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  4. [Form 4] KINGSWAY Corp Insider Trading Activity

Kingsway Corp (KWY) insider group sells 100K shares at $10 on Aug. 13

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

Rhea-AI Filing Summary

KINGSWAY Corp (KWY) insider group led by Joseph Stilwell reported sales of 100,000 shares of Common Stock on August 13, 2026 at $10.00 per share, executed indirectly through Stilwell Associates, L.P., Stilwell Activist Investments, L.P., and Stilwell Value Partners VII, L.P. Joseph Stilwell continues to hold 162,500 Common shares directly and has additional indirect positions in Class C and Class D Preferred Stock that are convertible into Common Stock at $9.50 per share, with conversions based on 2.63158 Common shares per preferred share and mandatory redemption dates in 2032. Footnotes state that these partnership-held shares are owned directly by the respective funds and only indirectly by Stilwell through control of their general partner, and he disclaims beneficial ownership beyond his pecuniary interest.

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Negative

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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 100,000 shs ($1.00M)
Type Security Shares Price Value
Sale Common Stock F2, F3 32,982 $10.00 $330K
Sale Common Stock F2, F4 26,168 $10.00 $262K
Sale Common Stock F2, F5 40,850 $10.00 $409K
holding Class D Preferred Stock F7, F3 -- -- --
holding Class C Preferred Stock F8, F4 -- -- --
holding Class C Preferred Stock F8, F6 -- -- --
holding Common Stock F1 -- -- --
holding Common Stock F6 -- -- --
Holdings After Transaction: Common Stock — 767,629 shares (Indirect, See footnote); Class D Preferred Stock — 52,631 shares (Indirect, See footnote); Class C Preferred Stock — 105,263 shares (Indirect, See footnote); Common Stock — 162,500 shares (Direct)
Footnotes (8)
  1. F1. These are shares owned directly by Joseph Stilwell.
  2. F2. This Form 4 reports the following sales on August 13, 2026: Stilwell Associates, L.P. ("Associates") sold 32,982 shares at $10.00; Stilwell Activist Investments, L.P. ("SAI") sold 26,168 shares at $10.00; and Stilwell Value Partners VII, L.P. ("SVP VII") sold 40,850 shares at $10.00.
  3. F3. 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. F4. These are shares owned directly by 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. F5. These are shares owned directly by 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.
  6. F6. 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.
  7. F7. The shares of Class D Preferred Stock of Kingsway Corporations (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. F8. 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.
Total shares sold 100,000 shares Aggregate Common Stock sales on August 13, 2026 by three Stilwell-affiliated LPs
Sale price $10.00 per share Price for each block of Common Stock sold on August 13, 2026
Shares sold by Stilwell Associates, L.P. 32,982 shares Common Stock sold at $10.00 on August 13, 2026
Shares sold by Stilwell Activist Investments, L.P. 26,168 shares Common Stock sold at $10.00 on August 13, 2026
Shares sold by Stilwell Value Partners VII, L.P. 40,850 shares Common Stock sold at $10.00 on August 13, 2026
Direct Common Stock held 162,500 shares Common Stock directly owned by Joseph Stilwell after reported transactions
Preferred conversion price $9.50 Conversion or exercise price for Class C and Class D Preferred Stock into Common Stock
Class D underlying shares 52,631 shares Common Stock underlying indirectly held Class D Preferred Stock position
indirectly financial
"These are shares owned directly by Associates and indirectly by Joseph Stilwell"
disclaims beneficial ownership financial
"Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly"
stated value financial
"have a stated value of $25 per share and are convertible at any time"
Stated value is an accounting figure a company assigns to a share when the share has no par (legal) value; it becomes the portion of proceeds recorded as the company’s permanent capital for regulatory and bookkeeping purposes. It matters to investors because it affects the equity reported on the balance sheet and the legal limits on distributions or dividend payments, but it is not the market price — think of it as a record-keeping sticker price rather than what buyers actually pay.
conversion basis financial
"at a conversion basis equal to 2.63158 shares of Common Stock"
redeemed financial
"All outstanding shares of Class D Preferred Stock shall be redeemed by the Company"

FAQ

Which entities actually sold Kingsway Corp (KWY) shares in this filing?
The filing states that Stilwell Associates, L.P. sold 32,982 shares, Stilwell Activist Investments, L.P. sold 26,168 shares, and Stilwell Value Partners VII, L.P. sold 40,850 shares, all at $10.00 per share on August 13, 2026.

How many KWY shares does Joseph Stilwell hold directly after these transactions?
The report shows that Joseph Stilwell holds 162,500 shares of Kingsway Corp Common Stock directly as of August 13, 2026, separate from additional indirect and preferred-share-based holdings reported through affiliated investment entities.

Does Joseph Stilwell claim full beneficial ownership of all reported KWY shares?
No. Footnotes state that many shares are owned directly by partnerships and only indirectly by him through control of their general partner; he disclaims beneficial ownership of indirectly held shares except to the extent of his pecuniary interest.

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Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED 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 PUERTO RICO 00901
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
KINGSWAY Corp [ KWY ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirectorX10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
08/13/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
Form filed by One Reporting Person
XForm filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
Common Stock162,500(1)D
Common Stock08/13/2026S(2)32,982D$10267,018ISee footnote(3)
Common Stock08/13/2026S(2)26,168D$102,228,803ISee footnote(4)
Common Stock08/13/2026S(2)40,850D$10330,718ISee footnote(5)
Common Stock436,911ISee 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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Class D Preferred Stock$9.5(7)05/07/202505/07/2032(7)Common Stock52,631(7)20,000ISee footnote(3)
Class C Preferred Stock$9.5(8)02/12/202502/12/2032(8)Common Stock88,421(8)33,600ISee footnote(4)
Class C Preferred Stock$9.5(8)02/12/202502/12/2032(8)Common Stock16,842(8)6,400ISee footnote(6)
1. Name and Address of Reporting Person*
Stilwell Joseph
(Last)(First)(Middle)
200 CALLE DEL SANTO CRISTO
(Street)
SAN JUAN PUERTO RICO 00901
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
XDirectorX10% 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 NEW YORK 10006
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
DirectorX10% 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 NEW YORK 10006
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
DirectorX10% 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 NEW YORK 10006
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
DirectorX10% 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 NEW YORK 10006
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
DirectorX10% 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 NEW YORK 10006
(City)(State)(Zip)
UNITED STATES
(Country)
Relationship of Reporting Person(s) to Issuer
DirectorX10% 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 August 13, 2026: Stilwell Associates, L.P. ("Associates") sold 32,982 shares at $10.00; Stilwell Activist Investments, L.P. ("SAI") sold 26,168 shares at $10.00; and Stilwell Value Partners VII, L.P. ("SVP VII") sold 40,850 shares at $10.00.
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 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 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.
6. 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.
7. The shares of Class D Preferred Stock of Kingsway Corporations (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 Stilwell08/17/2026
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC08/17/2026
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.08/17/2026
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.08/17/2026
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.08/17/2026
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.08/17/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR