KINGSWAY FINL SVCS INC KWY
COM NEW · Common Stock · CUSIP 496904202
- SectorFinancials
- IndustryFire, Marine & Casualty Insurance
- HeadquartersChicago, IL
- FilingsSEC EDGAR
* Summed across managers. Shares that two managers' reports both contain – a subsidiary's holdings that its parent's report includes too, or a sub-adviser's in its client's – are counted once ($4.4k this quarter). Holder counts are more reliable. Shares outstanding: 28.9m as of 2026-08-06, from the company's own SEC filing; the percentage can still exceed 100%: lent-out shares are counted by the lender and the buyer, and some reports overlap without saying so. Implied quarter-end price ≈ $10.42. Options: 0 managers hold calls (— notional), 2 hold puts ($126.1k).
Trends to Q2 2026
Institutional holders
Managers reporting a position, each quarter
Numbers
| Quarter | Holders |
|---|---|
| Q3 2022 | 23 |
| Q4 2022 | 24 |
| Q1 2023 | 39 |
| Q2 2023 | 45 |
| Q3 2023 | 49 |
| Q4 2023 | 47 |
| Q1 2024 | 49 |
| Q2 2024 | 50 |
| Q3 2024 | 56 |
| Q4 2024 | 61 |
| Q1 2025 | 66 |
| Q2 2025 | 67 |
| Q3 2025 | 70 |
| Q4 2025 | 74 |
| Q1 2026 | 75 |
| Q2 2026 | 73 |
Buyers vs sellers
Managers adding to or starting a position, vs cutting or selling out
Numbers
| Quarter | Bought or added | Cut or sold out |
|---|---|---|
| Q3 2024 | 29 | 12 |
| Q4 2024 | 31 | 20 |
| Q1 2025 | 26 | 24 |
| Q2 2025 | 42 | 26 |
| Q3 2025 | 40 | 20 |
| Q4 2025 | 33 | 27 |
| Q1 2026 | 32 | 34 |
| Q2 2026 | 40 | 30 |
Calls vs puts
Options held, notional value, last 4 quarters. P/C = puts ÷ calls
Numbers
| Quarter | Calls | Puts | P/C |
|---|---|---|---|
| Q3 2025 | $0 | $487.8k | — |
| Q4 2025 | $0 | $980.5k | — |
| Q1 2026 | $0 | $376.5k | — |
| Q2 2026 | $0 | $126.1k | — |
Biggest buyers
| VANGUARD CAPITAL MANAGEMENT LLC | Added | +122.0k |
| BlackRock, Inc. | Added | +121.9k |
| UNITED CAPITAL FINANCIAL ADVISORS, LLC | New | +82.8k |
| GOLDMAN SACHS GROUP INC | Added | +59.1k |
| CITADEL ADVISORS LLC | Added | +56.0k |
| GEODE CAPITAL MANAGEMENT, LLC | Added | +37.4k |
| Nuveen, LLC | Added | +27.9k |
| VANGUARD PORTFOLIO MANAGEMENT LLC | Added | +24.4k |
| OSAIC HOLDINGS, INC. | Added | +20.5k |
| CHARLES SCHWAB INVESTMENT MANAGEMENT INC | Added | +17.4k |
Biggest sellers
| Capricorn Fund Managers Ltd | Reduced | -374.4k |
| Greenhaven Road Investment Management, L.P. | Reduced | -155.6k |
| Waverly Advisors, LLC | Sold out | -125.0k |
| STATE OF WISCONSIN INVESTMENT BOARD | Sold out | -29.2k |
| JANE STREET GROUP, LLC | Sold out | -22.0k |
| MORGAN STANLEY | Reduced | -18.2k |
| RENAISSANCE TECHNOLOGIES LLC | Reduced | -16.9k |
| BANK OF AMERICA CORP /DE/ | Reduced | -16.3k |
| MERCER GLOBAL ADVISORS INC /ADV | Sold out | -11.6k |
| SIMPLEX TRADING, LLC | Reduced | -10.2k |
Biggest calls
| None |
Biggest puts
| SUSQUEHANNA INTERNATIONAL GROUP, LLP | Added | $124.0k11.9k shares |
| SIMPLEX TRADING, LLC | Reduced | $2.1k200 shares |
Options at notional value: the value of the shares the contracts control, as filers report them, not what the options cost. Not included in the holders, shares or buying above.
