Kingsway Financial (KFS) CEO reports ESPP stock purchase and holdings

Rhea-AI Filing Summary

Kingsway Financial Services Inc. insider John Taylor Maloney Fitzgerald, who serves as President, CEO and Director, reported acquiring additional common shares. On 12/16/2025 he acquired 195 shares of common stock at a price of $12.82 per share, increasing his directly held position to 1,489,534 common shares.

He also reports indirect ownership of 34,100 common shares in each of three separate trusts (Trust-GEF, Trust-LTF and Trust-MPF. According to the notes, the acquired shares were purchased under the Kingsway America Inc. Employee Share Purchase Plan, under which eligible employees can contribute up to 5% of adjusted salary and receive a 100% company match after 12 months of employment. The filing states that the total direct holdings include 400,000 shares of restricted stock granted on March 31, 2021.

Insights

Insider transactions analyst

CEO’s small ESPP purchase modestly increases already large shareholding.

The President and CEO of Kingsway Financial Services Inc. (KFS), John Taylor Maloney Fitzgerald, acquired 195 common shares at $12.82 per share on 12/16/2025. This was done through participation in the Kingsway America Inc. Employee Share Purchase Plan, which allows eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment.

Following this transaction, his directly held stake totals 1,489,534 common shares, which the disclosure notes includes 400,000 restricted shares granted on March 31, 2021. He also reports indirect ownership of 34,100 shares in each of three trusts, indicating additional aligned exposure. The size and nature of this purchase suggest a routine incremental increase rather than a transformative change, so its standalone impact on the investment case is limited.

Insider Trade Summary

Net Buyer: 195 shares ($2,500)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 195 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	195	$12.82	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,489,534 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)
12/16/2025

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	12/16/2025		P		195(1)	A	$12.82	1,489,534(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	12/17/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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FAQ

What insider transaction did KFS report for John Taylor Maloney Fitzgerald?

The filing reports that John Taylor Maloney Fitzgerald, President, CEO and Director of Kingsway Financial Services Inc. (KFS), acquired 195 shares of common stock on 12/16/2025 at a price of $12.82 per share.

How many KFS shares does the CEO beneficially own after this transaction?

After the reported transaction, John Taylor Maloney Fitzgerald beneficially owns 1,489,534 common shares directly, plus 34,100 common shares in each of three separate trusts reported as indirect ownership.

What is the Kingsway America Inc. Employee Share Purchase Plan mentioned in the KFS Form 4?

The Employee Share Purchase Plan allows eligible employees to contribute up to 5% of adjusted salary each pay period, and after 12 months of employment the company contributes a 100% matching amount. Both employee and company contributions are used to buy Kingsway Financial Services Inc. shares on the open market through a registered stockbroker.

Does the CEO’s KFS share total include restricted stock?

Yes. The filing explains that his direct holdings include 400,000 shares of restricted stock that were granted on March 31, 2021.

How are the ESPP shares for KFS acquired in the market?

The explanation states that the administrator of the Employee Share Purchase Plan uses employee and company contributions to purchase Kingsway Financial Services Inc. shares on the open market through a duly registered stockbroker.

What roles does John Taylor Maloney Fitzgerald hold at KFS?

He is disclosed as a Director and as an Officer, serving as President and CEO of Kingsway Financial Services Inc.