Kingsway Financial (NYSE: KFS) CEO boosts stake through ESPP stock buy

Rhea-AI Filing Summary

Kingsway Financial Services Inc. President and CEO John Taylor Maloney Fitzgerald reported a small open‑market acquisition of company stock through an employee plan. On 12/31/2025, he acquired 184 shares of common stock at a price of $13.58 per share under the Kingsway America Inc. Employee Share Purchase Plan, which uses both employee and company matching contributions to buy shares on the open market.

After this transaction, Fitzgerald beneficially owns 1,459,718 shares of Kingsway common stock directly, plus 34,100 shares held in each of three separate trusts. The direct holdings disclosed include 400,000 shares of restricted stock that were granted on March 31, 2021. The filing characterizes this transaction as part of an ongoing employee share purchase program rather than a one‑time discretionary trade.

Insider Trade Summary

Net Buyer: 184 shares ($2,499)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 184 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	184	$13.58	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,459,718 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF)

Footnotes (1)

1. 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. Includes 400,000 shares of restricted stock granted on March 31, 2021.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Fitzgerald John Taylor Maloney

(Last) (First) (Middle)

10 S. RIVERSIDE PLAZA

SUITE 1520

(Street)

CHICAGO IL 60606

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

3. Date of Earliest Transaction (Month/Day/Year)
12/31/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	12/31/2025		P		184(1)	A	$13.58	1,459,718(2)	D
Common Stock								34,100	I	Trust-GEF
Common Stock								34,100	I	Trust-LTF
Common Stock								34,100	I	Trust-MPF

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. 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.

2. Includes 400,000 shares of restricted stock granted on March 31, 2021.

	/s/ Robert E. Buckner II, attorney-in-fact for John Taylor Maloney Fitzgerald	01/05/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transaction did Kingsway Financial Services (KFS) report in this Form 4?

The filing reports that President and CEO John Taylor Maloney Fitzgerald acquired 184 shares of Kingsway Financial Services Inc. common stock on 12/31/2025 at a price of $13.58 per share.

How were the new Kingsway Financial Services (KFS) shares acquired by the CEO?

The 184 shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which allows eligible employees to contribute up to 5% of adjusted salary and receive a 100% company matching contribution, with all contributions used to purchase Kingsway shares on the open market.

How many Kingsway Financial Services (KFS) shares does the CEO own after this transaction?

Following the reported transaction, John Taylor Maloney Fitzgerald beneficially owns 1,459,718 shares of Kingsway common stock directly, and 34,100 shares in each of three trusts listed as indirect holdings.

Does the CEO’s Kingsway (KFS) stake include restricted stock?

Yes. The filing states that the reported holdings include 400,000 shares of restricted stock granted on March 31, 2021, which form part of the CEO’s direct beneficial ownership.

What are the key terms of the Kingsway America Inc. ESPP mentioned in the filing?

Under the ESPP, eligible employees may contribute up to 5% of adjusted salary each payroll period, and if they have been employed for 12 months, the company makes a 100% matching contribution. These combined contributions are then used to purchase Kingsway Financial Services Inc. shares on the open market through a registered stockbroker.

What roles does the reporting person hold at Kingsway Financial Services (KFS)?

The reporting person, John Taylor Maloney Fitzgerald, is identified as a Director and as an Officer with the title President and CEO of Kingsway Financial Services Inc.