Fitzgerald John Taylor Maloney 4

4 · KINGSWAY FINANCIAL SERVICES INC · Filed Mar 31, 2026

AI-generated summary of this filing

Updated Mar 31, 2026

Kingsway (KFS) CEO John Maloney Buys 244 Shares via ESPP

What Happened

John Taylor Fitzgerald Maloney, President & CEO and Director of Kingsway Financial Services Inc. (KFS), acquired 244 shares of KFS common stock on 2026-03-30 at $10.22 per share, for a total of about $2,494. This was a purchase (code P) reported on a Form 4 filed 2026-03-31.

Key Details

Transaction date and price: 2026-03-30 — 244 shares at $10.22/share (total ≈ $2,494).
Transaction type: Purchase under the Kingsway America Inc. Employee Share Purchase Plan (ESPP); shares were bought on the open market by the plan administrator through a broker.
Shares owned after transaction: Not specified in the provided filing summary; filing notes holdings include 400,000 restricted shares granted on 2021-03-31 (footnote F2).
Footnotes: F1 explains the ESPP lets eligible employees contribute up to 5% of adjusted salary with a 100% company match after 12 months; contributions are used to buy shares on the open market. F2 notes inclusion of 400,000 restricted shares granted 3/31/2021.
Filing timeliness: Form 4 was filed on 2026-03-31 for a 2026-03-30 transaction (timely filing).

Context

This was a routine ESPP purchase funded by payroll contributions and company matching rather than a direct market order by the insider. The purchase value is small (~$2.5k) and consistent with ongoing employee share plan participation; it should be viewed as a personal purchase rather than a material directional signal.

Form 4

Period: 2026-03-30

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|2026-03-31

1 file