FORM 4
[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

STILWELL JOSEPH
2. Issuer Name and Ticker or Trading Symbol

KINGSWAY FINANCIAL SERVICES INC [ KFS ]
5. Relationship of Reporting Person(s) to Issuer (Check all applicable)

__ X __ Director                      __ X __ 10% Owner
_____ Officer (give title below)      _____ Other (specify below)
(Last)          (First)          (Middle)

111 BROADWAY, 12TH FLOOR
3. Date of Earliest Transaction (MM/DD/YYYY)

3/20/2019
(Street)

NEW YORK, NY 10006
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
6. Individual or Joint/Group Filing (Check Applicable Line)

___ Form filed by One Reporting Person
_ X _ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock                  162500   (1) D    
Common Stock                  903066   I   See footnote   (2)
Common Stock   3/20/2019     P    17170   (3) A $2.2724   422813   I   See footnote   (4)
Common Stock   3/20/2019     P    8756   (3) A $2.2724   3322563   I   See footnote   (5)
Common Stock   3/20/2019     P    30000   (3) A $2.2724   310000   I   See footnote   (6)
Common Stock   3/21/2019     P    949   (3) A $2.3997   423762   I   See footnote   (4)
Common Stock   3/21/2019     P    7338   (3) A $2.3997   3329901   I   See footnote   (5)
Common Stock   3/21/2019     P    10000   (3) A $2.3997   320000   I   See footnote   (6)

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Explanation of Responses:
(1)  These are shares owned directly by Joseph Stilwell.
(2)  These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(3)  This Form 4 reports the following acquisitions: (a) on March 20, 2019, Stilwell Activist Fund, L.P. ("SAF") acquired 17,170 shares at $2.2724 USD per share; Stilwell Activist Investments, L.P. ("SAI") acquired 8,756 shares at $2.2724 USD per share; and Stilwell Value Partners VII, L.P. ("SVP VII") acquired 30,000 shares at $2.2724 USD per share; and (b) on March 21, 2019, SAF acquired 949 shares at $2.3997 USD per share; SAI acquired 7,338 shares at $2.3997 USD per share; and SVP VII acquired 10,000 shares at $2.3997 USD per share.
(4)  These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(5)  These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(6)  These are shares owned directly by SVP VII, and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
STILWELL JOSEPH
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006
X X

Stilwell Value LLC
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

STILWELL ASSOCIATES L P
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Activist Fund, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Activist Investments, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Value Partners VII, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X


Signatures
/s/ Pilar Torres as Attorney-in-Fact for Joseph Stilwell 3/22/2019
** Signature of Reporting Person Date

/s/ Pilar Torres as Attorney-in-Fact for Stilwell Value LLC 3/22/2019
** Signature of Reporting Person Date

/s/ Pilar Torres as Attorney-in-Fact for Stilwell Associates, L.P. 3/22/2019
** Signature of Reporting Person Date

/s/ Pilar Torres as Attorney-in-Fact for Stilwell Activist Fund, L.P. 3/22/2019
** Signature of Reporting Person Date

/s/ Pilar Torres as Attorney-in-Fact for Stilwell Activist Investments, L.P. 3/22/2019
** Signature of Reporting Person Date

/s/ Pilar Torres as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 3/22/2019
** Signature of Reporting Person Date


Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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