As of May 14, 2026, Kingsway Financial Services's top three insider holders are Gregory Paul Hannon (Director, 2.62Mn shares), Terence Michael Kavanagh (Director, 2.61Mn shares), Terence Michael Kavanagh (Director, 2.61Mn shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| Gregory Paul Hannon | - | 0 | 2,624,444 | 01 Jul, 2022 |
| Terence Michael Kavanagh | - | 0 | 2,611,444 | 01 Jul, 2022 |
| Terence Michael Kavanagh | - | 0 | 2,611,444 | 01 Jul, 2022 |
| Terence Michael Kavanagh | - | 0 | 2,611,444 | 01 Jul, 2022 |
| Terence Michael Kavanagh | - | 0 | 2,611,444 | 01 Jul, 2022 |
| Capital Inc Oakmont | - | 2,576,694 | 0 | 01 Jul, 2022 |
| Capital Inc Oakmont | - | 2,576,694 | 0 | 01 Jul, 2022 |
| Capital Inc Oakmont | - | 2,576,694 | 0 | 01 Jul, 2022 |
| Capital Inc Oakmont | - | 2,576,694 | 0 | 01 Jul, 2022 |
| Adam Jonathan Patinkin | - | 0 | 2,547,000 | 18 Dec, 2025 |
| Adam Jonathan Patinkin | - | 0 | 2,547,000 | 18 Dec, 2025 |
| Adam Jonathan Patinkin | - | 0 | 2,547,000 | 18 Dec, 2025 |
| Adam Jonathan Patinkin | - | 0 | 2,547,000 | 18 Dec, 2025 |
| Capital Inc Oakmont | - | 1,987,830 | 0 | 19 Dec, 2025 |
| Terence Michael Kavanagh | - | 0 | 1,987,830 | 19 Dec, 2025 |
| Capital Inc Oakmont | - | 1,987,830 | 0 | 19 Dec, 2025 |
| Capital Inc Oakmont | - | 1,987,830 | 0 | 19 Dec, 2025 |
| Terence Michael Kavanagh | - | 0 | 1,987,830 | 19 Dec, 2025 |
| Terence Michael Kavanagh | - | 0 | 1,987,830 | 19 Dec, 2025 |
| Terence Michael Kavanagh | - | 0 | 1,987,830 | 19 Dec, 2025 |
| Capital Inc Oakmont | - | 1,987,830 | 0 | 19 Dec, 2025 |
| Gregory Paul Hannon | - | 0 | 1,987,830 | 19 Dec, 2025 |
| John Taylor Maloney Fitzgerald | President And Ceo | 1,882,583 | 0 | 20 Mar, 2023 |
| Charles L Frischer | - | 1,600,898 | 0 | 14 Sep, 2023 |
| Charles L Frischer | - | 1,584,278 | 0 | 09 Dec, 2022 |
| John Taylor Maloney Fitzgerald | President And Ceo | 1,461,182 | 0 | 15 Apr, 2026 |
| Douglas Levine | - | 1,157,671 | 0 | 23 Mar, 2023 |
| Douglas Levine | - | 1,157,671 | 0 | 23 Mar, 2023 |
| Douglas Levine | - | 1,157,671 | 0 | 23 Mar, 2023 |
| Douglas Levine | - | 1,157,671 | 0 | 23 Mar, 2023 |
| Joshua Horowitz | - | 32,500 | 367,500 | 18 Dec, 2025 |
| Charles L Frischer | - | 0 | 234,900 | 12 Sep, 2023 |
| Charles L Frischer | - | 0 | 231,000 | 09 Jun, 2022 |
| Kent A Hansen | Cfo Evp | 120,260 | 0 | 31 Mar, 2026 |
| Kent A Hansen | Cfo Evp | 106,810 | 0 | 20 Mar, 2023 |
| John Taylor Maloney Fitzgerald | President And Ceo | 0 | 102,300 | 30 Sep, 2025 |
| Terence Michael Kavanagh | - | 0 | 34,750 | 27 Mar, 2023 |
| Terence Michael Kavanagh | - | 0 | 34,750 | 27 Mar, 2023 |
| Terence Michael Kavanagh | - | 0 | 34,750 | 27 Mar, 2023 |
| Terence Michael Kavanagh | - | 0 | 34,750 | 27 Mar, 2023 |
| Gregory Paul Hannon | - | 0 | 29,500 | 27 Mar, 2023 |
* 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 |
|---|---|---|---|---|---|---|---|---|
| 15 Apr, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 211 | $11.85 | 1,461,182 | D | P |
| 17 Mar, 2026 | Kent A Hansen | Common Stock | A | 14,568 | $11.02 | 134,675 | D | A |
| 30 Mar, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 244 | $10.22 | 1,460,971 | D | P |
| 30 Mar, 2026 | Kent A Hansen | Common Stock | A | 153 | $10.22 | 120,260 | D | P |
| 13 Mar, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 234 | $10.71 | 1,460,727 | D | P |
| 13 Mar, 2026 | Kent A Hansen | Common Stock | A | 146 | $10.71 | 120,107 | D | P |
| 27 Feb, 2026 | Kent A Hansen | Common Stock | A | 126 | $12.34 | 119,961 | D | P |
| 27 Feb, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 202 | $12.34 | 1,460,493 | D | P |
| 17 Feb, 2026 | Kent A Hansen | Common Stock | A | 128 | $12.19 | 119,835 | D | P |
| 17 Feb, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 205 | $12.19 | 1,460,291 | D | P |
| 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 | Kent A Hansen | Common Stock | A | 116 | $13.54 | 119,593 | D | P |
| 15 Jan, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 185 | $13.54 | 1,459,903 | 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 |
| 29 Dec, 2025 | Kent A Hansen | Common Stock | D | 7,500 | $13.67 | 128,850 | D | S |
| 30 Dec, 2025 | Kent A Hansen | Common Stock | D | 3,565 | $12.83 | 125,285 | 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 | 2,919 | $12.83 | 119,362 | D | F |