SEC Insider Transactions from Fitzgerald John Taylor Maloney.

Last updated: 2026-03-31 21:08 UTC | Total transactions: 98

Fitzgerald John Taylor Maloney, President and CEO of Kingsway Financial Services Inc ($KFS), made 23 open market purchases totaling $57,500 in the last 365 days, with the most recent on February 27, 2026. These buys rank 2,852nd among 4,983 individual insiders, below the average of $1.46 million per buyer and 3.29 transactions. He sold shares once for $399,714, most recently on December 23, 2025, ranking 6,949th out of 11,678 sellers versus an average of $8.6 million and 6.37 transactions.

Set Up your own filters →
Transaction Date Company Ticker Insider Name Title Transaction Type Security Shares Price Shares Owned Following Total Shares Outstanding % of Owned % of Outstanding
March 30, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 244 $10.22 1,563,271.0000 28,956,152 0.02% 0.00%
March 13, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 234 $10.71 1,563,027.0000 28,956,152 0.01% 0.00%
Feb. 27, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 202 $12.34 1,562,793.0000 28,956,152 0.01% 0.00%
Feb. 17, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 205 $12.19 1,562,591.0000 28,956,152 0.01% 0.00%
Feb. 2, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 183 $13.69 1,562,386.0000 28,956,152 0.01% 0.00%
Jan. 15, 2026 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 185 $13.54 1,562,203.0000 28,956,152 0.01% 0.00%
Dec. 31, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 184 $13.58 1,562,018.0000 28,956,152 0.01% 0.00%
Dec. 23, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO S Common Stock 30000 $13.32 1,561,834.0000 28,956,152 1.88% 0.10%
Dec. 16, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 195 $12.82 1,591,834.0000 28,956,152 0.01% 0.00%
Nov. 28, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 192 $13.03 1,591,639.0000 28,956,152 0.01% 0.00%
Nov. 17, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 197 $12.70 1,591,447.0000 28,956,152 0.01% 0.00%
Oct. 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 177 $14.08 1,591,250.0000 27,537,151 0.01% 0.00%
Oct. 15, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 157 $15.92 1,591,073.0000 27,537,151 0.01% 0.00%
Sept. 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 171 $14.63 1,590,916.0000 27,537,151 0.01% 0.00%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,590,745.0000 27,537,151 0.89% 0.05%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,604,845.0000 27,537,151 0.87% 0.05%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,618,945.0000 27,537,151 0.86% 0.05%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,590,745.0000 27,537,151 0.89% 0.05%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,590,745.0000 27,537,151 0.88% 0.05%
Sept. 26, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 14100 $14.57 1,590,745.0000 27,537,151 0.89% 0.05%
Sept. 15, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 174 $14.36 1,590,745.0000 27,537,151 0.01% 0.00%
Aug. 29, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 173 $14.49 1,590,571.0000 27,537,151 0.01% 0.00%
Aug. 18, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 176 $14.16 1,590,398.0000 27,537,151 0.01% 0.00%
July 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 174 $14.42 1,590,222.0000 27,537,151 0.01% 0.00%
July 15, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 172 $14.49 1,590,048.0000 27,537,151 0.01% 0.00%
July 1, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 179 $14.02 1,589,876.0000 27,537,151 0.01% 0.00%
June 13, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 181 $13.77 1,589,697.0000 27,537,151 0.01% 0.00%
May 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 195 $12.82 1,589,516.0000 27,537,151 0.01% 0.00%
May 15, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 247 $10.12 1,589,321.0000 27,537,151 0.02% 0.00%
April 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 287 $8.71 1,589,074.0000 27,537,151 0.02% 0.00%
April 15, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO A Common Stock 311 $8.02 1,588,787.0000 27,537,151 0.02% 0.00%
March 28, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 305 $8.20 1,588,476.0000 27,537,151 0.02% 0.00%
March 14, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 340 $7.35 1,588,171.0000 0 0.02% 0.00%
March 3, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 315 $7.95 1,587,831.0000 0 0.02% 0.00%
Sept. 24, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO A Class B Preferred Stock 8000 $25.00 8,000.0000 0 9999.99% 0.00%
Feb. 14, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 311 $8.03 1,587,516.0000 0 0.02% 0.00%
Jan. 30, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 300 $8.33 1,587,205.0000 0 0.02% 0.00%
Jan. 16, 2025 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 301 $8.30 1,586,905.0000 0 0.02% 0.00%
Dec. 31, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 297 $8.47 1,586,604.0000 0 0.02% 0.00%
Dec. 16, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 291 $8.56 1,586,307.0000 0 0.02% 0.00%
Nov. 29, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 279 $8.95 1,586,016.0000 0 0.02% 0.00%
Nov. 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 279 $8.96 1,585,737.0000 0 0.02% 0.00%
Oct. 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 266 $9.40 1,585,458.0000 0 0.02% 0.00%
Oct. 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 284 $8.81 1,585,192.0000 0 0.02% 0.00%
