Insider · CIK 0001584349
John Taylor Maloney Fitzgerald
ceopresidentofficerdirector
Files at KWY (KINGSWAY FINANCIAL SERVICES INC). First filing Oct 16, 2023, latest Sep 30, 2026.
In brief
John Taylor Maloney Fitzgerald files SEC Form 4 as CEO, president and director at KWY (KINGSWAY FINANCIAL SERVICES INC). Since Oct 16, 2023, John Taylor Maloney Fitzgerald has reported 65 open-market buys worth $163k and 3 open-market sells worth $554k, the latest filed on Sep 30, 2026.
After John Taylor Maloney Fitzgerald's past buys, the stock trailed the S&P 500 by a median 19.9% over six months (n = 33), and 30% of those buys were ahead of the index at six months. InsiderTell labels that a negative record.
The newest scored trade: bought $2,502 of KWY on Sep 30, 2026, filed Sep 30, 2026, scored 40 (moderate). In the last 12 months: 24 buys worth $60k and 3 sells worth $554k.
Track record
Negative
Past buys trailed the index over six months, median.
Median 6-month excess
-19.9%
after past buys, n = 33
Hit rate
30%
past buys that beat the index over 6 months
Open-market trades
65 / 3
$163k bought, $554k sold
Where the trades landed
Last year at the company this insider has traded most, with each buy and sell on the bar it happened.
KWY: KINGSWAY FINANCIAL SERVICES INC
KWYOct 12, 2026 · close 9.46
Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value. Click a marked bar to open the signal.Charts by TradingView Lightweight Charts™
Signals
This insider’s open-market buys and sells, scored: the newest 50 of 68.
| Score | Company | Value | Holdings | Price context | Filed |
|---|---|---|---|---|---|
| 40Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,502 269 shares | +0% | - | |
| 40Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,494 254 shares | +0% | - | |
| 43Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,498 239 shares | +0% | +20% from low-36% from high | |
| 43Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,507 254 shares | +0% | +14% from low-39% from high | |
| 46Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,496 278 shares | +0% | +4% from low-45% from high | |
| 46Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,499 256 shares | +0% | 0% from low-41% from high | |
| 46Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,498 239 shares | +0% | +6% from low-37% from high | |
| 61Notable | KINGSWAY FINANCIAL SERVICES INC | $2,503 240 shares | +0% | +6% from low-37% from high | |
| 68Notable | KINGSWAY FINANCIAL SERVICES INC | $2,508 250 shares | +0% | +1% from low-40% from high | |
| 37Weak | KWYsell KINGSWAY FINANCIAL SERVICES INC | $51k 5,000 shares | -15% | +3% from low-38% from high | |
| 45Moderate | KWYsell KINGSWAY FINANCIAL SERVICES INC | $104k 10,000 shares | -29% | +5% from low-37% from high | |
| 68Notable | KINGSWAY FINANCIAL SERVICES INC | $2,496 230 shares | +0% | +9% from low-35% from high | |
| 51Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,503 229 shares | +0% | +27% from low-35% from high | |
| 29Weak | KWYbuy KINGSWAY FINANCIAL SERVICES INC | $2,500 211 shares | +0% | +49% from low-29% from high | |
| 41Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,494 244 shares | +0% | +36% from low-38% from high | |
| 41Moderate | KINGSWAY FINANCIAL SERVICES INC | $2,506 234 shares | +0% | +42% from low-37% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,493 202 shares | +0% | +68% from low-26% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 205 shares | +0% | +66% from low-27% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,505 183 shares | +0% | +87% from low-18% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,505 185 shares | +0% | +82% from low-20% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 184 shares | +0% | +85% from low-19% from high | |
| 56Moderate | KINGSWAY FINANCIAL SERVICES INC | $400k 30,000 shares | -2% | +82% from low-20% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 195 shares | +0% | +74% from low-23% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,502 192 shares | +0% | +78% from low-22% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,502 197 shares | +0% | +72% from low-24% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,492 177 shares | +0% | +91% from low-16% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 157 shares | +0% | +118% from low-4% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,502 171 shares | +0% | +101% from low-12% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 174 shares | +0% | +96% from low-14% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,507 173 shares | +0% | +97% from low-13% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,492 176 shares | +0% | +93% from low-15% from high | |
| 37Weak | KINGSWAY FINANCIAL SERVICES INC | $2,509 174 shares | +0% | +91% from low-16% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,492 172 shares | +0% | +94% from low-15% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,510 179 shares | +0% | +93% from low-2% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,492 181 shares | +0% | +87% from low-3% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 195 shares | +0% | +76% from low-1% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 247 shares | +0% | +43% from low0% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 287 shares | +0% | +19% from low-9% from high | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,501 305 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 340 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,504 315 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,497 311 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,499 300 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,498 301 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,516 297 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,491 291 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,497 279 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 279 shares | +0% | - | |
| 33Weak | KINGSWAY FINANCIAL SERVICES INC | $2,500 266 shares | +0% | - | |
| 28Weak | KINGSWAY FINANCIAL SERVICES INC | $2,502 284 shares | +0% | - |
Planned sales
Form 144 notices this insider filed before selling restricted or control stock, newest first.
