benefits expected to be derived in the proposed transaction.
Morgan Stanley is not a legal, tax or regulatory advisor. Morgan Stanley is not an expert in the evaluation of allowance for credit losses, and it neither made an independent evaluation of the adequacy of the allowance for credit losses at Macatawa or Wintrust, nor did it examine any individual loan credit files of Macatawa or Wintrust nor was it requested to conduct such a review, and, as a result, Morgan Stanley assumed, that the aggregate allowance for credit losses of Macatawa and Wintrust are adequate. Morgan Stanley is a financial advisor only and relied upon, without independent verification, the assessments of Wintrust and Macatawa and their legal, tax or regulatory advisors with respect to legal, tax or regulatory matters. Morgan Stanley expressed no opinion with respect to the fairness of the amount or nature of the compensation to any of the officers, directors or employees of Macatawa or Wintrust, or any class of such persons, whether relative to the Per Share Merger Consideration or otherwise. Morgan Stanley did not make any independent valuation or appraisal of the assets or liabilities of Macatawa or Wintrust, nor was Morgan Stanley furnished with any such valuations or appraisals.
Morgan Stanley’s opinion was necessarily based on financial, economic, market and other conditions as in effect on, and the information made available to it, as of April 15, 2024. Events occurring after such date may affect Morgan Stanley’s opinion and the assumptions used in preparing it, and Morgan Stanley did not assume any obligation to update, revise or reaffirm its opinion.
Morgan Stanley’s opinion did not address the relative merits of the transactions contemplated by the merger agreement as compared to other business or financial strategies that might be available to Macatawa, nor did it address the underlying business decision of Macatawa to enter into the merger agreement or proceed with any other transaction contemplated by the merger agreement. Morgan Stanley did not express a view on and Morgan Stanley’s opinion did not address any other term or aspect of the merger agreement or the transactions contemplated thereby or any term or aspect of any other agreement or instrument contemplated by the merger agreement or entered into or amended in connection therewith. In addition, Morgan Stanley’s opinion did not in any manner address the prices at which Wintrust common stock will trade following the consummation of the proposed transaction or at any time and Morgan Stanley expressed no opinion or recommendation as to how the shareholders of Macatawa should vote at the shareholders’ meetings to be held in connection with the proposed transaction.
Summary of Financial Analyses of Morgan Stanley
The following is a summary of the material financial analyses performed by Morgan Stanley in connection with its oral opinion and the preparation of its written opinion letter dated April 15, 2024. The various financial analyses summarized below were based on closing prices of Macatawa common stock and other information available as of April 12, 2024, the last full trading day preceding the day of the meeting of the board of directors of Macatawa to consider, approve, adopt and authorize the merger agreement. Some of these summaries of financial analyses include information presented in tabular format. In order to fully understand the financial analyses used by Morgan Stanley, the tables must be read together with the text of each summary. The tables alone do not constitute a complete description of the financial analyses. Furthermore, mathematical analysis (such as determining the average or median) is not in itself a meaningful method of using the data referred to below.
 
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In performing the financial analysis summarized below and arriving at its opinion, Morgan Stanley used and relied upon certain financial projections provided by Macatawa’s management, referred to as the “Macatawa Management Projections” ​(see “— Certain unaudited prospective financial information of Macatawa” below) and certain mean equity research consensus estimates for Macatawa referred to as the “Macatawa Street Projections”.
Comparable Companies Analysis
Morgan Stanley performed a public trading comparables analysis, which is designed to provide an implied trading value of a company by comparing it to selected companies with similar characteristics. Morgan Stanley compared certain financial information of Macatawa with publicly available information for a group of selected companies. The selected companies were chosen based on Morgan Stanley’s knowledge of the industry and because these companies have businesses that may be considered similar to the business of Macatawa.
The group of selected companies consisted of U.S. publicly-traded banks that were listed on a major exchange, headquartered in Michigan and contiguous states (Indiana, Illinois, Ohio, and Wisconsin), had assets between two billion dollars and six billion dollars, and excluded announced merger targets and banks with a national business model. The selected companies consisted of:

Bank First Corporation

ChoiceOne Financial Services, Inc.

CF Bankshares Inc.

Civista Bancshares, Inc.

Farmers & Merchants Bancorp, Inc.

Farmers National Banc Corp.

Finward Bancorp

First Financial Corporation

First Savings Financial Group, Inc.

HBT Financial, Inc.

Independent Bank Corporation

LCNB Corp.

Mercantile Bank Corporation

Old Second Bancorp, Inc.

Waterstone Financial, Inc.
In all instances, multiples were based on closing stock prices on April 12, 2024. For each of the following analyses performed by Morgan Stanley, financial and market data for the group of selected companies were based on the most recent publicly available information and mean equity research consensus estimates.
With respect to the group of selected companies, Morgan Stanley reviewed:

multiple of price to estimated diluted earnings per share for 2024, or Price/2024E EPS;

multiple of price to estimated diluted earnings per share for 2025, or Price/2025E EPS; and

multiple of price to tangible book value per share, or Price/TBV.
Morgan Stanley also reviewed the same information for Macatawa based on the Macatawa Street Projections and, other than with respect to Price/TBV, the Macatawa Management Projections.
The following table presents the results of this analysis:
 
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Selected Companies
Macatawa
Bottom Quartile
Median
Top Quartile
Street
Management
Price/2024E EPS
7.7x 8.4x 10.5x 7.8x 7.3x
Price/2025E EPS
7.4x 8.1x 9.1x 7.5x 6.7x
Price/TBV
0.9x 1.2x 1.3x 1.1x N/A
Based on the results of this analysis and its professional judgment, Morgan Stanley selected ranges of multiples as described in the table below and applied these ranges of multiples to the relevant financial statistics for Macatawa to derive ranges of implied value per share of Macatawa common stock as of April 12, 2024, as set forth below:
Macatawa
Metric
Multiple Range
Implied Value Per Share of
Macatawa Common Stock
Price/2024E EPS (Macatawa Street Projections)
$ 1.24 7.4x – 9.4x
$9.18 – $11.66
Price/2025E EPS (Macatawa Street Projections)
$ 1.28 7.1x – 9.1x
$9.09 – $11.65
Price/2024E EPS (Macatawa Management Projections)
$ 1.31 7.4x – 9.4x
$9.69 – $12.31
Price/2025E EPS (Macatawa Management Projections)
$ 1.42 7.1x – 9.1x
$10.08 – $12.92
Price / Tangible Book Value
$ 8.35 1.1x – 1.3x
$9.19 – $10.86
Morgan Stanley also performed a regression-based analysis based on Price/TBV versus estimated 2024 return on tangible common equity for each of the selected companies. The range of estimated regression-based analysis implied values represents +/- 0.1x of the value implied by the regression line equation. Utilizing a 2024 return on tangible common equity estimate for Macatawa of 14.0%, as set forth in the Macatawa Street Projections, the regression-implied value would be 1.27x Price/TBV and the low-end of the range of $9.79 represents the implied value if Macatawa were valued at 1.17x of the value implied by the regression line and the high-end range of $11.46 represents the implied value if Macatawa were valued at 1.37x of the value implied by the regression line. Utilizing a 2024 return on tangible common equity estimate for Macatawa of 14.8%, as set forth in the Macatawa Management Projections, the regression-implied value would be 1.33x Price/TBV, and the low-end range of $10.24 represents the implied value if Macatawa were valued at 1.23x of the value implied by the regression line and the high-end range of $11.91 represents the implied value if Macatawa were valued at 1.43x of the value implied by the regression line.
Morgan Stanley compared these ranges with (i) the closing price per share of Macatawa common stock of $9.59 on April 12, 2024 and (ii) $14.85, the value assigned to a share of Macatawa common stock for purposes of calculating the Per Share Merger Consideration pursuant to the merger agreement assuming the Purchaser Common Stock Price is equal to or greater than $89.03 and less than or equal to $113.03.
No company used as a comparison in the comparable companies analysis is identical to Macatawa. In evaluating the group of selected companies, Morgan Stanley made judgments and assumptions with regard to industry performance, general business, economic, market and financial conditions and other matters, many of which are beyond the control of Macatawa and Wintrust, such as the impact of competition on the business of Macatawa or the industry generally, industry growth and the absence of any material adverse change in the financial condition and prospects of Macatawa or the industry or in the financial markets in general. Mathematical analysis, such as determining the average or median, is not in itself a meaningful method of using peer group data. Rather, it involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies involved.
Dividend Discount Analysis
Using the Macatawa Street Projections for 2024 and 2025 and the Macatawa Management Projections for 2024 to 2028 and assuming, at the direction of Macatawa management, (a) a 5.0% annual growth rate thereafter and (b) that Macatawa would make distributions of capital in excess of the amount necessary to achieve a 9.7% Tier 1 leverage ratio, which represents the average of the selected companies described above, Morgan Stanley performed a dividend discount analysis for Macatawa on a standalone basis. Morgan Stanley calculated a range of implied values per share of Macatawa common stock based on the sum of the
 
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discounted present values of (a) projected dividends on shares of Macatawa common stock for the period December 31, 2023 through December 31, 2028 and (b) a projected terminal value of Macatawa common stock as of December 31, 2029.
Morgan Stanley based its analysis on a range of terminal forward multiples of 7.4x to 9.4x to the terminal year 2029 estimated forward earnings, a range of discount rates of 9.9% to 11.9% (determined using the capital asset pricing model). Based on information provided by Macatawa management, Morgan Stanley also assumed a 4.5% opportunity cost of cash and a 19.5% effective tax rate. Utilizing the foregoing range of discount rates and terminal value multiples, Morgan Stanley derived a range of implied present values per share of Macatawa common stock of $10.54 to $12.97 using the Macatawa Street Projections and $12.19 to $14.84 using the Macatawa Management Projections.
Morgan Stanley compared these ranges with (i) the closing price per share of Macatawa common stock of $9.59 on April 12, 2024 and (ii) $14.85, the value assigned to a share of Macatawa common stock for purposes of calculating the Per Share Merger Consideration pursuant to the merger agreement assuming the Purchaser Common Stock Price is equal to or greater than $89.03 and less than or equal to $113.03.
Precedent Transaction Analysis
Morgan Stanley performed a precedent transactions analysis, which attempts to imply a value of a company based on publicly available financial terms of selected transactions. Morgan Stanley reviewed the publicly available financial information for certain bank transactions announced between January 1, 2021 and April 12, 2024 with a transaction value between $100 million and $1 billion, in which the target was headquartered in the Midwest Region. The transactions reviewed and the date that each transaction was announced were as follows:
Acquiror / Target
Date Announced
Byline Bancorp, Inc. / Inland Bancorp, Inc.
November 30, 2022
Peoples Bancorp Inc. / Limestone Bancorp, Inc. October 25, 2022
Southern Missouri Bancorp, Inc. / Citizens Bancshares Co.
September 20, 2022
HBT Financial, Inc. / Town and Country Financial Corporation August 23, 2022
Bank First Corporation / Hometown Bancorp, Ltd. July 26, 2022
Nicolet Bankshares, Inc. / Charter Bankshares, Inc. March 30, 2022
Bank First Corporation / Denmark Bancshares, Inc. January 19, 2022
QCR Holdings, Inc. / Guaranty Federal Bancshares, Inc.
November 9, 2021
First Merchants Corporation / Level One Bancorp, Inc.
November 4, 2021
German American Bancorp, Inc. / Citizens Union Bancorp of Shelbyville, Inc.
September 20, 2021
Arbor Bancorp, Inc. / FNBH Bancorp, Inc. August 9, 2021
Stock Yards Bancorp, Inc. / Commonwealth Bancshares, Inc. August 3, 2021
First Mid Bancshares, Inc. / Delta Bancshares Company July 29, 2021
Old Second Bancorp, Inc. / West Suburban Bancorp, Inc. July 26, 2021
Farmers National Banc Corp. / Cortland Bancorp June 23, 2021
Nicolet Bankshares, Inc. / County Bancorp, Inc. June 22, 2021
The Farmers & Merchants State Bank / Perpetual Federal Savings Bank May 4, 2021
Nicolet Bankshares, Inc. / Mackinac Financial Corporation April 12, 2021
Stock Yards Bancorp, Inc. / Kentucky Bancshares, Inc. January 27, 2021
First Busey Corporation / Cummins-American Corp. January 19, 2021
For purposes of this analysis, based on publicly available financial information, Morgan Stanley analyzed the multiple of price to forward estimated diluted earnings per share, or Price/Forward EPS, and the multiple of price to tangible book value per share, or Price/TBV, for each of the target companies in the selected transactions and the proposed transaction assuming the Per Share Merger Consideration has a
 
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value of $14.85 and assuming the forward estimated diluted earnings per share from the Macatawa Street Projections. The following table presents the results of this analysis:
Precedent Transactions
Bottom Quartile
Median
Top Quartile
Merger
Price/Forward EPS
11.2x 12.4x 14.0x 12.0x
Price/TBV
1.4x 1.6x 1.7x 1.8x
The selected precedent transactions varied significantly based upon company scale, business risks, growth prospects and geography, as well as prevailing market trends. Based on its experience and professional judgment, and taking into consideration, among other things, the prevailing market trends for the valuation and performance of companies in Macatawa’s industry at the time of each transaction as compared to the current prevailing market trends, Morgan Stanley selected a range of multiples and applied this range of multiples to the relevant financial statistics for Macatawa.
Based on the results of this analysis and its professional judgment, Morgan Stanley selected ranges of multiples as described in the table below and applied these ranges of multiples to the relevant financial statistics for Macatawa in the Macatawa Street Projections to derive ranges of implied value per share of Macatawa common stock as of April 12, 2024, as set forth below:
Macatawa Metric
Multiple Range
Implied Value Per Share of
Macatawa Common Stock
Price/Forward EPS
$ 1.24
11.4x – 13.4x
$ 14.14 – $16.62
Price/TBV
$ 8.35
1.5x – 1.7x
$ 12.53 – $14.20
Morgan Stanley compared these ranges with (i) the closing price per share of Macatawa common stock of $9.59 on April 12, 2024 and (ii) $14.85, the value assigned to a share of Macatawa common stock for purposes of calculating the Per Share Merger Consideration pursuant to the merger agreement assuming the Purchaser Common Stock Price is equal to or greater than $89.03 and less than or equal to $113.03.
No company or transaction used in the precedent transactions analysis is identical to Macatawa or the proposed transaction. In evaluating the precedent transactions, Morgan Stanley made judgments and assumptions with regard to industry performance, general business, economic, market and financial conditions and other matters, many of which are beyond the control of Macatawa and Wintrust, such as the impact of competition on the business of Macatawa or the industry generally, industry growth and the absence of any material adverse change in the financial condition and prospects of Macatawa or the industry or in the financial markets in general. Mathematical analysis, such as determining the average or median, is not in itself a meaningful method of using the precedent transactions data. Rather, it involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies involved.
Macatawa Analyst Price Targets Analysis
For reference only, and not as a component of its fairness analysis, Morgan Stanley reviewed and analyzed future public market trading price targets for Macatawa common stock prepared and published by three equity research analysts prior to April 12, 2024, as reported by Capital IQ. These targets reflected each analyst’s estimate of the future public market trading price of Macatawa common stock. The undiscounted analyst price targets for the Macatawa common stock ranged from $12.00 to $12.50 per share. Morgan Stanley discounted the analyst price targets for one year back to April 12, 2024 at a rate of 10.9%, which discount rate was selected by Morgan Stanley based upon the application of its professional judgment and experience and the capital asset pricing model, to reflect Macatawa’s cost of equity based on market data as of April 12, 2024. This analysis indicated a range of implied values per share of Macatawa common stock of $10.82 to $11.27. Morgan Stanley compared this range with (i) the closing price per share of Macatawa common stock of $9.59 on April 12, 2024 and (ii) $14.85, the value assigned to a share of Macatawa common stock for purposes of calculating the Per Share Merger Consideration pursuant to the merger agreement assuming the Purchaser Common Stock Price is equal to or greater than $89.03 and less than or equal to $113.03.
 
