Kingsway Financial Services Inc
NYSE: KFS · CONSUMER CYCLICAL · AUTO & TRUCK DEALERSHIPS
Updated 2026-05-13
Kingsway Financial Services Inc (KFS) Insider transactions
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-04-30 | HANSEN, KENT A | CFO & EVP | Buy | 143 | $10.93 | $1562.99 |
| 2026-04-30 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 229 | $10.93 | $2502.97 |
| 2026-04-15 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 211 | $11.85 | $2500.35 |
| 2026-03-30 | HANSEN, KENT A | CFO & EVP | Buy | 153 | $10.22 | $1563.66 |
| 2026-03-30 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 244 | $10.22 | $2493.68 |
| 2026-03-17 | HANSEN, KENT A | CFO & EVP | Buy | 14,568 | $11.02 | $160539.36 |
| 2026-03-13 | HANSEN, KENT A | CFO & EVP | Buy | 146 | $10.71 | $1563.66 |
| 2026-03-13 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 234 | $10.71 | $2506.14 |
| 2026-02-27 | HANSEN, KENT A | CFO & EVP | Buy | 126 | $12.34 | $1554.84 |
| 2026-02-27 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 202 | $12.34 | $2492.68 |
| 2026-02-17 | HANSEN, KENT A | CFO & EVP | Buy | 128 | $12.19 | $1560.32 |
| 2026-02-17 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 205 | $12.19 | $2498.95 |
| 2026-02-02 | HANSEN, KENT A | CFO & EVP | Buy | 114 | $13.69 | $1560.66 |
| 2026-02-02 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 183 | $13.69 | $2505.27 |
| 2026-01-15 | HANSEN, KENT A | CFO & EVP | Buy | 116 | $13.54 | $1570.64 |
| 2026-01-15 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 185 | $13.54 | $2504.90 |
| 2025-12-31 | HANSEN, KENT A | CFO & EVP | Buy | 115 | $13.58 | $1561.70 |
| 2025-12-31 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 184 | $13.58 | $2498.72 |
| 2025-12-30 | HANSEN, KENT A | CFO & EVP | Sale | 3,565 | $12.83 | $45738.95 |
| 2025-12-30 | HANSEN, KENT A | CFO & EVP | Sale | 3,004 | $12.83 | $38541.32 |
| 2025-12-30 | HANSEN, KENT A | CFO & EVP | Sale | 2,919 | $12.83 | $37450.77 |
| 2025-12-29 | HANSEN, KENT A | CFO & EVP | Sale | 7,500 | $13.67 | $102508.50 |
| 2025-12-23 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Sale | 30,000 | $13.32 | $399714.00 |
| 2025-12-22 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 19,229 | $12.80 | $246131.20 |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 1,295,411 | — | — |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 218,842 | — | — |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 215,477 | — | — |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 20,270 | — | — |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 1,295,411 | $8.25 | $10.69M |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 218,842 | $8.25 | $1.81M |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 215,477 | $8.25 | $1.78M |
| 2025-12-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 20,270 | $8.25 | $167227.50 |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Sale | 540,000 | — | — |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Sale | 500,000 | — | — |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Sale | 275,000 | — | — |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Buy | 540,000 | $8.25 | $4.46M |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Buy | 500,000 | $8.25 | $4.13M |
| 2025-12-17 | PATINKIN, ADAM JONATHAN | Director | Buy | 275,000 | $8.25 | $2.27M |
| 2025-12-17 | OAKMONT, CAPITAL INC | 10% Owner | Sale | 500,000 | — | — |
| 2025-12-17 | OAKMONT, CAPITAL INC | 10% Owner | Sale | 500,000 | $8.25 | $4.13M |
| 2025-12-17 | KAVANAGH, TERENCE MICHAEL | Director | Sale | 500,000 | — | — |
| 2025-12-17 | KAVANAGH, TERENCE MICHAEL | Director | Sale | 500,000 | $8.25 | $4.13M |
| 2025-12-17 | HOROWITZ, JOSHUA | Director | Sale | 252,500 | — | — |
| 2025-12-17 | HOROWITZ, JOSHUA | Director | Sale | 22,500 | — | — |
| 2025-12-17 | HOROWITZ, JOSHUA | Director | Buy | 252,500 | $8.25 | $2.08M |
| 2025-12-17 | HOROWITZ, JOSHUA | Director | Buy | 22,500 | $8.25 | $185625.00 |
| 2025-12-17 | HANNON, GREGORY PAUL | Director | Sale | 500,000 | — | — |
| 2025-12-17 | HANNON, GREGORY PAUL | Director | Sale | 500,000 | $8.25 | $4.13M |
| 2025-12-16 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 10,429 | $12.80 | $133491.20 |
| 2025-12-16 | HANSEN, KENT A | CFO & EVP | Buy | 122 | $12.82 | $1564.04 |
| 2025-12-16 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 195 | $12.82 | $2499.90 |
| 2025-12-15 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 34,269 | $12.80 | $438660.33 |
| 2025-12-11 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 67,500 | $12.80 | $864000.00 |
| 2025-12-09 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 20,000 | $12.80 | $256000.00 |