| Filed | Company | Shares | Value | Sale date | Past 3 months |
|---|---|---|---|---|---|
| May 21, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC. | 5,000 0.02% of outstanding | $51k | May 21, 2026 | $103k |
| May 20, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC. | 5,000 0.02% of outstanding | $51k | May 20, 2026 | $51k |
| May 19, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC. | 5,000 0.02% of outstanding | $52k | May 19, 2026 | none |
| Dec 23, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC. | 30,000 0.10% of outstanding | $398k | Dec 23, 2025 | none |
Transactions
The newest 50 of 85 rows this insider has filed.
| Date | Company | Transaction | Shares | Price | Value | Holdings after | Filed |
|---|---|---|---|---|---|---|---|
| Sep 30, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +269 | $9.30 | $2,502 | 1,427,430 | 14 d ago |
| Sep 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +254 | $9.82 | $2,494 | 1,427,161 | 28 d ago |
| Aug 31, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +239 | $10.45 | $2,498 | 1,426,907 | 43 d ago |
| Aug 17, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +254 | $9.87 | $2,507 | 1,426,668 | Aug 18, 2026 |
| Jul 30, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +278 | $8.98 | $2,496 | 1,426,414 | Jul 31, 2026 |
| Jul 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +256 | $9.76 | $2,499 | 1,426,136 | Jul 16, 2026 |
| Jun 30, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +239 | $10.45 | $2,498 | 1,425,880 | Jul 1, 2026 |
| Jun 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | FTax withholding Common Stock | -30,233 | $10.12 | $306k | 1,425,641 | Jun 17, 2026 |
| Jun 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +240 | $10.43 | $2,503 | 1,455,874 | Jun 15, 2026 |
| May 29, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +250 | $10.03 | $2,508 | 1,455,634 | Jun 1, 2026 |
| May 27, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | GGift Common Stock | -6,257 | $9.99 | $63k | 1,455,384 | May 29, 2026 |
| May 21, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | SOpen-market sale Common Stockindirect: Trust-MPF | -5,000 | $10.14 | $51k | 29,100 | May 22, 2026 |
| May 19, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | SOpen-market sale Common Stockindirect: Trust-GEF | -5,000 | $10.30 | $52k | 29,100 | May 21, 2026 |
| May 20, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | SOpen-market sale Common Stockindirect: Trust-LTF | -5,000 | $10.43 | $52k | 29,100 | May 21, 2026 |
| May 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +230 | $10.85 | $2,496 | 1,461,641 | May 19, 2026 |
| Apr 30, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +229 | $10.93 | $2,503 | 1,461,411 | May 4, 2026 |
| Apr 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +211 | $11.85 | $2,500 | 1,461,182 | Apr 15, 2026 |
| Mar 30, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +244 | $10.22 | $2,494 | 1,460,971 | Mar 31, 2026 |
| Mar 13, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +234 | $10.71 | $2,506 | 1,460,727 | Mar 16, 2026 |
| Feb 27, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +202 | $12.34 | $2,493 | 1,460,493 | Mar 2, 2026 |
| Feb 17, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +205 | $12.19 | $2,499 | 1,460,291 | Feb 18, 2026 |
| Feb 2, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +183 | $13.69 | $2,505 | 1,460,086 | Feb 2, 2026 |
| Jan 15, 2026 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +185 | $13.54 | $2,505 | 1,459,903 | Jan 29, 2026 |
