Over the past 12 months, 8 insiders at KINGSWAY FINANCIAL SERVICES INC filed 62 open-market SEC Form 4 transactions on KFS: 36 purchases worth $74K and 26 sales worth $6.3M. Insiders have been mixed over this period. The most recent filing was on Apr 30, 26.
| Date | Insider | Type | Shares | Price | Value |
|---|---|---|---|---|---|
| Apr 30, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 229 | $10.93 | $3K |
| Apr 15, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 211 | $11.85 | $3K |
| Mar 30, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 244 | $10.22 | $2K |
| Mar 30, 26 | Kent A HansenCFO & EVP | BUY | 153 | $10.22 | $2K |
| Mar 13, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 234 | $10.71 | $3K |
| Mar 13, 26 | Kent A HansenCFO & EVP | BUY | 146 | $10.71 | $2K |
| Feb 27, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 202 | $12.34 | $2K |
| Feb 27, 26 | Kent A HansenCFO & EVP | BUY | 126 | $12.34 | $2K |
| Feb 17, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 205 | $12.19 | $2K |
| Feb 17, 26 | Kent A HansenCFO & EVP | BUY | 128 | $12.19 | $2K |
| Feb 2, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 183 | $13.69 | $3K |
| Feb 2, 26 | Kent A HansenCFO & EVP | BUY | 114 | $13.69 | $2K |
| Jan 15, 26 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 185 | $13.54 | $3K |
| Jan 15, 26 | Kent A HansenCFO & EVP | BUY | 116 | $13.54 | $2K |
| Dec 31, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 184 | $13.58 | $2K |
| Dec 31, 25 | Kent A HansenCFO & EVP | BUY | 115 | $13.58 | $2K |
| Dec 29, 25 | Kent A HansenCFO & EVP | SELL | 7.5K | $13.67 | $103K |
| Dec 23, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | SELL | 30.0K | $13.32 | $400K |
| Dec 22, 25 | Stilwell Value LlcTenPercentOwner | SELL | 19.2K | $12.80 | $246K |
| Dec 16, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 195 | $12.82 | $3K |
| Dec 16, 25 | Kent A HansenCFO & EVP | BUY | 122 | $12.82 | $2K |
| Dec 16, 25 | Stilwell Associates, L.p.TenPercentOwner | SELL | 10.4K | $12.80 | $133K |
| Dec 15, 25 | Stilwell Associates, L.p.TenPercentOwner | SELL | 34.3K | $12.80 | $439K |
| Dec 11, 25 | Stilwell Activist Fund, L.p.TenPercentOwner | SELL | 67.5K | $12.80 | $864K |
| Dec 9, 25 | Stilwell Activist Fund, L.p.TenPercentOwner | SELL | 20.0K | $12.80 | $256K |
| Dec 8, 25 | Stilwell Activist Fund, L.p.TenPercentOwner | SELL | 35.0K | $12.82 | $449K |
| Nov 28, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 192 | $13.03 | $3K |
| Nov 28, 25 | Kent A HansenCFO & EVP | BUY | 120 | $13.03 | $2K |
| Nov 17, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 197 | $12.70 | $3K |
| Nov 17, 25 | Kent A HansenCFO & EVP | BUY | 123 | $12.70 | $2K |
| Oct 30, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 177 | $14.08 | $2K |
| Oct 30, 25 | Kent A HansenCFO & EVP | BUY | 111 | $14.08 | $2K |
| Oct 15, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 157 | $15.92 | $2K |
| Oct 15, 25 | Kent A HansenCFO & EVP | BUY | 98 | $15.92 | $2K |
| Sep 30, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 171 | $14.63 | $3K |
| Sep 30, 25 | Kent A HansenCFO & EVP | BUY | 107 | $14.63 | $2K |
| Sep 17, 25 | Stilwell Value Partners Vii, L.p.TenPercentOwner | SELL | 28.7K | $14.47 | $415K |
| Sep 16, 25 | Stilwell Value Partners Vii, L.p.TenPercentOwner | SELL | 11.9K | $14.40 | $172K |
| Sep 15, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 174 | $14.36 | $2K |
| Sep 15, 25 | Kent A HansenCFO & EVP | BUY | 109 | $14.36 | $2K |
| Sep 8, 25 | Joseph StilwellDirector,TenPercentOwner | SELL | 14.9K | $14.41 | $215K |
| Aug 29, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 173 | $14.49 | $3K |
| Aug 29, 25 | Kent A HansenCFO & EVP | BUY | 107 | $14.49 | $2K |
| Aug 22, 25 | Stilwell Activist Fund, L.p.TenPercentOwner | SELL | 44.8K | $14.18 | $635K |
| Aug 18, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 176 | $14.16 | $2K |
| Aug 18, 25 | Kent A HansenCFO & EVP | BUY | 111 | $14.16 | $2K |
| Aug 18, 25 | Stilwell Associates L PTenPercentOwner | SELL | 23.8K | $14.16 | $332K |
| Jul 30, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 174 | $14.42 | $3K |
| Jul 30, 25 | Kent A HansenCFO & EVP | BUY | 108 | $14.42 | $2K |
| Jul 15, 25 | Fitzgerald John Taylor MaloneyPresident and CEO | BUY | 172 | $14.49 | $2K |
Over the past 12 months, insiders at KINGSWAY FINANCIAL SERVICES INC filed 36 open-market purchases worth $74K and 26 sales worth $6.3M on KFS, which makes them mixed over the period. The most recent Form 4 was filed on Apr 30, 26.
The largest recent open-market KFS insider purchase in our data was $3K by Fitzgerald John Taylor Maloney, President and CEO, filed on Jul 30, 25.
8 different insiders at KINGSWAY FINANCIAL SERVICES INC filed open-market SEC Form 4 transactions on KFS over the last 12 months.
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