Kingsway (KFS) CEO Buys via ESPP; 1.53M Shares Held Including 400K Restricted

Rhea-AI Filing Summary

Kingsway Financial Services insider transaction summary: The company’s President and CEO, John Taylor Maloney Fitzgerald, acquired 173 shares of Common Stock under transaction code P at $14.49 per share through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Following the purchase, his total reported beneficial ownership in common stock is 1,530,571 shares, which includes 400,000 shares of restricted stock granted in March 2021. The filing also discloses three indirect holdings of 20,000 shares each held in specified trusts. The ESPP permits employee contributions up to 5% of adjusted salary with a 100% company match after 12 months, and purchases are made on the open market by the plan administrator.

Positive

• Executive participation in ESPP with company matching shows alignment with employee compensation programs
• Substantial beneficial ownership reported (1,530,571 shares), including 400,000 restricted shares, indicating long-term equity stake

Negative

• None.

Insights

Financial Analyst

TL;DR: Insider modestly purchased shares via ESPP; significant reported ownership largely from prior restricted grants.

The small acquisition of 173 shares at $14.49 appears to be routine participation in the ESPP rather than a material open-market purchase. The report shows substantial aggregate ownership of 1,530,571 shares, with a notable component of 400,000 restricted shares granted in 2021. For investors assessing insider alignment, the ESPP buying demonstrates continued executive participation in company compensation programs; however, the single, small purchase reported here is not by itself a material signal about near-term company prospects.

Corporate Governance Expert

TL;DR: Transaction reflects normal exercise of employee benefit; significant restricted stock holdings indicate prior compensation alignment.

The disclosure confirms the CEO holds long-term equity through restricted stock and participates in the ESPP with company matching. The use of plan mechanics (open-market purchases by the plan administrator) and the presence of trusts holding shares are standard governance features. This Form 4 shows compliance with Section 16 reporting and documents beneficial ownership structure without revealing unusual governance concerns.

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
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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)
08/29/2025

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	08/29/2025		P		173(1)	A	$14.49	1,530,571(2)	D
Common Stock								20,000	I	Trust-GEF
Common Stock								20,000	I	Trust-LTF
Common Stock								20,000	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/ Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	09/02/2025
	** 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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** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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FAQ

Who filed the Form 4 for KFS and what was the reported transaction?

The form was filed for John Taylor Maloney Fitzgerald, President and CEO, reporting acquisition of 173 common shares at $14.49 per share under the ESPP.

How many shares does the reporting person beneficially own after the transaction?

The filing reports 1,530,571 shares beneficially owned following the transaction, including 400,000 restricted shares granted in 2021.

How were the shares acquired under the ESPP purchased?

Shares purchased under the ESPP are acquired by the plan administrator on the open market through a registered stockbroker using employee and company contributions.

What are the ESPP contribution and matching terms disclosed in the filing?

Eligible employees may contribute up to 5% of adjusted salary and, after 12 months of employment, the company matches 100% of the employee contribution to purchase shares.

Are there any indirect holdings disclosed for the reporting person?

Yes, the filing shows indirect holdings of 20,000 shares each held in three trusts identified as GEF, LTF, and MPF.