Kingsway (KFS) director Stilwell details $8.25 option agreements and preferred stock terms
Rhea-AI Filing Summary
Kingsway Financial Services Inc. insider Joseph Stilwell and affiliated funds reported option-related share transactions. On December 17, 2025, entities associated with Stilwell, a director and 10% owner, reported dispositions of Kingsway common stock at a price of $8.25 per share through stock options described as an obligation to sell.
Footnotes explain that on March 31, 2025, Stilwell Value LLC entered into three option agreements granting buyers options to purchase 815,000, 660,000, and 275,000 Kingsway common shares, each at an exercise price of $8.25, later amended on December 17, 2025 to be exercisable at any time before 5:00 p.m. Eastern on December 29, 2025. The filing also notes indirect ownership of Kingsway shares and preferred stock (Class C and D) by several Stilwell-managed limited partnerships, with those preferred shares convertible into common stock at a stated conversion basis of 2.63158 common shares per preferred share.
Positive
- None.
Negative
- None.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| X | Stock Option (obligation to sell) | 215,477 | $0.00 | -- |
| X | Stock Option (obligation to sell) | 1,295,411 | $0.00 | -- |
| X | Stock Option (obligation to sell) | 20,270 | $0.00 | -- |
| X | Stock Option (obligation to sell) | 218,842 | $0.00 | -- |
| X | Common Stock | 215,477 | $8.25 | $1.78M |
| X | Common Stock | 1,295,411 | $8.25 | $10.69M |
| X | Common Stock | 20,270 | $8.25 | $167K |
| X | Common Stock | 218,842 | $8.25 | $1.81M |
| holding | Class D Preferred Stock | -- | -- | -- |
| holding | Class C Preferred Stock | -- | -- | -- |
| holding | Class C Preferred Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
Footnotes (1)
- These are shares owned directly by Joseph Stilwell. 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. 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. 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. 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. 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. 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. 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.
FAQ
What insider activity did KINGSWAY FINANCIAL SERVICES INC (KFS) report?
The report shows Joseph Stilwell, a director and 10% owner, and related entities engaged in transactions involving Kingsway common stock on December 17, 2025, at a price of $8.25 per share through stock options described as an obligation to sell.
When were the KFS option agreements amended and what changed?
The option agreements 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, instead of only at their original expiry.
What are the key terms of KFS Class C and Class D Preferred Stock mentioned?
The filing notes that both Class C and Class D Preferred Stock have a stated value of $25 per share and are convertible at any time into Kingsway common stock at a conversion basis of 2.63158 common shares per preferred share, subject to customary adjustments. All outstanding Class D Preferred shares are to be redeemed on May 7, 2032, and all outstanding Class C Preferred shares on February 12, 2032.