Sept. 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 299 $8.34 1,584,908.0000 0 0.02% 0.00%
Sept. 24, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO A Class B Preferred Stock 8000 $25.00 8,000.0000 0 9999.99% 0.00%
Sept. 13, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 320 $7.83 1,584,609.0000 0 0.02% 0.00%
Sept. 5, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO F Common Stock 43832 $8.01 1,584,289.0000 0 2.69% 0.00%
Aug. 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 304 $8.21 1,628,121.0000 0 0.02% 0.00%
Aug. 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 315 $7.96 1,627,817.0000 0 0.02% 0.00%
July 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 286 $8.74 1,627,502.0000 0 0.02% 0.00%
July 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 294 $8.49 1,627,216.0000 0 0.02% 0.00%
July 1, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 305 $8.20 1,626,922.0000 0 0.02% 0.00%
June 17, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 310 $8.06 1,626,617.0000 0 0.02% 0.00%
May 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 308 $8.11 1,626,307.0000 0 0.02% 0.00%
May 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 310 $8.07 1,625,999.0000 0 0.02% 0.00%
May 1, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 279 $8.97 1,625,689.0000 0 0.02% 0.00%
April 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 296 $8.44 1,625,410.0000 0 0.02% 0.00%
April 1, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 302 $8.27 1,625,114.0000 0 0.02% 0.00%
March 28, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO F Common Stock 221104 $8.34 1,624,812.0000 0 11.98% 0.00%
March 18, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 294 $8.49 1,845,916.0000 0 0.02% 0.00%
Feb. 29, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 282 $8.86 1,845,622.0000 0 0.02% 0.00%
Feb. 15, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 299 $8.37 1,845,340.0000 0 0.02% 0.00%
Jan. 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 283 $8.86 1,845,041.0000 0 0.02% 0.00%
Jan. 30, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 283 $8.86 1,845,041.0000 0 0.02% 0.00%
Jan. 12, 2024 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 307 $8.14 1,844,758.0000 0 0.02% 0.00%
Dec. 29, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 296 $8.46 1,844,451.0000 0 0.02% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,844,155.0000 0 1.07% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,884,155.0000 0 1.05% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,844,155.0000 0 1.10% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,864,155.0000 0 1.06% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,844,155.0000 0 1.10% 0.00%
Dec. 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO J Common Stock 20000 $8.38 1,844,155.0000 0 1.10% 0.00%
Dec. 15, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 300 $8.32 1,844,155.0000 0 0.02% 0.00%
Nov. 30, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 341 $7.31 1,843,855.0000 0 0.02% 0.00%
Nov. 15, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 337 $7.42 1,843,514.0000 0 0.02% 0.00%
Oct. 30, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 332 $7.53 1,843,177.0000 0 0.02% 0.00%
Oct. 13, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 359 $6.97 1,842,845.0000 0 0.02% 0.00%
Sept. 29, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 318 $7.85 1,842,486.0000 0 0.02% 0.00%
Sept. 15, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 301 $8.30 1,842,168.0000 0 0.02% 0.00%
Sept. 5, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO F Common Stock 43893 $8.76 1,841,867.0000 0 2.33% 0.00%
Aug. 30, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 283 $8.83 1,885,760.0000 0 0.02% 0.00%
Aug. 15, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 292 $8.58 1,885,477.0000 0 0.02% 0.00%
July 31, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 302 $8.28 1,885,185.0000 0 0.02% 0.00%
July 14, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 309 $8.10 1,884,883.0000 0 0.02% 0.00%
July 3, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 310 $8.06 1,884,574.0000 0 0.02% 0.00%
June 20, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 281 $8.90 1,884,264.0000 0 0.01% 0.00%
May 30, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 303 $8.23 1,883,983.0000 0 0.02% 0.00%
May 16, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 301 $8.34 1,883,680.0000 0 0.02% 0.00%
May 4, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 282 $8.86 1,883,379.0000 0 0.01% 0.00%
April 14, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 284 $8.53 1,883,097.0000 0 0.02% 0.00%
March 31, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Common Stock 230 $9.05 1,882,813.0000 0 0.01% 0.00%
March 16, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 249 $8.98 1,882,583.0000 0 0.01% 0.00%
March 1, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 216 $9.61 1,882,334.0000 0 0.01% 0.00%
Feb. 15, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 234 $8.88 1,882,118.0000 0 0.01% 0.00%
Jan. 30, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 258 $8.06 1,881,884.0000 0 0.01% 0.00%
Jan. 17, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 252 $8.25 1,881,626.0000 0 0.01% 0.00%
Jan. 3, 2023 KINGSWAY FINANCIAL SERVICES INC $KFS Fitzgerald John Taylor Maloney President and CEO P Commoon Stock 258 $8.06 1,881,374.0000 0 0.01% 0.00%