[SCHEDULE 13D/A] KINGSWAY FINANCIAL SERVICES INC SEC Filing
Filing Impact
Filing Sentiment
Form Type
SCHEDULE 13D/A
Kingsway Financial Services Inc. received an updated ownership disclosure from a shareholder group led by Oakmont Capital Inc. In an option agreement exercised on December 17, 2025, Oakmont sold 500,000 Kingsway common shares to David Capital Partners Special Situation Fund, LP at US$8.25 per share.
After this transaction, the group comprising Oakmont, E.J.K. Holdings Inc., 1272562 Ontario Inc., Terence M. Kavanagh and Gregory P. Hannon is reported to beneficially own 2,386,119 shares, or about 8.24% of Kingsway’s outstanding common stock as of that date. This percentage is based on 28,956,152 shares outstanding as of November 6, 2025, plus 315,789 shares issuable upon exercise of the group’s Series B warrants and conversion of its Class C preferred shares.
Positive
- None.
Negative
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SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549 |
SCHEDULE 13D
Under the Securities Exchange Act of 1934
(Amendment No. 6)
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KINGSWAY FINANCIAL SERVICES INC (Name of Issuer) |
Common Stock, $0.01 par value per share (Title of Class of Securities) |
496904202 (CUSIP Number) |
Terence M. Kavanagh 45 St. Clair Avenue West, Suite 400, Toronto, A6, M4V 1K9 (416) 923-1477 (Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications) |
12/17/2025 (Date of Event Which Requires Filing of This Statement) |
If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.
The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the
Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other
provisions of the Act (however, see the Notes).
SCHEDULE 13D
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| CUSIP No. | 496904202 |
| 1 |
Name of reporting person
Oakmont Capital Inc. | ||||||||
| 2 | Check the appropriate box if a member of a Group (See Instructions)
(a)
(b) | ||||||||
| 3 | SEC use only | ||||||||
| 4 |
Source of funds (See Instructions)
WC | ||||||||
| 5 |
Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)
| ||||||||
| 6 | Citizenship or place of organization
ONTARIO, CANADA
| ||||||||
| Number of Shares Beneficially Owned by Each Reporting Person With: |
| ||||||||
| 11 | Aggregate amount beneficially owned by each reporting person
2,386,119.00 | ||||||||
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)
| ||||||||
| 13 | Percent of class represented by amount in Row (11)
8.24 % | ||||||||
| 14 | Type of Reporting Person (See Instructions)
CO |
Comment for Type of Reporting Person:
In reference to Rows 11 and 13 above, see Item 5 herein.
SCHEDULE 13D
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| CUSIP No. | 496904202 |
| 1 |
Name of reporting person
E.J.K. Holdings Inc. | ||||||||
| 2 | Check the appropriate box if a member of a Group (See Instructions)
(a)
(b) | ||||||||
| 3 | SEC use only | ||||||||
| 4 |
Source of funds (See Instructions)
WC | ||||||||
| 5 |
Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)
| ||||||||
| 6 | Citizenship or place of organization
ONTARIO, CANADA
| ||||||||
| Number of Shares Beneficially Owned by Each Reporting Person With: |
| ||||||||
| 11 | Aggregate amount beneficially owned by each reporting person
2,386,119.00 | ||||||||
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)
| ||||||||
| 13 | Percent of class represented by amount in Row (11)
8.24 % | ||||||||
| 14 | Type of Reporting Person (See Instructions)
CO |
Comment for Type of Reporting Person:
In reference to Rows 11 and 13 above, see Item 5 herein.
SCHEDULE 13D
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| CUSIP No. | 496904202 |
| 1 |
Name of reporting person
1272562 Ontario Inc | ||||||||
| 2 | Check the appropriate box if a member of a Group (See Instructions)
(a)
(b) | ||||||||
| 3 | SEC use only | ||||||||
| 4 |
Source of funds (See Instructions)
WC | ||||||||
| 5 |
Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)
| ||||||||
| 6 | Citizenship or place of organization
ONTARIO, CANADA
| ||||||||
| Number of Shares Beneficially Owned by Each Reporting Person With: |
| ||||||||
| 11 | Aggregate amount beneficially owned by each reporting person
2,386,119.00 | ||||||||
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)
| ||||||||
| 13 | Percent of class represented by amount in Row (11)
8.24 % | ||||||||
| 14 | Type of Reporting Person (See Instructions)
CO |
Comment for Type of Reporting Person:
In reference to Rows 11 and 13 above, see Item 5 herein.
SCHEDULE 13D
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| CUSIP No. | 496904202 |
| 1 |
Name of reporting person
Terence M. Kavanagh | ||||||||
| 2 | Check the appropriate box if a member of a Group (See Instructions)
(a)
(b) | ||||||||
| 3 | SEC use only | ||||||||
| 4 |
Source of funds (See Instructions)
PF | ||||||||
| 5 |
Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)
| ||||||||
| 6 | Citizenship or place of organization
CANADA (FEDERAL LEVEL)
| ||||||||
| Number of Shares Beneficially Owned by Each Reporting Person With: |
| ||||||||
| 11 | Aggregate amount beneficially owned by each reporting person
2,386,119.00 | ||||||||
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)
| ||||||||
| 13 | Percent of class represented by amount in Row (11)
8.24 % | ||||||||
| 14 | Type of Reporting Person (See Instructions)
IN |
Comment for Type of Reporting Person:
In reference to Rows 11, 12 and 13 above, see Item 5 herein.
SCHEDULE 13D
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| CUSIP No. | 496904202 |
| 1 |
Name of reporting person
Gregory P. Hannon | ||||||||
| 2 | Check the appropriate box if a member of a Group (See Instructions)
(a)
(b) | ||||||||
| 3 | SEC use only | ||||||||
| 4 |
Source of funds (See Instructions)
PF | ||||||||
| 5 |
Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)
| ||||||||
| 6 | Citizenship or place of organization
CANADA (FEDERAL LEVEL)
| ||||||||
| Number of Shares Beneficially Owned by Each Reporting Person With: |
| ||||||||
| 11 | Aggregate amount beneficially owned by each reporting person
2,386,119.00 | ||||||||
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)
| ||||||||
| 13 | Percent of class represented by amount in Row (11)
8.24 % | ||||||||
| 14 | Type of Reporting Person (See Instructions)
IN |
Comment for Type of Reporting Person:
In reference to Rows 11 and 13 above, see Item 5 herein.
SCHEDULE 13D
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| Item 1. | Security and Issuer | |
| (a) | Title of Class of Securities:
Common Stock, $0.01 par value per share | |
| (b) | Name of Issuer:
KINGSWAY FINANCIAL SERVICES INC | |
| (c) | Address of Issuer's Principal Executive Offices:
10 S. RIVERSIDE PLAZA, SUITE 1520, CHICAGO,
ILLINOIS
, 60606. | |
Item 1 Comment:
This Amendment No. 6 to Schedule 13D (this "Amendment") amends the Statement on Schedule 13D filed on March 5, 2009, as previously amended on December 12, 2012, September 13, 2013, September 20, 2013, March 21, 2019 and April 9, 2025 (the "Schedule 13D") by Oakmont Capital Inc., an Ontario corporation ("Oakmont"), E.J.K. Holdings Inc., an Ontario corporation ("EJK"), 1272562 Ontario Inc., an Ontario corporation ("1272562"), and Gregory P. Hannon and Terence M. Kavanagh, each of whom is a citizen of Canada (collectively, the "Reporting Persons"). Capitalized terms used herein not otherwise defined shall have the meaning ascribed to them in the Schedule 13D. All references to common stock in this Amendment have been adjusted for the rights offering which expired on September 6, 2013 (the "Rights Offering"). | ||
| Item 4. | Purpose of Transaction | |
Item 4 of this Schedule 13D is hereby supplemented as follows:
On December 17, 2025, the option agreement described in Item 6 of this Amendment No. 6 was exercised. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special (as hereafter defined) at a price of US$8.25 per Share.
Except as disclosed in Item 6 of this Amendment No. 6, the Reporting Persons have no current plans or proposals which relate to or would result in any of the events described in Items (a) through (j) of the instructions to Item 4 of Schedule 13D. The information set forth in Item 6 of this Amendment No. 6 is incorporated herein by reference. | ||
| Item 5. | Interest in Securities of the Issuer | |
| (a) | (a) Item 5(a) and 5(b) of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:
As of the close of business on December 17, 2025, the Reporting Persons may be deemed to beneficially own, in the aggregate, 2,386,119 Shares, representing approximately 8.24% of the Issuer's outstanding Shares (based upon the 28,956,152 Shares stated to be outstanding as of November 6, 2025 in the Issuer's Form 10-Q dated November 6, 2025 for the quarter ended September 30, 2025 plus 315,789 Shares issuable upon exercise of the Reporting Persons' Series B Warrants and conversion of the Report Persons' Class C Preferred Shares).
Oakmont has sole voting power and sole dispositive power with respect to the 2,303,619 Shares that it owns directly. Oakmont may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.
EJK has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. EJK may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.
1272562 has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of its ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. 1272562 may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.
Mr. Kavanagh has sole voting power and sole dispositive power with respect to 34,750 Shares owned through a self-directed Retirement Savings Plan. Mr. Kavanagh has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of Mr. Kavanagh's ownership of all the outstanding voting stock of EJK, and EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. Mr. Kavanagh may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group.
Mr. Kavanagh's sister owns directly and through a registered retirement savings account 13,500 Shares as to which Mr. Kavanagh disclaims beneficial ownership.
Mr. Hannon has sole voting power and sole dispositive power with respect to the following 34,000 Shares:
(i) the 29,500 Shares owned directly by him or through a self-directed Retirement Savings Plan; and
(ii) the 4,500 Shares owned directly by two trusts for Mr. Hannon's children; Mr. Hannon is the sole trustee of each such trust.
Mr. Hannon has shared voting power and shared dispositive power with respect to the following 2,317,369 Shares:
(i) the 2,303,619 Shares owned directly by Oakmont, by virtue of his ownership of all of the capital stock of 1272562, and 1272562's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont; and
(ii) the 13,750 Shares owned directly by Mr. Hannon's spouse.
Mr. Hannon may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group. | |
| (b) | The information set forth in Item 5(a) of this Amendment No. 6 is incorporated herein by reference. | |
| (c) | The information set forth in Item 4 of this Amendment No. 6 is incorporated herein by reference. | |
| Item 6. | Contracts, Arrangements, Understandings or Relationships With Respect to Securities of the Issuer | |
Item 6 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:
On December 17, 2025, David Capital Partners Special Situation Fund, LP ("DCP Special") exercised in full the option agreement with Oakmont filed as Exhibit 99.1 to Amendment No. 5 to the 13D. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special at a price of US$8.25 per Share. | ||
| SIGNATURE | |
After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.
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