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The public market trading price targets published by research analysts do not necessarily reflect current market trading prices for Macatawa common stock, and these estimates are subject to uncertainties, including the future financial performance of Macatawa and future financial market conditions.
General
In connection with the review of the proposed transaction by the Macatawa Board, Morgan Stanley performed a variety of financial and comparative analyses for purposes of rendering its opinion. The preparation of a financial opinion is a complex process and is not necessarily susceptible to a partial analysis or summary description. In arriving at its opinion, Morgan Stanley considered the results of all of its analyses as a whole and did not attribute any particular weight to any analysis or factor it considered. Morgan Stanley believes that selecting any portion of its analyses, without considering all analyses as a whole, would create an incomplete view of the process underlying its analyses and opinion. In addition, Morgan Stanley may have given various analyses and factors more or less weight than other analyses and factors, and may have deemed various assumptions more or less probable than other assumptions. As a result, the ranges of valuations resulting from any particular analysis described above should not be taken to be Morgan Stanley’s view of the actual value of Macatawa or Wintrust. In performing its analyses, Morgan Stanley made numerous assumptions with regard to industry performance, general business, economic, market and financial conditions and other matters which are beyond the control of Macatawa. Any estimates contained in Morgan Stanley’s analyses are not necessarily indicative of future results or actual values, which may be significantly more or less favorable than those suggested by such estimates.
Morgan Stanley conducted the analyses described above solely as part of its analysis of the fairness from a financial point of view to the holders of Macatawa common stock of the Per Share Merger Consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement, and in connection with the delivery of its oral opinion, and its subsequent written opinion, to the Macatawa Board. These analyses do not purport to be an appraisal or to reflect the price at which Macatawa common stock or Wintrust common stock might actually trade. The consideration to be received by the holders of shares of Macatawa common stock was determined through arm’s-length negotiations between Macatawa and Wintrust and was approved by the Macatawa Board. Morgan Stanley provided advice to Macatawa during these negotiations but did not, however, recommend any specific form, mix or amount of consideration to Macatawa, or that any specific form, mix or amount of consideration constituted the only appropriate consideration for the proposed transaction.
Morgan Stanley’s opinion and its presentation to the Macatawa Board was one of many factors taken into consideration by the Macatawa Board in deciding to approve, adopt and authorize the merger agreement and approve the transactions contemplated thereby, including the proposed transaction. Consequently, the analyses as described above should not be viewed as determinative of the opinion of the board of directors of Macatawa with respect to the consideration to be received by the holders of shares of Macatawa common stock pursuant to the merger agreement or of whether the board of directors of Macatawa would have been willing to agree to different consideration. Morgan Stanley’s opinion was approved by a committee of Morgan Stanley investment banking and other professionals in accordance with its customary practice.
The Macatawa Board retained Morgan Stanley based upon Morgan Stanley’s qualifications, experience and expertise. Morgan Stanley is a global financial services firm engaged in the securities, investment management and individual wealth management businesses. Its securities business is engaged in securities underwriting, trading and brokerage activities, foreign exchange, commodities and derivatives trading, prime brokerage, as well as providing investment banking, financing and financial advisory services. Morgan Stanley, its affiliates, directors and officers may at any time invest on a principal basis or manage funds that invest, hold long or short positions, finance positions, and may trade or otherwise structure and effect transactions, for their own account or the accounts of its customers, in debt or equity securities or loans of Wintrust, Macatawa, or any other company, or any currency or commodity, that may be involved in this transaction, or any related derivative instrument.
Under the terms of its engagement letter, as compensation for its services relating to the proposed transaction, Macatawa has agreed to pay Morgan Stanley a fee of $6.6 million in the aggregate, $500,000 of which was payable upon the rendering of its opinion and $6.1 million of which is contingent upon the consummation of the proposed transaction. Macatawa has also agreed to reimburse Morgan Stanley for its
 
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reasonable expenses incurred in performing its services. In addition, Macatawa has agreed to indemnify Morgan Stanley and its affiliates, their respective directors, officers, agents and employees and each person, if any, controlling Morgan Stanley or any of its affiliates against certain liabilities and expenses, related to or arising out of Morgan Stanley’s engagement. During the two years preceding the date of delivery of Morgan Stanley’s written opinion, Morgan Stanley and its affiliates have not received any fees from Macatawa or Wintrust for financial advisory or financial services. Morgan Stanley may also seek to provide financial advisory and financing services to Macatawa, Wintrust and their respective affiliates in the future and would expect to receive fees for the rendering of these services.
Certain unaudited prospective financial information of Macatawa
Macatawa does not as a matter of course publicly disclose forecasts or internal projections as to future performance, revenues, earnings, financial condition or other results due to, among other reasons, the inherent uncertainty unpredictability and subjectivity of the underlying assumptions and estimates. However, in connection with the evaluation of a potential merger, Macatawa management prepared or approved for use certain projections of Macatawa’s future financial performance for 2024 through 2028, without reference to the merger, which we refer to as the “Macatawa Management Projections”, which contain unaudited prospective financial information with respect to Macatawa on a standalone, pre-merger basis, and which were made available to Macatawa’s financial advisor, Morgan Stanley, the Macatawa Board and Wintrust management and used by Morgan Stanley for the purposes of performing its financial analysis in connection with its opinion as described above under the heading “Opinion of Macatawa’s Financial Advisor”. The Macatawa Management Projections were not prepared for the purpose of or with a view toward public disclosure and the inclusion of the Macatawa Management Projections in this document should not be regarded as an indication that Macatawa or any other recipient of the Macatawa Management Projections considered, or now considers, them to be necessarily predictive of actual future results. The Macatawa Management Projections were not prepared with a view toward complying with the guidelines of the SEC, the guidelines established by the Public Company Accounting Oversight Board for preparation or presentation of financial information, or generally accepted accounting principles in the United States. Neither Macatawa’s current independent registered public accounting firm, BDO USA, P.C., nor any other independent accountants, have compiled, examined or performed any procedures with respect to the Macatawa Management Projections, or expressed any opinion or any other form of assurance on such information or its achievability. The report of BDO USA, P.C. that is incorporated by reference into this document relates only to Macatawa’s historical financial information. It does not extend or apply to any prospective financial information. In addition, since the Macatawa Management Projections cover multiple years, such information by its nature becomes more speculative with each successive year.
The Macatawa Management Projections reflect numerous estimates and assumptions made by Macatawa management with respect to industry performance, general business, economic, regulatory, market and financial conditions and other future events, as well as matters specific to Macatawa’s business, all of which are difficult to predict and many of which are beyond Macatawa’s control. The Macatawa Management Projections also reflect assumptions as to certain business decisions that are subject to change. The Macatawa Management Projections reflect subjective judgment in many respects and thus are susceptible to multiple interpretations and periodic revisions based on actual experience and business developments. As such, the Macatawa Management Projections constitute forward-looking information and are subject to risks and uncertainties that could cause actual results to differ materially from the results forecasted in such prospective information, including, but not limited to, Macatawa’s performance, industry performance, general business and economic conditions, customer requirements, competition, adverse changes in applicable laws, regulations or rules, interest rates, the regulatory environment, and the various risks set forth in this proxy statement/prospectus under the heading “Risk Factors” beginning on page 15 and “Special Notes Concerning Forward-Looking Statements” beginning on page 19 and in Macatawa’s reports filed with the SEC. Neither Macatawa, Wintrust nor any of their respective affiliates or advisors assumes any responsibility for the validity, accuracy or completeness of the Macatawa Management Projections described below. The Macatawa Management Projections do not take into account any circumstances or events occurring after the date they were prepared, including the transactions contemplated by the merger agreement. Further, the Macatawa Management Projections do not take into account the effect of any failure of the merger to occur. Neither Macatawa, Wintrust nor any of their respective affiliates or advisors intends to, and each of them disclaims any obligation to, update, revise or correct such Macatawa
 
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Management Projections if they are or become inaccurate (even in the short term). The inclusion of the Macatawa Management Projections herein should not be deemed an admission or representation by Macatawa, Wintrust or any of their respective affiliates that they are viewed by Macatawa as material information of Macatawa, particularly in light of the inherent risks and uncertainties associated with such forecasts.
These tables set forth the financial projections on which Morgan Stanley relied for purposes of its analysis.
Macatawa Management Projections:
2024E
2025E
2026E
2027E
2028E
Net Income ($MM)
$ 44.8 $ 48.8 $ 51.2 $ 53.9 $ 56.2
Earnings per Share ($)
$ 1.31 $ 1.42 $ 1.49 $ 1.57 $ 1.64
Total Assets ($MM)
$ 2,778 $ 2,910 $ 3,005 $ 3,064 $ 3,171
Avg. Assets for Leverage Ratio ($MM)
$ 2,772 $ 2,844 $ 2,958 $ 3,035 $ 3,118
Return on Tangible Common Equity (%)
14.8%
Macatawa’s reasons for the merger and recommendation of Macatawa board of directors
In determining that the merger, the merger agreement and the Per Share Merger Consideration are fair to and in the best interest of Macatawa and its shareholders and in compliance with all applicable laws, in authorizing and approving the merger, in adopting and approving the merger agreement and in recommending that Macatawa shareholders vote for approval of the merger agreement, the Macatawa Board consulted with members of Macatawa’s management, and with representatives of Morgan Stanley and Warner Norcross, and also considered a number of factors that the Macatawa Board viewed as relevant to its decisions, including, without limitation, the following factors:

the current and prospective business and economic environment of the markets in which Macatawa operates, including consolidation in the banking industry and recent mergers and acquisitions;

a review of the risks and prospects of Macatawa remaining independent, including the challenges of the current financial and regulatory climate and the significant costs associated with increasing regulatory and technological burdens;

the process conducted by Macatawa to identify potential merger partners, with the assistance of its advisors;

the business, financial condition, safety and soundness, size, operating model, brand, acquisition history and experience, regulatory standing, culture and earnings prospects of Wintrust;

the competence, experience, and integrity of Wintrust and its management;

the findings of reverse due diligence conducted on Wintrust;

the nature and value of the Merger Consideration;

the social and economic impact of the merger on Macatawa and its employees, customers, suppliers and communities which it serves and the fact that many members of senior management, officers and employees will be retained as employees post-transaction;

the fact that Macatawa Bank will remain a separately chartered bank subsidiary of Wintrust with a separate, legally constituted board of directors;

the community impact of the merger, including the fact that Macatawa Bank will continue to operate under the Macatawa Bank name and brand in Michigan with local decision making expected to remain largely intact;

the fact that the Chairman of the Macatawa Board is expected to serve on the Wintrust board of directors post-transaction;

the provisions of the merger agreement that permit Macatawa to, in the event Wintrust’s common stock price falls more than 20% relative to the KBW Nasdaq Regional Banking Index, either
 
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(i) continue with the merger as is; (ii) ask Wintrust to increase the Merger Consideration; or (iii) terminate and abandon the merger;

analyses of comparable transactions involving banking organizations in the Midwest;

the structure, terms and conditions of the merger as provided in the merger agreement;

provisions of the merger agreement which permit the board of directors under certain circumstances to consider and negotiate another proposal which the board of directors determines to be a superior proposal and to terminate the merger agreement and enter into an agreement for a superior proposal with payment of the Termination Fee to Wintrust;

the amount of the Termination Fee (4% of transaction value) which Macatawa would be required to pay if it terminates the merger agreement and enters into an agreement with respect to a superior proposal, which fee the Macatawa Board believes is reasonable and would not economically preclude a capable party from submitting a superior proposal;

Macatawa’s and Wintrust’s shared values, common cultures and commitment to serve their clients and communities;

the ability of Wintrust to complete a merger transaction from a financial and regulatory perspective;

Wintrust’s demonstrated ability to successfully complete a merger transaction;

the geographic fit and increased product offerings for Macatawa customers through the combined company;

the likelihood of successful integration and operation of the combined company;

the likelihood of obtaining the shareholder and regulatory approvals needed to complete the merger;

advice from Warner Norcross, including regarding the fiduciary and legal obligations applicable to directors when considering a sale or merger of a company and that a merger with Wintrust will comply with all applicable laws; and

the financial analyses presented to the Macatawa Board by representatives of Morgan Stanley and the oral opinion of Morgan Stanley, subsequently confirmed by delivery of a written opinion dated April 15, 2024, to the effect that, as of such date and based upon and subject to the various assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth in its written opinion, the Per Share Consideration to be received by the holders of Macatawa common stock pursuant to the merger agreement was fair from a financial point of view to the holders of Macatawa common stock, as more fully described in the section entitled “— Opinion of Macatawa’s Financial Advisor”.
The Macatawa Board also considered a number of potential risks and uncertainties in connection with its consideration of the proposed merger, including, without limitation, the following:

the risk that Wintrust will be unable to obtain necessary regulatory approvals when expected or at all (and the risk that such approvals may result in a materially burdensome regulatory condition (as defined in the merger agreement));

the risk that Macatawa will not obtain shareholder approval for the merger;

the risk that either party may fail to satisfy any of the other closing conditions to the transaction on a timely basis or at all;

the potential occurrence of an event, change or other circumstances that could give rise to the right of one or both of the parties to terminate the merger agreement;

the possibility that the anticipated benefits of the transaction are not realized when expected, in the amounts anticipated or at all, including as a result of the impact of, or problems arising from, the integration of the two companies or as a result of changes in the economy, competitive factors in the areas where Macatawa and Wintrust do business, or as a result of other unexpected factors or events;
 
