Welcome to our dedicated page for KINGSWAY SEC filings (Ticker: KWY), 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.
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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.
KFS insider filed a Form 144 reporting the proposed sale of 5,000 shares of Common Stock through Goldman Sachs & Co. LLC. The filing lists that 3,054 shares were acquired on 06/21/2016 and 1,946 shares were acquired on 06/20/2016, both described as acquired as compensation — stock options with cashless exercise / same-day sale.
Kingsway Financial Services President and CEO John Taylor Maloney bought 230 shares of Common Stock on May 15, 2026 at $10.85 per share through the company’s employee share purchase plan. This increased his direct holdings to 1,461,641 shares, alongside indirect holdings of 34,100 shares in each of three trusts, including 400,000 restricted shares granted on March 31, 2021.