Insider Transactions Reported by 10 Insiders of KINGSWAY FINANCIAL SERVICES INC

Symbol
KFS on NYSE
Location
Chicago, IL

Insiders trading volume in the past year

KINGSWAY FINANCIAL SERVICES INC executives and other stock owners filed with the SEC include:

Name Relationship Holdings Value Past Year Net Change Change % Report Date
Adam Jonathan Patinkin Director $21,662,750 17 Dec 2025
Gregory Paul Hannon Director $20,000,292 17 Dec 2025
Terence Michael Kavanagh Director $19,836,752 17 Dec 2025
OAKMONT CAPITAL INC 10%+ Owner $19,399,597 17 Dec 2025
John Taylor Maloney Fitzgerald President and CEO, Director $19,396,372 -$342,216 -1.7% 27 Feb 2026
DOUGLAS LEVINE Director $14,820,399 12 May 2025
Charles L. Frischer Director $14,608,974 24 Sep 2024
Joseph Stilwell Director, 10%+ Owner $6,758,227 -$16,054,456 -70% 22 Dec 2025
Joshua Horowitz Director $3,650,000 17 Dec 2025
Kent A. Hansen Cfo & Evp $1,480,318 -$72,518 -4.7% 27 Feb 2026

Recent Insider Transactions by Companies or Individuals for KINGSWAY FINANCIAL SERVICES INC