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the impact of purchase accounting with respect to the transaction, or any change in the assumptions used regarding the assets purchased and liabilities assumed to determine their fair value;

diversion of management’s attention from ongoing business operations and opportunities;

potential adverse reactions or changes to business or employee relationships, including those resulting from the announcement or completion of the transaction; and

the outcome of any legal proceedings that may be instituted against Macatawa or Wintrust.
This discussion of the information and factors considered by the Macatawa Board in reaching its conclusions and recommendation includes the factors identified above but is not intended to be exhaustive and may not include all of the factors considered by the Macatawa Board. In view of the wide variety of factors considered in connection with its evaluation of the merger and the other transactions contemplated by the merger agreement, and the complexity of these matters, the Macatawa Board did not find it useful and did not attempt to quantify, rank or assign any relative or specific weights to the various factors that it considered in reaching its determination to approve the merger and the other transactions contemplated by the merger agreement, and to make its recommendation to Macatawa shareholders. Rather, the Macatawa Board viewed its decisions as being based on the totality of the information presented to it and the factors it considered, including its discussions with and questioning of members of Macatawa’s management and outside legal and financial advisors. In addition, individual members of the Macatawa Board may have assigned different weights to different factors.
Certain of Macatawa’s directors and executive officers have financial interests in the merger that are different from, or in addition to, those of Macatawa’s shareholders generally. The Macatawa Board was aware of and considered these potential interests, among other matters, in evaluating the merger and in making its recommendation to Macatawa shareholders. For a discussion of these interests, see “Interests of Directors and Executive Officers in the Merger” below.
The Macatawa Board unanimously determined that the merger, the merger agreement and the Per Share Merger Consideration are fair to and in the best interests of Macatawa and its shareholders and that entering into the merger agreement and completing the merger will comply with all applicable laws. The Macatawa Board unanimously recommends that Macatawa shareholders vote “FOR” the proposal to approve the merger agreement, “FOR” the proposal to approve, on a non-binding, advisory basis, the compensation that may be paid or become payable to Macatawa’s named executive officers that is based on or otherwise related to the proposed transactions and “FOR” the proposal to approve the adjournment of the Macatawa special meeting, if necessary or appropriate, to permit further solicitation of proxies.
Wintrust’s reasons for the merger
Wintrust’s board of directors believes that the merger is in the best interests of Wintrust and its shareholders. In deciding to approve the merger, Wintrust’s board of directors considered a number of factors, including:

management’s view that the acquisition provides an attractive opportunity for Wintrust to expand in the west Michigan area;

Macatawa’s community banking orientation and its compatibility with Wintrust and its subsidiaries;

a review of the demographic, economic and financial characteristics of the markets in which Macatawa operates, including existing and potential competition and history of the market areas with respect to financial institutions;

management’s review of Macatawa’s business, operations, earnings and financial condition, including capital levels and asset quality of Macatawa Bank;

efficiencies to come from integrating certain of Macatawa’s operations into Wintrust’s existing operations; and

the likelihood that the merger will be approved by the relevant bank regulatory authorities without undue burden and in a timely manner.
 
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The above discussion of the information and factors considered by Wintrust’s board of directors is not intended to be exhaustive, but includes a description of all material factors considered by Wintrust’s board. In view of the wide variety of factors considered by the Wintrust board of directors in connection with its evaluation of the merger, the Wintrust board did not consider it practical to, nor did it attempt to, quantify, rank or otherwise assign relative weights to the specific factors that it considered. In considering the factors described above, individual directors may have given differing weights to different factors. Wintrust’s board of directors collectively made its determination with respect to the merger based on the conclusion reached by its members, based on the factors that each of them considered appropriate, that the merger is in the best interests of Wintrust’s shareholders.
Material U.S. federal income tax consequences of the merger
The following summary describes the material U.S. federal income tax consequences of the merger to U.S. holders (as defined below) of Macatawa common stock. The summary is based upon the Internal Revenue Code, applicable U.S. Treasury regulations, judicial decisions and administrative rulings and practice, all as in effect as of the date hereof, and all of which are subject to change, possibly with retroactive effect. This summary does not address any tax consequences of the merger under state, local or foreign laws, or any federal laws other than those pertaining to income tax.
For purposes of this discussion, the term “U.S. holder” means a beneficial owner that is: an individual citizen or resident of the United States; a corporation (or other entity taxable as a corporation for U.S. federal income tax purposes) created or organized under the laws of the United States or any of its political subdivisions; a trust that (1) is subject to the supervision of a court within the United States and the control of one or more U.S. persons or (2) has a valid election in effect under applicable U.S. Treasury regulations to be treated as a U.S. person; or an estate that is subject to U.S. federal income taxation on its income regardless of its source.
This discussion addresses only those U.S. holders of Macatawa common stock that hold their Macatawa common stock as a capital asset within the meaning of Section 1221 of the Internal Revenue Code and does not address all the U.S. federal income tax consequences that may be relevant to particular holders of Macatawa common stock in light of their individual circumstances or to holders of Macatawa common stock that are subject to special rules, such as non-U.S. holders (as defined below) (except to the extent discussed under the subheading “Tax Implications to Non-U.S. Shareholders” below); financial institutions; qualified insurance plans; qualified retirement plans and individual retirement accounts; investors in pass-through entities; persons who are subject to alternative minimum tax; insurance companies; mutual funds; tax-exempt organizations; dealers or brokers in securities or currencies; traders in securities that elect to use a mark-to-market method of accounting; persons that hold Macatawa common stock as part of a straddle, hedge, constructive sale or conversion or other integrated transaction; regulated investment companies; real estate investment trusts; persons whose “functional currency” is not the U.S. dollar; U.S. expatriates or certain former citizens or long-term residents of the U.S.; and holders who acquired their shares of Macatawa common stock through the exercise of an employee stock option or otherwise as compensation.
If a partnership (or other entity that is taxed as a partnership for federal income tax purposes) holds Macatawa common stock, the tax treatment of a partner in that partnership generally will depend upon the status of the partner, the activities of the partnership and certain determinations made at the partner level. Partnerships and partners in partnerships should consult their own tax advisors about the tax consequences of the merger to them.
The parties intend for the merger to be treated as a “reorganization” for U.S. federal income tax purposes. Each of Warner Norcross and ArentFox have delivered opinions, filed as exhibits to the registration statement of which this proxy statement/prospectus is a part, to the effect that, subject to the exceptions, qualifications and limitations set forth therein, the merger will constitute a “reorganization” within the meaning of Section 368(a) of the Internal Revenue Code. Additionally, it is a condition to Macatawa’s obligation to complete the merger that Macatawa receive an opinion from Warner Norcross, dated as of the closing date of the merger, and it is a condition to Wintrust’s obligation to complete the merger that Wintrust receive an opinion from ArentFox, dated as of the closing date of the merger, each to the same effect as the opinions described in the preceding sentence. These conditions are waivable, and Wintrust and Macatawa undertake to recirculate and resolicit if either of these conditions is waived and the change in tax
 
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consequences is material. These opinions are and will be based upon representation letters provided by Wintrust and Macatawa and upon customary factual assumptions. Neither Wintrust nor Macatawa has sought, and neither of them will seek, any ruling from the Internal Revenue Service regarding any matters relating to the merger, and the opinions described above will not be binding on the Internal Revenue Service or any court. Consequently, there can be no assurance that the Internal Revenue Service will not assert, or that a court would not sustain, a position contrary to any of the conclusions set forth below. In addition, if any of the representations or assumptions upon which the opinions are based are inconsistent with the actual facts, the U.S. federal income tax consequences of the merger could be adversely affected.
The actual tax consequences of the merger to you may be complex and will depend upon your specific situation and upon factors that are not within the control of Wintrust or Macatawa. You should consult with your own tax advisor as to the tax consequences of the merger in light of your particular circumstances, including the applicability and effect of the alternative minimum tax and any state, local or foreign and other tax laws.
The following discussion summarizes the material U.S. federal income tax consequences of the merger to U.S. holders, assuming the merger qualifies as a reorganization within the meaning of Section 368(a) of the Internal Revenue Code.
Tax Consequences of the merger for U.S. holders of Macatawa common stock.   Except as discussed below in “— Cash in Lieu of Fractional Shares of Wintrust Common Stock,” a U.S. holder of Macatawa common stock will generally not recognize any gain or loss as a result of the merger. Pursuant to the merger, a U.S. holder of Macatawa common stock will receive shares of Wintrust common stock in exchange for its shares of Macatawa common stock. Generally, a U.S. holder’s aggregate tax basis in the Wintrust common stock received by such U.S. holder in the merger in exchange for its Macatawa common stock, including any fractional shares deemed received by the U.S. holder under the treatment discussed below in “— Cash in Lieu of Fractional Shares of Wintrust Common Stock,” will equal such U.S. holder’s aggregate tax basis in the Macatawa common stock surrendered in the merger. The holding period for the shares of Wintrust common stock received in the merger, including any fractional shares deemed received by the U.S. holder under the treatment discussed below in “— Cash in Lieu of Fractional Shares of Wintrust Common Stock,” generally will include the holding period for the shares of Macatawa common stock exchanged therefor.
Cash in Lieu of Fractional Shares of Wintrust Common Stock.   A U.S. holder who receives cash instead of a fractional share of Wintrust common stock will be treated as having received the fractional share of Wintrust common stock pursuant to the merger and then as having exchanged the fractional share of Wintrust common stock for cash in a redemption by Wintrust. In general, this deemed redemption will be treated as a sale or exchange, and a U.S. holder will recognize gain or loss equal to the difference between (i) the amount of cash received by such U.S. holder and (ii) the portion of the basis of the shares of Macatawa common stock allocable to such fractional interest. Such gain or loss generally will constitute capital gain or loss and will be long-term capital gain or loss if the U.S. holder’s holding period for the Macatawa common stock exchanged by such U.S. holder is greater than one year as of the effective time of the merger.
Medicare Tax on Unearned Income.   A U.S. holder that is an individual is subject to a 3.8% tax on the lesser of (i) his or her “net investment income” for the relevant taxable year or (ii) the excess of his or her modified adjusted gross income for the taxable year over a certain threshold (between $125,000 and $250,000 depending on the individual’s U.S. federal income tax filing status). A similar regime applies to estates and trusts. Net investment income generally would include any capital gain incurred in connection with the merger.
Backup Withholding and Information Reporting.   Payments of cash instead of a fractional share of Wintrust common stock to a U.S. holder of Macatawa common stock pursuant to the merger may, under certain circumstances, be subject to information reporting and backup withholding unless the holder provides proof of an applicable exemption satisfactory to Wintrust and the exchange agent or, in the case of backup withholding, furnishes its taxpayer identification number and otherwise complies with all applicable requirements of the backup withholding rules. Any amounts withheld from payments to a U.S. holder under the backup withholding rules are not additional tax and generally will be allowed as a refund or credit against the U.S. holder’s U.S. federal income tax liability, provided the required information is timely furnished to the Internal Revenue Service.
 
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A U.S. holder of Macatawa common stock, as a result of having received Wintrust common stock in the merger, will be required to retain records pertaining to the merger. In addition, each U.S. holder of Macatawa common stock who is a “significant holder” will be required to file a statement with such holder’s U.S. federal income tax return in accordance with Treasury Regulations Section 1.368-3(b) setting forth the fair market value and such holder’s basis in the Macatawa common stock surrendered in the merger. A “significant holder” is a holder of Macatawa common stock who, immediately before the merger, owned at least five percent of the vote or value of the outstanding stock of Macatawa or securities of Macatawa with a basis for federal income taxes of at least one million dollars.
Tax Implications to Non-U.S. Shareholders.   For purposes of this discussion, the term “non-U.S. holder” means a beneficial owner of Macatawa common stock (other than an entity treated as a partnership for U.S. federal income tax purposes) that is not a U.S. holder. The rules governing the U.S. federal income taxation of non-U.S. holders are complex, and no attempt will be made herein to provide more than a limited summary of those rules. Any gain a non-U.S. holder recognizes in connection with receiving cash instead of a fractional share of Wintrust common stock generally will not be subject to U.S. federal income taxation unless (a) the gain is effectively connected with a trade or business conducted by the non-U.S. holder in the U.S., or (b) in the case of a non-U.S. holder who is an individual, such shareholder is present in the U.S. for 183 days or more in the taxable year of the sale and other conditions are met. Non-U.S. holders described in (a) above will be subject to tax on gain recognized at applicable U.S. federal income tax rates and, in addition, non-U.S. holders that are corporations (or treated as corporations for U.S. federal income tax purposes) may be subject to a branch profits tax equal to 30% (or a lesser rate under an applicable income tax treaty) on their effectively connected earnings and profits for the taxable year, which would include such gain. Non-U.S. holders described in (b) above will be subject to a flat 30% tax on any gain recognized, which may be offset by U.S. source capital losses.
If any gain a non-U.S. holder recognizes on the receipt of cash instead of a fractional share of Wintrust common stock in the merger is effectively connected with the conduct of such trade or business, then the gain will be subject to U.S. federal income tax at graduated rates for non-U.S. holders other than corporations and the flat corporate rate (currently 21%) for non-U.S. holders that are corporations (including, if applicable, special lower rates that may be applicable to certain gain and dividends). If the non-U.S. holder is eligible for the benefits of a tax treaty between the U.S. and the non-U.S. holder’s country of residence, any effectively connected gain or dividend income would generally be subject to U.S. federal income tax only if it is also attributable to a permanent establishment or fixed place of business maintained by the non-U.S. holder in the U.S. To claim exemption from withholding for any effectively connected dividend or gain, the non-U.S. holder must certify its qualification, which can be done by providing Form W-8ECI. In addition, non-U.S. holders that are corporations (or treated as corporations for U.S. federal income tax purposes) may be subject to a branch profits tax equal to 30% (or a lesser rate under an applicable income tax treaty), referenced above, on their effectively connected earnings and profits for the taxable year, which would include such gain.
This discussion does not address tax consequences that may vary with, or are contingent upon, individual circumstances. Moreover, it does not address any non-income tax or any foreign, state or local tax consequences of the merger. Tax matters are very complicated, and the tax consequences of the merger to you will depend upon the facts of your particular situation. Accordingly, we strongly urge you to consult with a tax advisor to determine the particular federal, state, local or foreign tax consequences to you as a result of the merger.
Regulatory approvals
The completion of the merger is subject to the receipt of approvals from, or the making of filings with, applicable U.S. federal bank regulatory authorities and other regulatory authorities. Subject to the terms of the merger agreement, Wintrust and Macatawa have agreed to cooperate with each other and use commercially reasonable efforts to take, or cause to be taken, all actions, and to do, or cause to be done, all things necessary, proper, or advisable under applicable laws and regulations to consummate and make effective the merger. In addition, Wintrust and Macatawa have agreed in the merger agreement to use commercially reasonable efforts to obtain as promptly as practical consents, approvals and authorizations of all third parties and governmental entities necessary or desirable for the consummation of the merger.
 
