KINGSWAY Corp
KWY · Fire, Marine & Casualty Insurance · 28.9M shares · +5%/yr ↑ shares · EDGAR filings ↗
Net buyback after stock comp: $719K (gross $3M, SBC $2M)
Reference price $10.43 · est. market cap ~$302M — last insider purchase, 2026-06-15 (estimated from the dated SEC Form 4 price × shares outstanding — not a live quote)
Grade
D48Kingsway Co — small insurance/services holding company with high leverage.
Strengths
- Diversified small-business (warranty, search-acquisition) model
Risks
- Operating loss; very high leverage (D/E 4.7, 97th)
- Thin liquidity (cash 8th pct)
Notable findings
- High leverageHigh leverage (debt/equity 4.66)
- Net lossNet loss (net margin -7.6%)
- Insider buyingInsider buying — 25 open-market buy(s) by 3 insider(s) (cluster of 3 insiders, last 6mo) Form 4 ↗
Quarterly revenue
Last 4 quarters · from SEC filings.
Key metrics
Operating margin
-1.8%
Net margin
-7.6%
Return on equity
-67.6%
Return on assets
-4.4%
ROIC
-2.2%
Revenue growth (QoQ)
1.0%
Debt / equity
4.7×
Net debt / EBITDA
9.1×
EBITDA
$7M
Tangible book value
-$106M
Cash & investments
$8M
Stock comp / revenue
1.3%
Insider transactions · last 18 months
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| 2026-06-15 | Hansen Kent A | Buy | 150 | $10.43 |
| 2026-06-15 | Fitzgerald John Taylor Maloney | Buy | 240 | $10.43 |
| 2026-06-15 | Fitzgerald John Taylor Maloney | Tax withheld | 30K | $10.12 |
| 2026-05-29 | Hansen Kent A | Buy | 156 | $10.03 |
| 2026-05-29 | Horowitz Joshua | Buy | 3.8K | $9.91 |
| 2026-05-29 | Fitzgerald John Taylor Maloney | Buy | 250 | $10.03 |
| 2026-05-28 | Horowitz Joshua | Buy | 700 | $9.95 |
| 2026-05-27 | Fitzgerald John Taylor Maloney | Gift | 6.3K | $9.99 |
| 2026-05-21 | Fitzgerald John Taylor Maloney | Sell | 5.0K | $10.13 |
| 2026-05-20 | Fitzgerald John Taylor Maloney | Sell | 5.0K | $10.43 |
| 2026-05-19 | Fitzgerald John Taylor Maloney | Sell | 5.0K | $10.30 |
| 2026-05-15 | Fitzgerald John Taylor Maloney | Buy | 230 | $10.85 |
| 2026-05-15 | Hansen Kent A | Buy | 144 | $10.85 |
| 2026-04-30 | Hansen Kent A | Buy | 143 | $10.93 |
| 2026-04-30 | Fitzgerald John Taylor Maloney | Buy | 229 | $10.93 |
| 2026-04-15 | Fitzgerald John Taylor Maloney | Buy | 211 | $11.85 |
| 2026-03-30 | Hansen Kent A | Buy | 153 | $10.22 |
| 2026-03-30 | Fitzgerald John Taylor Maloney | Buy | 244 | $10.22 |
| 2026-03-17 | Hansen Kent A | Grant | 15K | $11.02 |
| 2026-03-13 | Fitzgerald John Taylor Maloney | Buy | 234 | $10.71 |
| 2026-03-13 | Hansen Kent A | Buy | 146 | $10.71 |
| 2026-02-27 | Hansen Kent A | Buy | 126 | $12.34 |
| 2026-02-27 | Fitzgerald John Taylor Maloney | Buy | 202 | $12.34 |
| 2026-02-17 | Hansen Kent A | Buy | 128 | $12.19 |
| 2026-02-17 | Fitzgerald John Taylor Maloney | Buy | 205 | $12.19 |
| 2026-02-02 | Fitzgerald John Taylor Maloney | Buy | 183 | $13.69 |
| 2026-02-02 | Hansen Kent A | Buy | 114 | $13.69 |
| 2026-01-15 | Fitzgerald John Taylor Maloney | Buy | 185 | $13.54 |
| 2026-01-15 | Hansen Kent A | Buy | 116 | $13.54 |
| 2025-12-31 | Hansen Kent A | Buy | 115 | $13.58 |
| 2025-12-31 | Fitzgerald John Taylor Maloney | Buy | 184 | $13.58 |
| 2025-12-30 | Hansen Kent A | Tax withheld | 3.6K | $12.83 |
| 2025-12-30 | Hansen Kent A | Tax withheld | 3.0K | $12.83 |
| 2025-12-30 | Hansen Kent A | Tax withheld | 2.9K | $12.83 |
| 2025-12-29 | Hansen Kent A | Sell | 7.5K | $13.67 |
