Every Form 4 that Kingsway Corporation (KWY) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow KWY and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full KWY filings page.
KINGSWAY Corp (KWY) President and CEO and director John Taylor Maloney Fitzgerald purchased 357 common shares on October 15, 2026, at $9.74 per share through the Kingsway America Inc. Employee Share Purchase Plan. The plan administrator acquires shares on the open market; eligible employees may contribute up to 5% of adjusted salary per regular payroll period, and a 100% company match applies after 12 months of employment. Direct holdings after the purchase were 1,427,787 shares, including 300,000 restricted shares. Trust-GEF, Trust-LTF and Trust-MPF each reported indirect holdings of 29,100 shares. No Rule 10b5-1 plan is reported.
Kingsway Corp CFO & EVP Kent A. Hansen purchased 160 shares of common stock at $9.74 per share on October 16, 2026, under the Kingsway America Inc. Employee Share Purchase Plan (ESPP). The plan administrator acquired the shares on the open market through a registered stockbroker. Hansen reported direct holdings of 136,832 shares after the purchase, including 6,909 restricted shares granted December 4, 2024, and 14,568 restricted shares granted March 17, 2026. No Rule 10b5-1 plan is reported.
Kingsway Corp director Joshua Horowitz reported that Palm Global Small Cap Master Fund LP purchased 2,717 common shares on September 28, 2026, at a weighted average $9.2757 per share, and 858 shares on September 30, 2026, at $9.23 per share. As reported on September 28, 2026, the fund held 14,000 Class D Preferred Stock shares, convertible at the holder’s option at an initial $9.50 per-share price; Horowitz directly held 32,500 common shares. Horowitz disclaimed beneficial ownership except to the extent of his pecuniary interest.
Kingsway Corp President and CEO John Taylor Maloney Fitzgerald purchased 269 common shares at $9.30 per share on September 30, 2026, through Kingsway America Inc.’s Employee Share Purchase Plan; the plan administrator acquired the shares on the open market. The filing does not indicate a Rule 10b5-1 plan. His reported direct holdings after the purchase were 1,427,430 shares, including 300,000 shares of restricted stock granted March 31, 2021. Separate indirect holdings are listed as 29,100 shares each in Trust-GEF, Trust-LTF, and Trust-MPF.
Kingsway Corp (KWY) CFO & EVP Kent A. Hansen purchased 169 common shares at $9.30 per share on September 30, 2026. His reported direct holdings after the purchase were 136,672 shares, including restricted stock grants of 6,909 shares on December 4, 2024, and 14,568 shares on March 17, 2026. The purchase was under the Kingsway America Inc. Employee Share Purchase Plan, which permits eligible employees to contribute up to 5% of adjusted salary per regular payroll period; for employees with 12 months of service, the company matches employee contributions at 100%. The transaction was not reported as made under a Rule 10b5-1 plan.
KINGSWAY Corp (KWY) chief financial officer and executive vice president Kent A. Hansen purchased 159 shares of common stock on September 15, 2026 at $9.82 per share, through participation in Kingsway America Inc.’s Employee Share Purchase Plan. After this purchase, he directly holds 136,503 shares, including 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.
KINGSWAY Corp (KWY) reported that President and CEO, and director, John Taylor Maloney purchased 254 shares of Common Stock on September 15, 2026 at $9.82 per share through the company’s Employee Share Purchase Plan. Following this, he directly holds 1,427,161 shares, including 300,000 restricted shares, plus additional indirect holdings through family trusts. No Rule 10b5-1 trading plan is reported.
KINGSWAY Corp (KWY) reported that its CFO & EVP, Kent A. Hansen, purchased common stock. On August 31, 2026, he acquired 149 shares of common stock at $10.45 per share, in a transaction reported as a purchase in the open market or a private transaction. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). After this transaction, Hansen directly holds 136,344 shares of KINGSWAY Corp common stock, which include 6,909 restricted shares granted on December 4, 2024, and 14,568 restricted shares granted on March 17, 2026.
KINGSWAY Corp (KWY) director and President & CEO John Taylor Maloney purchased 239 shares of Common Stock on August 31, 2026 at $10.45 per share, through the Kingsway America Inc. Employee Share Purchase Plan. Following this purchase, his direct holdings total 1,426,907 shares, including 300,000 restricted shares granted on March 31, 2021. The filing also reports three indirect holdings of 29,100 shares each in separate trusts.
KINGSWAY Corp (KWY) director Joshua Horowitz reported indirect open-market purchases of Common Stock through Palm Global Small Cap Master Fund LP on August 18–20, 2026, totaling 9,103 shares at weighted-average prices around $9.75–$9.89 per share. Horowitz also reports 32,500 Common shares held directly and an indirect derivative position in Class D Preferred Stock convertible into 36,842.4 Common shares at a $9.50 conversion price. Palm Management (US) LLC and Horowitz may be deemed beneficial owners of Palm Global’s holdings but each disclaims beneficial ownership except to the extent of pecuniary interest.
KINGSWAY Corp (KWY) reported that President and CEO Fitzgerald John Taylor Maloney purchased 254 shares of common stock on August 17, 2026 at $9.87 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, which allows up to 5% of adjusted salary to be contributed with a 100% company match after 12 months of employment. Following this ESPP purchase, he directly owns 1,426,668 shares, including 300,000 restricted shares granted on March 31, 2021, and also reports indirect ownership of 29,100 shares in each of three separate trusts.
