Kingsway CEO John Fitzgerald sells 30,000 KFS shares at $13.32

Kingsway Financial Services Inc. reported an insider share sale by its President and CEO, John Taylor Maloney Fitzgerald, who is also a director.

Rhea-AI Filing Summary

Kingsway Financial Services Inc. reported an insider share sale by its President and CEO, John Taylor Maloney Fitzgerald, who is also a director. On 12/23/2025, he sold 30,000 shares of Kingsway common stock in an open market transaction coded as a sale at a price of $13.3238 per share.

After this transaction, he beneficially owned 1,459,534 shares directly, which include 400,000 shares of restricted stock granted on March 31, 2021. He also had indirect beneficial ownership of additional shares through trusts, including 34,100 shares held in each of three trusts identified as Trust‑GEF, Trust‑LTF, and Trust‑MPF.

Insider Trade Summary

Net Seller: 30,000 shares

Net Sell 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Sold 30,000 shs ($400K)

Type	Security	Shares	Price	Value
Sale	Common Stock	30,000	$13.3238	$400K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,459,534 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF); Common Stock — 34,100 shares (Indirect, Trust-LTF); Common Stock — 34,100 shares (Indirect, Trust-MPF)

Footnotes (1)

1. F1. Includes 400,000 shares of restricted stock granted on March 31, 2021.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Kingsway Financial Services (KFS) report?

Kingsway Financial Services reported that its President, CEO, and director, John Taylor Maloney Fitzgerald, sold 30,000 shares of common stock on 12/23/2025 in a transaction coded as a sale.

At what price were the KFS shares sold in this insider transaction?

The 30,000 Kingsway Financial Services common shares were sold at a price of $13.3238 per share.

How many Kingsway Financial Services (KFS) shares does the insider own after the sale?

Following the sale, John Taylor Maloney Fitzgerald beneficially owned 1,459,534 shares of Kingsway common stock directly, plus additional indirect holdings through several trusts.

Does the CEO’s direct KFS shareholding include any restricted stock?

Yes. The direct beneficial ownership of 1,459,534 shares includes 400,000 shares of restricted stock granted on March 31, 2021.

What indirect Kingsway (KFS) shareholdings are reported for the insider?

In addition to his direct holdings, John Taylor Maloney Fitzgerald reported indirect ownership of Kingsway common stock through trusts, including 34,100 shares held in each of three trusts named Trust‑GEF, Trust‑LTF, and Trust‑MPF.

What is John Taylor Maloney Fitzgerald’s role at Kingsway Financial Services (KFS)?

John Taylor Maloney Fitzgerald is reported as both a director and an officer of Kingsway Financial Services, serving as President and CEO.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 12/29/2025 - 04:27 PM EST Learn about SEC filing dates

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)
12/23/2025

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	12/23/2025		S		30,000	D	$13.3238	1,459,534(1)	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. 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	12/29/2025
	** 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.