Fitzgerald John Taylor Maloney 4

What Happened John Taylor Fitzgerald Maloney, President, CEO and a Director of Kingsway Financial Services Inc. (KFS), acquired 229 shares of KFS common stock on April 30, 2026 at $10.93 per share, for a total purchase of approximately $2,503. The acquisition was made under the company’s Employee Share Purchase Plan (ESPP) and executed on the open market by the plan administrator. This was a purchase (code P), typically seen as a routine employee/insider buy via payroll contributions rather than a large, discretionary market buy.

Key Details

• Transaction date and price: 2026-04-30, 229 shares @ $10.93 each.
• Total value: approximately $2,503.
• Transaction type: Purchase (ESPP acquisition, code P). Shares were bought on the open market by the ESPP administrator through a broker (see footnote).
• Shares owned after transaction: not specified in the provided filing excerpt.
• Footnotes: F1 — shares acquired pursuant to Kingsway America Inc.’s ESPP (employee contributions up to 5% of salary with a 100% company match after 12 months; administrator purchases shares on open market). F2 — filing notes Maloney holds 400,000 shares of restricted stock granted March 31, 2021.
• Filing timeliness: Report filed 2026-05-04 for an April 30 transaction; this appears to meet the two-business-day Form 4 filing requirement and is not late.

Context ESPP purchases are typically routine payroll-driven transactions: employees contribute from paychecks and the company (after eligibility) may match contributions, with shares bought by the plan administrator. The size of this purchase (~$2.5k) is modest and more consistent with routine plan participation than a significant directional bet by the insider.