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Under the terms of the merger agreement, Wintrust and Macatawa will not be required to take any action, or commit to take any action, or agree to any condition or restriction which the Wintrust board of directors reasonably determines in good faith would, individually or in the aggregate, materially and adversely reduce the economic benefits of the merger to such a degree that Wintrust would not have entered into the merger agreement had such action, condition or restriction been known at the date hereof (a “materially burdensome regulatory condition”).
Wintrust and Macatawa believe that the merger does not raise significant regulatory concerns and that all requisite regulatory approvals will be obtained. However, there can be no assurance that the regulatory approvals described below will be obtained. If the regulatory approvals are obtained, there can be no assurances regarding the timing of the receipt of the approvals, the terms of the approvals or the absence of any litigation challenging the approvals. In addition, there can be no assurance that the approvals will not impose conditions or requirements that, individually or in the aggregate, would or could reasonably be expected to have a material adverse effect on the financial condition, results of operations, assets or business of Wintrust following the completion of the merger. There can also be no assurances that U.S. federal or state regulatory authorities will not attempt to challenge the merger or, if such a challenge is made, what the result of such challenge will be.
The merger is subject to the approval of the Federal Reserve Board pursuant to section 3 of the Bank Holding Company Act (the “BHC Act”). The Federal Reserve Board takes into account various factors when considering applications under section 3 of the BHC Act, including the effect of the merger on competitiveness in the affected banking markets, and the financial and managerial resources and future prospects of the combined company. The Federal Reserve Board also considers the convenience and needs of the communities being served, and the extent to which the proposal would result in greater or more concentrated risks to the stability of the U.S. banking or financial system. The Federal Reserve Board may not approve an application that would have significant adverse effects on competition or on the concentration of resources in any banking market.
In considering an application under section 3 of the BHC Act, the Federal Reserve Board also reviews the records of performance of the relevant insured depository institutions under the CRA, pursuant to which the Federal Reserve Board must take into account the record of performance of each of Wintrust and Macatawa in meeting the credit needs of the entire community, including low- and moderate-income neighborhoods, served by their depository institution subsidiaries. As part of the review process, the Federal Reserve Board may receive comment letters from community groups and others. In their most recent CRA performance evaluations, Wintrust’s subsidiary banks each received CRA ratings of “outstanding” or “satisfactory,” and Macatawa Bank received a “satisfactory” CRA rating.
The initial submission of the applications to the Federal Reserve Board occurred on April 30, 2024.
In addition to the Federal Reserve Board, the Antitrust Division of the Department of Justice (the “DOJ”) conducts a concurrent review of the merger’s competitive effects to determine whether the merger would result in a violation of antitrust laws. Transactions approved under Section 3 of the BHC Act generally may not be completed until 30 days after the approval of the Federal Reserve Board is received, during which time the DOJ may challenge the transaction on antitrust grounds. With the approval of the Federal Reserve Board and the DOJ, the waiting period may be, and customarily is, reduced to no less than 15 days. The commencement of an antitrust action by the DOJ would stay the effectiveness of the merger’s approval unless a court of competent jurisdiction orders otherwise. In reviewing the merger, the DOJ could reach a different conclusion than the Federal Reserve Board regarding the merger’s effects on competition. The DOJ deciding not to object to the merger does not prohibit the filing of antitrust actions by private persons or state attorneys general.
Interests of Directors and Executive Officers in the Merger
The directors and executive officers of Macatawa and its subsidiaries may have interests in the merger that are different from, or are in addition to, the interests of Macatawa shareholders generally. The Macatawa Board was aware of these interests and considered them, among other matters, in evaluating, negotiating and adopting the merger agreement and in recommending that the Macatawa shareholders vote for approval of the merger agreement. These interests are described in more detail below, and certain of them are
 
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quantified within the narrative disclosure and in the section entitled “— Quantification of Potential Payments and Benefits to Macatawa’s Named Executive Officers in Connection with the Merger” below. The merger will constitute a “change in control” for purposes of the compensation arrangements described below. The amounts presented in the following discussion do not reflect the impact of applicable withholding or other taxes.
Certain Assumptions
Except as otherwise specifically noted, for purposes of quantifying the potential payments and benefits described in this section, the following assumptions were used:

the relevant price per share of Macatawa common stock is $13.92, which is the average closing price per share of Macatawa common stock as reported on Nasdaq over the five business days following the public announcement of the merger on April 15, 2024;

the merger occurs on December 31, 2024, which is the assumed completion date of the merger solely for purposes of the disclosure in this section;

unless otherwise noted, each executive officer of Macatawa experiences a qualifying termination as defined in the relevant agreements, as applicable, on the assumed merger completion date of December 31, 2024 and immediately following the completion of the merger; and

for purposes of this section, the “Named Executive Officers” are Jon W. Swets, Craig A. Hankinson, and Jill A. Walcott.
As a result of these assumptions, which may or may not actually occur or be accurate on the relevant date, the actual amounts, if any, to be received by Macatawa’s executive officers and directors may differ materially from the amounts set forth in this section. For purposes of the discussion in this section, “single trigger” refers to benefits that arise solely as a result of the completion of the merger and “double trigger” refers to benefits that require two conditions, which are the completion of the merger and a qualifying termination of employment on or following the completion of the merger.
Treatment of Macatawa Equity Awards
Macatawa has granted restricted stock awards under its Macatawa Bank Corporation Stock Incentive Plan of 2015. At the effective time, each unvested restricted stock award will vest and be converted into the right to receive a number of shares of Wintrust common stock, determined by dividing the Aggregate Share Amount (as defined below) by the number of shares of Macatawa common stock outstanding as of the effective time. The “Aggregate Share Amount” is determined by dividing (i) the product of (A) $14.85 and (B) the number of shares of Macatawa common stock outstanding as of the effective time by (ii) the volume weighted average price per share of Wintrust common stock on Nasdaq for the ten consecutive trading days ending the two trading days prior to the closing of the merger as reported on the Bloomberg Page for Wintrust (such price, the “Wintrust Share Price”), provided, however, that if the Wintrust Share Price is greater than $113.03, $113.03 will replace the Wintrust Share Price in the Aggregate Share Amount calculation and if the Wintrust Share Price is less than $89.03, $89.03 will replace the Wintrust Share Price in such calculation.
See the section entitled “— Quantification of Potential Payments and Benefits to Macatawa’s Named Executive Officers in Connection with the Merger” below for the estimated value of unvested restricted stock awards held by Macatawa’s Named Executive Officers. Based on the assumptions described above under “— Certain Assumptions”, the estimated aggregated amount that would be realized by the two Macatawa executive officers who are not named executive officers in respect of their unvested Macatawa restricted stock awards on a “single trigger” basis is $229,220.24.
Change in Control Agreements
Each of the executive officers referred to herein is party to a Change in Control Agreement pursuant to which the applicable executive is entitled to severance benefits if, within six months before or 24 months after the change in control of Macatawa, the executive’s employment is terminated by Macatawa without “Cause” or by such Named Executive Officer for “Good Reason” ​(as such terms are defined below).
 
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Upon such a qualifying termination, Messrs. Swets and Hankinson would be entitled to a lump sum cash payment equal to 1.5 times the average of the sum of the executive’s base salary, cash bonus paid, and grant date value of stock awards in the three most recent complete calendar years (such average, the “Average Compensation”) and a lump sum health coverage payment equal to 18 months of Macatawa’s share of health and dental insurance costs for the executive and the executive’s dependents. Ms. Walcott and the executive officers who are not Named Executive Officers would be entitled to a lump sum cash payment equal to 1.0 times the executive’s Average Compensation and a lump sum health coverage payment equal to 12 months of Macatawa’s share of health and dental insurance costs for the executive and the executive’s dependents.
Under the Change in Control Agreements, “Cause” means (i) the executive’s removal from office by order of a regulatory agency having jurisdiction over Macatawa, or the executive’s willful and repeated failure to perform the executive’s duties of employment, which failure has not been cured within 30 days after Macatawa provides the executive notice of such failure; it being expressly understood that negligence or bad judgment does not constitute “Cause” so long as such act or omission was without intent of personal profit and was reasonably believed by the executive to be in or not adverse to the best interests of Macatawa.
“Good Reason” means a material negative change to the employment relationship between the executive and Macatawa because:

the executive is removed from any of the executive’s principal positions with Macatawa or its affiliates;

the authority, duties or responsibilities of the executive’s principal positions is materially diminished;

the executive’s base compensation is materially reduced;

the authority, duties or responsibilities of the supervisor to whom the executive is required to report is materially diminished, which includes a requirement that the executive report to anyone other than Macatawa’s Chief Executive Officer or the Macatawa Board;

of any requirement imposed by Macatawa that the executive be based anywhere other than in Ottawa County or Kent County, Michigan, or any substantial increase in the business travel required of the executive; or

of any material breach by Macatawa or any successor of its obligations to the executive under the relevant Change in Control Agreement.
Severance benefits are conditioned upon the executive’s execution of a release of claims. and compliance with certain post-termination restrictive covenants. These covenants include a (i) a perpetual confidentiality covenant, (ii) a six month prohibition on competing with Macatawa (18 months for Mr. Hankinson), and (iii) a 12 month prohibition on solicitation of personnel and customers (18 months for Messrs. Swets and Hankinson).
The Change in Control Agreements also limit the amount of the severance payments that may be paid under each agreement such that severance benefits will be reduced to the highest dollar amount of payments that will not result in the executive receiving an “excess parachute payment” under Section 280G of the Internal Revenue Code. According to the analysis completed by Macatawa, it is not expected that any severance benefits will be reduced as a result of this Section 280G provision.
See the section entitled “— Quantification of Potential Payments and Benefits to Macatawa’s Named Executive Officers in Connection with the Merger” below for the estimated value of severance payments to Macatawa’s Named Executive Officers in the event of a qualifying termination under the Change in Control Agreements. Based on the assumptions described above under “— Certain Assumptions”, the estimated aggregate amount of cash severance and health coverage payments that would be realized by the two Macatawa executive officers who are not named executive officers on a “double trigger” basis is $496,757.60.
New Employment and Compensation Arrangements with Wintrust
Upon the effective time, it is expected that Wintrust will award to Jon Swets, Craig Hankinson, and Jill Walcott restricted stock units that will vest ratably over a three-year period. Any other executive officers who become officers or employees or who otherwise are retained to provide services to the combined company
 
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may enter into new individualized compensation arrangements and may participate in cash or equity incentive or other benefit plans maintained by the combined company. As of the date of this proxy statement/prospectus, no new individualized compensation arrangements between such persons and Wintrust have been established.
Indemnification and Insurance
Pursuant to the terms of the merger agreement, Wintrust has agreed to provide to each director or officer of Macatawa or its subsidiaries for not less than six years after the effective time of the merger with continued or substantially the same directors’ and officers’ liability insurance and fiduciary liability insurance as maintained by Macatawa prior to the merger with respect to matters occurring at or prior to effective time of the merger. Alternatively, Wintrust may elect to pay for a six-year prepaid “tail” policy providing substantially equivalent benefits as Macatawa’s current policies of directors’ and officers’ liability insurance and fiduciary liability insurance with respect to matters occurring at or prior to the effective time of the merger. In either case, Wintrust is not required to pay policy premiums in excess of 300% of the last annual premium paid by Macatawa for such coverage, which we refer to as the maximum premium. If such continued coverage or “tail” coverage is not available for the maximum premium, the insurance obtained shall be the best coverage as is reasonably available for such maximum premium.
Wintrust has agreed to indemnify Macatawa’s and its subsidiaries’ past and current directors and officers to the fullest extent permitted by applicable law with respect to any action or omission occurring at or before the effective time of the merger, including in connection with the transactions contemplated by the merger agreement.
Quantification of Potential Payments and Benefits to Macatawa’s Named Executive Officers in Connection with the Merger
The information set forth in the table below is intended to comply with Item 402(t) of the SEC’s Regulation S-K, which requires disclosure of information about certain compensation for each named executive officer of Macatawa that is based on, or otherwise relates to, the merger. This compensation is referred to as “golden parachute” compensation by the applicable SEC disclosure rules, and is subject to a non-binding advisory vote of the shareholders of Macatawa.
The amounts shown in the table below are estimates based on multiple assumptions that may or may not actually occur or be accurate on the relevant date, including the assumptions described above under “— Certain Assumptions” and in the footnotes to the table, and do not reflect certain compensation actions that may occur after the date hereof and before completion of the merger. The calculations in the table below do not include amounts the Macatawa Named Executive Officers were already entitled to receive or vested in as of the date hereof. In addition, these amounts do not attempt to forecast any additional equity or cash award grants, issuances or forfeitures that may occur, or future dividend equivalents that may be accrued, prior to the closing of the merger. As a result of the foregoing assumptions, which may or may not actually occur or be accurate on the relevant date, including the assumptions described in the footnotes to the table, the actual amounts, if any, to be received by a Named Executive Officer may materially differ from the amounts set forth below.
The table below does not include amounts for Ronald Haan, who retired effective November 1, 2023. Mr. Haan was included as a named executive officer of Macatawa in Macatawa’s most recently filed Form 10-K/A but he will not receive compensation or benefits in connection with the merger.
Golden Parachute Compensation
Named Executive Officer
Cash
($)(1)
Equity
($)(2)
Total
($)
Jon W. Swets
718,182 253,984 972,166
Craig A. Hankinson
719,053 245,076 964,129
Jill A. Walcott
350,494 157,867 508,361
 
