| FORM 4 |
UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940 |
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| Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b). | |||||||||||||||||
| Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10. | |||||||||||||||||
1. Name and Address of Reporting Person*
(Street)
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2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ] |
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
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3. Date of Earliest Transaction
(Month/Day/Year) 05/08/2025 | ||||||||||||||||||||||||||
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4. If Amendment, Date of Original Filed
(Month/Day/Year) |
6. Individual or Joint/Group Filing (Check Applicable Line)
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| Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned | ||||||||||
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| 1. Title of Security (Instr. 3) | 2. Transaction Date (Month/Day/Year) | 2A. Deemed Execution Date, if any (Month/Day/Year) | 3. Transaction 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 | 162,500(1) | D | ||||||||
| Common Stock | 3,786,820 | I | See footnote(2) | |||||||
| Common Stock | 498,937 | I | See footnote(3) | |||||||
| Common Stock | 712,866 | I | See footnote(4) | |||||||
| Common Stock | 701,904 | I | See footnote(5) | |||||||
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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities) | |||||||||||||||
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| 1. Title of Derivative Security (Instr. 3) | 2. Conversion or Exercise Price of Derivative Security | 3. Transaction Date (Month/Day/Year) | 3A. Deemed Execution Date, if any (Month/Day/Year) | 4. Transaction 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 (Month/Day/Year) | 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: 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 | ||||||||
| Class D Preferred Stock | $9.5(6) | 05/08/2025 | A | 20,000 | 05/07/2025 | 05/07/2032(6) | Common Stock | 52,631(6) | $25 | 20,000 | I | See footnote(5) | |||
| Class C Preferred Stock | $9.5(7) | 02/12/2025 | 02/12/2032(7) | Common Stock | 88,421(7) | 33,600 | I | See footnote(2) | |||||||
| Class C Preferred Stock | $9.5(7) | 02/12/2025 | 02/12/2032(7) | Common Stock | 16,842(7) | 6,400 | I | See footnote(3) | |||||||
1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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1. Name and Address of Reporting Person*
(Street)
Relationship of Reporting Person(s) to Issuer
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| Explanation of Responses: |
| 1. These are shares owned directly by Joseph Stilwell. |
| 2. These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") 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 SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. |
| 3. These are shares owned directly by Stilwell Activist Fund, L.P. ("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. |
| 4. These are shares owned directly by Stilwell Value Partners VII, L.P. ("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. |
| 5. 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 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. |
| 6. The shares of Class D Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032. |
| 7. The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032. |
| /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell | 05/12/2025 | |
| /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC | 05/12/2025 | |
| /s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P. | 05/12/2025 | |
| /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P. | 05/12/2025 | |
| /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P. | 05/12/2025 | |
| /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P. | 05/12/2025 | |
| ** 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 Number. | ||