There have been 50 recent insider transactions recorded for Kingsway Financial Services Inc. (KFS), including 30 buys and 18 sells. Total insider buying was valued at $264.82K and total insider selling at $23.46M.
Notable insiders with recent activity include Fitzgerald John Taylor Maloney, Hansen Kent A, Horowitz Joshua. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — KFS
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-03-30 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
244 |
$10.22 |
$2.49K |
1,460,971 |
| 2026-03-30 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
153 |
$10.22 |
$1.56K |
120,260 |
| 2026-03-13 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
234 |
$10.71 |
$2.51K |
1,460,727 |
| 2026-03-13 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
146 |
$10.71 |
$1.56K |
120,107 |
| 2026-02-27 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
202 |
$12.34 |
$2.49K |
1,460,493 |
| 2026-02-27 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
126 |
$12.34 |
$1.55K |
119,961 |
| 2026-02-17 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
205 |
$12.19 |
$2.5K |
1,460,291 |
| 2026-02-17 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
128 |
$12.19 |
$1.56K |
119,835 |
| 2026-02-02 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
183 |
$13.69 |
$2.51K |
1,460,086 |
| 2026-02-02 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
114 |
$13.69 |
$1.56K |
119,707 |
| 2026-01-15 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
185 |
$13.54 |
$2.5K |
1,459,903 |
| 2026-01-15 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
116 |
$13.54 |
$1.57K |
119,593 |
| 2025-12-31 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
184 |
$13.58 |
$2.5K |
1,459,718 |
| 2025-12-31 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
115 |
$13.58 |
$1.56K |
119,477 |
| 2025-12-30 |
Hansen Kent A |
CFO & EVP |
Tax Withholding of RSU |
2,919 |
$12.83 |
$37.45K |
119,362 |
| 2025-12-29 |
Horowitz Joshua |
Director |
Unknown |
252,500 |
$8.25 |
$2.08M |
- |
| 2025-12-29 |
Patinkin Adam Jonathan |
Director |
Unknown |
500,000 |
$8.25 |
$4.13M |
- |
| 2025-12-29 |
Hansen Kent A |
CFO & EVP |
Informative Sell |
7,500 |
$13.67 |
$102.51K |
128,850 |
| 2025-12-23 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Sell |
30,000 |
$13.32 |
$399.71K |
1,459,534 |
| 2025-12-22 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
19,229 |
$12.80 |
$246.13K |
300,000 |
| 2025-12-17 |
Horowitz Joshua |
Director |
Option Exercise (ITM) |
252,500 |
$8.25 |
$2.08M |
- |
| 2025-12-17 |
Patinkin Adam Jonathan |
Director |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
- |
| 2025-12-17 |
Oakmont Capital Inc |
10 Percent Owner |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
- |
| 2025-12-17 |
Stilwell Joseph |
10 Percent Owner |
Option Exercise (ITM) |
218,842 |
$8.25 |
$1.81M |
- |
| 2025-12-17 |
Kavanagh Terence Michael |
Director |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
- |
| 2025-12-17 |
Hannon Gregory Paul |
Director |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
- |
| 2025-12-16 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
10,429 |
$12.80 |
$133.49K |
534,706 |
| 2025-12-16 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
195 |
$12.82 |
$2.5K |
1,489,534 |
| 2025-12-16 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
122 |
$12.82 |
$1.56K |
136,472 |
| 2025-12-15 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
34,269 |
$12.80 |
$438.66K |
545,135 |
| 2025-12-11 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
67,500 |
$12.80 |
$864K |
579,404 |
| 2025-12-09 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
20,000 |
$12.80 |
$256K |
646,904 |
| 2025-12-08 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
35,000 |
$12.82 |
$448.7K |
666,904 |
| 2025-11-28 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
192 |
$13.03 |
$2.5K |
1,489,339 |
| 2025-11-28 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
120 |
$13.03 |
$1.56K |
136,350 |
| 2025-11-17 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
197 |
$12.70 |
$2.5K |
1,489,147 |
| 2025-11-17 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
123 |
$12.70 |
$1.56K |
136,230 |
| 2025-10-30 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
177 |
$14.08 |
$2.49K |
1,488,950 |
| 2025-10-30 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
111 |
$14.08 |
$1.56K |
136,107 |
| 2025-10-15 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
157 |
$15.92 |
$2.5K |
1,488,773 |
| 2025-10-15 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
98 |
$15.92 |
$1.56K |
135,996 |
| 2025-09-30 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
171 |
$14.63 |
$2.5K |
1,488,616 |
| 2025-09-30 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
107 |
$14.63 |
$1.57K |
135,898 |
| 2025-09-26 |
Fitzgerald John Taylor Maloney |
President and CEO |
Other (Buy) |
14,100 |
$14.57 |
$205.44K |
34,100 |
| 2025-09-17 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
5,055 |
$14.47 |
$73.15K |
457,181 |
| 2025-09-16 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
2,106 |
$14.40 |
$30.33K |
462,236 |
| 2025-09-15 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
174 |
$14.36 |
$2.5K |
1,530,745 |
| 2025-09-15 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
109 |
$14.36 |
$1.57K |
135,791 |
| 2025-09-08 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
2,551 |
$14.41 |
$36.76K |
464,342 |
| 2025-08-29 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
173 |
$14.49 |
$2.51K |
1,530,571 |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