KINGSWAY Corp (KWY) executive Kent A. Hansen, CFO & EVP, purchased 158 shares of common stock on 2026-08-17 at $9.87 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, under which eligible employees can contribute up to 5% of adjusted salary with a 100% company match. Following this transaction, Hansen directly holds 136,195 shares of common stock, including 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.
KINGSWAY Corp (KWY) insider group led by Joseph Stilwell reported sales of 100,000 shares of Common Stock on August 13, 2026 at $10.00 per share, executed indirectly through Stilwell Associates, L.P., Stilwell Activist Investments, L.P., and Stilwell Value Partners VII, L.P. Joseph Stilwell continues to hold 162,500 Common shares directly and has additional indirect positions in Class C and Class D Preferred Stock that are convertible into Common Stock at $9.50 per share, with conversions based on 2.63158 Common shares per preferred share and mandatory redemption dates in 2032. Footnotes state that these partnership-held shares are owned directly by the respective funds and only indirectly by Stilwell through control of their general partner, and he disclaims beneficial ownership beyond his pecuniary interest.
Kent A. Hansen, CFO & EVP of Kingsway Corp, purchased 174 shares of Common Stock at $8.98 per share on July 30, 2026 through the Kingsway America Inc. Employee Share Purchase Plan. Under this ESPP, eligible employees may contribute up to 5% of adjusted salary with a 100% company match after 12 months to buy shares on the open market. Following this purchase, Hansen directly owns 136,037 shares, including 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.
Kingsway Corp President and CEO Fitzgerald John Taylor Maloney purchased 278 shares of Common Stock on July 30, 2026 at $8.98 per share through the company’s Employee Share Purchase Plan. Following this purchase, he directly holds 1,426,414 shares, including 300,000 shares of restricted stock granted March 31, 2021, and also reports indirect holdings of 29,100 shares in each of three trusts.
KINGSWAY Corp reports that its CFO & EVP, Kent A. Hansen, acquired 161 shares of common stock on July 15, 2026 at $9.76 per share. The purchase was made under the Kingsway America Inc. Employee Share Purchase Plan, which uses employee contributions and company matching funds to buy shares on the open market.
Following this transaction, Hansen directly holds 135,863 shares of common stock, including 6,909 shares of restricted stock granted on December 4, 2024 and 14,568 shares of restricted stock granted on March 17, 2026. Under the plan, eligible employees may contribute up to 5% of adjusted salary, with a 100% company matching contribution after 12 months of employment.
Kingsway Corp President and CEO Fitzgerald John Taylor Maloney acquired 256 common shares on 2026-07-15 at $9.76 per share through the company’s Employee Share Purchase Plan, bringing his direct holdings to 1,426,136 shares, including 300,000 shares of restricted stock. He also reports indirect ownership of 29,100 shares in each of three family trusts.
KINGSWAY Corp CFO & EVP Kent A. Hansen bought 149 shares of common stock at $10.45 per share in an open-market purchase made through the company’s Employee Share Purchase Plan. After this transaction, he directly owns 135,702 common shares, including restricted stock granted on December 4, 2024 and March 17, 2026.
KINGSWAY Corp President and CEO John Taylor Maloney increased his direct holdings of common stock through a small open-market purchase. He bought 239 shares on June 30, 2026 at $10.45 per share, bringing his direct ownership to 1,425,880 shares.
The shares were acquired under Kingsway America Inc.’s Employee Share Purchase Plan (ESPP), which allows employees to contribute up to 5% of adjusted salary and receive a 100% company match, with purchases executed on the open market. His direct holdings include 300,000 shares of restricted stock granted on March 31, 2021. He also has separate indirect holdings of 29,100 shares in each of three trusts.
Kingsway Corp President and CEO John Taylor Maloney reported a tax-related share disposition. On June 15, 2026, he surrendered 30,233 shares of Kingsway common stock at $10.12 per share to cover tax withholding obligations triggered by the vesting of restricted stock.
After this tax-withholding transaction, he directly holds 1,425,641 common shares, which include 300,000 restricted shares granted on March 31, 2021. He also reports indirect ownership of common stock through several family trusts, reflecting additional indirect exposure to Kingsway shares.
Kingsway Corp CFO and EVP Kent A. Hansen reported an open-market purchase of company stock through the Kingsway America Inc. Employee Share Purchase Plan. He acquired 150 shares of common stock at $10.43 per share.
Following this transaction, he directly owns 135,553 shares of Kingsway common stock. These holdings include 6,909 shares of restricted stock granted on December 4, 2024 and 14,568 shares of restricted stock granted on March 17, 2026, as described in the footnotes.
KINGSWAY Corp President and CEO John Taylor Maloney increased his stake through the company’s employee share purchase plan. He bought 240 shares of Common Stock at $10.43 per share in an open-market purchase, bringing his directly held position to 1,455,874 shares, including 400,000 shares of restricted stock granted on March 31, 2021. He also has indirect ownership of 29,100 shares in each of three personal trusts.
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 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.