If the filing person has previously filed a statement on Schedule 13G
to report the acquisition which is the subject of this Schedule 13D, and is filing this schedule because of Rule 13d-1(e), 13d-1(f) or
13d-1(g), check the following box. ☐
*The remainder of this cover page shall be filled out for a reporting
person’s initial filing on this form with respect to the subject class of securities, and for any subsequent amendment containing
information which would alter disclosures provided in a prior cover page.
The information required on the remainder of this cover page shall
not be deemed to be “filed” for the purpose of Section 18 of the Securities Exchange Act of 1934 or otherwise subject to the
liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the
Notes).
CUSIP No. 496904202
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SCHEDULE 13D
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Page 2 of 5
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1
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NAME OF REPORTING PERSON OR
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John T. Fitzgerald
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2
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CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP
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(a)
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☐
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(b)
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☐
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3
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SEC USE ONLY
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4
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SOURCE OF FUNDS
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SC, PF
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5
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CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEMS 2(d) or 2(e)
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☐
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6
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CITIZENSHIP OR PLACE OF ORGANIZATION
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United States of America
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NUMBER OF
SHARES
BENEFICIALLY
OWNED BY EACH
REPORTING
PERSON
WITH
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7
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SOLE VOTING POWER
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1,439,190
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8
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SHARED VOTING POWER
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0
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9
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SOLE DISPOSITIVE POWER
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1,439,190
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10
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SHARED DISPOSITIVE POWER
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0
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11
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AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
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1,439,190
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12
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CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES
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☐
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13
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PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
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6.3%
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14
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TYPE OF REPORTING PERSON
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IN
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CUSIP No. 496904202
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SCHEDULE 13D
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Page 3 of 5
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Item 1.
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Security and Issuer
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This Schedule 13D relates to the common stock,
$0.01 par value per share (the “Common Stock”), of Kingsway Financial Services Inc., a Delaware corporation (the “Issuer”).
The address of the Issuer’s principal executive offices is 150 Pierce Road, Suite 600, Itasca, Illinois 60143.
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Item 2.
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Identity and Background
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(a) This Schedule 13D is being filed by
John T. Fitzgerald (the “Reporting Person”).
(b) The principal business address for the
Reporting Person is c/o Kingsway Financial Services Inc. 150 Pierce Road, Suite 600, Itasca, Illinois 60143.
(c) The Reporting Person serves as the Issuer’s
Chief Executive Officer, President and Director.
(d), (e) During the last five years, the Reporting
Person has not been (i) convicted in a criminal proceeding (excluding traffic violations or similar misdemeanors) or (ii) a party to a
civil proceeding of a judicial or administrative body of competent jurisdiction and as a result of such proceeding was or is subject to
a judgment, decree or final order enjoining future violations of, or prohibiting or mandating activities subject to, federal or state
securities laws or finding any violation with respect to such laws.
(f) The Reporting Person is a citizen of the
United States of America.
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Item 3.
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Source and Amount of Funds
or Other Consideration
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The Reporting Person has acquired the shares of
Common Stock beneficially owned by him for cash using personal funds or as compensation for serving as an executive officer and a director
of the Issuer.
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Item 4.
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Purpose of Transaction
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The Reporting Person holds the shares of Common
Stock reported in this Schedule 13D for general investment purposes and retains the right to change his investment intent. The Reporting
Person may acquire additional shares of Common Stock for cash or as compensation, may otherwise acquire or dispose of Common Stock in
the future, or may engage in discussions with the Issuer concerning investments in the Issuer. Other than as described herein, the Reporting
Person has no current plans or proposals which relate to, or could result in, any of the matters referred to in paragraphs (a) through
(j), inclusive, of Item 4 of Schedule 13D.
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Item 5.
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Interest in Securities of the
Issuer
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(a) The Reporting Person beneficially
owns 1,439,190 shares of Common Stock of the Issuer. Of these 1,439,190 shares of Common Stock, 800,000 are restricted shares that vest
equally in 100,000 share tranches every September 5, until 2028. The Reporting Person is entitled to dividend, voting and other ownership
rights of a stockholder with respect to these 800,000 restricted shares. The Reporting Person does not own any options to purchase shares
of Common Stock that are exercisable within sixty (60) days of the date hereof. The Reporting Person beneficially owns 6.3% of the shares
of Common Stock outstanding, assuming 22,711,069 shares of Common Stock outstanding (based on disclosure in the Issuer’s Annual
Report on Form 10-K filed with the SEC on March 29, 2021).
In addition, the Reporting Person was issued 500,000 restricted shares of Common Stock of the Issuer on September 5, 2018. These restricted
shares vest on March 28, 2024 and do not permit the Reporting Person to vote these shares until they have vested. Furthermore, until
these restricted shares have vested, any dividends or any other rights to participate in any capital adjustment applicable to all holders
of Common Stock shall be deposited with the Issuer and subject to the same restrictions as the restricted shares themselves. As such,
the Reporting Person does not exercise voting or investment control over these restricted shares but does have the opportunity, directly
or indirectly, to profit or share in any profit derived from a transaction applicable to these restricted shares.
(b) The Reporting Person has
sole voting and dispositive power with respect to the indicated shares of Common Stock.
(c) On March 31, 2021, the
Issuer granted 1,000,000 restricted shares to the Reporting Person, 200,000 of which vested immediately and 800,000 of which vest equally
in 100,000 share tranches every September 5, until 2028. The restricted shares were granted for no consideration. Other than as described
herein, no transactions in the shares of Common Stock of the Issuer have been effected by the Reporting Person in the last sixty (60)
days.
CUSIP No. 496904202
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SCHEDULE 13D
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Page 4 of 5
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Item 6.
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Contracts, Arrangements, Understandings
or Relationships With Respect to Securities of the Issuer
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As the Issuer’s Chief
Executive Officer, President and Director, the Reporting Person has in the past and may receive in the future compensation in the form
of Common Stock, options, restricted shares or other securities convertible into Common Stock. Other than as described herein, there are
no other contracts, arrangements, understandings or relationships (legal or otherwise) between the Reporting Person and any other person
with respect to any securities of the Issuer, including, but not limited to, transfer or voting of any other securities, finder’s
fees, joint ventures, loan or option arrangements, puts or calls, guarantees of profits, division of profits or loss, or the giving or
withholding of proxies.
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Item 7.
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Material to be Filed as Exhibits
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None.
CUSIP No. 496904202
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SCHEDULE 13D
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Page 5 of 5
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After reasonable inquiry and to the best of my
knowledge and belief, the undersigned certifies that the information set forth in this statement is true, complete and correct.
Dated: April 2, 2021
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/s/ John T. Fitzgerald
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John T. Fitzgerald
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