Major shareholders (over 5%)
Anyone who owns more than 5% of a class of the company's shares has to say so: on Schedule 13D if they may try to influence or control the company, on 13G if they're a passive investor, and update it as the stake changes. Each holder's latest filing, from 19 Dec 2024 on; percentages are of the share class, as the holder worked them out.
| Holder | Stake |
|---|---|
Stilwell Joseph
13D · may seek influence
-6.1 pts · filed 2025-12-19
Stated purposeWe are filing this Forty-Ninth Amendment to report that members of the Group have sold shares of Common Stock pursuant to the terms of the Option Agreements dated March 31, 2025, as amended each on December 17, 2025, by the Option Agreement Amendments. The Option Agreements and the Option Agreement Amendments are defined and further discussed in Item 6 of this Forty-Ninth Amendment. A copy of the form of an Option Agreement Amendment is attached as Exhibit 18 to this Forty-Ninth Amendment. Our purpose in acquiring shares of Common Stock of the Issuer was to profit from the appreciation in the market price of the shares of Common Stock through asserting shareholder rights. We have succeeded and intend to gradually reduce our position over time. Members of the Group may seek to make additi… Full filing |
12.7% |
David Capital Partners, LLC
13D · may seek influence
+1.3 pts · filed 2026-05-20
Stated purposeMr. Patinkin was appointed as Chairman of the Board of Directors of the Company on March 11, 2026. On May 18, 2026, in connection with his appointment as Chairman, the Company granted to Mr. Patinkin a 10-year option to purchase up to 400,000 shares of Common Stock, which will vest in four equal annual installments beginning on the grant date, or May 18, 2026. The first and second installments have an exercise price of $20.00 per share, while the third and fourth installments have an exercise price of $30.00 per share. In addition, on May 18, 2026, certain employees of David Capital Partners, LLC who provide consulting services to the Company were granted 10-year options to purchase up to 200,000 shares of Common Stock in the aggregate, which have an exercise price of $25.00 per share and … Full filing |
10.3% |
Hannon Gregory Paul
13D · may seek influence
-2.1 pts · filed 2025-12-18
Stated purposeItem 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. Full filing |
8.2% |
| Greenhaven Road Investment Management, L.P. 13G · passive investor new · filed 2025-11-06 | 6.8% |
| Frischer Charles L 13D · may seek influence filed 2025-05-14 | 6.8% |
Fell to 5% or below in the last year: Capricorn Fund Managers Ltd (4.9%, 2026-07-13), MIRABELLA FINANCIAL SERVICES LLP (0.0%, 2026-04-10), Palm Management (US) LLC (1.5%, 2025-12-18)
Insider purchases and sales since 1 Apr 2026
Shares bought or sold by the company's own officers, directors and 10% owners, in the open market or privately, as they reported to the SEC on Form 4 (due within two business days of the trade). Grants, option exercises, shares withheld for tax and gifts aren't included.
