4//SEC Filing
Stilwell Associates, L.P. 4
Accession 0001104659-25-122064
CIK 0001072627other
Filed
Dec 16, 7:00 PM ET
Accepted
Dec 17, 4:30 PM ET
Size
25.5 KB
Accession
0001104659-25-122064
Insider Transaction Report
Form 4
Stilwell Joseph
Director10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Stilwell Value LLC
Director10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Stilwell Associates, L.P.
10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Stilwell Activist Fund, L.P.
10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Stilwell Activist Investments, L.P.
10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Stilwell Value Partners VII, L.P.
10% Owner
Transactions
- Sale
Common Stock
2025-12-15$12.80/sh−34,269$438,660→ 545,135 total(indirect: See footnote) - Sale
Common Stock
2025-12-16$12.80/sh−10,429$133,491→ 534,706 total(indirect: See footnote)
Holdings
- 162,500
Common Stock
- 3,550,382(indirect: See footnote)
Common Stock
- 457,181(indirect: See footnote)
Common Stock
- 590,410(indirect: See footnote)
Common Stock
- 20,000(indirect: See footnote)
Class D Preferred Stock
Exercise: $9.50From: 2025-05-07Exp: 2032-05-07→ Common Stock (52,631 underlying) - 33,600(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (88,421 underlying) - 6,400(indirect: See footnote)
Class C Preferred Stock
Exercise: $9.50From: 2025-02-12Exp: 2032-02-12→ Common Stock (16,842 underlying)
Footnotes (8)
- [F1]These are shares owned directly by Joseph Stilwell.
- [F2]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.
- [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.
- [F4]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.
- [F5]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.
- [F6]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.
- [F7]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.
- [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.
Documents
Issuer
KINGSWAY FINANCIAL SERVICES INC
CIK 0001072627
Entity typeother
IncorporatedDE
Related Parties
1- filerCIK 0000913960
Filing Metadata
- Form type
- 4
- Filed
- Dec 16, 7:00 PM ET
- Accepted
- Dec 17, 4:30 PM ET
- Size
- 25.5 KB