Data spanning the past 90 days through February 07, 2026 reveals that Kingsway Financial Services's three principal insider shareholders consist of TenPercentOwner Capital Inc Oakmont (1.99Mn shares), Director Terence Michael Kavanagh (1.99Mn shares), Director Gregory Paul Hannon (1.99Mn shares).
| Holder | Position | Shares | Report Date |
|---|---|---|---|
| Capital Inc Oakmont | 1,987,830 | 19 Dec, 2025 | |
| Terence Michael Kavanagh | 1,987,830 | 27 Mar, 2023 | |
| Gregory Paul Hannon | 1,987,830 | 19 Dec, 2025 | |
| Charles L Frischer | 1,835,798 | 14 Sep, 2023 | |
| Adam Jonathan Patinkin | 1,524,000 | 18 Dec, 2025 | |
| John Taylor Maloney Fitzgerald | President And Ceo | 1,494,186 | 02 Feb, 2026 |
| Douglas Levine | 1,157,671 | 23 Mar, 2023 | |
| Joseph Stilwell | 599,411 | 29 Dec, 2025 | |
| Joshua Horowitz | 400,000 | 18 Dec, 2025 | |
| Kent A Hansen | Cfo & Evp | 119,707 | 02 Feb, 2026 |
| Paul R. Hogan | Secretary And General Counsel | 3,968 | 02 Apr, 2021 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 02 Feb, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 183 | $13.69 | 1,460,086 | D | P |
| 02 Feb, 2026 | Kent A Hansen | Common Stock | A | 114 | $13.69 | 119,707 | D | P |
| 15 Jan, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 185 | $13.54 | 1,459,903 | D | P |
| 15 Jan, 2026 | Kent A Hansen | Common Stock | A | 116 | $13.54 | 119,593 | D | P |
| 31 Dec, 2025 | John Taylor Maloney Fitzgerald | Common Stock | A | 184 | $13.58 | 1,459,718 | D | P |
| 31 Dec, 2025 | Kent A Hansen | Common Stock | A | 115 | $13.58 | 119,477 | D | P |
| 30 Dec, 2025 | Kent A Hansen | Common Stock | D | 2,919 | $12.83 | 119,362 | D | F |
| 30 Dec, 2025 | Kent A Hansen | Common Stock | D | 3,004 | $12.83 | 122,281 | D | F |
| 30 Dec, 2025 | Kent A Hansen | Common Stock | D | 3,565 | $12.83 | 125,285 | D | F |
| 29 Dec, 2025 | Kent A Hansen | Common Stock | D | 7,500 | $13.67 | 128,850 | D | S |
| 23 Dec, 2025 | John Taylor Maloney Fitzgerald | Common Stock | D | 30,000 | $13.32 | 1,459,534 | D | S |
| 22 Dec, 2025 | Joseph Stilwell | Common Stock | D | 19,229 | $12.80 | 162,500 | D | S |
| 17 Dec, 2025 | Capital Inc Oakmont | Common Stock | D | 500,000 | $8.25 | 1,987,830 | D | X |
| 17 Dec, 2025 | Joseph Stilwell | Common Stock | D | 215,477 | $8.25 | 162,500 | D | X |
| 17 Dec, 2025 | Joseph Stilwell | Common Stock | D | 1,295,411 | $8.25 | 319,229 | I | X |
| 17 Dec, 2025 | Joseph Stilwell | Common Stock | D | 218,842 | $8.25 | 436,911 | I | X |
| 17 Dec, 2025 | Joseph Stilwell | Common Stock | D | 20,270 | $8.25 | 2,254,971 | I | X |
| 17 Dec, 2025 | Joseph Stilwell | - | - | 436,911 | I | |||
| 17 Dec, 2025 | Terence Michael Kavanagh | Common Stock | D | 500,000 | $8.25 | 1,987,830 | I | X |
| 17 Dec, 2025 | Gregory Paul Hannon | - | - | 1,987,830 | I |