Fitzgerald John Taylor Maloney 4

What Happened
Fitzgerald John Taylor Maloney, President & CEO and Director of Kingsway Financial Services Inc. (KFS), purchased 185 shares of common stock on January 15, 2026 at $13.54 per share for a total of $2,505. The acquisition was a purchase (code P) made through the company’s Employee Share Purchase Plan.

Key Details

• Transaction date and price: 2026-01-15 at $13.54 per share; total value $2,505.
• Transaction type: P = Purchase; shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan (ESPP) and bought on the open market by the plan administrator (Footnote F1).
• Shares owned after transaction: Not specified in the Form 4. Footnote F2 notes holdings include 400,000 shares of restricted stock granted March 31, 2021.
• Filing timeliness: Report filed 2026-01-29; the Form 4 was filed late relative to the 2-business-day reporting requirement (filed 14 days after the trade).

Context
The purchase was made under the ESPP, which allows eligible employees to contribute up to 5% of adjusted salary and—after 12 months of employment—receive a 100% company match that is used to buy shares. The administrator purchases shares on the open market through a broker, so this reflects plan activity rather than necessarily a discretionary open-market buy by the executive. The amount is modest ($2.5K).