STOCK TITAN

Kingsway (KFS) Insider Trust Transfers; Beneficial Ownership Unchanged

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

John Taylor Maloney, President and CEO and a director of Kingsway Financial Services Inc. (KFS), reported transactions dated 09/26/2025 on a Form 4. The filing shows repeated entries of 14,100-share movements coded J(1) at a price of $14.57 involving transfers between the reporting person’s direct holdings and three trusts (GEF, LTF, MPF). The filing states the reporting person transferred shares to trusts for which he serves as trustee but retained voting and investment power, so his beneficial ownership did not change. The report notes total direct beneficial holdings in the ranges shown: approximately 1,516,645, 1,502,545, and 1,488,445 shares after specific transactions, and discloses inclusion of 400,000 restricted shares granted on 03/31/2021. The Form 4 was signed by an attorney-in-fact, Debra Rouse, on 09/30/2025.

Positive

  • Beneficial ownership unchanged after the reported transfers, indicating no reduction in insider economic or voting exposure
  • Transparent disclosure of trust transfers and retention of voting and investment power
  • 400,000 restricted shares from 03/31/2021 are explicitly disclosed

Negative

  • None.

Insights

TL;DR Insider transferred shares into trusts but retained control; beneficial ownership unchanged, indicating estate/planning reallocation rather than a sale.

The Form 4 records multiple identical J(1)-coded transactions on 09/26/2025 moving 14,100 shares at $14.57 into separate trusts (GEF, LTF, MPF) while the reporting person remains trustee with retained voting and investment power. From an equity-stake perspective, reported direct beneficial totals remain in excess of one million shares across the reported lines, with 400,000 restricted shares noted from a 03/31/2021 grant. These entries are administrative transfers and do not change the economic or voting exposure disclosed on the filing.

TL;DR Transactions appear to be trust transfers with retained control, a routine governance/estate-planning action, not a change in insider intent.

The documentation explicitly states the reporting person retains voting and investment power after transferring shares to trusts for which he serves as trustee. That language is standard when insiders reposition holdings for governance or estate purposes while maintaining control. The signature by an attorney-in-fact and the disclosure of restricted shares from 03/31/2021 are properly noted. No suspension of Section 16 obligations is indicated.

Insider Fitzgerald John Taylor Maloney
Role President and CEO
Type Security Shares Price Value
Other Common Stock 14,100 $14.57 $205K
Other Common Stock 14,100 $14.57 $205K
Other Common Stock 14,100 $14.57 $205K
Other Common Stock 14,100 $14.57 $205K
Other Common Stock 14,100 $14.57 $205K
Other Common Stock 14,100 $14.57 $205K
Holdings After Transaction: Common Stock — 1,516,645 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF)
Footnotes (1)
  1. Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership. Includes 400,000 shares of restricted stock granted on March 31, 2021.
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).
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)
09/26/2025
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 09/26/2025 J(1) 14,100 D $14.57 1,516,645(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 34,100 I Trust-GEF
Common Stock 09/26/2025 J(1) 14,100 D $14.57 1,502,545(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 34,100 I Trust-LTF
Common Stock 09/26/2025 J(1) 14,100 D $14.57 1,488,445(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 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. Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.
2. Includes 400,000 shares of restricted stock granted on March 31, 2021.
/s/ Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald 09/30/2025
** 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.

FAQ

What transactions did John Taylor Maloney report on Form 4 for KFS?

The filing reports multiple 09/26/2025 J(1)-coded movements of 14,100 shares at $14.57 into trusts (GEF, LTF, MPF).

Did the insider reduce his beneficial ownership in KFS?

No. The filing states the reporting person retained voting and investment power, so beneficial ownership did not change.

How many restricted shares does the filing disclose for John Taylor Maloney?

The Form 4 discloses 400,000 restricted shares granted on 03/31/2021.

Who signed the Form 4 and when was it signed?

The Form 4 was signed by Debra Rouse, attorney-in-fact, on 09/30/2025.

What is the reporting person's role at Kingsway Financial Services (KFS)?

The reporting person is listed as Director and as an Officer with the title President and CEO.