Adam Jonathan Patinkin - 17 Dec 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Reporting relationship: Director
Issuer ticker: KFS
Reported as of: 17 Dec 2025
Net transaction value: +$10,848,750
SEC form: 4
Accepted by SEC: 18 Dec 2025, 16:25:54 UTC
Prior SEC filing: 09 May 2025
Next SEC filing: 20 May 2026
Source filing: View source filing
Reporting owner signature: /s/ Robert E. Buckner II, attorney-in-fact for Adam Jonathan Patinkin

Key filing fact

Adam Jonathan Patinkin filed Form 4 for KINGSWAY FINANCIAL SERVICES INC (KFS) on 18 Dec 2025.

Key facts

This page summarizes Adam Jonathan Patinkin's Form 4 filing for KINGSWAY FINANCIAL SERVICES INC (KFS).
6 reported transactions and 4 derivative rows are listed below.
Accepted by SEC: 18 Dec 2025, 16:25.

Change

Previous filing in this sequence was filed on 09 May 2025.
Current net transaction value: +$10,848,750.

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 (1)

CIK 0002063594 Primary reporting owner

Patinkin Adam Jonathan

Relationship: Director
Address: 737 N. MICHIGAN AVE., SUITE 1405, CHICAGO
Signature: /s/ Robert E. Buckner II, attorney-in-fact for Adam Jonathan Patinkin
Signature date: 18 Dec 2025

Reported non-derivative transactions

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

KFS transaction

Common Stock

Exercise of in-the-money or at-the-money derivative security

Transaction value: $2,268,750
Shares: +275,000
Change %: +37%
Price: $8.25
Shares after: 1,023,000
Date: 17 Dec 2025
Ownership: by David Capital Partners Fund, LP
Footnotes: F1

KFS transaction

Common Stock

Exercise of in-the-money or at-the-money derivative security

Transaction value: $4,455,000
Shares: +540,000
Change %: +112%
Price: $8.25
Shares after: 1,024,000
Date: 17 Dec 2025
Ownership: by David Capital Partners Special Situation Fund, LP
Footnotes: F2

KFS transaction

Common Stock

Exercise of in-the-money or at-the-money derivative security

Transaction value: $4,125,000
Shares: +500,000
Change %: +49%
Price: $8.25
Shares after: 1,524,000
Date: 17 Dec 2025
Ownership: by David Capital Partners Special Situation Fund, LP
Footnotes: F2

Reported derivative securities

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

KFS transaction Derivative

Stock Option (Right to Buy)

Exercise of in-the-money or at-the-money derivative security

Transaction value: $0
Shares: -275,000
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: by David Capital Partners Fund, LP
Underlying class: Common Stock
Underlying amount: 275,000
Exercise price: $8.25
Footnotes: F4

KFS transaction Derivative

Stock Option (Right to Buy)

Exercise of in-the-money or at-the-money derivative security

Transaction value: $0
Shares: -540,000
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: by David Capital Partners Special Situation Fund, LP
Underlying class: Common Stock
Underlying amount: 540,000
Exercise price: $8.25
Footnotes: F4

KFS transaction Derivative

Stock Option (Right to Buy)

Exercise of in-the-money or at-the-money derivative security

Transaction value: $0
Shares: -500,000
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: by David Capital Partners Special Situation Fund, LP
Underlying class: Common Stock
Underlying amount: 500,000
Exercise price: $8.25
Footnotes: F5

KFS holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 26,000
Date: 17 Dec 2025
Ownership: by David Capital Partners Special Situation Fund, LP
Underlying class: Common Stock
Underlying amount: 68,421
Exercise price: $9.50
Footnotes: F3

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 5 footnotes

Footnote F1

David Capital Partners, LLC, as the investment manager and general partner of David Capital Partners Fund, LP ("DCP Fund"), may be deemed to be a beneficial owner of the shares of common stock disclosed as directly owned by DCP Fund. Due to his position as managing partner of David Capital Partners, LLC, Mr. Patinkin may be deemed to be a beneficial owner of the shares of common stock disclosed as directly owned by DCP Fund. David Capital Partners, LLC and Mr. Patinkin expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

Footnote F2

David Capital Partners, LLC, as the investment manager and general partner of David Capital Partners Special Situation Fund, LP ("DCP Special"), may be deemed to be a beneficial owner of the shares of common stock disclosed as directly owned by DCP Special. Due to his position as managing partner of David Capital Partners, LLC, Mr. Patinkin may be deemed to be a beneficial owner of the shares of common stock disclosed as directly owned by DCP Special. David Capital Partners, LLC and Mr. Patinkin expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

Footnote F3

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 8, 2032.

Footnote F4

DCP Fund and DCP Special entered into an option agreement, dated March 31, 2025, with Stilwell Value LLC, to acquire 275,000 and 540,000 shares of common stock, respectively, at an exercise price of $8.25 per share, which options were originally exercisable by DCP Fund and DCP Special together in whole, and not in part, on December 29, 2025 and which were set to expire at 5:00 p.m. Eastern Time on December 29, 2025. The option agreement was amended on December 17, 2025, so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.

Footnote F5

DCP Special entered into an option agreement, dated March 31, 2025, with Oakmont Capital Inc., to acquire 500,000 shares of common stock at an exercise price of $8.25 per share, which option was originally exercisable in whole, and not in part, on December 29, 2025 and which was set to expire at 5:00 p.m. Eastern Time on December 29, 2025. The option agreement was amended on December 17, 2025, so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.

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