# EDGAR Filing Document

**Accession Number:** 0001072627
**File Stem:** 0001072627-25-000047
**Filing Date:** 2025-12
**Character Count:** 9579
**Document Hash:** 85ff294696bc0b1c85ba3a6bed935c9c
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001072627-25-000047.hdr.sgml**: 20251218

**ACCESSION NUMBER**: 0001072627-25-000047

**CONFORMED SUBMISSION TYPE**: 4

**PUBLIC DOCUMENT COUNT**: 1

**CONFORMED PERIOD OF REPORT**: 20251217

**FILED AS OF DATE**: 20251218

**DATE AS OF CHANGE**: 20251218

**REPORTING-OWNER**: 

**OWNER DATA:**
- **COMPANY CONFORMED NAME:** Patinkin Adam Jonathan
- **CENTRAL INDEX KEY:** 0002063594

**ORGANIZATION NAME:**

**FILING VALUES:**
- **FORM TYPE:** 4
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-15204
- **FILM NUMBER:** 251583411

**MAIL ADDRESS:**
- **STREET 1:** 737 N. MICHIGAN AVENUE
- **STREET 2:** SUITE 1405
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60611
**ISSUER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** KINGSWAY FINANCIAL SERVICES INC
- **CENTRAL INDEX KEY:** 0001072627
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 999999999
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**BUSINESS ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606
- **BUSINESS PHONE:** (312) 766-2144

**MAIL ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606

### UNITED STATES SECURITIES AND EXCHANGE COMMISSION
**Washington, D.C. 20549**

## FORM 4

### STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

[ ] 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**<sup>*</sup><br>Patinkin Adam Jonathan<br><sub>(Last) (First) (Middle)</sub><br>737 N. MICHIGAN AVE.<br>SUITE 1405<br><sub>(Street)</sub><br>CHICAGO, IL 60611<br><sub>(City) (State) (Zip)</sub> | **3. Date of Earliest Transaction (Month/Day/Year)**<br>2025-12-17 | **5. Relationship of Reporting Person(s) to Issuer**<br>(Check all applicable)<br>[X] Director [ ] 10% Owner<br>[ ] Officer (give title below) [ ] Other (specify below)<br>_ _ |
| **2. Issuer Name and Ticker or Trading Symbol**<br>KINGSWAY FINANCIAL SERVICES INC [ KFS ] | **4. If Amendment, Date of Original Filed (Month/Day/Year)**<br>  | **6. Individual or Joint/Group Filing (Check Applicable Line)**<br>[X] Form filed by One Reporting Person<br>[ ] Form filed by More than One Reporting Person |

---

## Table I - Non-Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | 3. Transaction Code (V) | 3. Transaction Code (V) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | Code | V | Amount | (A) or (D) | Price | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| Common Stock | 2025-12-17 |  | X |  | 275000 | A | $8.25 | 1023000 | I | by David Capital Partners Fund, LP<sup>(1)</sup> |
| Common Stock | 2025-12-17 |  | X |  | 540000 | A | $8.25 | 1024000 | I | by David Capital Partners Special Situation Fund, LP<sup>(2)</sup> |
| Common Stock | 2025-12-17 |  | X |  | 500000 | A | $8.25 | 1524000 | I | by David Capital Partners Special Situation Fund, LP<sup>(2)</sup> |

---

## Table II - Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | 4. Transaction Code (V) | 4. Transaction Code (V) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 6. Date Exercisable and Expiration Date | 6. Date Exercisable and Expiration Date | 7. Title and Amount of Underlying Securities | 7. Title and Amount of Underlying Securities | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | Code | V | (A) | (D) | Date Exercisable | Expiration Date | Title | Amount or Number of Shares | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| Class D Preferred Stock | 9.50<sup>(3)</sup> |  |  |  |  |  |  | 2025-05-08 | 2032-05-08<sup>(3)</sup> | Common Stock | 68421.08<sup>(3)</sup> |  | 26000 | I | by David Capital Partners Special Situation Fund, LP |
| Stock Option (Right to Buy) | 8.25<sup>(4)</sup> | 2025-12-17 |  | X |  |  | 275000 | 2025-12-17<sup>(4)</sup> | 2025-12-29<sup>(4)</sup> | Common Stock | 275000 | $0 | 0 | I | by David Capital Partners Fund, LP |
| Stock Option (Right to Buy) | 8.25<sup>(4)</sup> | 2025-12-17 |  | X |  |  | 540000 | 2025-12-17<sup>(4)</sup> | 2025-12-29<sup>(4)</sup> | Common Stock | 540000 | $0 | 0 | I | by David Capital Partners Special Situation Fund, LP |
| Stock Option (Right to Buy) | 8.25<sup>(5)</sup> | 2025-12-17 |  | X |  |  | 500000 | 2025-12-17<sup>(5)</sup> | 2025-12-29<sup>(5)</sup> | Common Stock | 500000 | $0 | 0 | I | by David Capital Partners Special Situation Fund, LP |

---

### Footnotes:

(1) 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.

(2) 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.

(3) 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.

(4) 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.

(5) 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.

**Signature:** /s/ Robert E. Buckner II, attorney-in-fact for Adam Jonathan Patinkin  
**Date:** 2025-12-18

### Remarks:

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.**