KINGSWAY FINANCIAL SERVICES INC
Total Trades
255
Buys
224
Sells
30
Largest Trade
$1M+
Insiders
8
Institutional Funds
54
Inst. Value
$1M+
Activist Filings
29
Insider Trades
| Insider | Title | Type | Value | Shares | Price | Date |
|---|---|---|---|---|---|---|
| Kavanagh Terence Michael | Director | BUY | $50K–$100K | 8K | $9.04 | Mar 27, 2023 |
| Kavanagh Terence Michael | Director | SELL | $50K–$100K | 8K | $8.97 | Mar 27, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 249 | $8.98 | Mar 20, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 184 | $8.98 | Mar 20, 2023 |
| STILWELL JOSEPH | Director | SELL | $1M+ | 161K | $9.01 | Mar 15, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 156 | $9.61 | Mar 1, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 216 | $9.61 | Mar 1, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 234 | $8.88 | Feb 15, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 168 | $8.88 | Feb 15, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 258 | $8.06 | Jan 30, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 186 | $8.06 | Jan 30, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 181 | $8.25 | Jan 17, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 252 | $8.25 | Jan 17, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 186 | $8.06 | Jan 4, 2023 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 258 | $8.06 | Jan 4, 2023 |
| STILWELL JOSEPH | Director | SELL | $50K–$100K | 7K | $8.02 | Jan 3, 2023 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 205 | $7.30 | Dec 16, 2022 |
| Hansen Kent A | CFO & EVP | GRANT | $100K–$500K | 25K | $7.17 | Dec 16, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 285 | $7.30 | Dec 16, 2022 |
| Frischer Charles L | Director | BUY | $15K–$50K | 3K | $7.13 | Dec 9, 2022 |
| Frischer Charles L | Director | BUY | $50K–$100K | 12K | $7.13 | Dec 8, 2022 |
| Frischer Charles L | Director | BUY | $50K–$100K | 7K | $7.22 | Dec 6, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 205 | $7.31 | Nov 30, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 284 | $7.31 | Nov 30, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 208 | $7.18 | Nov 16, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 290 | $7.18 | Nov 16, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 300 | $6.94 | Nov 1, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 216 | $6.94 | Nov 1, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 348 | $5.98 | Oct 14, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 250 | $5.98 | Oct 14, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 293 | $7.11 | Oct 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 211 | $7.11 | Oct 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 217 | $6.90 | Sep 19, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 302 | $6.90 | Sep 19, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 210 | $7.11 | Aug 31, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 293 | $7.11 | Aug 31, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 199 | $7.53 | Aug 16, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 276 | $7.53 | Aug 16, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 328 | $6.33 | Aug 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 236 | $6.33 | Aug 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 246 | $6.07 | Jul 18, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 343 | $6.07 | Jul 18, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 261 | $5.73 | Jul 1, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 363 | $5.73 | Jul 1, 2022 |
