KWY insider trading — Kingsway Corp
Over the last 90 days, insiders at Kingsway Corp (KWY) made 15 open-market purchases worth $143K and 1 open-market sale worth $1.00M, making them net sellers by $857K. The largest purchase was by Horowitz Joshua (Director), who bought 7,034 shares for $69K on Aug 19, 2026. The largest sale was by Stilwell Joseph, Stilwell Value Llc, Stilwell Associates, L.P., Stilwell Activist Fund, L.P., Stilwell Activist Investments, L.P., Stilwell Value Partners Vii, L.P. (Director, 10% Owner), who sold 100,000 shares for $1.00M on Aug 13, 2026. 3 different insiders bought shares in this period — a cluster buy, which many investors watch closely.
Updated Oct 16, 2026.
Recent KWY insider transactions
Every Form 4 filed by Kingsway Corp officers, directors and 10% owners in the last 90 days, newest first. P = open-market purchase, S = open-market sale; other codes are awards, option exercises, tax withholding or gifts.
| Trade date | Insider | Role | Type | Ownership | Shares | Price | Value | Filing |
|---|---|---|---|---|---|---|---|---|
| Sep 30, 2026 | Horowitz Joshua | Director | P · Purchase | Indirect | 858 | $9.23 | $8K | Form 4 |
| Sep 28, 2026 | Horowitz Joshua | Director | P · Purchase | Indirect | 2,717 | $9.28 | $25K | Form 4 |
| Sep 30, 2026 | Fitzgerald John Taylor Maloney | President and CEO | P · Purchase | Direct | 269 | $9.30 | $3K | Form 4 |
| Sep 30, 2026 | Hansen Kent A | CFO & EVP | P · Purchase | Direct | 169 | $9.30 | $2K | Form 4 |
| Sep 15, 2026 | Hansen Kent A | CFO & EVP | P · Purchase | Direct | 159 | $9.82 | $2K | Form 4 |
| Sep 15, 2026 | Fitzgerald John Taylor Maloney | President and CEO | P · Purchase | Direct | 254 | $9.82 | $2K | Form 4 |
| Aug 31, 2026 | Hansen Kent A | CFO & EVP | P · Purchase | Direct | 149 | $10.45 | $2K | Form 4 |
| Aug 31, 2026 | Fitzgerald John Taylor Maloney | President and CEO | P · Purchase | Direct | 239 | $10.45 | $2K | Form 4 |
| Aug 20, 2026 | Horowitz Joshua | Director | P · Purchase | Indirect | 769 | $9.89 | $8K | Form 4 |
| Aug 19, 2026 | Horowitz Joshua | Director | P · Purchase | Indirect | 7,034 | $9.84 | $69K | Form 4 |
| Aug 18, 2026 | Horowitz Joshua | Director | P · Purchase | Indirect | 1,300 | $9.75 | $13K | Form 4 |
| Aug 17, 2026 | Fitzgerald John Taylor Maloney | President and CEO | P · Purchase | Direct | 254 | $9.87 | $3K | Form 4 |
| Aug 17, 2026 | Hansen Kent A | CFO & EVP | P · Purchase | Direct | 158 | $9.87 | $2K | Form 4 |
| Aug 13, 2026 | Stilwell Joseph, Stilwell Value Llc, Stilwell Associates, L.P., Stilwell Activist Fund, L.P., Stilwell Activist Investments, L.P., Stilwell Value Partners Vii, L.P. | Director, 10% Owner | S · Sale | Indirect | 100,000 | $10.00 | $1.00M | Form 4 |
| Jul 30, 2026 | Hansen Kent A | CFO & EVP | P · Purchase | Direct | 174 | $8.98 | $2K | Form 4 |
| Jul 30, 2026 | Fitzgerald John Taylor Maloney | President and CEO | P · Purchase | Direct | 278 | $8.98 | $2K | Form 4 |
KWY insider trading FAQ
Are insiders buying KWY stock?
Yes. In the last 90 days, Kingsway Corp insiders made 15 open-market purchases totaling $143K, and 1 open-market sale totaling $1.00M. Purchases with the insider's own money are generally seen as a stronger signal than sales, which happen for many reasons (taxes, diversification, planned 10b5-1 sales).
Who are the insiders trading KWY?
Recent buyers: Fitzgerald John Taylor Maloney, Hansen Kent A, Horowitz Joshua. Recent sellers: Stilwell Joseph, Stilwell Value Llc, Stilwell Associates, L.P., Stilwell Activist Fund, L.P., Stilwell Activist Investments, L.P., Stilwell Value Partners Vii, L.P..
Where does KWY insider trading data come from?
Every transaction comes from SEC Form 4 filings on EDGAR. Company officers, directors and 10% owners must file a Form 4 within two business days of buying or selling. InsiderBolt reads these filings directly from the SEC.
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Insider trading data is for informational purposes only and is not investment advice. Filings can be amended; always confirm details on SEC EDGAR.