| 2025-12-23 | Fitzgerald John Taylor Maloney | Sell | 30K | $13.32 |
| 2025-12-22 | Stilwell Joseph | Sell | 19K | $12.80 |
| 2025-12-17 | Stilwell Joseph | Option exercise | 215K | $8.25 |
| 2025-12-17 | Stilwell Joseph | Option exercise | 1.3M | $8.25 |
| 2025-12-17 | Stilwell Joseph | Option exercise | 20K | $8.25 |
| 2025-12-17 | Patinkin Adam Jonathan | Option exercise | 275K | $8.25 |
| 2025-12-17 | OAKMONT CAPITAL INC | Option exercise | 500K | $8.25 |
| 2025-12-17 | Kavanagh Terence Michael | Option exercise | 500K | $8.25 |
| 2025-12-17 | Hannon Gregory Paul | Option exercise | 500K | $8.25 |
| 2025-12-17 | Horowitz Joshua | Option exercise | 22K | $8.25 |
| 2025-12-17 | Horowitz Joshua | Option exercise | 252K | $8.25 |
| 2025-12-17 | Stilwell Joseph | Option exercise | 219K | $8.25 |
| 2025-12-17 | Patinkin Adam Jonathan | Option exercise | 540K | $8.25 |
| 2025-12-17 | Patinkin Adam Jonathan | Option exercise | 500K | $8.25 |
| 2025-12-16 | Stilwell Joseph | Sell | 10K | $12.80 |
| 2025-12-16 | Hansen Kent A | Buy | 122 | $12.82 |
| 2025-12-16 | Fitzgerald John Taylor Maloney | Buy | 195 | $12.82 |
| 2025-12-15 | Stilwell Joseph | Sell | 34K | $12.80 |
| 2025-12-11 | Stilwell Joseph | Sell | 68K | $12.80 |
| 2025-12-09 | Stilwell Joseph | Sell | 20K | $12.80 |
| 2025-12-08 | Stilwell Joseph | Sell | 35K | $12.82 |
| 2025-11-28 | Fitzgerald John Taylor Maloney | Buy | 192 | $13.03 |
| 2025-11-28 | Hansen Kent A | Buy | 120 | $13.03 |
| 2025-11-17 | Hansen Kent A | Buy | 123 | $12.70 |
| 2025-11-17 | Fitzgerald John Taylor Maloney | Buy | 197 | $12.70 |
| 2025-10-30 | Hansen Kent A | Buy | 111 | $14.08 |
| 2025-10-30 | Fitzgerald John Taylor Maloney | Buy | 177 | $14.08 |
| 2025-10-15 | Hansen Kent A | Buy | 98 | $15.92 |
| 2025-10-15 | Fitzgerald John Taylor Maloney | Buy | 157 | $15.92 |
| 2025-09-30 | Hansen Kent A | Buy | 107 | $14.63 |
| 2025-09-30 | Fitzgerald John Taylor Maloney | Buy | 171 | $14.63 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-26 | Fitzgerald John Taylor Maloney | Other | 14K | $14.57 |
| 2025-09-17 | Stilwell Joseph | Sell | 29K | $14.47 |
| 2025-09-17 | Stilwell Joseph | Sell | 5.1K | $14.47 |
| 2025-09-17 | Stilwell Joseph | Sell | 14K | $14.47 |
| 2025-09-16 | Stilwell Joseph | Sell | 2.1K | $14.40 |
| 2025-09-16 | Stilwell Joseph | Sell | 12K | $14.40 |
| 2025-09-16 | Stilwell Joseph | Sell | 6.0K | $14.40 |
| 2025-09-15 | Fitzgerald John Taylor Maloney | Buy | 174 | $14.36 |
| 2025-09-15 | Hansen Kent A | Buy | 109 | $14.36 |
| 2025-09-08 | Stilwell Joseph | Sell | 15K | $14.41 |
| 2025-09-08 | Stilwell Joseph | Sell | 2.6K | $14.41 |
| 2025-09-08 | Stilwell Joseph | Sell | 7.5K | $14.41 |
| 2025-08-29 | Hansen Kent A | Buy | 107 | $14.49 |
| 2025-08-29 | Fitzgerald John Taylor Maloney | Buy | 173 | $14.49 |
| 2025-08-22 | STILWELL JOSEPH | Sell | 45K | $14.18 |
| 2025-08-22 | STILWELL JOSEPH | Sell | 7.6K | $14.18 |
| 2025-08-22 | STILWELL JOSEPH | Sell | 23K | $14.18 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 24K | $13.95 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 4.1K | $13.95 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 12K | $13.95 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 19K | $14.16 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 3.2K | $14.16 |