| 2025-12-08 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 35,000 | $12.82 | $448700.00 |
| 2025-11-28 | HANSEN, KENT A | CFO & EVP | Buy | 120 | $13.03 | $1563.60 |
| 2025-11-28 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 192 | $13.03 | $2501.76 |
| 2025-11-17 | HANSEN, KENT A | CFO & EVP | Buy | 123 | $12.70 | $1562.10 |
| 2025-11-17 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 197 | $12.70 | $2501.90 |
| 2025-10-30 | HANSEN, KENT A | CFO & EVP | Buy | 111 | $14.08 | $1562.88 |
| 2025-10-30 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 177 | $14.08 | $2492.16 |
| 2025-10-15 | HANSEN, KENT A | CFO & EVP | Buy | 98 | $15.92 | $1560.16 |
| 2025-10-15 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 157 | $15.92 | $2499.44 |
| 2025-09-30 | HANSEN, KENT A | CFO & EVP | Buy | 107 | $14.63 | $1565.41 |
| 2025-09-30 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 171 | $14.63 | $2501.73 |
| 2025-09-26 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Sale | 14,100 | $14.57 | $205437.00 |
| 2025-09-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 28,657 | $14.47 | $414666.79 |
| 2025-09-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 14,288 | $14.47 | $206747.36 |
| 2025-09-17 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 5,055 | $14.47 | $73145.85 |
| 2025-09-16 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 11,941 | $14.40 | $171950.40 |
| 2025-09-16 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 5,953 | $14.40 | $85723.20 |
| 2025-09-16 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 2,106 | $14.40 | $30326.40 |
| 2025-09-15 | HANSEN, KENT A | CFO & EVP | Buy | 109 | $14.36 | $1565.24 |
| 2025-09-15 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 174 | $14.36 | $2498.64 |
| 2025-09-08 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 14,944 | $14.41 | $215343.04 |
| 2025-09-08 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 7,505 | $14.41 | $108147.05 |
| 2025-09-08 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 2,551 | $14.41 | $36759.91 |
| 2025-08-29 | HANSEN, KENT A | CFO & EVP | Buy | 107 | $14.49 | $1550.43 |
| 2025-08-29 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 173 | $14.49 | $2506.77 |
| 2025-08-22 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 44,772 | $14.18 | $634795.32 |
| 2025-08-22 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 22,586 | $14.18 | $320233.34 |
| 2025-08-22 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 7,642 | $14.18 | $108351.33 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 23,779 | $13.95 | $331717.05 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 18,835 | $14.16 | $266761.99 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 12,123 | $13.95 | $169115.85 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 9,410 | $14.16 | $133274.77 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 4,098 | $13.95 | $57167.10 |
| 2025-08-18 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 3,184 | $14.16 | $45095.31 |
| 2025-08-18 | HANSEN, KENT A | CFO & EVP | Buy | 111 | $14.16 | $1571.76 |
| 2025-08-18 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 176 | $14.16 | $2492.16 |
| 2025-07-30 | HANSEN, KENT A | CFO & EVP | Buy | 108 | $14.42 | $1557.36 |
| 2025-07-30 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 174 | $14.42 | $2509.08 |
| 2025-07-15 | HANSEN, KENT A | CFO & EVP | Buy | 108 | $14.49 | $1564.92 |
| 2025-07-15 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 172 | $14.49 | $2492.28 |
| 2025-07-01 | HANSEN, KENT A | CFO & EVP | Buy | 111 | $14.02 | $1556.22 |
| 2025-07-01 | FITZGERALD, JOHN TAYLOR MALONEY | Director, President and CEO | Buy | 179 | $14.02 | $2509.58 |
| 2025-06-30 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 18,763 | $13.90 | $260897.64 |
| 2025-06-30 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 8,319 | $13.90 | $115674.86 |
| 2025-06-30 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 5,896 | $13.90 | $81983.29 |
| 2025-06-27 | STILWELL, JOSEPH | Director, 10% Owner | Sale | 85,191 | $14.03 | $1.20M |
Frequently asked questions
Are KFS insiders buying or selling?
Over the transactions on record, KFS insiders have been net sellers, with about $35.09M in stock sold across 53 sales, against 47 open-market purchases.
Does insider selling at KFS mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which KFS insiders are selling the most?
Recent selling is concentrated in a few names. STILWELL, JOSEPH accounts for the largest share on record, with about $21.89M sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.