🕵️ Kingsway Corp ($KWY)

SEC insider & ownership activity, last 12 months · CIK 1072627 · every row links its SEC filing

Over the last 12 months insiders sold $5.0M against $230K of open-market buying. Stilwell Joseph sold $4.4M (Sep–Aug). Stilwell Joseph trimmed 18.8% → 12.7%; Stilwell Value LLC trimmed 18.8% → 12.7%. No red-flag 8-Ks in the window.

🚨 2 signals active — planned-vs-executed verdicts, pre-event flags, and cluster context live in the API and the alerts bot.
Oct 2025: net +$8K Nov 2025: net +$8K Dec 2025: net -$2.9M Jan 2026: net +$4K Feb 2026: net +$12K Mar 2026: net +$8K Apr 2026: net +$7K May 2026: net -$102K Jun 2026: net +$8K Jul 2026: net +$8K Aug 2026: net -$902K Sep 2026: net +$4K
Monthly net open-market insider flow, last 12 months (up = net buying)

Insider flow

3 buyers, $230K (52 lots) · 3 sellers, $5.0M (20 lots)

InsiderBuysBoughtSellsSoldLast
Stilwell Joseph0 15$4.4MAug 13, 2026
Fitzgerald John Taylor Maloney24$60K 4$554KSep 15, 2026
Kent A. Hansen23$36K 1$103KSep 15, 2026
Horowitz Joshua5$134K 0Aug 20, 2026

5%+ holders

HolderStakeClassScheduleEvent
Stilwell Joseph 12.7% 13DDec 17, 2025 filing ↗
Stilwell Value LLC 12.7% 13DDec 17, 2025 filing ↗
Stilwell Activist Fund, L.P. 12.7% 13DDec 17, 2025 filing ↗
Stilwell Activist Investments, L.P. 12.7% 13DDec 17, 2025 filing ↗
Stilwell Value Partners VII, L.P. 12.7% 13DDec 17, 2025 filing ↗
Stilwell Associates L. P. 12.7% 13DDec 17, 2025 filing ↗
1272562 Ontario Inc. 10.4% 13DMar 31, 2025 filing ↗
Oakmont Capital Inc. 10.4% 13DMar 31, 2025 filing ↗
Terence M. Kavanagh 10.4% 13DMar 31, 2025 filing ↗
Adam J. Patinkin 10.3% 13DMay 18, 2026 filing ↗
David Capital Partners, LLC 9.0% 13DMay 18, 2026 filing ↗
Oakmont Capital Inc. 8.2% 13DDec 17, 2025 filing ↗
E.J.K. Holdings Inc. 8.2% 13DDec 17, 2025 filing ↗
1272562 Ontario Inc 8.2% 13DDec 17, 2025 filing ↗
Terence M. Kavanagh 8.2% 13DDec 17, 2025 filing ↗
Gregory P. Hannon 8.2% 13DDec 17, 2025 filing ↗
Greenhaven ROAD Investment Management, L.P. 6.8% 13GNov 6, 2025 filing ↗
MVM Funds LLC 6.8% 13GNov 6, 2025 filing ↗
Miller Scott Stewart 6.8% 13GNov 6, 2025 filing ↗
Charles Frischer 6.8% 13DApr 11, 2025 filing ↗
David Capital Partners Special Situation Fund, LP 5.5% 13DMay 18, 2026 filing ↗

Planned insider sales (Form 144)

SellerPlannedApprox. sale date
John T. Fitzgerald$51KMay 21, 2026 filing ↗
John T. Fitzgerald$51KMay 20, 2026 filing ↗
John T. Fitzgerald$52KMay 19, 2026 filing ↗
Kent A. Hansen$105KDec 29, 2025 filing ↗
John T. Fitzgerald$398KDec 23, 2025 filing ↗

Material events (8-K)

ItemEvent date
Earnings (2.02)Aug 6, 2026 filing ↗
Financial Statements and Exhibits (9.01)Aug 6, 2026 filing ↗
Shareholder vote (5.07)May 18, 2026 filing ↗
Charter/bylaw changes (5.03)May 18, 2026 filing ↗
Reg FD disclosure (7.01)May 18, 2026 filing ↗
Other events (8.01)May 18, 2026 filing ↗
Financial Statements and Exhibits (9.01)May 18, 2026 filing ↗
Material agreement (1.01)May 8, 2026 filing ↗
Reg FD disclosure (7.01)May 8, 2026 filing ↗
Financial Statements and Exhibits (9.01)May 8, 2026 filing ↗
Earnings (2.02)May 7, 2026 filing ↗
Financial Statements and Exhibits (9.01)May 7, 2026 filing ↗
Reg FD disclosure (7.01)Mar 16, 2026 filing ↗
Financial Statements and Exhibits (9.01)Mar 16, 2026 filing ↗
Earnings (2.02)Mar 12, 2026 filing ↗
Financial Statements and Exhibits (9.01)Mar 12, 2026 filing ↗
Earnings (2.02)Nov 6, 2025 filing ↗
Financial Statements and Exhibits (9.01)Nov 6, 2025 filing ↗