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(1)
Cash.   Consists of the cash severance payments calculated based on a multiple of the executive’s Average Compensation and a payment covering Macatawa’s share of health and dental coverage for a specified number of months. The cash lump sum severance payments are “double trigger” and become payable only upon a qualifying termination under the terms of the Change in Control Agreements during the six months prior to, or 24 months following, the completion of the merger (see the section entitled “— Change in Control Agreements”). The estimated amount of each such payment is shown in the following table.
Named Executive Officer
Severance Based on
Average Compensation ($)
Health Coverage
Payment ($)
Total ($)
Jon W. Swets
697,979 20,202 718,182
Craig A. Hankinson
692,124 26,928 719,053
Jill A. Walcott
340,413 10,081 350,494
(2)
Equity.   Amounts shown reflect the estimated value received by the Macatawa named executive officers in respect of unvested restricted stock awards (as more fully described under “— Treatment of Macatawa Equity Awards”). The value of the unvested restricted stock awards was estimated using a Macatawa common stock price of $13.92.
Voting agreement
On April 15, 2024, certain directors and executive officers of Macatawa who own shares of Macatawa common stock entered into a voting agreement with Wintrust. Under this agreement, these shareholders have each agreed to vote their respective shares of Macatawa common stock:

in favor of the merger and the transactions contemplated by the merger agreement;

against any Company Takeover Proposal involving any party other than Wintrust or one of its affiliates; and

against any action or agreement that would reasonably be expected to result in a material breach of any covenant, representation or warranty or any other obligation under the merger agreement.
Furthermore, each of these shareholders has also agreed not to transfer or otherwise dispose of any shares of Macatawa common stock that they own (other than under certain circumstances) and not to vote or execute any written consent to rescind or amend any prior vote or written consent to approve or adopt the merger or the merger agreement. The shares subject to the voting agreement represented approximately 6.9% of Macatawa’s outstanding shares of common stock as of March 31, 2024. The voting agreement will terminate upon the earlier of the favorable vote of the Macatawa shareholders with respect to approval of the merger or termination of the merger agreement in accordance with its terms.
Restrictions on resale of Wintrust common stock
The shares of Wintrust common stock to be issued in connection with the merger will be registered under the Securities Act, and will be freely transferable, except for shares issued to any shareholder who may be deemed to be an “affiliate” of Wintrust for purposes of Rule 144 under the Securities Act. Persons who may be deemed to be affiliates of Wintrust include individuals or entities that control, are controlled by, or are under common control with, Wintrust and may include the executive officers, directors and significant shareholders of Wintrust.
Macatawa’s shareholder dissenters’ rights
Under Section 762 of the MBCA, Macatawa shareholders will not be entitled to dissenters’ rights in connection with the merger.
 
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DESCRIPTION OF THE MERGER AGREEMENT
The following is a summary of the material terms of the merger agreement. This summary does not purport to describe all the terms of the merger agreement and is qualified by reference to the complete text of the merger agreement which is attached as Annex A to this proxy statement/prospectus, and is incorporated by reference into this proxy statement/prospectus. You should read the merger agreement completely and carefully as it, rather than this description, is the legal document that governs the merger.
The text of the merger agreement has been included to provide you with information regarding its terms. The terms of the merger agreement (such as the representations and warranties) are intended to govern the contractual rights and relationships, and allocate risks, between the parties in relation to the merger. The merger agreement contains representations and warranties Wintrust, Merger Sub and Macatawa made to each other as of specific dates. The representations and warranties were negotiated between the parties with the principal purpose of setting forth their respective rights with respect to their obligations to complete the merger. The statements embodied in those representations and warranties may be subject to important limitations and qualifications as set forth therein, including a contractual standard of materiality different from that generally applicable under federal securities laws.
General
The merger agreement provides for the merger of Macatawa with and into Merger Sub, with Merger Sub continuing as the surviving company. After the consummation of the merger, Merger Sub will continue to be a wholly-owned subsidiary of Wintrust. It is expected that, after completion of the merger at such time as Wintrust may determine, Merger Sub will be merged with and into, or dissolved by, Wintrust.
Closing and effective time
Closing.   The closing of the merger will take place on a date to be agreed upon by Macatawa and Wintrust upon five business days’ written notice after the satisfaction (or waiver) of the conditions to closing set forth in the merger agreement, or on another date that the parties mutually agree upon. See “— Conditions to completion of the merger” below for a more complete description of the conditions that must be satisfied prior to closing. The date of completion of the merger sometimes is referred to in this proxy statement/prospectus as the closing date.
Completion of the Merger.   The merger will become effective on the date set forth in the certificate of merger filed with the Michigan Department of Licensing and Regulatory Affairs, Corporations, Securities & Commercial Licensing Bureau, which if requested by Wintrust, shall be either the last day of the month in which, or the first day of the month after which, the closing occurs. The time at which the merger becomes effective is sometimes referred to in this proxy statement/prospectus as the effective time.
Consideration to be received in the merger
Macatawa Common Stock.   If the merger is completed, the shares of Macatawa common stock which you own immediately before the completion of the merger will be converted into a right to receive shares of Wintrust common stock, subject in each case to the adjustment procedures described below under “— Adjustment to Merger Consideration.” The Merger Consideration paid by Wintrust to Macatawa shareholders will be the product of $14.85 and the number of share of Macatawa common stock issued and outstanding immediately prior to the effective time of the merger, subject to adjustment as described below. The Merger Consideration would be $510.3 million, based on 34,361,562 shares of Macatawa common stock outstanding as of April 12, 2024, the last trading day before public announcement of the execution of the merger agreement. All of the Merger Consideration will be paid to holders of Macatawa common stock in shares of Wintrust common stock, no par value per share, calculated based on the Per Share Merger Consideration described below, other than cash to be paid in lieu of any fractional shares. Immediately prior to the effective time, all unvested shares of Macatawa restricted stock will automatically vest and be eligible to receive the respective portion of the Merger Consideration.
Merger Consideration.   At closing, for each share of Macatawa common stock, Macatawa shareholders will be entitled to receive the Per Share Merger Consideration in the form of shares of Wintrust common
 
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stock in an amount equal to the quotient obtained by dividing (a) the aggregate share amount (as defined below) by (b) the number of shares of Macatawa common stock issued and outstanding immediately prior to the effective time of the merger. The Per Share Merger Consideration will be determined based on the average of the volume-weighted average price of Wintrust common stock as reported under the heading “Bloomberg VWAP” on the Bloomberg page for Wintrust for each trading day during the ten trading day period ending on the second trading day prior to completion of the merger, which we refer to as the reference price, subject to a minimum and maximum reference price equal to $89.03 and $113.03, respectively.
For purposes of determining the Per Share Merger Consideration, the merger agreement provides that the “aggregate share amount” will be determined as follows:

if the reference price is less than $89.03, the aggregate share amount shall be obtained by dividing (i) the Merger Consideration by (ii) $89.03;

if the reference price is more than $113.03, the aggregate share amount shall be obtained by dividing (i) the Merger Consideration by (ii) $113.03; and

if the reference price is greater than or equal to $89.03 and no more than $113.03, the aggregate share amount shall be obtained by dividing (i) the Merger Consideration by (ii) the reference price.
Adjustment to Per Share Merger Consideration.
If, before the merger becomes effective, there is a reorganization, reclassification, recapitalization, stock split, split-up, stock dividend or stock distribution, combination, exchange, or readjustment of shares with respect to Wintrust common stock or Macatawa common stock, the Per Share Merger Consideration will be proportionately and appropriately adjusted to provide to Macatawa shareholders the same economic effect as contemplated in the merger agreement. No adjustment shall be made in the event of the issuance of additional shares of Wintrust common stock pursuant to any dividend or direct reinvestment, exercise of stock options awarded under stock option plans, or grant or sale of shares or rights to receive shares.
Upset Condition
If the Upset Condition (as defined below) exists as of the last day of the Pricing Period (as defined below), Macatawa will have the right to:
(a)   proceed with the merger on the basis of the Per Share Merger Consideration as described above (the “Base Per Share Merger Consideration”); or
(b)   request Wintrust to adjust the aggregate share amount used to calculate the Per Share Merger Consideration, to an aggregate share amount computed by (i) multiplying the aggregate share amount by (ii) a fraction (A) that has as its numerator the Floor Purchaser Price (as defined below) and (B) that has as its denominator the Average Purchaser Closing Price (as defined below) (such amount resulting from such computation, the “Adjusted Per Share Merger Consideration”).
If Macatawa exercises its right to make such a request described in the foregoing clause (b), Wintrust shall either accept or decline the Adjusted Per Share Merger Consideration. If Wintrust declines the Adjusted Per Share Merger Consideration or fails to deliver written notice of its decision to accept or decline the Adjusted Per Share Merger Consideration in the time period specified in the merger agreement, Macatawa may elect to proceed with the merger on the basis of the Base Per Share Merger Consideration by delivering written notice of such election within the time period specified in the merger agreement, otherwise, the merger agreement will automatically terminate.
An “Upset Condition” occurs if both of the following conditions exist as of the last day of the Pricing Period:
(a)   the Average Purchaser Closing Price is less than $80.82 (the “Floor Purchaser Price”); and
(b)   the number determined by dividing the Average Purchaser Closing Price by $101.03 is less than the number obtained by subtracting (i) 20% from (ii) the quotient obtained by dividing the Final Index Price by the Initial Index Price.
 
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The “Average Purchaser Closing Price” is the average volume weighted trading price per share of Wintrust common stock on which shares of Wintrust common stock were actually traded in transactions reported on Nasdaq during the 20 trading days immediately preceding the first date on which all Requisite Regulatory Approvals (and waivers, if applicable) necessary for the consummation of the merger have been received (disregarding any waiting period) (the “Pricing Period”).
The “Initial Index Price” means the $94.81 closing price of the KBW Nasdaq Regional Banking Index (KRX) on April 12, 2024. The “Final Index Price” means the closing price of the KBW Nasdaq Regional Banking Index (KRX) on the last day of the Pricing Period.
Fractional shares
No fractional shares of Wintrust common stock will be issued in the merger. No dividends or other distributions of Wintrust shall be paid with respect to such fractional share interests, and such fractional share interests will not entitle the owner to vote or to have any rights of a holder of shares of Wintrust common stock. Instead, Wintrust will pay to each holder of Macatawa common stock who would otherwise be entitled to a fractional share of Wintrust common stock an amount in cash (without interest) determined by multiplying the fractional part of a share of Wintrust common stock to which such Macatawa shareholder would otherwise be entitled by the reference price.
Exchange of certificates
Wintrust has engaged Equiniti Trust Company, LLC to act as its exchange agent to handle the exchange of Macatawa common stock for the Merger Consideration and the payment of cash for any fractional share interest. As soon as reasonably practicable after the effective time, Wintrust will cause the exchange agent to send to each Macatawa shareholder a letter of transmittal for use in the exchange with instructions explaining how to surrender Macatawa common stock certificates and book-entry shares to the exchange agent. Macatawa shareholders that surrender their certificates or book-entry shares to the exchange agent, together with a properly completed letter of transmittal, will receive the Merger Consideration. Macatawa shareholders that do not exchange their Macatawa common stock will not be entitled to receive the Merger Consideration or any dividends or other distributions by Wintrust until their certificates or book-entry shares are surrendered. After surrender of the certificates or book-entry shares representing Macatawa shares, any unpaid dividends or distributions with respect to the Wintrust common stock represented by the certificates will be paid without interest.
Conduct of business pending the merger and certain covenants
Under the merger agreement, Macatawa has agreed to certain restrictions on its activities and the activities of its subsidiaries until the merger is completed or the merger agreement is terminated. In general, Macatawa and its subsidiaries are required to conduct their business in the ordinary course of business, consistent with past practice in all material respects.
The following is a summary of the more significant restrictions imposed upon Macatawa, subject to the exceptions set forth in the merger agreement. Macatawa will not, and will cause its subsidiaries to not, without Wintrust’s prior written consent, which consent will not be unreasonably withheld, delayed or conditioned (other than with respect to those items marked with a “*” below, with respect to which Wintrust may withhold its consent as its sole discretion):

amend its articles of incorporation or bylaws (or other comparable organizational documents);*

split, combine or reclassify any securities issued by Macatawa or its subsidiaries or issue or authorize the issuance of any other securities in respect of, in lieu of or in substitution for shares of its securities;*

purchase, repurchase, redeem or otherwise acquire any securities issued by Macatawa or its subsidiaries;*

declare, set aside or pay any dividend or distribution (whether in cash, stock, property or otherwise) in respect of, or enter into any contract with respect to the voting of, any shares of its capital stock, except for distributions by a direct or indirect subsidiary of Macatawa to its parent, and except for
 
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quarterly cash dividends by Macatawa in an amount not to exceed $0.09 per share and paid in a manner consistent with past practice with respect to the timing of the declaration, payment and record date of such dividend;*

issue, offer, deliver, sell, pledge, grant, dispose of or otherwise permit to become outstanding any shares of its capital stock, any other voting securities or any securities convertible into or exchangeable for, or any rights, warrants or options to acquire, any such shares, voting securities or convertible or exchangeable securities, or encumber any securities issued by Macatawa or any of its subsidiaries;*

subject to certain exceptions, increase the compensation, benefits, severance, or termination pay of any employee or independent contractor of Macatawa or any of its subsidiaries, pay any bonuses, amend existing agreements with any employee or independent contractor, fund compensation under any company benefit plan or hire any new employees except in the ordinary course of business;

subject to certain exceptions, enter into any new or amend in any material respect any existing employment or similar agreement with any of its past or present officers, directors, employees or independent contractors, establish, amend, terminate, or take action to accelerate rights under any company benefit plan, grant any severance or termination pay unless provided under any company benefit plan, grant any compensatory award in relation to the value of Macatawa common stock, or establish, amend or terminate any collective bargaining agreement;*

subject to certain exceptions, acquire any businesses or division of business, or make any capital contributions to any person;

subject to certain exceptions, dispose of or permit any lien (other than Permitted Liens, as defined in the merger agreement), to attach to, any assets, including the capital stock or other equity interests in any Macatawa subsidiary;

adopt or effect a plan of complete or partial liquidation, dissolution, restructuring, recapitalization or other reorganization;

adopt any shareholder rights plan;

subject to certain exceptions, incur any indebtedness for borrowed money or guarantee of such;

make any application for the opening, relocation, or closing of any branch office, loan production office or other material office or facility;

enter into or amend or modify in any material respect, or consent to the termination of (other than at its stated expiration date), any Macatawa material contract or lease, other than in the ordinary course of business consistent with past practice;

make any material change in any method of financial accounting principles or practices except as required by law or generally accepted accounting principles;*

subject to certain exceptions, institute, settle or compromise any tax claims or audits, or actions pending or threatened, as specified in the merger agreement;*

subject to certain exceptions, make any capital expenditure or permit any of the Macatawa subsidiaries to make any capital expenditure;

enter into any material new line of business or change in any material respect its material banking or operating policies or practices, except in the ordinary course of business consistent with past practice or as required by law;

restructure or materially change the nature of the composition of its investment securities portfolio;

fail to charge off loans and maintain its allowance for credit losses, except in a manner in conformity with prior practices;

subject to certain exceptions, fail to promptly notify Wintrust of the threat or the commencement, of certain material actions;

except as and to the extent required by applicable law, take any action that would reasonably be expected to prevent, materially impede or delay the merger, or take any action reasonably likely to result in any of the conditions to the merger, as specified in the merger agreement, not being satisfied;
 
