Kingsway Finl SEC Filings

Joseph Stilwell and affiliated entities reported insider sales of Kingsway Financial Services Inc. (KFS) common stock on September 16-17, 2025. The Form 4 shows aggregate sales by three affiliated investment vehicles of 68,000 common shares: 20,000 shares sold on 09/16/2025 at $14.40 and 48,000 shares sold on 09/17/2025 at $14.47. After these transactions certain indirect holdings remain large, with the largest reported indirect position totaling 3,550,382 shares following the 09/17 trades and other indirect holdings reported at 457,181, 590,410 and 701,904 through affiliated entities. The filing also discloses convertible Class C and Class D preferred stakes that convert into common shares (conversion rate 2.63158) and remaining derivative common equivalents reported as 52,631 and 88,421/16,842 across certain preferred positions. The Form 4 is signed by an attorney-in-fact on behalf of Stilwell and his affiliated entities.

John Taylor Maloney Fitzgerald, President & CEO and Director of Kingsway Financial Services Inc. (KFS), acquired 174 shares of KFS common stock on 09/15/2025 at $14.36 per share under the company's Employee Share Purchase Plan (ESPP). The ESPP allows employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months; purchases are executed on the open market by the plan administrator. After the transaction, Mr. Fitzgerald beneficially owns 1,530,745 shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. The Form 4 was signed by an attorney-in-fact on behalf of Mr. Fitzgerald on 09/16/2025.

Kent A. Hansen, Chief Financial Officer and Executive Vice President of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan on 09/15/2025. The filing shows a purchase (code P) at $14.36 per share for 109 shares acquired through the ESPP administrator. Following the transaction, Mr. Hansen beneficially owns 135,791 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares from 2022, March 2024 and December 2024 respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of service; shares are purchased on the open market by the plan administrator.

Kingsway Financial Services Inc. insider sale disclosure: This Form 4 shows that on September 8, 2025 multiple Stilwell-related entities sold common stock of KFS at $14.41 per share. Stilwell Activist Investments, L.P. sold 14,944 shares, Stilwell Activist Fund, L.P. sold 2,551 shares, and Stilwell Value Partners VII, L.P. sold 7,505 shares. Joseph Stilwell is identified as a director and >10% owner and directly owns 162,500 common shares. Several Stilwell entities and affiliates report substantial indirect holdings, including reported beneficial ownership figures of 3,590,980, 464,342, 610,651, and 701,904 common shares. The filing also discloses convertible Class D and Class C preferred shares with stated value $25 and conversion ratio 2.63158 common shares per preferred share, and redemption dates in 2032.

Kent A. Hansen, Chief Financial Officer and EVP of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan (ESPP). On 08/29/2025 Mr. Hansen acquired 107 shares of KFS common stock at $14.49 per share through the ESPP. After the purchase he beneficially owns 135,682 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares granted on December 15, 2022, March 26, 2024, and December 4, 2024, respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment; shares are bought on the open market by the plan administrator. The Form 4 was signed by an attorney-in-fact for Mr. Hansen on 09/02/2025.

Kingsway Financial Services insider transaction summary: The company’s President and CEO, John Taylor Maloney Fitzgerald, acquired 173 shares of Common Stock under transaction code P at $14.49 per share through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Following the purchase, his total reported beneficial ownership in common stock is 1,530,571 shares, which includes 400,000 shares of restricted stock granted in March 2021. The filing also discloses three indirect holdings of 20,000 shares each held in specified trusts. The ESPP permits employee contributions up to 5% of adjusted salary with a 100% company match after 12 months, and purchases are made on the open market by the plan administrator.

Kingsway Financial Services, Inc. (KFS) Form 4 summary: Joseph Stilwell and affiliated entities reported multiple sales of KFS common stock on 08/22/2025. Stilwell Activist Investments, L.P. sold 44,772 shares, Stilwell Activist Fund, L.P. sold 7,642 shares, and Stilwell Value Partners VII, L.P. sold 22,586 shares, each at $14.1784 per share. After the reported transactions, the reporting parties hold significant common stock positions: Joseph Stilwell directly holds 162,500 shares and beneficially holds additional shares through affiliated entities for totals shown on the form. The filing also discloses ownership of Class C and Class D preferred shares convertible into common stock at 2.63158 shares per preferred share, with redemption dates in 2032. The Form 4 is signed by Debra Rouse as attorney-in-fact for the reporting persons.

Kingsway Financial Services, Inc. insider filing reports multiple August 18, 2025 sales by entities affiliated with Joseph Stilwell while retaining substantial ownership. The Form 4 shows aggregated dispositions of 71,429 common shares across Stilwell Activist Investments, L.P., Stilwell Activist Fund, L.P., and Stilwell Value Partners VII, L.P., at prices between $13.95 and $14.1631. After the transactions, certain affiliated entities and Mr. Stilwell continue to beneficially own large positions, including reported indirect holdings of 3,650,696, 701,904 (derivative-convertible basis noted), and other specified share counts. The filing also discloses convertible Class C and D preferred stakes convertible into common shares.