Kingsway Financial Services's top three insider shareholders as of March 23, 2026 are Terence Michael Kavanagh (Director, 1.99Mn shares), Capital Inc Oakmont (TenPercentOwner, 1.99Mn shares), Gregory Paul Hannon (Director, 1.99Mn shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| Gregory Paul Hannon | 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 | |
| Charles L Frischer | 1,600,898 | 0 | 14 Sep, 2023 | |
| Adam Jonathan Patinkin | 0 | 1,524,000 | 18 Dec, 2025 | |
| John Taylor Maloney Fitzgerald | President And Ceo | 1,460,727 | 0 | 16 Mar, 2026 |
| John Taylor Maloney Fitzgerald | President And Ceo | 1,460,493 | 0 | 02 Mar, 2026 |
| Douglas Levine | 1,157,671 | 0 | 23 Mar, 2023 | |
| Joshua Horowitz | 32,500 | 367,500 | 18 Dec, 2025 | |
| Joseph Stilwell | 0 | 300,000 | 29 Dec, 2025 | |
| Charles L Frischer | 0 | 234,900 | 12 Sep, 2023 | |
| Kent A Hansen | Cfo Evp | 120,107 | 0 | 16 Mar, 2026 |
| Kent A Hansen | Cfo Evp | 119,961 | 0 | 02 Mar, 2026 |
| John Taylor Maloney Fitzgerald | President And Ceo | 0 | 34,100 | 30 Sep, 2025 |
| John Taylor Maloney Fitzgerald | President And Ceo | 0 | 34,100 | 30 Sep, 2025 |
| Paul R. Hogan | Secretary And General Counsel | 3,968 | 0 | 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 |
|---|---|---|---|---|---|---|---|---|
| 13 Mar, 2026 | Kent A Hansen | Common Stock | A | 146 | $10.71 | 120,107 | D | P |
| 13 Mar, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 234 | $10.71 | 1,460,727 | D | P |
| 27 Feb, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 202 | $12.34 | 1,460,493 | D | P |
| 27 Feb, 2026 | Kent A Hansen | Common Stock | A | 126 | $12.34 | 119,961 | 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 |
| 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 | Kent A Hansen | Common Stock | A | 114 | $13.69 | 119,707 | D | P |
| 02 Feb, 2026 | John Taylor Maloney Fitzgerald | Common Stock | A | 183 | $13.69 | 1,460,086 | 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 |
| 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 | Kent A Hansen | Common Stock | A | 115 | $13.58 | 119,477 | D | P |
| 31 Dec, 2025 | John Taylor Maloney Fitzgerald | Common Stock | A | 184 | $13.58 | 1,459,718 | D | P |