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enter into any new credit or new lending relationships that would require an exception to Macatawa Bank’s formal loan policy as in effect as of the date of the merger agreement or that are not in compliance with the provisions of such loan policy; and

other than incident to a reasonable loan restructuring, extend additional credit to certain persons which constitutes a nonperforming loan or against any part of such indebtedness Macatawa or any of its subsidiaries has established loss reserves or any part of which has been charged-off by Macatawa or any of its subsidiaries.
Wintrust has agreed to file all applications and notices to obtain the necessary regulatory approvals for the transactions contemplated by the merger agreement. Both parties agreed:

to use commercially reasonable efforts to take all actions necessary to consummate and make effective the merger;

to use commercially reasonable efforts to obtain as promptly as practical approvals of all third parties and government entities necessary or desirable for the consummation of the merger; and

to notify the other of any pending or, to their respective knowledge, threatened action or order by any governmental entity or person seeking material damages in connection with the merger or to restrain or prohibit the consummation of the merger. If an action is instituted, Wintrust and Macatawa shall cooperate and make commercially reasonable efforts to contest the action.
Macatawa has also agreed to the following:

to provide prompt notice to Wintrust of the threat, filing, defense or settlement of any securityholder action against it or its directors or officers relating to the merger or the other transactions contemplated by the merger agreement;

to give Wintrust the opportunity to participate in the defense or settlement of any such securityholder action; and

not to settle any such action without Wintrust’s prior written consent (such consent not to be unreasonably withheld, conditioned or delayed).
The merger agreement also contains certain covenants relating to employee benefits and other matters pertaining to officers and directors. See “— Employee benefit matters.”
No solicitation of or discussions relating to a Company Takeover Proposal
The merger agreement contains provisions that prohibit Macatawa from soliciting or engaging in discussions or negotiations regarding a Company Takeover Proposal. A “Company Takeover Proposal” includes any inquiry, proposal or offer from any person or group relating to, in a single transaction or series of transactions, any direct or indirect acquisition of Macatawa assets equal to more than 15% of Macatawa’s consolidated assets or net income on a consolidated basis, any acquisition of more than 15% of the outstanding Macatawa common stock or the capital stock of any Macatawa subsidiary, any tender offer or exchange offer that if consummated would result in any person or group beneficially owning more than 15% of the outstanding Macatawa common stock, any merger, reorganization, liquidation or similar transaction involving Macatawa or any of its subsidiaries, or any combination of the foregoing types of transactions if the sum of the percentage of consolidated assets, consolidated net income and Macatawa common stock involved is more than 15% (in each case, other than the merger). Macatawa has agreed that it will not directly or indirectly solicit, initiate, facilitate or knowingly encourage (including by way of furnishing information) inquiries regarding, or the making of any proposal or offer that constitutes or could reasonably be expected to lead to a Company Takeover Proposal, enter into any agreement, negotiations or discussions with, or furnish information to, any person or entity concerning any proposals relating to or in connection with any Company Takeover Proposal or grant any waiver of, or fail to enforce, any confidentiality, standstill or similar provision of any other contract. However, the merger agreement provides that if, before receipt of shareholder approval of the merger agreement, Macatawa receives a bona fide unsolicited Company Takeover Proposal, it may contact the person or group submitting such proposal to clarify any term or condition in the proposal that the Macatawa board of directors determines to be unclear
 
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and upon receipt of a bona fide written Company Takeover Proposal to acquire 50% or more of the consolidated assets or net income of Macatawa or 50% of more of the outstanding stock of Macatawa if the Macatawa board of directors determines in its good faith judgment after consultation with its independent financial advisors and outside legal counsel that the Company Takeover Proposal is reasonably likely to result in the consummation of a transaction that is more favorable to Macatawa’s shareholders from a financial point of view than the merger, taking into account all legal, regulatory and financial aspects of the proposal and any changes to the Merger Consideration proposed by Wintrust in response to such proposal (a “Company Superior Proposal”), it may furnish information regarding Macatawa and its subsidiaries to such person or group pursuant to a permitted confidentiality agreement and engage in discussions or negotiations with such person or group with respect to the Company Superior Proposal. Macatawa is required to notify and provide a summary of the material terms of any Company Takeover Proposal to Wintrust. Macatawa must also keep Wintrust informed of related developments, discussions or negotiations on a reasonably current basis, and concurrently provide to Wintrust copies of all nonpublic information made available to such third party.
Pursuant to the merger agreement, the Macatawa Board, or any committee thereof, shall not:

fail to recommend to the Macatawa shareholders that shareholder approval be given or fail to include the Macatawa Board recommendation in the proxy statement;

change, qualify, withhold, or withdraw, or publicly propose such, the recommendation in a manner adverse to Wintrust;

fail to recommend against any tender offer or exchange offer that is a Company Takeover Proposal within ten business days after the commencement thereof other than a temporary “stop, look and listen” communication;

adopt, approve or recommend, or submit to shareholder vote, or publicly propose to approve or recommend to shareholders, a Company Takeover Proposal;

make any public statement inconsistent with the recommendation of the Macatawa Board that Macatawa shareholders vote in favor of approval of the merger agreement (a “Company Adverse Recommendation Change”); or

cause or permit Macatawa or any of its subsidiaries to enter into any agreement with respect to any Company Takeover Proposal.
However, prior to receipt of the Macatawa shareholder approval, the Macatawa Board may, in connection with a bona fide written Company Takeover Proposal made after execution of the merger agreement and which does not result from a breach of the merger agreement, make a Company Adverse Recommendation Change or terminate the merger agreement in accordance with its terms to enter into a definitive merger agreement or other definitive purchase or acquisition agreement with respect to such Company Takeover Proposal, if and only if, prior to taking such action, Macatawa has complied with its obligations under the merger agreement and the Macatawa Board has determined in good faith, after consultation with its independent financial advisors and outside legal counsel, that such Company Takeover Proposal constitutes a Company Superior Proposal and that the failure to take the actions contemplated by this sentence are reasonably likely to be inconsistent with its fiduciary duties under applicable law. Prior to taking any such action, it is required that (a) Macatawa has given Wintrust at least four business days prior written notice of its intention to take such action (which notice shall specify the material terms and conditions of any such Company Superior Proposal, including the identity of the party making such Company Superior Proposal) and has contemporaneously provided a copy to Wintrust of all written materials (including all transaction agreements and related documents) with or from the party making such Company Superior Proposal, (b) Macatawa has negotiated in good faith with Wintrust during such notice period to the extent Wintrust wishes to negotiate, to enable Wintrust to revise the terms of the merger agreement such that it would cause the Company Superior Proposal to no longer constitute a Company Superior Proposal and (c) following the end of such notice period, the Macatawa board of directors shall have considered in good faith any changes to the merger agreement proposed in writing by Wintrust, and shall have determined that the Company Superior Proposal would continue to constitute a Company Superior Proposal if such revisions were given effect and that the failure to take the actions contemplated by this paragraph would be reasonably likely to be inconsistent with its fiduciary duties under applicable law.
 
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In the event of any material revisions to a Company Takeover Proposal, Macatawa shall deliver a new written notice to Wintrust pursuant to the foregoing clause (a) and again comply with the requirements of this paragraph with respect to such new written notice; provided, however, that the four business day notice period shall be reduced to two business days. See also “— Termination fee” below.
Representations and warranties
The merger agreement contains representations and warranties made by Macatawa, Wintrust and Merger Sub. These include, among other things, representations relating to:

valid corporate organization and existence;

corporate power and authority to enter into the merger and the merger agreement;

capitalization;

financial statements;

certain tax matters;

absence of material adverse effect;

absence of undisclosed investigations and litigation;

compliance with laws and regulations;

required approvals;

filing of necessary reports with regulatory authorities;

ownership of its subsidiaries;

investment bankers and brokers;

agreements with bank regulators;

allowance for credit losses; and

the accuracy of information supplied for inclusion in the registration statement; and absence of any breach of organizational documents, law, regulatory restrictions, material agreements or governmental orders as a result of the merger.
Macatawa makes additional representations and warranties to Wintrust in the merger agreement relating to, among other things:

organizational documents, minutes and stock records;

real property, personal property and other material assets;

insurance matters;

employee matters and employee benefits;

environmental matters;

fiduciary matters;

data security and customer privacy matters;

absence of indemnification claims;

compliance with, absence of default under and information regarding material contracts;

loans and its allowance for loan losses;

investment securities;

compliance with the CRA;

changes in business relationships;
 
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technology and intellectual property;

absence of “excess parachute payments” resulting from the transactions contemplated in the merger agreement;

absence of undisclosed liabilities; and

related party transactions.
Conditions to completion of the merger
Conditions to Each Party’s Obligation to Effect the Merger.   The respective obligations of each party to effect the merger are subject to fulfillment of certain conditions, including:

adoption of the merger agreement at the special meeting by the holders of at least a majority of the outstanding shares of Macatawa common stock entitled to vote;

receipt of all regulatory approvals required in connection with the transaction contemplated by the merger agreement, the expiration of all applicable notice periods and waiting periods, and all such regulatory approvals must be in effect;

no provision of any applicable law making illegal or otherwise prohibiting the consummation of the merger, temporary restraining order, preliminary or permanent injunction or other order issued by a court of competent jurisdiction preventing the consummation of the merger;

neither party shall be subject to any order of a court or agency of competent jurisdiction that enjoins or prohibits the consummation of the merger;

this registration statement shall have been declared effective under the Securities Act, no stop order suspending the effectiveness of the registration statement can have been issued by the SEC and no proceedings for that purpose can have been commenced or threated by the SEC; and

the Wintrust common stock issuable pursuant to the merger agreement shall have been accepted for listing on Nasdaq.
Conditions to Wintrust’s Obligation to Effect the Merger.   Wintrust’s obligations are subject to fulfillment of certain conditions, including:

accuracy of representations and warranties of Macatawa in the merger agreement as of the closing date, except as otherwise set forth in the merger agreement;

performance by Macatawa in all material respects of its covenants under the merger agreement;

receipt of a certificate from Macatawa’s chief executive officer or chief financial officer certifying the satisfaction of conditions including the accuracy of representations and warranties of Wintrust, performance by Wintrust and Merger Sub of all covenants and obligations, and no material adverse effects of Macatawa;

no Macatawa material adverse effect shall have occurred and Macatawa shall not have been subject to any regulatory agreement, in each case since the date the merger agreement was signed; and

receipt of a tax opinion of ArentFox, acting as counsel to Wintrust;
Conditions to Macatawa’s Obligation to Effect the Merger.   Macatawa’s obligations are subject to fulfillment of certain conditions, including:

accuracy of representations and warranties of Wintrust and Merger Sub in the merger agreement as of the closing date, except as otherwise set forth in the merger agreement;

performance by Wintrust and Merger Sub in all material respects of all of the covenants and obligations under the merger agreement;

receipt of a certificate from Wintrust’s chief executive officer, chief financial officer, or general counsel certifying the satisfaction of conditions including the accuracy of representations and warranties of Wintrust, performance by Wintrust and Merger Sub of all covenants and obligations, and no material adverse effects of Macatawa;
 
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no Wintrust material adverse effect shall have occurred; and

receipt of a tax opinion from Warner Norcross, acting as counsel to Macatawa.
Termination
By written agreement, Wintrust and Macatawa may mutually agree to terminate the merger agreement and abandon the merger at any time. Subject to conditions and circumstances described in the merger agreement, Wintrust or Macatawa, as the case may be, may also terminate the merger agreement as follows:

by either party if the merger is not completed by April 15, 2025;

in certain circumstances, by either party in the event that a material breach or failure to perform any representation, warranty or covenant results in a failure of a closing condition and is not cured within a specified period of time;

in certain circumstances by either party if the merger agreement and the transactions contemplated therein are not approved by Macatawa’s shareholders;

by Wintrust, before receipt of Macatawa’s shareholder approval if the Macatawa Board effected a Company Adverse Recommendation Change, the Macatawa Board failed to reject a Company Takeover Proposal, Macatawa enters into a Company Acquisition Agreement or the Macatawa Board fails to publicly reaffirm its recommendation of the merger within three business days of a written request by Wintrust, as further described in “— No solicitation of or discussions relating to a Company Takeover Proposal”;

by Macatawa, prior to receipt of Macatawa’s shareholder approval in order to enter into a Company Acquisition Agreement in respect of a Company Superior Proposal provided Macatawa pays Wintrust the Termination Fee, as further described in “— Termination fee”;

in certain circumstances, by either party, if any governmental entity has issued an order or taken any other action permanently enjoining, restraining or otherwise prohibiting consummation of the merger;

by Wintrust, if Macatawa Bank is examined for compliance with the CRA and receives written notification of a rating lower than “Satisfactory”; and

in certain circumstances, in the event the Upset Condition shall have occurred and the Adjusted Per Share Merger Consideration is not accepted by Wintrust and Macatawa does not elect to proceed with the merger under the terms of the merger agreement.
Any termination of the merger agreement will not affect any rights accrued prior to such termination, except as otherwise provided in the merger agreement.
Termination fee
Macatawa has agreed to pay Wintrust $20,400,000 (the “Termination Fee”) if the merger agreement is terminated and within 12 months of such termination Macatawa consummates or enters into a definitive agreement with respect to a Company Takeover Proposal (provided that, for purposes hereof, references to 15% in the definition of Company Takeover Proposal shall be deemed to be references to 50%) under the following circumstances:

