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 |
|---|---|---|---|---|---|---|
| STILWELL JOSEPH | Director | BUY | $1K–$15K | 500 | $5.34 | Jun 27, 2022 |
| OAKMONT CAPITAL INC | 10% Owner | BUY | $100K–$500K | 44K | $5.30 | Jun 24, 2022 |
| Hannon Gregory Paul | Director | BUY | $100K–$500K | 44K | $5.30 | Jun 24, 2022 |
| Kavanagh Terence Michael | Director | BUY | $100K–$500K | 44K | $5.30 | Jun 24, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 15K | $5.31 | Jun 23, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 10K | $5.30 | Jun 21, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 388 | $5.36 | Jun 17, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 279 | $5.36 | Jun 17, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 16K | $5.30 | Jun 16, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 11K | $5.29 | Jun 14, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 26K | $5.36 | Jun 10, 2022 |
| Frischer Charles L | Director | BUY | $50K–$100K | 11K | $5.35 | Jun 9, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 17K | $5.40 | Jun 8, 2022 |
| Frischer Charles L | Director | BUY | $100K–$500K | 27K | $5.40 | Jun 2, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.39 | Jun 2, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 276 | $5.42 | May 31, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 384 | $5.42 | May 31, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 11K | $5.39 | May 31, 2022 |
| Frischer Charles L | Director | BUY | $50K–$100K | 11K | $5.40 | May 26, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 10K | $5.39 | May 26, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 10K | $5.32 | May 24, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.38 | May 19, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 278 | $5.40 | May 18, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 386 | $5.40 | May 18, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.40 | May 17, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.42 | May 13, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 365 | $5.70 | May 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 263 | $5.70 | May 4, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 383 | $5.43 | Apr 20, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 276 | $5.43 | Apr 20, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 369 | $5.63 | Apr 4, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 266 | $5.63 | Apr 4, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 35K | $5.50 | Apr 1, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 13K | $5.50 | Mar 30, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.50 | Mar 28, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.50 | Mar 24, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 13K | $5.50 | Mar 22, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.50 | Mar 18, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 378 | $5.51 | Mar 16, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 272 | $5.51 | Mar 16, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 11K | $5.50 | Mar 16, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 11K | $5.50 | Mar 14, 2022 |
| STILWELL JOSEPH | Director | BUY | $50K–$100K | 10K | $5.39 | Mar 10, 2022 |
| STILWELL JOSEPH | Director | BUY | $100K–$500K | 20K | $5.50 | Mar 8, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 406 | $5.13 | Mar 1, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 292 | $5.13 | Mar 1, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 396 | $5.26 | Feb 18, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 285 | $5.26 | Feb 18, 2022 |
| Fitzgerald John Taylor Maloney | President and CEO | BUY | $1K–$15K | 392 | $5.31 | Feb 1, 2022 |
| Hansen Kent A | CFO & EVP | BUY | $1K–$15K | 282 | $5.31 | Feb 1, 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