Joseph Stilwell - 13 Aug 2026 Form 4 Insider Report for KINGSWAY Corp (KWY)

Reporting relationship
Director, 10%+ Owner
Issuer ticker
KWY
Reported as of
13 Aug 2026
Net transaction value
-$1,000,000
Source evidence Original filing metadata and source links for verification. 4 source fields
SEC form
4
Accepted by SEC
17 Aug 2026, 16:19:04 UTC
Prior SEC filing
03 Aug 2026
Source filing
View source filing
Reporting owner 1 detail
Reporting owner signature
/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell

Key filing fact

Joseph Stilwell filed Form 4 for KINGSWAY Corp (KWY) on 17 Aug 2026.

Key facts

  • This page summarizes Joseph Stilwell's Form 4 filing for KINGSWAY Corp (KWY).
  • 3 reported transactions and 18 derivative rows are listed below.
  • Accepted by SEC: 17 Aug 2026, 16:19.

Change

  • Previous filing in this sequence was filed on 03 Aug 2026.
  • Current net transaction value: -$1,000,000.

Research use

  • This tells you what this filing adds before you inspect full transaction and derivative tables.
  • You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (6)

CIK 0001113303 Primary reporting owner

Stilwell Joseph

Relationship
Director, 10%+ Owner
Address
200 CALLE DEL SANTO CRISTO, SAN JUAN
Signature
/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell
Signature date
17 Aug 2026
CIK 0001397076

Stilwell Value LLC

Relationship
10%+ Owner
Address
111 BROADWAY, 12TH FLOOR, NEW YORK
Signature
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC
Signature date
17 Aug 2026
CIK 0000913960

Stilwell Associates, L.P.

Relationship
10%+ Owner
Address
111 BROADWAY, 12TH FLOOR, NEW YORK
Signature
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.
Signature date
17 Aug 2026
CIK 0001564452

Stilwell Activist Fund, L.P.

Relationship
10%+ Owner
Address
111 BROADWAY, 12TH FLOOR, NEW YORK
Signature
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.
Signature date
17 Aug 2026
CIK 0001573720

Stilwell Activist Investments, L.P.

Relationship
10%+ Owner
Address
111 BROADWAY, 12TH FLOOR, NEW YORK
Signature
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.
Signature date
17 Aug 2026
CIK 0001555931

Stilwell Value Partners VII, L.P.

Relationship
10%+ Owner
Address
111 BROADWAY, 12TH FLOOR, NEW YORK
Signature
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.
Signature date
17 Aug 2026

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$329,820
Shares
-32,982
Change %
-11%
Price
$10.00
Shares after
267,018
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F3
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$261,680
Shares
-26,168
Change %
-1.2%
Price
$10.00
Shares after
2,228,803
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F4
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY transaction

Common Stock

Sale

Transaction value
$408,500
Shares
-40,850
Change %
-11%
Price
$10.00
Shares after
330,718
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F2, F5
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
162,500
Date
13 Aug 2026
Ownership
Direct
Footnotes
F1
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6
KWY holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
436,911
Date
13 Aug 2026
Ownership
See footnote
Footnotes
F6

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
20,000
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
52,631
Exercise price
$9.50
Footnotes
F3, F7
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
33,600
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
88,421
Exercise price
$9.50
Footnotes
F4, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
KWY holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after
6,400
Date
13 Aug 2026
Ownership
See footnote
Underlying class
Common Stock
Underlying amount
16,842
Exercise price
$9.50
Footnotes
F6, F8
* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 8 footnotes

Footnote F1

These are shares owned directly by Joseph Stilwell.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

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