Kingsway Corporation (KWY)
NYSE: KWY · Fire, Marine & Casualty Insurance · Chicago, IL · filing with the SEC since 1998
Grade3.6
◀ Past 3.7● Present 2.9▶ Future 4.4
Who owns Kingsway Corporation
As filed with the SECHolders of 5% or more
5
Stilwell Activist Fund, L.P. holds 12.7% of Common Shares, no par value, as its SCHEDULE 13D/A filed Dec 19, 2025 says.
Directors and officers
11
report now, of 19 people on the record since 2012. Their holdings as a group are not read here.
Institutions as a whole
n/a
The record does not read the share held by managers that file Form 13F, so none is printed and no split of the rest is estimated. What it holds is the 5 named at left.
Holders of 5% or moreshare of the class, as filed
Stilwell Activist Fund, L.P.
SCHEDULE 13D/A · filed Dec 19, 2025 · Common Shares, no par value · 18.8% in Dec 15, 2025
Adam J. Patinkin
SCHEDULE 13D/A · filed May 20, 2026 · Common Stock, par value $0.01 per share · 9% in Dec 18, 2025
Oakmont Capital Inc.
SCHEDULE 13D/A · filed Dec 18, 2025 · Common Stock, $0.01 par value per share · 10.4% in Apr 9, 2025
Greenhaven Road Investment Management, L.P.
SCHEDULE 13G · filed Nov 6, 2025 · Common Stock, par value $0.01 per share
Charles Frischer
SCHEDULE 13D/A · filed May 14, 2025 · Common Stock, $0.01 par value per share
Capricorn Fund Managers Ltd
SCHEDULE 13G/A · filed Jul 13, 2026 · Common Stock · reported falling below 5%, from 6.6% in Feb 5, 2026
Joshua S. Horowitz
SCHEDULE 13D/A · filed Dec 18, 2025 · Common Stock, par value $0.01 per share · reported falling below 5%, from 1.5% in Apr 2, 2025
Mirabella Financial Services LLP
SCHEDULE 13G/A · filed Apr 10, 2026 · Common Stock, par value $0.01 per share · reported falling below 5%, from 6.85% in Jan 9, 2026
What KWY reports owning in othersstakes of 5% or more, and other ties
Other ties the annual report names
Digital Diagnostics Imaging, Inc. ("DDI")
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
Kingsway Plumbing Holdco LLC
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
Longhorns LLC
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
Nursing Service LLC
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
PWI Holdings
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
Ravix Financial, Inc
An entity · legal entity · owns, named in the 10-K filed Mar 12, 2026
Advanced Plumbing and Drain
A company bought · acquisition · Jul 2025 · owns, named in the 10-K filed Mar 12, 2026
Image Solutions, LLC
A company bought · acquisition, legal entity · Jul 2025 · owns, named in the 10-K filed Mar 12, 2026
36 subsidiaries in 4 countries, from the list filed with the 10-K filed Mar 12, 2026.
Insider tradesForm 4
14sales
54purchases
0sales on a scheduled plan
6people selling
$4.0Msold, in dollars
$300,000bought, in dollars
Open-market trades on Form 4 from Nov 3, 2025 to Nov 3, 2026. A scheduled plan is a selling program set in advance under SEC rule 10b5-1. The trades are listed as filed and do not feed the grade.
By calendar yearSoldBought
2026 runs to Nov 3, 2026. Dollars as filed, summed by the transaction date.
People who traded in the window7 of 21 on the roster
| Person | Role as filed | Sales | Sold | On a plan | Buys | Bought |
|---|---|---|---|---|---|---|
| Stilwell Activist Fund, L.P. | director | 3 | $1.6M | 0 | 0 | $0 |
| Stilwell Joseph | director | 3 | $1.0M | 0 | 0 | $0 |
| Fitzgerald John Taylor Maloney | President and CEO | 4 | $600,000 | 0 | 24 | $100,000 |
| Stilwell Associates L P | director | 2 | $600,000 | 0 | 0 | $0 |
| Stilwell Value LLC | director | 1 | $200,000 | 0 | 0 | $0 |
| Hansen Kent A | CFO & EVP | 1 | $100,000 | 0 | 23 | $0 |
| Horowitz Joshua | director | 0 | $0 | 0 | 7 | $200,000 |