STOCK TITAN

Kingsway Financial (NYSE: KFS) insider Stilwell discloses share sales

Filing Impact
(Very High)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

Kingsway Financial Services Inc. director and 10% owner Joseph Stilwell, together with affiliated fund Stilwell Associates, L.P., reported sales of Kingsway common stock on December 15 and 16, 2025. Associates sold 34,269 shares at $12.8005 on December 15 and 10,429 shares at $12.80 on December 16.

After these trades, the report shows Stilwell directly owning 162,500 Kingsway common shares and indirect interests in several large positions, including 545,135 shares held by Stilwell Associates, 3,550,382 shares held by Stilwell Activist Investments, L.P., 457,181 shares held by Stilwell Activist Fund, L.P., and 590,410 shares held by Stilwell Value Partners VII, L.P. He reports these as indirectly owned through his role at Stilwell Value LLC and disclaims beneficial ownership beyond his pecuniary interest.

The filing also lists indirect holdings of 20,000 shares of Class D Preferred Stock and 33,600 and 6,400 shares of Class C Preferred Stock. The Class C and Class D Preferred Stock each have a stated value of $25 per share and are convertible at any time into Kingsway common stock at a conversion basis of 2.63158 common shares per preferred share, with all outstanding Class D Preferred Stock to be redeemed on May 7, 2032 and all outstanding Class C Preferred Stock to be redeemed on February 12, 2032.

Positive

  • None.

Negative

  • None.
Insider Stilwell Joseph, Stilwell Value LLC, Stilwell Associates, L.P., Stilwell Activist Fund, L.P., Stilwell Activist Investments, L.P., Stilwell Value Partners VII, L.P.
Role Director, 10% Owner | 10% Owner | 10% Owner | 10% Owner | 10% Owner | 10% Owner
Sold 44,698 shs ($572K)
Type Security Shares Price Value
Sale Common Stock 10,429 $12.80 $133K
Sale Common Stock 34,269 $12.8005 $439K
holding Class D Preferred Stock -- -- --
holding Class C Preferred Stock -- -- --
holding Class C Preferred Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 534,706 shares (Indirect, See footnote); Class D Preferred Stock — 52,631 shares (Indirect, See footnote); Class C Preferred Stock — 88,421 shares (Indirect, See footnote); Common Stock — 162,500 shares (Direct)
Footnotes (1)
  1. These are shares owned directly by Joseph Stilwell. This Form 4 reports the following sales: on December 15, 2025, Stilwell Associates, L.P. ("Associates") sold 34,269 shares at $12.8005; and on December 16, 2025, Associates sold 10,429 shares at $12.80. These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. The shares of Class D Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032. The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032.
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*
Stilwell Joseph

(Last) (First) (Middle)
200 CALLE DEL SANTO CRISTO

(Street)
SAN JUAN PR 00901

(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 X 10% Owner
Officer (give title below) Other (specify below)
3. Date of Earliest Transaction (Month/Day/Year)
12/15/2025
4. If Amendment, Date of Original Filed (Month/Day/Year)
6. Individual or Joint/Group Filing (Check Applicable Line)
Form filed by One Reporting Person
X 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 162,500(1) D
Common Stock 12/15/2025 S(2) 34,269 D $12.8005 545,135 I See footnote(3)
Common Stock 12/16/2025 S(2) 10,429 D $12.8 534,706 I See footnote(3)
Common Stock 3,550,382 I See footnote(4)
Common Stock 457,181 I See footnote(5)
Common Stock 590,410 I See footnote(6)
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
Class D Preferred Stock $9.5(7) 05/07/2025 05/07/2032(7) Common Stock 52,631(7) 20,000 I See footnote(3)
Class C Preferred Stock $9.5(8) 02/12/2025 02/12/2032(8) Common Stock 88,421(8) 33,600 I See footnote(4)
Class C Preferred Stock $9.5(8) 02/12/2025 02/12/2032(8) Common Stock 16,842(8) 6,400 I See footnote(5)
1. Name and Address of Reporting Person*
Stilwell Joseph

(Last) (First) (Middle)
200 CALLE DEL SANTO CRISTO

(Street)
SAN JUAN PR 00901

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
X Director X 10% Owner
Officer (give title below) Other (specify below)
1. Name and Address of Reporting Person*
Stilwell Value LLC

(Last) (First) (Middle)
111 BROADWAY, 12TH FLOOR

(Street)
NEW YORK NY 10006

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
Director X 10% Owner
Officer (give title below) Other (specify below)
1. Name and Address of Reporting Person*
Stilwell Associates, L.P.

