Kingsway KWY Insider Ownership

Updated Oct 16, 2026

Over the past year, KWY insiders bought $259,112 of stock (25.41K shares) and sold $4.04 million (338.93K shares) on the open market.

• A count shows 3 insiders buying KWY stock on the open market over the past 12 months and 3 insiders selling.
• Among Kingsway's insiders, the largest open-market purchases in the past 12 months were by Joshua Horowitz (Director), totaling $167,230 (17.18K shares), most recently on September 30, 2026.
• On the selling side, Joseph Stilwell (Director and 10% owner) was the top open-market seller of Kingsway over the past 12 months, with $3.39 million sold (286.43K shares) and the latest sale on August 13, 2026.
• Beyond open-market trades, insiders at Kingsway received 14.57K shares in stock awards, acquired 1.59Mn shares through option exercises and conversions, gave up 39.72K shares to cover taxes or exercise prices and gave away 6.26K shares as gifts in the last 12 months.
• Per Business Quant, KWY insiders together hold 13.09Mn shares based on their latest Form 4 filings, down 0.64% from 13.17Mn shares at the end of Q2 2026 and up 2.77% from 12.73Mn shares at the end of Q3 2025.
• Direct holdings account for 6.51Mn shares (49.71%) of KWY's insider total, and indirect holdings through trusts, partnerships and family members for 6.58Mn shares (50.29%).
• The insider holdings in Kingsway belong to 10 insiders who have reported on Form 4 within the past two years.
• KWY's largest insider holders by reported holdings are Joseph Stilwell (Director and 10% owner, 3.43Mn shares), Adam Jonathan Patinkin (Director, 2.55Mn shares) and Oakmont Capital Inc (10% owner, 1.99Mn shares).
• The holding of Joseph Stilwell makes up 26.18% of all shares held by Kingsway insiders.
• Institutions owned 42.23% of KWY shares as of Q2 2026; insiders' latest Form 4 filings account for about 45.73%, leaving roughly 12.04% with other investors, including the public.
• In the past year, 8 insiders of Kingsway submitted 69 Form 4 filings reporting trades, awards or other transactions.
• Insider figures for KWY include Form 4 filings through September 30, 2026.