Kingsway Financial Services Inc. (KFS) has 15 known insider and institutional holders on record. The largest holder is Stilwell Value Partners VII, L.P. with 5,048,333 shares. Other notable holders include Fitzgerald John Taylor Maloney and SWETS LARRY G JR.
Over the last 12 months, insiders have made 75 transactions in KFS stock — 53 buys (valued at $1.06M) and 15 sells (valued at $3.42M). Insider buying has outpaced selling during this period, which may signal confidence in the company's prospects.
KFS Insider Ownership
Top Holder
Stilwell Value Partners VII, L.P.
5,048,333 shares
Buys (12 mo)
53
$1.06M value
Sells (12 mo)
15
$3.42M value
12-Month Transaction Activity
Top Insider Holders
| # |
Name |
Role |
Shares Owned |
Last Filed |
Relative Size |
| 1 |
Stilwell Value Partners Vii, L.p. |
Director |
5,048,333 |
2022-06-27 |
|
| 2 |
Fitzgerald John Taylor Maloney |
President and CEO |
1,460,971 |
2026-03-31 |
|
| 3 |
Swets Larry G Jr |
Director |
963,273 |
2018-09-17 |
|
| 4 |
Stilwell Joseph |
10 Percent Owner |
300,000 |
2025-12-29 |
|
| 5 |
Hickey William August Jr |
CFO & EVP |
198,831 |
2020-03-03 |
|
| 6 |
Baqar Hassan |
Vice President |
160,512 |
2019-02-01 |
|
| 7 |
Hansen Kent A |
CFO & EVP |
120,260 |
2026-03-31 |
|
| 8 |
Hannon Gregory Paul |
Director |
40,000 |
2025-02-14 |
|
| 9 |
Kavanagh Terence Michael |
Director |
40,000 |
2025-02-14 |
|
| 10 |
Oakmont Capital Inc |
10 Percent Owner |
40,000 |
2025-02-14 |
|
| 11 |
Patinkin Adam Jonathan |
Director |
26,000 |
2025-05-09 |
|
| 12 |
Levine Douglas |
Director |
20,000 |
2025-05-12 |
|
| 13 |
Horowitz Joshua |
Director |
14,000 |
2025-05-09 |
|
| 14 |
Frischer Charles L |
Director |
4,000 |
2024-09-27 |
|
| 15 |
Hogan Paul R. |
Secretary and General Counsel |
3,968 |
2021-04-02 |
|
Recent Transactions (last 12 months)
| Date |
Name |
Role |
Type |
Shares |
Price |
Value |
| 2026-03-30 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
153 |
$10.22 |
$1.56K |
| 2026-03-30 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
244 |
$10.22 |
$2.49K |
| 2026-03-13 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
146 |
$10.71 |
$1.56K |
| 2026-03-13 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
234 |
$10.71 |
$2.51K |
| 2026-02-27 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
126 |
$12.34 |
$1.55K |
| 2026-02-27 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
202 |
$12.34 |
$2.49K |
| 2026-02-17 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
128 |
$12.19 |
$1.56K |
| 2026-02-17 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
205 |
$12.19 |
$2.5K |
| 2026-02-02 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
114 |
$13.69 |
$1.56K |
| 2026-02-02 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
183 |
$13.69 |
$2.51K |
| 2026-01-15 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
116 |
$13.54 |
$1.57K |
| 2026-01-15 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
185 |
$13.54 |
$2.5K |
| 2025-12-31 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
115 |
$13.58 |
$1.56K |
| 2025-12-31 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Buy |
184 |
$13.58 |
$2.5K |
| 2025-12-30 |
Hansen Kent A |
CFO & EVP |
Tax Withholding of RSU |
2,919 |
$12.83 |
$37.45K |
| 2025-12-29 |
Hansen Kent A |
CFO & EVP |
Informative Sell |
7,500 |
$13.67 |
$102.51K |
| 2025-12-23 |
Fitzgerald John Taylor Maloney |
President and CEO |
Informative Sell |
30,000 |
$13.32 |
$399.71K |
| 2025-12-22 |
Stilwell Joseph |
10 Percent Owner |
Informative Sell |
19,229 |
$12.80 |
$246.13K |
| 2025-12-17 |
Hannon Gregory Paul |
Director |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
| 2025-12-17 |
Kavanagh Terence Michael |
Director |
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 |
Oakmont Capital Inc |
10 Percent Owner |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
| 2025-12-17 |
Patinkin Adam Jonathan |
Director |
Option Exercise (ITM) |
500,000 |
$8.25 |
$4.13M |
| 2025-12-16 |
Hansen Kent A |
CFO & EVP |
Informative Buy |
122 |
$12.82 |
$1.56K |
| 2025-12-17 |
Horowitz Joshua |
Director |
Option Exercise (ITM) |
252,500 |
$8.25 |
$2.08M |
