KFS · Insider Trading
Kingsway Financial Services, Inc.
Every open-market purchase and sale reported by KFS officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-05-04 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +229 | +$2.50K |
| 2026-05-04 | Kent A Hansen | CFO & EVP | Buy | +143 | +$1.56K |
| 2026-04-15 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +211 | +$2.50K |
| 2026-04-08 | Kent A Hansen | CFO & EVP | A | +14,568 | +$160.54K |
| 2026-03-16 | Kent A Hansen | CFO & EVP | Buy | +146 | +$1.56K |
| 2026-03-16 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +234 | +$2.51K |
| 2026-03-02 | Kent A Hansen | CFO & EVP | Buy | +126 | +$1.55K |
| 2026-03-02 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +202 | +$2.49K |
| 2026-02-18 | Kent A Hansen | CFO & EVP | Buy | +128 | +$1.56K |
| 2026-02-18 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +205 | +$2.50K |
| 2026-02-02 | Kent A Hansen | CFO & EVP | Buy | +114 | +$1.56K |
| 2026-02-02 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +183 | +$2.51K |
| 2026-01-29 | Kent A Hansen | CFO & EVP | Buy | +116 | +$1.57K |
| 2026-01-29 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +185 | +$2.50K |
| 2026-01-05 | Kent A Hansen | CFO & EVP | Buy | +115 | +$1.56K |
| 2026-01-05 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +184 | +$2.50K |
| 2025-12-31 | Kent A Hansen | CFO & EVP | MIXED | −16,988 | −$224.24K |
| 2025-12-29 | John Taylor Maloney Fitzgerald | President and CEO | Sell | −30,000 | −$399.71K |
| 2025-12-29 | Stilwell Value LLC | 10%+ Owner | Sell | −115,374 | −$1.48M |
| 2025-12-19 | OAKMONT CAPITAL INC | 10%+ Owner | X | −500,000 | −$4.12M |
| 2025-12-19 | Terence Michael Kavanagh | Director | X | −500,000 | −$4.12M |
| 2025-12-19 | Joseph Stilwell | Director | X | −10,500,000 | −$86.62M |
| 2025-12-19 | Gregory Paul Hannon | Director | X | −500,000 | −$4.12M |
| 2025-12-18 | Kent A Hansen | CFO & EVP | Buy | +122 | +$1.56K |
| 2025-12-18 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +195 | +$2.50K |
| 2025-12-18 | Adam Jonathan Patinkin | Director | X | +1,315,000 | +$10.85M |
| 2025-12-18 | Joshua Horowitz | Director | X | +275,000 | +$2.27M |
| 2025-12-17 | Stilwell Value Partners VII, L.P. | 10%+ Owner | Sell | −268,188 | −$3.43M |
| 2025-12-15 | Stilwell Activist Fund, L.P. | 10%+ Owner | Sell | −405,000 | −$5.18M |
| 2025-12-10 | Stilwell Activist Investments, L.P. | 10%+ Owner | Sell | −330,000 | −$4.23M |
| 2025-12-02 | Kent A Hansen | CFO & EVP | Buy | +120 | +$1.56K |
| 2025-12-02 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +192 | +$2.50K |
| 2025-11-19 | Kent A Hansen | CFO & EVP | Buy | +123 | +$1.56K |
| 2025-11-19 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +197 | +$2.50K |
| 2025-11-03 | Kent A Hansen | CFO & EVP | Buy | +111 | +$1.56K |
| 2025-11-03 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +177 | +$2.49K |
| 2025-10-17 | Kent A Hansen | CFO & EVP | Buy | +98 | +$1.56K |
| 2025-10-17 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +157 | +$2.50K |
| 2025-10-02 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +171 | +$2.50K |
| 2025-10-02 | Kent A Hansen | CFO & EVP | Buy | +107 | +$1.57K |
| 2025-09-30 | John Taylor Maloney Fitzgerald | President and CEO | J | — | — |
| 2025-09-18 | Stilwell Activist Fund, L.P. | 10%+ Owner | Sell | −408,000 | −$5.90M |
| 2025-09-16 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +174 | +$2.50K |
| 2025-09-16 | Kent A Hansen | CFO & EVP | Buy | +109 | +$1.57K |
| 2025-09-10 | Stilwell Value Partners VII, L.P. | 10%+ Owner | Sell | −150,000 | −$2.16M |
| 2025-09-02 | John Taylor Maloney Fitzgerald | President and CEO | Buy | +173 | +$2.51K |
| 2025-09-02 | Kent A Hansen | CFO & EVP | Buy | +107 | +$1.55K |
| 2025-08-26 | Stilwell Value LLC | 10%+ Owner | Sell | −450,000 | −$6.38M |
| 2025-08-20 | Stilwell Activist Fund, L.P. | 10%+ Owner | Sell | −428,574 | −$6.02M |
| 2025-08-18 | Kent A Hansen | CFO & EVP | Buy | +111 | +$1.57K |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| Stilwell Activist Fund, L.P. | 10%+ Owner | 3,712,882 | $39.84M |
| Stilwell Activist Investments, L.P. | Director | 3,712,882 | $39.84M |
| OAKMONT CAPITAL INC | 10%+ Owner | 1,987,830 | $21.33M |
| Gregory Paul Hannon | Director | 1,987,830 | $21.33M |
| Charles L Frischer | Director | 1,835,798 | $19.70M |
| John Taylor Maloney Fitzgerald | President and CEO | 1,495,511 | $16.05M |
| Douglas Levine | Director | 1,247,871 | $13.39M |
| Stilwell Associates, L.P. | 10%+ Owner | 1,081,286 | $11.60M |
| Adam Jonathan Patinkin | Director | 1,023,000 | $10.98M |
| Stilwell Value Partners VII, L.P. | 10%+ Owner | 752,910 | $8.08M |
| Joseph Stilwell | Director | 599,411 | $6.43M |
| Stilwell Value LLC | 10%+ Owner | 462,500 | $4.96M |
| Joshua Horowitz | Director | 400,000 | $4.29M |
| Kent A Hansen | CFO & EVP | 135,103 | $1.45M |
| Terence Michael Kavanagh | Director | 34,750 | $372.87K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the KFS quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.