Kingsway Financial (KFS) insider Stilwell reports 55,000-share sale and large holdings
Rhea-AI Filing Summary
Kingsway Financial Services Inc. insider activity: Director and 10% owner Joseph Stilwell, reporting jointly with several Stilwell investment partnerships, disclosed open-market sales of a total of 55,000 shares of Kingsway common stock. Stilwell Associates, L.P. sold 35,000 shares on December 8, 2025 at $12.82 per share and 20,000 shares on December 9, 2025 at $12.80 per share.
Following these trades, Stilwell Associates reports indirect beneficial ownership of 646,904 common shares, while other Stilwell entities report additional indirect holdings of 3,550,382, 457,181 and 590,410 common shares. The group also reports Class C and Class D preferred stock that is convertible into common stock at 2.63158 common shares per preferred share, with all outstanding Class D preferred to be redeemed on May 7, 2032 and all outstanding Class C preferred to be redeemed on February 12, 2032. Stilwell disclaims beneficial ownership of indirectly held shares except to the extent of his pecuniary interest.
Positive
- None.
Negative
- None.
Insights
Insider group sold a small block of common shares but retains a large, complex equity and convertible preferred stake in the company.
The filing shows entities affiliated with Joseph Stilwell, a director and 10% owner of Kingsway Financial Services Inc. (KFS), selling 55,000 shares of common stock on
The group also owns several series of convertible preferred stock with stated value
The transactions may be viewed as a modest trimming of holdings in one affiliated fund rather than an exit, given the remaining multi‑million share indirect ownership. The specified conversion terms and redemption dates for the preferred stock define a clear timeframe, through
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Sale | Common Stock | 20,000 | $12.80 | $256K |
| Sale | Common Stock | 35,000 | $12.82 | $449K |
| holding | Class D Preferred Stock | -- | -- | -- |
| holding | Class C Preferred Stock | -- | -- | -- |
| holding | Class C Preferred Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
Footnotes (1)
- These are shares owned directly by Joseph Stilwell. This Form 4 reports the following sales: on December 8, 2025 Stilwell Associates, L.P. ("Associates") sold 35,000 shares at $12.82; and on December 9, 2025 Associates sold 20,000 shares at $12.80. These are shares owned directly by 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. 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 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. 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.