Insider Symbol Class Transaction % Value $ * Price $ Shares Shares Owned Date Ownership
Kent A. Hansen KFS Common Stock Purchase 0.11% $1,555 $12.34 126 119,961 27 Feb 2026 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,493 $12.34 202 1,460,493 27 Feb 2026 Direct
Kent A. Hansen KFS Common Stock Purchase 0.11% $1,560 $12.19 128 119,835 17 Feb 2026 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,499 $12.19 205 1,460,291 17 Feb 2026 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,505 $13.69 183 1,460,086 02 Feb 2026 Direct
Kent A. Hansen KFS Common Stock Purchase 0.1% $1,561 $13.69 114 119,707 02 Feb 2026 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,505 $13.54 185 1,459,903 15 Jan 2026 Direct
Kent A. Hansen KFS Common Stock Purchase 0.1% $1,571 $13.54 116 119,593 15 Jan 2026 Direct
Kent A. Hansen KFS Common Stock Purchase 0.1% $1,562 $13.58 115 119,477 31 Dec 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,499 $13.58 184 1,459,718 31 Dec 2025 Direct
Kent A. Hansen KFS Common Stock Tax liability -7.36% -9,488 119,362 30 Dec 2025 Direct
Kent A. Hansen KFS Common Stock Sale -5.5% $102,508 $13.67 -7,500 128,850 29 Dec 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Sale -2.01% $399,714 $13.32 -30,000 1,459,534 23 Dec 2025 Direct
Joseph Stilwell KFS Common Stock Sale -6.02% $246,131 $12.80 -19,229 300,000 22 Dec 2025 See footnote
Joseph Stilwell KFS Common Stock Exercise of in-the-money or at-the-money derivative security -84.6% -1,750,000 319,229 17 Dec 2025 See footnote
Joseph Stilwell KFS Stock Option (obligation to sell) Exercise of in-the-money or at-the-money derivative security -100% -1,750,000 0 17 Dec 2025 See footnote
Oakmont Capital Inc KFS Common Stock Exercise of in-the-money or at-the-money derivative security -20.1% -500,000 1,987,830 17 Dec 2025 Direct
Oakmont Capital Inc KFS Stock Option (obligation to sell) Exercise of in-the-money or at-the-money derivative security -100% -500,000 0 17 Dec 2025 Direct
Terence Michael Kavanagh KFS Common Stock Exercise of in-the-money or at-the-money derivative security -20.1% -500,000 1,987,830 17 Dec 2025 By Oakmont Capital Inc.
Terence Michael Kavanagh KFS Stock Option (obligation to sell) Exercise of in-the-money or at-the-money derivative security -100% -500,000 0 17 Dec 2025 By Oakmont Capital Inc.
Gregory Paul Hannon KFS Common Stock Exercise of in-the-money or at-the-money derivative security -20.1% -500,000 1,987,830 17 Dec 2025 By Oakmont Capital Inc
Gregory Paul Hannon KFS Stock Option (obligation to sell) Exercise of in-the-money or at-the-money derivative security -100% -500,000 0 17 Dec 2025 By Oakmont Capital Inc.
Adam Jonathan Patinkin KFS Common Stock Exercise of in-the-money or at-the-money derivative security 214.9% 1,040,000 1,524,000 17 Dec 2025 by David Capital Partners Special Situation Fund, LP
Adam Jonathan Patinkin KFS Common Stock Exercise of in-the-money or at-the-money derivative security 36.8% 275,000 1,023,000 17 Dec 2025 by David Capital Partners Fund, LP
Adam Jonathan Patinkin KFS Stock Option (Right to Buy) Exercise of in-the-money or at-the-money derivative security -100% -1,040,000 0 17 Dec 2025 by David Capital Partners Special Situation Fund, LP
Adam Jonathan Patinkin KFS Stock Option (Right to Buy) Exercise of in-the-money or at-the-money derivative security -100% -275,000 0 17 Dec 2025 by David Capital Partners Fund, LP
Joshua Horowitz KFS Common Stock Exercise of in-the-money or at-the-money derivative security 219.6% 252,500 367,500 17 Dec 2025 by Palm Global Small Cap Master Fund LP
Joshua Horowitz KFS Common Stock Exercise of in-the-money or at-the-money derivative security 225% 22,500 32,500 17 Dec 2025 Direct
Joshua Horowitz KFS Stock Option (Right to Buy) Exercise of in-the-money or at-the-money derivative security -100% -252,500 0 17 Dec 2025 by Palm Global Small Cap Master Fund LP
Joshua Horowitz KFS Stock Option (Right to Buy) Exercise of in-the-money or at-the-money derivative security -100% -22,500 0 17 Dec 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.09% $1,564 $12.82 122 136,472 16 Dec 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,500 $12.82 195 1,489,534 16 Dec 2025 Direct
Joseph Stilwell KFS Common Stock Sale -1.91% $133,491 $12.80 -10,429 534,706 16 Dec 2025 See footnote
Joseph Stilwell KFS Common Stock Sale -5.91% $438,660 $12.80 -34,269 545,135 15 Dec 2025 See footnote
Joseph Stilwell KFS Common Stock Sale -10.4% $864,000 $12.80 -67,500 579,404 11 Dec 2025 See footnote
Joseph Stilwell KFS Common Stock Sale -3% $256,000 $12.80 -20,000 646,904 09 Dec 2025 See footnote
Joseph Stilwell KFS Common Stock Sale -4.99% $448,700 $12.82 -35,000 666,904 08 Dec 2025 See footnote
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,502 $13.03 192 1,489,339 28 Nov 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.09% $1,564 $13.03 120 136,350 28 Nov 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.09% $1,562 $12.70 123 136,230 17 Nov 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,502 $12.70 197 1,489,147 17 Nov 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.08% $1,563 $14.08 111 136,107 30 Oct 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,492 $14.08 177 1,488,950 30 Oct 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.07% $1,560 $15.92 98 135,996 15 Oct 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,499 $15.92 157 1,488,773 15 Oct 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Purchase 0.01% $2,502 $14.63 171 1,488,616 30 Sep 2025 Direct
Kent A. Hansen KFS Common Stock Purchase 0.08% $1,565 $14.63 107 135,898 30 Sep 2025 Direct
John Taylor Maloney Fitzgerald KFS Common Stock Other 70.5% 14,100 34,100 26 Sep 2025 Trust-MPF
John Taylor Maloney Fitzgerald KFS Common Stock Other 70.5% 14,100 34,100 26 Sep 2025 Trust-LTF
John Taylor Maloney Fitzgerald KFS Common Stock Other 70.5% 14,100 34,100 26 Sep 2025 Trust-GEF
* An asterisk sign (*) next to the price indicates that the price is likely invalid.