InsiderFlow

KFS

Kingsway Financial Services Inc.$10.24+0.00 ()
Prev Close$10.76·MCap$293.1M·P/E·Vol·Yield

Buys (12M)

43

$87.8K

Sells (12M)

10

$8.45M

Net Activity

Net Seller

$8.37M

Active Insiders

5

last 12 mo

Over the past 12 months, insider activity at Kingsway Financial Services Inc. (KFS) has been dominated by selling, with 43 insider purchases totaling $87.8K and 10 insider sales totaling $8.45M. The most recent insider transaction was by Fitzgerald John Taylor Maloney (director, officer: President and CEO), who purchased $2.5K worth of shares on May 4, 2026. Kingsway Financial Services Inc. operates in the Consumer Cyclical sector, within the Auto - Dealerships industry, with a market cap of $293.1M.

KFS Insider Trading Activity

DateInsiderTypeValue
May 4, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
May 4, 2026 Hansen Kent ABuy$1.6K
Apr 15, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 31, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 31, 2026 Hansen Kent ABuy$1.6K
Mar 16, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 16, 2026 Hansen Kent ABuy$1.6K
Mar 2, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 2, 2026 Hansen Kent ABuy$1.6K
Feb 17, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Feb 17, 2026 Hansen Kent ABuy$1.6K
Feb 2, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Feb 2, 2026 Hansen Kent ABuy$1.6K
Jan 29, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Jan 29, 2026 Hansen Kent ABuy$1.6K
Jan 5, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Jan 5, 2026 Hansen Kent ABuy$1.6K
Dec 29, 2025 Fitzgerald John Taylor MaloneySell$399.7K
Dec 29, 2025 Stilwell JosephSell$246.1K
Dec 18, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Dec 18, 2025 Hansen Kent ABuy$1.6K
Dec 17, 2025 Stilwell JosephSell$572.2K
Dec 15, 2025 Stilwell JosephSell$864.0K
Dec 10, 2025 Stilwell JosephSell$704.7K
Dec 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Dec 2, 2025 Hansen Kent ABuy$1.6K
Nov 19, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Nov 19, 2025 Hansen Kent ABuy$1.6K
Nov 3, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Nov 3, 2025 Hansen Kent ABuy$1.6K
Oct 17, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Oct 17, 2025 Hansen Kent ABuy$1.6K
Oct 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Oct 2, 2025 Hansen Kent ABuy$1.6K
Sep 18, 2025 Stilwell JosephSell$982.6K
Sep 16, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Sep 16, 2025 Hansen Kent ABuy$1.6K
Sep 10, 2025 Stilwell JosephSell$360.3K
Sep 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Sep 2, 2025 Hansen Kent ABuy$1.6K
Aug 26, 2025 STILWELL JOSEPHSell$1.06M
Aug 20, 2025 STILWELL JOSEPHSell$1.00M
Aug 18, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Aug 18, 2025 Hansen Kent ABuy$1.6K
Jul 31, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 31, 2025 Hansen Kent ABuy$1.6K
Jul 16, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 16, 2025 Hansen Kent ABuy$1.6K
Jul 1, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 1, 2025 Hansen Kent ABuy$1.6K
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KFS Insider Buying Activity

The following table shows recent insider purchases of Kingsway Financial Services Inc. (KFS) stock reported via SEC Form 4 filings.

DateInsiderTypeValue
May 4, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
May 4, 2026 Hansen Kent ABuy$1.6K
Apr 15, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 31, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 31, 2026 Hansen Kent ABuy$1.6K
Mar 16, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 16, 2026 Hansen Kent ABuy$1.6K
Mar 2, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Mar 2, 2026 Hansen Kent ABuy$1.6K
Feb 17, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Feb 17, 2026 Hansen Kent ABuy$1.6K
Feb 2, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Feb 2, 2026 Hansen Kent ABuy$1.6K
Jan 29, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Jan 29, 2026 Hansen Kent ABuy$1.6K
Jan 5, 2026 Fitzgerald John Taylor MaloneyBuy$2.5K
Jan 5, 2026 Hansen Kent ABuy$1.6K
Dec 18, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Dec 18, 2025 Hansen Kent ABuy$1.6K
Dec 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Dec 2, 2025 Hansen Kent ABuy$1.6K
Nov 19, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Nov 19, 2025 Hansen Kent ABuy$1.6K
Nov 3, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Nov 3, 2025 Hansen Kent ABuy$1.6K
Oct 17, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Oct 17, 2025 Hansen Kent ABuy$1.6K
Oct 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Oct 2, 2025 Hansen Kent ABuy$1.6K
Sep 16, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Sep 16, 2025 Hansen Kent ABuy$1.6K
Sep 2, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Sep 2, 2025 Hansen Kent ABuy$1.6K
Aug 18, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Aug 18, 2025 Hansen Kent ABuy$1.6K
Jul 31, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 31, 2025 Hansen Kent ABuy$1.6K
Jul 16, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 16, 2025 Hansen Kent ABuy$1.6K
Jul 1, 2025 Fitzgerald John Taylor MaloneyBuy$2.5K
Jul 1, 2025 Hansen Kent ABuy$1.6K

KFS Insider Selling Activity

The following table shows recent insider sales of Kingsway Financial Services Inc. (KFS) stock reported via SEC Form 4 filings.

DateInsiderTypeValue
Dec 29, 2025 Fitzgerald John Taylor MaloneySell$399.7K
Dec 29, 2025 Stilwell JosephSell$246.1K
Dec 17, 2025 Stilwell JosephSell$572.2K
Dec 15, 2025 Stilwell JosephSell$864.0K
Dec 10, 2025 Stilwell JosephSell$704.7K
Sep 18, 2025 Stilwell JosephSell$982.6K
Sep 10, 2025 Stilwell JosephSell$360.3K
Aug 26, 2025 STILWELL JOSEPHSell$1.06M
Aug 20, 2025 STILWELL JOSEPHSell$1.00M

KFS Insiders

Hansen Kent A

officer: CFO & EVP

Bought $128.8K
92 tradesLast: May 4, 2026
Fitzgerald John Taylor Maloney

President and CEO

Bought $224.0KSold $399.7K
94 tradesLast: May 4, 2026
Stilwell Joseph

Director

Sold $3.73M
6 tradesLast: Dec 29, 2025
STILWELL JOSEPH

Director

Bought $6.67MSold $20.11M
62 tradesLast: Aug 26, 2025
Frischer Charles L

Director

Bought $172.3K
3 tradesLast: Sep 14, 2023
Hannon Gregory Paul

Director

Bought $197.0KSold $971.9K
6 tradesLast: Jun 22, 2023
Kavanagh Terence Michael

Director

Bought $71.2KSold $70.7K
2 tradesLast: Mar 27, 2023
Hogan Paul R.

Secretary and General Counsel

Bought $3.0K
3 tradesLast: Apr 2, 2021