Wintrust terminates the merger agreement because Macatawa has breached any of its representations, warranties, covenants, obligations or other agreements in the merger agreement and a Company Takeover Proposal (provided that, for purposes hereof, references to 15% in the definition of Company Takeover Proposal shall be deemed to be references to 50%) was made on or after the date of the merger agreement, but prior to the date that the merger agreement is terminated;

Wintrust or Macatawa terminates the merger agreement because Macatawa shareholders failed to approve the merger at the Macatawa special meeting and a Company Takeover Proposal (provided that, for purposes hereof, references to 15% in the definition of Company Takeover Proposal shall be deemed to be references to 50%) was made on or after the date of the merger agreement, but prior to the Macatawa special meeting; or
 
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Wintrust or Macatawa terminates the merger agreement because the merger failed to occur on or before April 15, 2025 and a Company Takeover Proposal (provided that, for purposes hereof, references to 15% in the definition of Company Takeover Proposal shall be deemed to be references to 50%) is made on or after the date of the merger agreement, but prior to the date of any such termination.
Macatawa also agreed to pay Wintrust the Termination Fee if the merger agreement is terminated under the following circumstances:

Wintrust terminates the merger agreement because, before receipt of shareholder approval, (i) the Macatawa Board effected a Company Adverse Recommendation Change, (ii) the Macatawa Board failed to reject a Company Takeover Proposal and reaffirm the Macatawa Board’s recommendation within three business days following the public announcement of such Company Takeover Proposal and, in any event, at least two business days prior to the Macatawa special meeting, (iii) Macatawa enters into a Company Acquisition Agreement or (iv) the Macatawa Board fails to publicly reaffirm its recommendation of the merger within three business days of a written request by Wintrust (or such less time as remains prior to the Macatawa special meeting); or

Macatawa terminates the merger agreement prior to receipt of the Macatawa shareholder approval, in order to enter into a Company Acquisition Agreement in respect of a Company Superior Proposal.
Governance matters
After the merger, the Wintrust board of directors will remain the same, except that Wintrust has agreed that it will take all appropriate action to appoint one individual serving on Macatawa’s board of directors that is mutually agreeable to Wintrust and Macatawa to serve on Wintrust’s board of directors, effective immediately following the effective time. It is currently expected that this individual will be Richard L. Postma, who currently serves as chairman of the Macatawa Board.
The managers, if any, of the surviving company shall be the managers of Merger Sub immediately before the effective time.
Following the effective time of the merger, Macatawa’s bank subsidiary, Macatawa Bank will maintain its separate bank charter and will continue to operate under the Macatawa Bank name in Michigan. Macatawa Bank will maintain a separate, legally constituted board of directors consisting of certain existing directors and new directors generally residing and doing business locally in the west Michigan community.
Employee benefit matters
All employees of Macatawa or any of the its subsidiaries immediately before the merger becomes effective shall automatically become employees of the surviving company or its affiliates. Under the merger agreement, Wintrust has agreed to provide each employee of Macatawa or any Macatawa subsidiary who becomes employed by Wintrust or any of its affiliates as a result of the merger with the same employee benefits then provided to similarly situated employees at Wintrust.
Expenses
All expenses incurred in connection with the merger agreement will be paid by the party incurring the expenses, except that Wintrust shall pay and bear the cost of (a) each regulatory filing, application, notification, registration or similar fee required to be paid by any party in connection with the merger agreement and the transactions contemplated by the merger agreement under the Securities Act, the Exchange Act, applicable banking laws and other applicable laws and (b) any fees and expenses (excluding each party’s internal costs and fees and expenses of attorneys, accountants and financial and other advisors) payable to the SEC in respect of filing the registration statement and this proxy statement/prospectus.
Nasdaq stock listing
Wintrust common stock is currently listed on Nasdaq under the symbol “WTFC.” The shares to be issued to Macatawa’s shareholders as Merger Consideration also will be eligible for trading on Nasdaq.
 
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Amendment
The merger agreement may be amended by the parties before or after receipt of shareholder approval of the merger agreement.
 
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SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF MACATAWA
Five Percent Shareholders
The following table sets forth the number of shares of Macatawa common stock reported to be beneficially owned by each person or group which is known to Macatawa to be a beneficial owner of five percent or more of Macatawa’s outstanding shares of common stock as of March 31, 2024.
Name of Beneficial Owner
Sole Voting
Power
Sole
Dispositive
Power
Shared Voting
or Dispositive
Power
Total
Beneficial
Ownership
Percent of
Class(1)
White Bay Capital, LLLP(2)
3133 Orchard Vista Drive, S.E.
Grand Rapids, Michigan 49546
5,319,788 5,319,788 5,319,788 15.5%
AllianceBernstein L.P.(3)
501 Commerce Street
Nashville, Tennessee 37203
2,038,609 2,038,609 2,038,609 5.9%
(1)
The percentage set forth in this column was calculated on the basis of 34,361,562 shares of common stock outstanding as of March 31, 2024.
(2)
Based on a Form 4 dated November 17, 2023 filed by White Bay Capital, LLLP. The Stephen A. Van Andel 2009 WBC Trust is the general partner of White Bay Capital, LLLP. Stephen A. Van Andel is the sole trustee of the Trust and has the authority to vote its common stock. Macatawa is not responsible for the accuracy of this information.
(3)
Based on a Schedule 13G dated December 31, 2023 filed by AllianceBernstein L.P. on February 14, 2024.
Ownership of Management
The table below sets forth the number of shares of Macatawa common stock that each of its directors, each named executive officer, and all directors and executive officers of Macatawa as a group are deemed to have beneficially owned as of March 31, 2024. Ownership of less than one percent of the outstanding shares of common stock is indicated by asterisk.
Amount and Nature of Beneficial Ownership(1)
Name of Beneficial Owner
Sole Voting and
Dispositive Power
Shared Voting
or Dispositive
Power(2)
Total Beneficial
Ownership
Percent of
Class(3)
Nicole S. Dandridge
*
Charles A. Geenen
123,724 123,724 *
Ronald L. Haan
170,039 144,048 314,087 *
Craig A. Hankinson
17,606 64,136 81,742 *
Robert L. Herr
4,767 23,310 28,077 *
Birgit M. Klohs
17,269 17,269 *
Michael K. Le Roy
12,702 12,702 *
Douglas B. Padnos
120,087 15,781 135,868 *
Richard L. Postma
1,559,639 1,559,639 4.5%
Thomas P. Rosenbach
75,702 75,702 *
Jon W. Swets
148,512 1,995 150,507 *
Jill Walcott
87,970 393,152 481,122 1.4%
All directors and executive officers as a group (12 persons)
2,338,017
642,422
2,980,439
8.7%
 
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(1)
The number of shares stated is based on information provided by each person listed and includes shares personally owned by the person and shares which, under applicable regulations, are considered to be otherwise beneficially owned by the person as of March 31, 2024.
(2)
These numbers include shares over which the listed person is legally entitled to share voting or dispositive power by reason of joint ownership, trust or other contract or property right, and shares held by spouses, children or other relatives over whom the listed person may have influence by reason of relationship.
(3)
The percentages set forth in this column were calculated on the basis of 34,361,562 shares of common stock outstanding as of March 31, 2024.
 
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COMPARISON OF RIGHTS OF WINTRUST SHAREHOLDERS AND MACATAWA SHAREHOLDERS
General
As a shareholder of Macatawa, your rights are governed by Macatawa’s articles of incorporation and its bylaws, each as currently in effect, as well as the rules and regulations applying to public companies. Upon completion of the merger, the rights of Macatawa shareholders who receive shares of Wintrust common stock in exchange for their shares of Macatawa common stock and become shareholders of Wintrust will be governed by Wintrust’s amended and restated articles of incorporation, as amended, and amended and restated by-laws, as well as the rules and regulations applying to public companies. Wintrust is incorporated in Illinois and subject to the Illinois Business Corporation Act (“IBCA”), while Macatawa is incorporated in Michigan and subject to the MBCA.
The following discussion summarizes material similarities and differences between the rights of Macatawa shareholders and Wintrust shareholders and is not a complete description of all of the differences. This discussion is qualified in its entirety by reference to the IBCA, MBCA and Wintrust’s and Macatawa’s respective articles of incorporation and by-laws.
Wintrust Shareholder Rights
Macatawa Shareholder Rights
Authorized Capital Stock:
Wintrust is authorized to issue 100 million shares of common stock, no par value per share, and 20 million shares of preferred stock, no par value per share, which we refer to as Wintrust preferred stock. Of the 20 million shares of Wintrust preferred stock, five million have been designated as Fixed-to-Floating Rate Non-Cumulative Perpetual Preferred Stock, Series D (“Wintrust Series D Preferred”). Another 14,000 shares of Wintrust preferred stock have been designated as Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series E (“Wintrust Series E Preferred”).
On March 31, 2024, Wintrust had 61,736,715 shares of common stock outstanding, 5,000,000 shares of Wintrust Series D Preferred outstanding, and 11,500 shares of Wintrust Series E Preferred outstanding. Further issuance of shares of Wintrust’s preferred stock could affect the relative rights of the holders of its common stock, depending upon the exact terms, qualifications, limitations and relative rights and preferences, if any, of the shares of the preferred stock as determined by Wintrust’s board of directors.
Macatawa is authorized to issue 200 million shares of common stock, no par value per share, and 500,000 shares of preferred stock, no par value per share.
On March 31, 2024, Macatawa had 34,361,562 shares of common stock outstanding.
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
Dividends:
Subject to any rights to receive dividends to which holders of Wintrust preferred stock may be entitled, Wintrust may pay dividends if, as and when declared payable from time to time by its board of directors from any funds legally available therefor.
Macatawa may pay dividends as may be declared from time to time by its board of directors upon Macatawa’s outstanding shares out of funds legally available for such purposes which may be payable in cash or other property permitted by law.
Under Section 345 of the MBCA, Macatawa may not pay a dividend if, after giving it effect, Macatawa would not be able to pay its debts as the debts become due in the usual course of business, or Macatawa’s total assets would be less than the sum of its total liabilities plus the amount that would be needed, if Macatawa were to be dissolved at the time of the dividend, to satisfy the preferential rights upon dissolution of shareholders of any class having preference over the common stock as to the payment of dividends.
Voting Securities Held by the Corporation
Wintrust’s by-laws provide that voting securities belonging to the corporation shall not be voted, directly or indirectly, at any meeting and shall not be counted in determining the total number of outstanding shares at any given time, but shares of its own stock held by the corporation in a fiduciary capacity may be voted and shall be counted in determining the total number of outstanding shares at any given time. Macatawa’s bylaws provide that voting securities of another corporation or entity standing in the name of Macatawa, which are entitled to vote may be voted, in person or by proxy, by the chairman of the board or the president of Macatawa or by other persons as may be designated by the board of directors. Macatawa’s bylaws do not explicitly provide for voting shares of its own stock held by Macatawa.
Number of Directors, Classification:
The Wintrust board of directors currently consists of 14 members. Wintrust’s by-laws provide, however, that the number may be increased or decreased (provided the number is never less than eleven or more than 14) by an amendment of the by-laws by the shareholders, or by a resolution adopted by the majority of the board of directors.
Wintrust’s board of directors consists of a single class of directors.
The Macatawa Board currently consists of ten members. Macatawa’s articles of incorporation provide that the number of directors may be determined from time to time by resolution adopted by at least 80% of the board of directors and a majority of the Continuing Directors. “Continuing Director” means any member of the board of directors of Macatawa who is unaffiliated with the interested shareholder and was a member of
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
the board prior to the time that the interested shareholder became an interested shareholder, and any successor of a Continuing Director who is unaffiliated with the interested shareholder and is recommended to succeed a Continuing Director by a majority of Continuing Directors then on the board.
The Macatawa Board is divided into three classes, with each class as equal in number as possible. Directors are elected for a three year term.
Election of Directors; Vacancies:
Each Wintrust shareholder is entitled to vote the number of shares owned by such shareholder for as many persons as there are directors to be elected. The IBCA requires that directors be elected by the affirmative vote of a majority of the shares represented at the meeting and entitled to vote thereon.
The Wintrust by-laws provide that no cumulative voting is permitted.
Wintrust’s by-laws provide that any vacancy on the board of directors may be filled at an annual meeting or special meeting of the shareholders called for such purpose, or if such vacancy arises between meetings of shareholders, by a majority vote of the board of directors then in office.
Each holder of Macatawa common stock is entitled to one vote for each share of stock entitled to vote. A plurality of the shares voted is required to elect a director. This means that, if there are more nominees than positions to be filled, the nominees who receive the most votes will be elected to the open director positions.
The Macatawa organizational documents do not provide for cumulative voting.
Macatawa’s articles of incorporation provide that any vacancy on the board of directors that arises for any reason may be filled only by the board of directors acting by an affirmative vote of a majority of the Continuing Directors and an 80% majority of all the directors then in office, even if less than a quorum.
Removal of Directors:
A Wintrust director may be removed at a shareholders’ meeting, with or without cause, by the affirmative vote of a majority of the outstanding shares entitled to vote. Any Macatawa director may be removed at any time, with or without cause, by either (i) the affirmative vote of a majority of the Continuing Directors and at least 80% of the board of directors or (ii) the affirmative vote of the holders of at least 80% of the voting power of the outstanding shares of capital stock of Macatawa entitled to vote generally in the election directors, voting together as a single class.
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
Call of Special Meeting of Directors:
Wintrust’s by-laws provide that a special meeting of the board of directors may be called by or at the request of the chairman of the board, president or a majority of then-acting directors. Macatawa’s bylaws provide that a special meeting of the board of directors may be called by the chairman of the board or the president. The chairman of the board or the president are required to call a special meeting on the request of any two directors.
Limitation on Director Liability:
Wintrust’s articles of incorporation provide that no director will be personally liable to the corporation or any of its shareholders for monetary damages for any breach of fiduciary duty except for liability:

for any breach of the director’s duty of loyalty to the corporation or its shareholders;

for acts and omissions not in good faith or that involve intentional misconduct or a knowing violation of law;

under Section 8.65 of the IBCA (which creates liability for unlawful distributions to shareholders), as it exists or hereafter may be amended; or