| 2025-08-18 | STILWELL JOSEPH | Sell | 9.4K | $14.16 |
| 2025-08-18 | Fitzgerald John Taylor Maloney | Buy | 176 | $14.16 |
| 2025-08-18 | Hansen Kent A | Buy | 111 | $14.16 |
| 2025-07-30 | Fitzgerald John Taylor Maloney | Buy | 174 | $14.42 |
| 2025-07-30 | Hansen Kent A | Buy | 108 | $14.42 |
| 2025-07-15 | Hansen Kent A | Buy | 108 | $14.49 |
| 2025-07-15 | Fitzgerald John Taylor Maloney | Buy | 172 | $14.49 |
| 2025-07-01 | Fitzgerald John Taylor Maloney | Buy | 179 | $14.02 |
| 2025-07-01 | Hansen Kent A | Buy | 111 | $14.02 |
| 2025-06-30 | STILWELL JOSEPH | Sell | 8.3K | $13.90 |
| 2025-06-30 | STILWELL JOSEPH | Sell | 19K | $13.90 |
| 2025-06-30 | STILWELL JOSEPH | Sell | 5.9K | $13.90 |
| 2025-06-27 | STILWELL JOSEPH | Sell | 32K | $14.03 |
| 2025-06-27 | STILWELL JOSEPH | Sell | 85K | $14.03 |
| 2025-06-27 | STILWELL JOSEPH | Sell | 11K | $14.03 |
| 2025-06-13 | Hansen Kent A | Buy | 114 | $13.77 |
| 2025-06-13 | Fitzgerald John Taylor Maloney | Buy | 181 | $13.77 |
| 2025-05-30 | Hansen Kent A | Buy | 24 | $12.82 |
| 2025-05-30 | Fitzgerald John Taylor Maloney | Buy | 195 | $12.82 |
| 2025-05-15 | Fitzgerald John Taylor Maloney | Buy | 247 | $10.12 |
| 2025-05-15 | Hansen Kent A | Buy | 31 | $10.12 |
| 2025-04-30 | Hansen Kent A | Buy | 36 | $8.71 |
| 2025-04-30 | Fitzgerald John Taylor Maloney | Buy | 287 | $8.71 |
| 2025-04-15 | Hansen Kent A | Buy | 39 | $8.02 |
| 2025-04-15 | Fitzgerald John Taylor Maloney | Grant | 311 | $8.02 |
| 2025-03-28 | Hansen Kent A | Buy | 38 | $8.20 |
| 2025-03-28 | Fitzgerald John Taylor Maloney | Buy | 305 | $8.20 |
| 2025-03-26 | STILWELL JOSEPH | Sell | 523K | $8.00 |
| 2025-03-26 | STILWELL JOSEPH | Sell | 69K | $8.00 |
| 2025-03-26 | STILWELL JOSEPH | Sell | 206K | $8.00 |
| 2025-03-26 | STILWELL JOSEPH | Sell | 203K | $8.00 |
| 2025-03-14 | Hansen Kent A | Buy | 42 | $7.35 |
| 2025-03-14 | Fitzgerald John Taylor Maloney | Buy | 340 | $7.35 |
| 2025-03-03 | Fitzgerald John Taylor Maloney | Buy | 315 | $7.95 |
| 2025-03-03 | Hansen Kent A | Buy | 40 | $7.95 |
| 2025-02-14 | Hansen Kent A | Buy | 39 | $8.03 |
| 2025-02-14 | Fitzgerald John Taylor Maloney | Buy | 311 | $8.03 |
| 2025-01-30 | Hansen Kent A | Buy | 37 | $8.33 |
| 2025-01-30 | Fitzgerald John Taylor Maloney | Buy | 300 | $8.33 |
| 2025-01-16 | Hansen Kent A | Buy | 38 | $8.30 |
| 2025-01-16 | Fitzgerald John Taylor Maloney | Buy | 301 | $8.30 |
| 2024-12-31 | Hansen Kent A | Buy | 37 | $8.47 |
| 2024-12-31 | Fitzgerald John Taylor Maloney | Buy | 297 | $8.47 |
All non-derivative Form 4 activity (SEC), newest first.
Notable events (8-K)
Recent filings
| Form | Filed | Period | Accession |
|---|---|---|---|
| 8-K | 2026-05-21 | 2026-05-18 | 0001437749-26-018057 ↗ |
| 8-K | 2026-05-19 | 2026-05-18 | 0001437749-26-017693 ↗ |
| 8-K | 2026-05-11 | 2026-05-08 | 0001437749-26-016149 ↗ |
| 10-Q | 2026-05-07 | 2026-03-31 | 0001437749-26-015567 ↗ |
| 8-K | 2026-05-07 | 2026-05-07 | 0001437749-26-015595 ↗ |
| 8-K | 2026-03-16 | 2026-03-16 | 0001437749-26-008317 ↗ |
| 10-K | 2026-03-12 | 2025-12-31 | 0001437749-26-007961 ↗ |
| 8-K | 2026-03-12 | 2026-03-12 | 0001437749-26-007967 ↗ |
| 10-Q | 2025-11-06 | 2025-09-30 | 0001437749-25-033593 ↗ |
| 8-K | 2025-11-06 | 2025-11-06 | 0001437749-25-033603 ↗ |
| 8-K | 2025-08-07 | 2025-08-07 | 0001437749-25-025428 ↗ |
| 10-Q | 2025-08-07 | 2025-06-30 | 0001437749-25-025403 ↗ |