[Form 4] Kingsway Financial Services, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Stagwell Inc. (STGW) – Form 4 insider transaction

Director Eli Samaha elected to take his Q2-2025 board fee in equity rather than cash, receiving 4,444 fully-vested Class A shares on 01-Jul-2025. The implied conversion of a US$20,000 fee equates to an estimated price of roughly $4.50 per share (based on the prior-day close). Following the grant, Samaha’s direct ownership rises to 134,281 shares. In addition, he continues to indirectly control 8,014,322 shares through funds managed by Madison Avenue Partners, LP, for which he serves as managing partner. The transaction is coded “A” (acquisition) and reflects routine non-cash director compensation rather than an open-market purchase. No derivative securities were reported.

The filing modestly increases insider ownership but does not represent a material capital commitment or signal a directional view on the company’s valuation.

Positive

• Director equity election modestly strengthens alignment between board member and common shareholders.

Negative

• None.

Insights

Corporate Governance Analyst

TL;DR: Routine equity fee; small, aligns interests, negligible market impact.

This Form 4 shows Mr. Samaha opting for stock instead of cash, a common governance practice that marginally improves board-member alignment with shareholders. The absolute size—4.4k shares or ~US$20k—is immaterial versus the director’s existing 8 million indirect shares and STGW’s 281 million fully-diluted share count. Because it is a fee conversion, not an out-of-pocket purchase, signaling value is weak. The move is governance-friendly but not financially impactful.

Securities Analyst

TL;DR: Neutral; insider equity grant does not alter investment thesis.

The equity-in-lieu arrangement increases Samaha’s direct stake to 134k shares, but his economic exposure already lies in the 8.0 million shares held via Madison Avenue funds. No derivatives or sales were disclosed. Given the small dollar value and routine nature, I classify the filing as neutral for valuation and liquidity. Investors typically watch for sizeable cash purchases or sales; this event lacks that signaling power.

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)
07/01/2025

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	07/01/2025		P		179(1)	A	$14.02	1,529,876(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	07/01/2025
	** 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

How many Stagwell (STGW) shares did Director Eli Samaha acquire on 01-Jul-2025?

4,444 Class A shares were issued as payment for his quarterly board fee.

What is Eli Samaha’s total direct ownership in STGW after the transaction?

His direct holdings increased to 134,281 shares.

Does the director hold additional shares indirectly?

Yes, 8,014,322 shares are held by funds managed by Madison Avenue Partners, LP.

Was this an open-market purchase?

No; it was an equity-in-lieu-of-cash board fee under the company’s Non-Employee Director Compensation Policy.

What price was used to calculate the number of shares issued?

The filing implies a price of about $4.50 per share (US$20,000 fee ÷ 4,444 shares).

Were any derivative securities reported?

No derivative positions were listed in Table II.