| OAKMONT CAPITAL INC | 10% Owner | BUY | $100K–$500K | 54K | $5.67 | Jul 1, 2022 |
| Hannon Gregory Paul | Director | BUY | $100K–$500K | 54K | $5.67 | Jul 1, 2022 |
| Kavanagh Terence Michael | Director | BUY | $100K–$500K | 54K | $5.67 | Jul 1, 2022 |
| OAKMONT CAPITAL INC | 10% Owner | BUY | $50K–$100K | 10K | $5.37 | Jun 28, 2022 |
| Kavanagh Terence Michael | Director | BUY | $50K–$100K | 10K | $5.37 | Jun 28, 2022 |
| Hannon Gregory Paul | Director | BUY | $50K–$100K | 10K | $5.37 | Jun 28, 2022 |
Institutional Ownership
13F filings as of Dec 31, 2025 · 54 funds holding
| Fund | Shares | Value | Type |
|---|---|---|---|
| Stilwell Value LLC | 3.4M | $1M+ | SH |
| Greenhaven Road Investment Management, L.P. | 1.9M | $1M+ | SH |
| GEODE CAPITAL MANAGEMENT, LLC | 401K | $1M+ | SH |
| Belpointe Asset Management LLC | 356K | $1M+ | SH |
| STATE STREET CORP | 286K | $1M+ | SH |
| BARD ASSOCIATES INC | 279K | $1M+ | SH |
| RENAISSANCE TECHNOLOGIES LLC | 261K | $1M+ | SH |
| VANGUARD GROUP INC | 139K | $1M+ | SH |
| Annandale Capital, LLC | 128K | $1M+ | SH |
| STIFEL FINANCIAL CORP | 78K | $1M+ | SH |
| CHARLES SCHWAB INVESTMENT MANAGEMENT INC | 58K | $500K+ | SH |
| Steward Partners Investment Advisory, LLC | 48K | $500K+ | SH |
| Squarepoint Ops LLC | 45K | $500K+ | SH |
| Informed Momentum Co LLC | 43K | $500K+ | SH |
| BARCLAYS PLC | 33K | $100K–$500K | SH |
| GOLDMAN SACHS GROUP INC | 32K | $100K–$500K | SH |
| JANE STREET GROUP, LLC | 31K | $100K–$500K | SH |
| SEI INVESTMENTS CO | 26K | $100K–$500K | SH |
| RHUMBLINE ADVISERS | 24K | $100K–$500K | SH |
| Nuveen, LLC | 24K | $100K–$500K | SH |
Activist & 5%+ Owners
SC 13D/13G filings — investors holding 5%+ of outstanding shares
SC 13G · Feb 5, 2026
6.6%
1.9M shares
Mirabella Financial Services LLP
SC 13G/A · Jan 9, 2026
6.8%
2.0M shares
SC 13D/A · Dec 19, 2025
12.7%
3.7M shares
SC 13D/A · Dec 18, 2025
9.0%
2.6M shares
SC 13D/A · Dec 18, 2025
1.4%
404K shares
SC 13D/A · Dec 18, 2025
8.2%
2.4M shares
SC 13D/A · Dec 16, 2025
18.8%
5.5M shares
Greenhaven Road Investment Management, L.P.
SC 13G · Nov 6, 2025
6.8%
2.0M shares
SC 13D/A · Aug 19, 2025
19.9%
5.8M shares
SC 13D/A · May 14, 2025
6.8%
1.9M shares
SC 13D/A · May 12, 2025
21.7%
6.0M shares
SC 13D/A · Apr 9, 2025
10.4%
2.9M shares
SC 13D/A · Apr 3, 2025
21.6%
6.0M shares
SC 13D · Apr 2, 2025
1.3%
368K shares
SC 13D · Apr 2, 2025
9.2%
2.5M shares
SC 13D/A · Mar 27, 2025
21.6%
6.0M shares
SC 13D/A · Feb 14, 2025
25.2%
7.0M shares
Mirabella Financial Services LLP
SC 13G · Jan 31, 2025
5.8%
1.6M shares
SC 13D/A · Dec 20, 2024
24.9%
6.9M shares
SC 13G/A · Jan 12, 2024
3.2%
900K shares
SC 13D/A · Nov 21, 2023
26.9%
7.6M shares
SC 13D/A · May 11, 2023
28.9%
7.6M shares
SC 13D/A · Mar 14, 2023
30.4%
7.6M shares
SC 13G/A · Jan 12, 2023
7.9%
1.9M shares
SC 13D/A · Jan 4, 2023
32.1%
7.8M shares
SC 13D/A · Jul 18, 2022
32.2%
7.8M shares
SC 13D/A · Jun 22, 2022
32.2%
7.8M shares
SC 13D/A · Mar 28, 2022
31.1%
7.5M shares
SC 13G/A · Jan 12, 2022
8.8%
2.1M shares