Welcome to our dedicated page for Kingsway Finl SEC filings (Ticker: KFS), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Kingsway Financial Services, Inc. filings document an operating company that uses a Search Fund model to acquire and operate B2B and B2C services businesses. Form 8-K disclosures cover operating results and financial condition, including segment reporting for Kingsway Search Xcelerator and Extended Warranty, as well as material-event and Regulation FD updates tied to governance and board leadership.
Proxy materials describe director elections, auditor ratification, executive compensation votes, equity incentive plan matters, and certificate-of-incorporation amendments. Registration and capital-structure filings address common stock listed under KFS on the New York Stock Exchange, securities registration mechanics, offering disclosures, and related risk and governance information.
KINGSWAY Corp executive Kent A. Hansen, the CFO and EVP, bought 156 shares of Common Stock in an open-market employee purchase on May 29, 2026 at $10.03 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan.
Under this plan, eligible employees may contribute up to 5% of adjusted salary, and, after 12 months of employment, the company makes a 100% matching contribution, with all contributions used to buy shares on the open market. Following this transaction, Hansen directly owns 135,403 shares, including 6,909 shares of restricted stock granted on December 4, 2024 and 14,568 shares of restricted stock granted on March 17, 2026.
KINGSWAY Corp President and CEO John Taylor Maloney increased his stake through the company’s employee share plan. On May 29, he bought 250 shares of Common Stock in an open-market purchase at $10.03 per share under the Employee Share Purchase Plan.
After this transaction, his direct ownership rose to 1,455,634 Common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. He also reports indirect holdings of 29,100 shares of Common Stock in each of three family trusts labeled MPF, LTF, and GEF.
Kingsway Corp director-linked fund increases stake with open-market buys. Palm Global Small Cap Master Fund LP, an entity associated with director Joshua Horowitz, purchased 3,800 shares of Kingsway common stock on May 29, 2026 at $9.9105 per share and 700 shares on May 28, 2026 at $9.95 per share, for a total of 4,500 shares. After these trades, Palm Global indirectly holds 372,000 common shares, while Horowitz directly holds 32,500 shares. In addition, Palm Global holds Class D Preferred Stock that is convertible into 36,842.4 common shares at a $9.50 conversion price, with all such preferred shares to be redeemed for cash on May 8, 2032. The filing notes Palm Management (US) LLC and Horowitz may be deemed beneficial owners of Palm Global’s holdings but expressly disclaim beneficial ownership except to the extent of their pecuniary interest.
KINGSWAY Corp President and CEO John Taylor Maloney reported a bona fide charitable gift of 6,257 shares of common stock on May 27, 2026 at a value of $9.99 per share. After the gift, he directly holds 1,455,384 shares, including 400,000 restricted shares granted on March 31, 2021, and reports additional indirect holdings through three family trusts.
KINGSWAY Corp President and CEO Fitzgerald John Taylor Maloney reported an indirect open-market sale of 5,000 shares of Common Stock at $10.135 per share through a trust identified as Trust-MPF. After the sale, he reports 29,100 shares held indirectly in that trust and 1,461,641 shares held directly.
KFS disclosed insider dispositions by John T. Fitzgerald. The filing lists two reported sales of 5,000 shares each on 05/19/2026 and 05/20/2026, with reported amounts of 51,255.43 and 51,892.92 respectively. Shares outstanding were listed as 28,946,664 as of 05/21/2026.
KINGSWAY Corp President and CEO John Taylor Maloney reported selling a total of 10,000 shares of common stock in open-market transactions through family trusts. The sales occurred on May 19 and May 20 at prices of about $10.30–$10.43 per share. After these transactions, he continues to hold 1,461,641 shares directly as of May 19, along with additional indirect holdings through trusts, so the sales represent a small portion of his overall position.
Kingsway Corporation held its 2026 annual stockholder meeting, with 21,157,092 common shares represented, about 73.09% of shares entitled to vote. Stockholders elected all nine director nominees, each receiving a majority of votes cast, with broker non-votes reported for each director.
Stockholders ratified Plante & Moran, PLLC as independent registered public accounting firm for 2026 and approved an amendment to the Certificate of Incorporation to change the corporate name. They also approved an amendment to the 2020 Equity Incentive Plan to increase shares reserved for issuance and supported, on a nonbinding basis, the company’s named executive officer compensation.
KFS files a Form 144 reporting a proposed resale of 5,000 shares of Common stock. The notice lists 05/20/2026 and shows a prior sale of 5,000 shares on 05/19/2026 by John T. Fitzgerald. The filing also lists shares acquired as compensation via stock option exercises on 06/13/2016 (3,706 shares) and 06/10/2016 (1,294 shares).
KINGSWAY Corp director Adam Jonathan Patinkin received a grant of 400,000 nonqualified stock options for Kingsway common stock. The options are split into 200,000 at an exercise price of $20 per share and 200,000 at $30 per share, all with a 10-year term.
According to the vesting schedule, 100,000 options at $20 vested on the grant date, another 100,000 at $20 vest on the first anniversary, 100,000 at $30 vest on the second anniversary, and the final 100,000 at $30 vest on the third anniversary, subject to his continued service.
Entities managed by David Capital Partners, LLC hold 1,524,000 and 1,023,000 Kingsway common shares, and 68,421.08 shares of Class D Preferred Stock that are convertible at a basis of 2.63158 common shares per preferred share and are redeemable by the company on May 8, 2032.