Form 4 for KWY KINGSWAY Corp
Accepted 2025-12-19 00:00:00 ET · period of report 2025-12-17 · accession 0001104659-25-123371 · SEC index · Original document
Summary rows
Aggregated the way they appear in lists: one row per insider, transaction code and security table.
| X | Filed | Traded | Ticker | Insider | Title | Type | Price | Qty | Owned | ΔOwn | Value |
|---|---|---|---|---|---|---|---|---|---|---|---|
| DMI | 2025-12-19 | 2025-12-17 | KWY | Stilwell Activist Fund, L.P. | 10% | X - OptEx | $8.25 | -1.75M | 371.6K | -82% | -$14.44M |
| DMI | 2025-12-19 | 2025-12-17 | KWY | Stilwell Activist Fund, L.P. | 10% | X - OptEx | $0.00 | -1.75M | 0 | -100% | $0 |
Purchase Sale Sale after option exercise All abbreviations
Every reported transaction
| # | Table | Security | Date | Code | A/D | Shares | Price | Owned after | Own | Exercise / expiry | Underlying | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Common | Common Stock | 2025-12-17 | X | D | 215,477 | $8.25 | 319,229 | I See footnote | — | — | (F3) These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. |
| 2 | Common | Common Stock | 2025-12-17 | X | D | 1,295,411 | $8.25 | 2,254,971 | I See footnote | — | — | (F4) These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. |
| 3 | Common | Common Stock | 2025-12-17 | X | D | 20,270 | $8.25 | 436,911 | I See footnote | — | — | (F5) These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. |
| 4 | Common | Common Stock | 2025-12-17 | X | D | 218,842 | $8.25 | 371,568 | I See footnote | — | — | (F6) These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. |
| 5 | Derivative | Stock Option (obligation to sell) | 2025-12-17 | X | D | 218,842 | $0.00 | 0 | I See footnote | $8.25 · — to 2025-12-29 | 218,842 Common Stock | (F6) These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. (F2) On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025. |
| 6 | Derivative | Stock Option (obligation to sell) | 2025-12-17 | X | D | 20,270 | $0.00 | 0 | I See footnote | $8.25 · — to 2025-12-29 | 20,270 Common Stock | (F5) These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. (F2) On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025. |
| 7 | Derivative | Stock Option (obligation to sell) | 2025-12-17 | X | D | 215,477 | $0.00 | 0 | I See footnote | $8.25 · — to 2025-12-29 | 215,477 Common Stock | (F3) These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. (F2) On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025. |
| 8 | Derivative | Stock Option (obligation to sell) | 2025-12-17 | X | D | 1,295,411 | $0.00 | 0 | I See footnote | $8.25 · — to 2025-12-29 | 1,295,411 Common Stock | (F4) These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein. (F2) On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025. |