Stilwell Associates, L.P. 4
4 · KINGSWAY FINANCIAL SERVICES INC · Filed Dec 19, 2025
Insider Transaction Report
Form 4
Stilwell Joseph
Director10% Owner
Transactions
- Exercise of In-Money
Common Stock
2025-12-17$8.25/sh−215,477$1,777,685→ 319,229 total(indirect: See footnote) - Exercise of In-Money
Common Stock
2025-12-17$8.25/sh−1,295,411$10,687,141→ 2,254,971 total(indirect: See footnote) - Exercise of In-Money
Common Stock
2025-12-17$8.25/sh−20,270$167,228→ 436,911 total(indirect: See footnote) - Exercise of In-Money
Common Stock
2025-12-17$8.25/sh−218,842$1,805,447→ 371,568 total(indirect: See footnote) - Exercise of In-Money
Stock Option (obligation to sell)
2025-12-17−215,477→ 0 total(indirect: See footnote)Exercise: $8.25Exp: 2025-12-29→ Common Stock (215,477 underlying) - Exercise of In-Money
Stock Option (obligation to sell)
2025-12-17−1,295,411→ 0 total(indirect: See footnote)Exercise: $8.25Exp: 2025-12-29→ Common Stock (1,295,411 underlying) - Exercise of In-Money
Stock Option (obligation to sell)
2025-12-17−20,270→ 0 total(indirect: See footnote)Exercise: $8.25Exp: 2025-12-29→ Common Stock (20,270 underlying) - Exercise of In-Money
Stock Option (obligation to sell)
2025-12-17−218,842→ 0 total(indirect: See footnote)Exercise: $8.25Exp: 2025-12-29→ Common Stock (218,842 underlying)
Holdings
- 162,500
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Footnotes (8)
- [F1]These are shares owned directly by Joseph Stilwell.
- [F2]On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.
- [F3]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.
- [F4]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 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.
- [F5]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.
- [F6]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.
- [F7]The shares of Class D 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 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.
- [F8]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.