Officers and directors buying vs selling
Number of people, by quarter (10% owners not included)
Numbers
| Quarter | Buying | Bought | Selling | Sold | Sold under a plan |
|---|---|---|---|---|---|
| Q4 2024 | 2 | $23.1k | 1 | $5.3m | $95.5k |
| Q1 2025 | 2 | $16.9k | 1 | $8.0m | — |
| Q2 2025 | 2 | $12.8k | 1 | $2.3m | — |
| Q3 2025 | 2 | $28.4k | 1 | $3.4m | — |
| Q4 2025 | 2 | $24.4k | 3 | $2.9m | — |
| Q1 2026 | 2 | $24.4k | 0 | — | — |
| Q2 2026 | 3 | $67.4k | 1 | $154.3k | — |
| Q3 2026 | 3 | $147.0k | 1 | $1.0m | — |
| Date | Insider | Trade | Value |
|---|---|---|---|
| 2026-09-30 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $7.9k858 shares |
| 2026-09-30 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k269 shares |
| 2026-09-30 | Hansen Kent A CFO & EVP | Bought | $1.6k169 shares |
| 2026-09-28 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $25.2k2.7k shares |
| 2026-09-15 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k254 shares |
| 2026-09-15 | Hansen Kent A CFO & EVP | Bought | $1.6k159 shares |
| 2026-08-31 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k239 shares |
| 2026-08-31 | Hansen Kent A CFO & EVP | Bought | $1.6k149 shares |
| 2026-08-20 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $7.6k769 shares |
| 2026-08-19 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $69.2k7.0k shares |
| 2026-08-18 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $12.7k1.3k shares |
| 2026-08-17 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k254 shares |
| 2026-08-17 | Hansen Kent A CFO & EVP | Bought | $1.6k158 shares |
| 2026-08-13 | Stilwell Joseph +5 Director · See footnote | Sold | $1.0m100.0k shares |
| 2026-07-30 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k278 shares |
| 2026-07-30 | Hansen Kent A CFO & EVP | Bought | $1.6k174 shares |
| 2026-07-15 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k256 shares |
| 2026-07-15 | Hansen Kent A CFO & EVP | Bought | $1.6k161 shares |
| 2026-06-30 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k239 shares |
| 2026-06-30 | Hansen Kent A CFO & EVP | Bought | $1.6k149 shares |
| 2026-06-15 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k240 shares |
| 2026-06-15 | Hansen Kent A CFO & EVP | Bought | $1.6k150 shares |
| 2026-05-29 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $37.7k3.8k shares |
| 2026-05-29 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k250 shares |
| 2026-05-29 | Hansen Kent A CFO & EVP | Bought | $1.6k156 shares |
| 2026-05-28 | Horowitz Joshua Director · by Palm Global Small Cap Master Fund LP | Bought | $7.0k700 shares |
| 2026-05-21 | Fitzgerald John Taylor Maloney President and CEO, director · Trust-MPF | Sold | $50.7k5.0k shares |
| 2026-05-20 | Fitzgerald John Taylor Maloney President and CEO, director · Trust-LTF | Sold | $52.1k5.0k shares |
| 2026-05-19 | Fitzgerald John Taylor Maloney President and CEO, director · Trust-GEF | Sold | $51.5k5.0k shares |
| 2026-05-15 | Fitzgerald John Taylor Maloney President and CEO, director | Bought | $2.5k230 shares |
The latest 30 of 34 trades.
Their holding: how much the trade added to or took from the insider's holding (direct, or the trust or fund named). The same trade is sometimes reported by more than one insider, such as a fund and the director who represents it; totals count it once. A value is left blank where the reported price is far from the market price (usually a typo).