(Last) (First) (Middle)
111 BROADWAY, 12TH FLOOR

(Street)
NEW YORK NY 10006

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
Director X 10% Owner
Officer (give title below) Other (specify below)
1. Name and Address of Reporting Person*
Stilwell Activist Fund, L.P.

(Last) (First) (Middle)
111 BROADWAY, 12TH FLOOR

(Street)
NEW YORK NY 10006

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
Director X 10% Owner
Officer (give title below) Other (specify below)
1. Name and Address of Reporting Person*
Stilwell Activist Investments, L.P.

(Last) (First) (Middle)
111 BROADWAY, 12TH FLOOR

(Street)
NEW YORK NY 10006

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
Director X 10% Owner
Officer (give title below) Other (specify below)
1. Name and Address of Reporting Person*
Stilwell Value Partners VII, L.P.

(Last) (First) (Middle)
111 BROADWAY, 12TH FLOOR

(Street)
NEW YORK NY 10006

(City) (State) (Zip)

Relationship of Reporting Person(s) to Issuer
Director X 10% Owner
Officer (give title below) Other (specify below)
Explanation of Responses:
1. These are shares owned directly by Joseph Stilwell.
2. This Form 4 reports the following sales: on December 15, 2025, Stilwell Associates, L.P. ("Associates") sold 34,269 shares at $12.8005; and on December 16, 2025, Associates sold 10,429 shares at $12.80.
3. These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
4. These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
5. These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
6. These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
7. The shares of Class D Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032.
8. The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032.
/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell 12/17/2025
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC 12/17/2025
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P. 12/17/2025
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P. 12/17/2025
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P. 12/17/2025
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 12/17/2025
** 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 Kingsway Financial (KFS) share sales did Joseph Stilwell report in December 2025?

Stilwell Associates, L.P., an affiliate of Joseph Stilwell, reported selling 34,269 Kingsway Financial common shares at $12.8005 on December 15, 2025, and 10,429 shares at $12.80 on December 16, 2025.

What is Joseph Stilwells relationship to Kingsway Financial (KFS)?

The report identifies Joseph Stilwell as both a director and a 10% owner of Kingsway Financial Services Inc., making him an insider with significant shareholdings.

How many Kingsway Financial (KFS) shares does Joseph Stilwell directly and indirectly own after these transactions?

After the reported sales, Stilwell directly owns 162,500 Kingsway common shares. Indirect positions reported through entities he controls include 545,135 shares held by Stilwell Associates, L.P., 3,550,382 shares held by Stilwell Activist Investments, L.P., 457,181 shares held by Stilwell Activist Fund, L.P., and 590,410 shares held by Stilwell Value Partners VII, L.P., with Stilwell stating he disclaims beneficial ownership beyond his pecuniary interest.

Which affiliated investment partnerships hold Kingsway Financial (KFS) shares for Joseph Stilwell?

The filing attributes Kingsway common share holdings to several Stilwell-affiliated partnerships: Stilwell Associates, L.P., Stilwell Activist Investments, L.P., Stilwell Activist Fund, L.P., and Stilwell Value Partners VII, L.P., all linked to Joseph Stilwell through Stilwell Value LLC.

When will Kingsway Financials Class C and Class D Preferred Stock be redeemed?

The report states that all outstanding Class D Preferred Stock of Kingsway Financial Services Inc. will be redeemed on May 7, 2032, and all outstanding Class C Preferred Stock will be redeemed on February 12, 2032.