Stilwell Joseph sold KFS

December 17, 2025 · Form 4 insider transaction

Stilwell Joseph sold 20,270 shares of Kingsway Financial Services Inc at $8.25 per share, a transaction worth $167.2K. The trade was recorded as exercise of in-the-money option and disclosed on an SEC Form 4, filed 2 days after the transaction.

Direction
Disposed (sell-side)
Shares
20,270
Price
$8.25
Total value
$167.2K
Role10% owner
SecurityCommon Stock
Transaction codeX: Exercise of in-the-money option
Transaction dateDecember 17, 2025
Filing dateDecember 19, 2025
Shares owned after436,911
OwnershipIndirect
10b5-1 planNo
AmendedNo

Footnotes

On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.; These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

View the original Form 4 on SEC EDGAR