Fitzgerald John Taylor Maloney 4

4 · KINGSWAY Corp · Filed May 19, 2026

AI-generated summary of this filing

Updated May 19, 2026

KINGSWAY (KWY) CEO Fitzgerald Maloney Buys 230 Shares

What Happened

Fitzgerald John Taylor Maloney (President, CEO and Director) purchased 230 shares of KINGSWAY Corp (KWY) on May 15, 2026 at $10.85 per share, for a total cash outlay of $2,496. The shares were acquired through the company’s Employee Share Purchase Plan (ESPP).

Key Details

Transaction date and price: 2026-05-15, 230 shares at $10.85 each.
Total value: $2,496.
Acquisition method: Shares purchased under the Kingsway America Inc. ESPP; the plan administrator buys shares on the open market through a broker (Footnote F1).
Ownership note: Filing references 400,000 restricted shares granted March 31, 2021 (Footnote F2). The filing does not state a full post-transaction total beneficial ownership figure.
Filing timeliness: Report filed May 19, 2026; based on the May 15 transaction date, the Form 4 was filed within the standard two-business-day window (timely).

Context

This was a small open‑market purchase made under an ESPP (payroll contributions with possible company matching), a routine way executives accumulate shares. Purchases can be interpreted as a modest affirmative action by the insider, but the size ($2.5k) is small and should be weighed alongside other signals and company fundamentals.

Form 4

Period: 2026-05-15

DirectorPresident and CEO

Transactions

Holdings

Footnotes (2)

[F1]The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.
[F2]Includes 400,000 shares of restricted stock granted on March 31, 2021.

Signature

/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald|2026-05-19

1 file