for any transaction from which the director derived an improper personal benefit.
Macatawa’s articles of incorporation provide that no director will be personally liable to Macatawa or its shareholders for monetary damages for breach of fiduciary duty except for limitations on liability not permitted under the MBCA including:

for any transaction from which the director derived a financial benefit to which they were not entitled;

for intentionally inflicted harm on Macatawa or its shareholders;

for violating Section 551 of the MBCA; or

for intentionally committing a criminal act.
Indemnification:
Wintrust’s articles of incorporation and by-laws provide that Wintrust has the power to indemnify its directors, officers, employees and agents to the fullest extent authorized by the IBCA.
The by-laws provide that, to the extent a present or former director, officer or employee of the corporation (or of any subsidiary, as the case may be) has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, the corporation shall indemnify the director or officer against expenses actually and reasonably incurred by him or her in connection with such proceeding to the extent he or
Macatawa’s bylaws and articles of incorporation provide that the corporation has the power to indemnify its directors and executive officers to the fullest extent permitted by law.
Macatawa’s bylaws and articles of incorporation provide that, to the extent a present or former director, officer or employee of Macatawa (or of any subsidiary, as the case may be) has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, Macatawa shall indemnify the director or officer against expenses actually and reasonably incurred by him or her in connection with such proceeding
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
she was a party as a result of being a director, officer or employee, provided that such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of the corporation. The board may indemnify agents of the corporation in this context.
Wintrust has entered into individual indemnification agreements with each of its non-employee directors and certain of its executive officers, which we refer to as the “indemnification agreements,” which implement with more specificity the indemnification provisions provided by Wintrust’s by-laws and provide, among other things, that to the fullest extent permitted by applicable law, Wintrust will indemnify such director or officer against any and all losses, expenses and liabilities arising out of such director’s or officer’s service as a director or officer of Wintrust, as the case may be. The indemnification agreements also contain detailed provisions concerning expense advancement and reimbursement. The indemnification agreements are in addition to any other rights each non-employee director or officer may be entitled to under Wintrust’s articles of incorporation, by-laws and applicable law.
to the extent he or she was a party as a result of being a director, officer or employee, provided that such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of Macatawa. The articles of incorporation provide that the right of indemnity is not exclusive and Macatawa can provide indemnification to anyone on terms that the board of directors approve and that are not inconsistent with the MBCA.
Call of Special Meetings of Shareholders:
Wintrust’s by-laws provide that a special meeting of its shareholders may be called by the board of directors, the president or the holders of not less than one-fifth of all the outstanding shares entitled to vote on the matter for which the meeting is called, for the purpose(s) stated in the call of the meeting.
Written notice stating the place, date, hour and purpose(s) of the special meeting must be delivered, either personally or by mail, not
Macatawa’s bylaws provide that a special meeting of the shareholders may be called by resolution of a majority of the board of directors, by the chairman of the board, or by the president and must be held on a date fixed by the board of directors, the chairman of the board or the president.
Written notice stating the time, place, if any, and purpose(s) of the special meeting must be delivered, either personally or by mail or, if permitted by the board of
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
less than ten nor more than 60 days before the date of the meeting. directors, by a form of electronic transmission to which the shareholder has consented, not less than ten nor more than 60 days before the date of the meeting.
Quorum of Shareholders:
Wintrust’s by-laws provide that a majority of the votes of shares entitled to vote on a matter, present in person or represented by proxy, constitutes a quorum at any meeting of shareholders. Macatawa’s bylaws provide that the number of shares entitled to cast a majority of the votes at a meeting constitute a quorum at the meeting.
Advance Notice Regarding Shareholders Proposals (other than Nomination of Candidates for Election to the Board of Directors):
Wintrust’s by-laws provide that, for a shareholder to properly bring business before an annual or special meeting of shareholders, written notice of such shareholder’s intent to make such proposal(s) must be given by personal delivery or U.S. mail postage prepaid and received by the secretary of the corporation no later than the following dates: (i) with respect to an annual meeting of shareholders, not less than 90 days nor more than 120 days prior to the anniversary date of the immediately preceding annual meeting of shareholders (provided, however, that in the event that the annual meeting is called for a date that is not within 30 days before or after such anniversary date, notice by the shareholder to be timely must be so delivered or received not later than the close of business on the tenth day following the earlier of the date on which such notice or public disclosure of the date of the meeting was given or made); and (ii) with respect to any special meeting of shareholders, the close of business on the tenth day following the date of public disclosure of the date of such meeting.
A shareholder’s notice to the secretary shall set forth as to each item of business the shareholder proposes to bring before such meeting: (a) a brief description of the business desired to be brought
Macatawa’s articles of incorporation provide that, in order for a shareholder to properly bring business before an annual or special meeting of shareholders, a notice of proposal must be given, either by personal delivery or by U.S. mail, postage prepaid, and received by Macatawa no later than the following dates: (i) with respect to an annual meeting of shareholders, not later than 60 days nor more than 90 days prior to the first anniversary of the preceding year’s annual meeting (or, if the date of the annual meeting is changed by more than 20 days from such anniversary date, within ten days after the date Macatawa mails or otherwise gives notice of the date of such meeting); and (ii) with respect to any special meeting of shareholders, not later than the close of business on the tenth day following the date on which notice of the special meeting was first mailed to the shareholders by Macatawa.
A shareholder’s notice of proposal must set forth: (a) the name and address of the shareholder submitting the proposal, as they appear on Macatawa’s books and records; (b) a representation that the shareholder (i) is a holder of record of stock of Macatawa entitled to vote at such meeting, (ii) will continue to hold such stock through the date on which the meeting is held, and (iii) intends to
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
before the meeting and the reasons for conducting the business at the meeting; (b) the name and record address of the shareholder who proposes such business; (c) the number and class of shares of stock of the corporation beneficially owned by such shareholder; (d) whether and the extent to which any derivative instrument, hedging or other transaction or series of transactions has been entered into by or on behalf of, or any other agreement, arrangement or understanding (including any short position or any borrowing or lending of shares) has been made the effect or intent of any of which is to increase or decrease economic interest in the corporation’s stock or manage the risk or benefit of share price changes for, or to increase or decrease the voting power of, such shareholder with respect to the corporation’s stock (which information shall be updated by such shareholder as of the record date for the meeting, such update to be provided not later than ten days after the record date for the meeting); (e) a representation that the shareholder intends to appear in person or by proxy at the meeting to introduce the item of business proposed to be brought before the meeting; (f) a description of all arrangements or understandings between the shareholder and any other person(s) pursuant to which the proposal or proposals are to be made by the shareholder and any material interest of the shareholder in the business being proposed; and (g) all other information which would be required to be included in a proxy statement filed with the SEC if, with respect to any such item of business or nomination, such shareholder were a participant in a solicitation subject to Section 14 of the Exchange Act. appear in person or by proxy at the meeting to submit the proposal for shareholder vote; (c) a brief description of the proposal desired to be submitted to the meeting for shareholder vote and the reasons for conducting such business at the meeting; and (d) a description of any financial or other interest of such shareholder in the proposal.
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
Advance Notice Regarding Shareholders Nomination of Candidates for Election to the Board of Directors:
Wintrust’s by-laws provide that nominations of persons for election to the board of directors may be made at an annual or special meeting of shareholders by a shareholder of Wintrust. Macatawa’s articles of incorporation provide that nominations of person for election to the board of directors may be made by any shareholder of record entitled to vote in the election of directors.
For nominations for election to the board of directors of Wintrust to be properly brought before an annual or special meeting, written notice of such shareholder’s intent to make such proposal(s) must be given by personal delivery or U.S. mail postage prepaid and received by the secretary of the corporation no later than the following dates: (i) with respect to an election to be held at an annual meeting of shareholders, not less than 90 days nor more than 120 days prior to the anniversary date of the immediately preceding annual meeting of shareholders (provided, however, that in the event that the annual meeting is called for a date that is not within 30 days before or after such anniversary date, notice by the shareholder to be timely must be so delivered or received not later than the close of business on the tenth day following the earlier of the date on which such notice or public disclosure of the date of the meeting was given or made); and (ii) with respect to an election to be held at any special meeting of shareholders called for the purpose of electing directors, the close of business on the tenth day following the date of public disclosure of the date of such meeting.
A shareholder’s notice to the secretary shall set forth each item described above under “Advance Notice Regarding Shareholders Proposals (other than Nomination of Candidates for Election to the Board of Directors)” as well as (a) the nominee’s name, age, principal occupation and
For a shareholder’s nomination for election to the board of directors of Macatawa to be properly brought before an annual or special meeting, written notice must be given by personal delivery or U.S. mail, postage prepaid and received by the corporation no later than the following dates: (i) with respect to an election to be held at an annual meeting of shareholders, not later than 60 days nor more than 90 days prior to the first anniversary of the preceding year’s annual meeting (or, if the date of the annual meeting is changed by more than 20 days from such anniversary date, within ten days after the date Macatawa mails or otherwise gives notice of the date of such meeting); and (b) with respect to an election to be held at a special meeting of shareholders called for that purpose, not later than the close of business on the tenth day following the date on which notice of the special meeting was first mailed to the shareholders by Macatawa.
A shareholder’s notice of intent to make a nomination shall set forth: (i) the name(s) and address(es) of the shareholder who intends to make the nomination and of the person or persons to be nominated; (ii) a representation that the shareholder (a) is a holder of record of stock of Macatawa entitled to vote at such meeting, (b) will continue to hold such stock through the date on which the meeting is held, and (c) intends to appear in person or by proxy at the meeting to nominate the person or persons specified in the notice;
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
employment, business and residence addresses and qualifications, (b) a description of all arrangements or understandings between the shareholder and each nominee of the shareholder and any other person or persons (naming such person or persons) pursuant to which the nominations are to be made by the shareholder and (c) the consent of each nominee to be named in any proxy statement and to serve as a director of Wintrust if so elected. (iii) a description of all arrangements or understandings between the shareholder and each nominee and any other person or persons (naming such person or persons) pursuant to which the nomination is to be made by the shareholder; (iv) such other information regarding each nominee proposed by such shareholder as would be required to be included in a proxy statement filed pursuant to Regulation 14A promulgated under Section 14 of the Exchange Act, as amended, as now in effect or hereafter modified; and (v) the consent of each nominee to serve as a director of Macatawa if so elected.
Shareholder Action by Written Consent:
Wintrust’s articles of incorporation and by-laws provide that its shareholders are not permitted to act by written consent. Any action required or permitted to be taken at a meeting of the shareholders must be effected at a duly called annual or special meeting. Macatawa’s articles of incorporation do not permit shareholders to act by written consent. Any action required or permitted to be taken at a meeting of the shareholders must be effected at a duly called annual or special meeting
Appointment and Removal of Officers:
Wintrust’s by-laws provide that the officers shall be elected annually by the board of directors at the first meeting of the board of directors held after each annual meeting of the shareholders. Each officer will hold office until his successor is duly elected and qualified or until his prior death, resignation or removal.
Any officer may be removed by the board of directors whenever in its judgment the best interests of the corporation will be served thereby.
Macatawa’s bylaws provide that the board of directors shall appoint officers of Macatawa. Each officer will hold office for an indefinite term at the pleasure of the board.
Any officer may be removed by the board of directors at any time and for any reason.
Required Vote for Certain Transactions:
The Wintrust articles of incorporation do not specifically discuss the required vote for transactions involving merger, consolidation, or sale, lease or exchange of all or substantially all of the property or assets of the corporation. However, the applicable IBCA provisions state that such a transaction must be approved by two-thirds of the The Macatawa bylaws specify that any action to be taken by vote of the shareholders, other than the election of directors, shall be authorized by a majority of the votes cast by the holders of shares entitled to vote thereon unless a greater plurality is required by the express provisions of the MBCA. The MBCA provides that a transaction, such as the merger,
 
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Wintrust Shareholder Rights
Macatawa Shareholder Rights
outstanding shares of stock entitled to vote on the matter. The corporation may, however, without approval by a vote of shareholders, merge into itself any corporation of which at least 90% of the outstanding shares of each class is owned by the corporation. must be recommended by the board of directors to the shareholders and receive an affirmative vote of the holders of a majority of the outstanding shares of Macatawa unless a greater vote is required in the articles of incorporation.
Amendment to Charter and By-laws:
An amendment to the articles of incorporation that relates to certain provisions, including, the prohibition of cumulative voting, shareholder purchase rights, the prohibition of shareholder action by written consent, director liability, indemnification and insurance, number, tenure and qualification of directors or the amendment process, must be approved by the affirmative vote of the holders of 85% or more of the voting power of the then-outstanding shares of stock entitled to vote generally in the election of directors, voting together as a single class.
Otherwise, as provided by the IBCA, the articles of incorporation may be amended by the affirmative vote of at least two-thirds of the shares entitled to vote on the proposal after the board of directors has passed a resolution by majority vote setting forth the proposed amendment and directing that it be submitted to a vote at a shareholders’ meeting.
The power to make, alter, amend or repeal the by-laws of the corporation is vested in the shareholders or the board of directors by a resolution adopted by a majority of the board of directors.
An amendment to or repeal of Article VIII, Article IX, Article X, Article XI or XII of the articles of incorporation requires the affirmative vote of the holders of 80% or more of the outstanding shares of capital stock entitled to vote for the election of directors, voting together as a single class unless such amendment or repeal has been recommended for approval by at least 80% of all directors then holding office and by a majority of the Continuing Directors. Otherwise, the MBCA provides that amendments to the Macatawa articles of incorporation generally may be proposed by the Macatawa board of directors and approved by the affirmative vote of a majority of the outstanding shares entitled to vote on the proposed amendment.
Macatawa’s bylaws may be amended by a majority vote of the board of directors at any regular or special meeting, without prior notice of intent to do so, or by vote of the holders of a majority of the outstanding voting shares of Macatawa at any annual or special meeting if notice of the proposed amendment is contained in the notice of the meeting.
Certain anti-takeover effects of Wintrust’s articles and by-laws and Illinois law and federal law
Certain provisions of Wintrust’s articles of incorporation, by-laws, Illinois law and certain applicable banking regulations may have the effect of impeding the acquisition of control of Wintrust by means of a tender offer, a proxy fight, open-market purchases or otherwise in a transaction not approved by Wintrust’s board of directors.
These provisions may have the effect of discouraging a future takeover attempt which is not approved by Wintrust’s board of directors but which individual Wintrust shareholders may deem to be in their best
 
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