Fitzgerald John Taylor Maloney 4

What Happened
John Taylor Fitzgerald Maloney (President, CEO and Director) acquired 250 shares of KINGSWAY Corporation (KWY) on May 29, 2026 through an open-market purchase under the company’s Employee Share Purchase Plan (ESPP). The shares were bought at $10.03 per share for a total transaction value of $2,508. This is a purchase (insider acquisition), a relatively small, routine ESPP transaction.

Key Details

• Transaction date: 2026-05-29; Form 4 filed: 2026-06-01 (Period of Report: 2026-05-29).
• Transaction type/code: Purchase (P) — 250 shares at $10.03; total $2,508.
• Acquisition method: Shares acquired pursuant to the Kingsway America Inc. ESPP; administrator purchases shares on the open market through a broker (Footnote F1).
• Shares owned after transaction: Filing notes inclusion of 400,000 restricted shares granted March 31, 2021 (Footnote F2). The summary data provided does not state a complete total of beneficially owned shares after this purchase.
• Timeliness: Filed on June 1, 2026 for a May 29 transaction; filing appears timely under the Form 4 two-business-day rule.

Context
This was a small ESPP purchase (about $2.5k) consistent with routine employee share plan participation and company matching described in F1 (employees may contribute up to 5% of salary and, after 12 months, receive a 100% matching contribution). Such ESPP transactions are common and reflect plan participation rather than an explicit market view by the insider.