Holders, Q2 2026
| Manager | Shares | Change |
|---|---|---|
| STILWELL VALUE LLC 20.10% of their portfolio | 3.4m $35.0m | Unchanged |
| Greenhaven Road Investment Management, L.P. 11.47% of their portfolio | 1.7m $17.7m | Reduced -155.6k |
| Capricorn Fund Managers Ltd 1.18% of their portfolio | 1.4m $14.7m | Reduced -374.4k |
| BlackRock, Inc. 0.00% of their portfolio | 1.3m $13.2m | Added +121.9k |
| VANGUARD CAPITAL MANAGEMENT LLC 0.00% of their portfolio | 856.4k $8.9m | Added +122.0k |
| GEODE CAPITAL MANAGEMENT, LLC 0.00% of their portfolio | 515.7k $5.4m | Added +37.4k |
| Belpointe Asset Management LLC 0.12% of their portfolio | 358.5k $3.7m | Reduced -2.0k |
| RENAISSANCE TECHNOLOGIES LLC 0.00% of their portfolio | 302.8k $3.2m | Reduced -16.9k |
| STATE STREET CORP 0.00% of their portfolio | 298.0k $3.1m | Reduced -5.8k |
| BARD ASSOCIATES INC 0.65% of their portfolio | 279.3k $2.9m | Added +1.4k |
| GOLDMAN SACHS GROUP INC 0.00% of their portfolio | 183.9k $1.9m | Added +59.1k |
| NORTHERN TRUST CORP 0.00% of their portfolio | 170.5k $1.8m | Added +2.9k |
| VANGUARD PORTFOLIO MANAGEMENT LLC 0.00% of their portfolio | 149.2k $1.6m | Added +24.4k |
| VANGUARD FIDUCIARY TRUST CO 0.00% of their portfolio | 148.2k $1.5m | Added +9.0k |
| Annandale Capital, LLC 0.20% of their portfolio | 128.2k $1.3m | Unchanged |
| CITADEL ADVISORS LLC 0.00% of their portfolio | 114.8k $1.2m | Added +56.0k |
| UNITED CAPITAL FINANCIAL ADVISORS, LLC 0.00% of their portfolio | 82.8k $863.1k | New |
| Squarepoint Ops LLC 0.00% of their portfolio | 75.9k $791.3k | Added +2.2k |
| Steward Partners Investment Advisory, LLC 0.00% of their portfolio | 72.5k $755.6k | Added +4.4k |
| CHARLES SCHWAB INVESTMENT MANAGEMENT INC 0.00% of their portfolio | 70.3k $732.4k | Added +17.4k |
| STIFEL FINANCIAL CORP 0.00% of their portfolio | 68.0k $708.6k | Added +2.0k |
| Nuveen, LLC 0.00% of their portfolio | 51.9k $540.4k | Added +27.9k |
| Bank of New York Mellon Corp 0.00% of their portfolio | 45.6k $475.3k | Added +3.6k |
| BRIDGEWAY CAPITAL MANAGEMENT, LLC 0.01% of their portfolio | 32.1k $334.5k | Added +1.0k |
| BANK OF AMERICA CORP /DE/ 0.00% of their portfolio | 30.3k $315.4k | Reduced -16.3k |
| OSAIC HOLDINGS, INC. 0.00% of their portfolio | 25.1k $261.2k | Added +20.5k |
| RHUMBLINE ADVISERS 0.00% of their portfolio | 24.0k $250.5k | Added +189 |
| DEUTSCHE BANK AG\ 0.00% of their portfolio | 23.2k $241.4k | Added +1.5k |
| MORGAN STANLEY 0.00% of their portfolio | 21.8k $227.2k | Reduced -18.2k |
| WELLS FARGO & COMPANY/MN 0.00% of their portfolio | 19.8k $205.9k | Added +12.1k |
| LPL Financial LLC 0.00% of their portfolio | 16.6k $173.0k | Reduced -700 |
| ALLIANCEBERNSTEIN L.P. 0.00% of their portfolio | 16.2k $168.5k | Added +1.2k |
| PRICE T ROWE ASSOCIATES INC /MD/ 0.00% of their portfolio | 15.6k $163.0k | Added +880 |
| SUSQUEHANNA INTERNATIONAL GROUP, LLP 0.00% of their portfolio | 12.0k $124.6k | Reduced -4.2k |
| O'SHAUGHNESSY ASSET MANAGEMENT, LLC 0.00% of their portfolio | 11.7k $122.0k | New |
| MetLife Investment Management, LLC 0.00% of their portfolio | 11.7k $121.9k | Added +4.5k |
| Invesco Ltd. 0.00% of their portfolio | 11.7k $121.7k | Reduced -6.5k |
| XTX Topco Ltd 0.00% of their portfolio | 11.2k $116.5k | New |
| CITIGROUP INC 0.00% of their portfolio | 10.4k $107.9k | Added +9.1k |
| MIRAE ASSET GLOBAL ETFS HOLDINGS Ltd. 0.00% of their portfolio | 10.0k $103.9k | Reduced -64 |
| FMR LLC 0.00% of their portfolio | 9.3k $97.2k | Added +2.0k |
| JPMORGAN CHASE & CO 0.00% of their portfolio | 9.2k $94.9k | Added +632 |
| UBS Group AG 0.00% of their portfolio | 8.7k $90.3k | Reduced -1.1k |
| Russell Investments Group, Ltd. 0.00% of their portfolio | 8.2k $85.7k | Added +3.8k |
| Vanguard Global Advisers, LLC 0.00% of their portfolio | 7.5k $78.6k | Unchanged |
| NEW YORK STATE COMMON RETIREMENT FUND 0.00% of their portfolio | 6.8k $70.9k | Unchanged |
| Police & Firemen's Retirement System of New Jersey 0.00% of their portfolio | 5.4k $56.7k | Unchanged |
| BNP PARIBAS FINANCIAL MARKETS 0.00% of their portfolio | 4.2k $43.3k | Reduced -724 |
| BARCLAYS PLC 0.00% of their portfolio | 3.2k $33.0k | Reduced -953 |
| ROYAL BANK OF CANADA 0.00% of their portfolio | 2.4k $25.0k | Added +737 |
| Tower Research Capital LLC (TRC) 0.00% of their portfolio | 1.9k $20.0k | Reduced -2.5k |
| Legal & General Group Plc 0.00% of their portfolio | 1.9k $20.0k | Unchanged |
| NISA INVESTMENT ADVISORS, LLC 0.00% of their portfolio | 1.9k $19.8k | Unchanged |
| Ameritas Investment Partners, Inc. 0.00% of their portfolio | 1.9k $19.3k | Unchanged |
| UBS AM, a distinct business unit of UBS ASSET MANAGEMENT AMERICAS LLC 0.00% of their portfolio | 426 $4.4k | Unchanged |
| Federation des caisses Desjardins du Quebec 0.00% of their portfolio | 358 $3.7k | Reduced -712 |
| CALIFORNIA STATE TEACHERS RETIREMENT SYSTEM 0.00% of their portfolio | 296 $3.1k | Reduced -846 |
| HUNTINGTON NATIONAL BANK 0.00% of their portfolio | 281 $2.9k | Unchanged |
| TD Waterhouse Canada Inc. 0.00% of their portfolio | 250 $2.6k | New |
| SIMPLEX TRADING, LLC 0.00% of their portfolio | 206 $2.1k | Reduced -10.2k |
| NORTHWESTERN MUTUAL WEALTH MANAGEMENT CO 0.00% of their portfolio | 166 $1.7k | New |
| GAMMA Investing LLC 0.00% of their portfolio | 131 $1.4k | Unchanged |
| Arax Advisory Partners 0.00% of their portfolio | 114 $1.2k | New |
| ZIONS BANCORPORATION, NATIONAL ASSOCIATION /UT/ 0.00% of their portfolio | 93 $969 | Unchanged |
| EverSource Wealth Advisors, LLC 0.00% of their portfolio | 80 $834 | Reduced -11 |
| Sterling Capital Management LLC 0.00% of their portfolio | 76 $792 | Reduced -61 |
| PNC Financial Services Group, Inc. 0.00% of their portfolio | 63 $656 | Added +8 |
| MassMutual Private Wealth & Trust, FSB 0.00% of their portfolio | 18 $188 | Unchanged |
| Integrated Wealth Concepts LLC 0.00% of their portfolio | 11 $114 | New |
| ASSETMARK, INC 0.00% of their portfolio | 10 $104 | New |
| Allworth Financial LP 0.00% of their portfolio | 8 $84 | Added +6 |
| Clearstead Advisors, LLC 0.00% of their portfolio | 4 $42 | New |
| Caitong International Asset Management Co., Ltd 0.00% of their portfolio | 3 $31 | New |