| Dec 31, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +184 | $13.58 | $2,499 | 1,459,718 | Jan 5, 2026 |
| Dec 23, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | SOpen-market sale Common Stock | -30,000 | $13.32 | $400k | 1,459,534 | Dec 29, 2025 |
| Dec 16, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +195 | $12.82 | $2,500 | 1,489,534 | Dec 18, 2025 |
| Nov 28, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +192 | $13.03 | $2,502 | 1,489,339 | Dec 2, 2025 |
| Nov 17, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +197 | $12.70 | $2,502 | 1,489,147 | Nov 19, 2025 |
| Oct 30, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +177 | $14.08 | $2,492 | 1,488,950 | Nov 3, 2025 |
| Oct 15, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +157 | $15.92 | $2,499 | 1,488,773 | Oct 17, 2025 |
| Sep 30, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +171 | $14.63 | $2,502 | 1,488,616 | Oct 2, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stock | -14,100 | $14.57 | $205k | 1,516,645 | Sep 30, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stockindirect: Trust-GEF | +14,100 | $14.57 | $205k | 34,100 | Sep 30, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stock | -14,100 | $14.57 | $205k | 1,502,545 | Sep 30, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stockindirect: Trust-LTF | +14,100 | $14.57 | $205k | 34,100 | Sep 30, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stock | -14,100 | $14.57 | $205k | 1,488,445 | Sep 30, 2025 |
| Sep 26, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | JOther Common Stockindirect: Trust-MPF | +14,100 | $14.57 | $205k | 34,100 | Sep 30, 2025 |
| Sep 15, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +174 | $14.36 | $2,499 | 1,530,745 | Sep 16, 2025 |
| Aug 29, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +173 | $14.49 | $2,507 | 1,530,571 | Sep 2, 2025 |
| Aug 18, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +176 | $14.16 | $2,492 | 1,530,398 | Aug 18, 2025 |
| Jul 30, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +174 | $14.42 | $2,509 | 1,530,222 | Jul 31, 2025 |
| Jul 15, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +172 | $14.49 | $2,492 | 1,530,048 | Jul 16, 2025 |
| Jul 1, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +179 | $14.02 | $2,510 | 1,529,876 | Jul 1, 2025 |
| Jun 13, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +181 | $13.77 | $2,492 | 1,529,697 | Jun 16, 2025 |
| May 30, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +195 | $12.82 | $2,500 | 1,529,516 | Jun 2, 2025 |
| May 15, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +247 | $10.12 | $2,500 | 1,529,321 | May 19, 2025 |
| Apr 30, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +287 | $8.71 | $2,500 | 1,529,074 | May 1, 2025 |
| Apr 15, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | AGrant or award Common Stock | +311 | $8.02 | $2,494 | 1,528,787 | Apr 16, 2025 |
| Mar 28, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +305 | $8.20 | $2,501 | 1,528,476 | Mar 31, 2025 |
| Mar 14, 2025 | KWY KINGSWAY FINANCIAL SERVICES INC | POpen-market purchase Common Stock | +340 | $7.35 | $2,499 | 1,528,171 | Mar 17, 2025 |
50 of 85 rows shown.
Questions about John Taylor Maloney Fitzgerald
Answered from the filings on this page, as of the latest one.
Is John Taylor Maloney Fitzgerald buying or selling?
In the last 12 months John Taylor Maloney Fitzgerald reported 24 open-market buys worth $60k and 3 open-market sells worth $554k on SEC Form 4; the latest was bought $2,502 of KWY on Sep 30, 2026. Grants, option exercises and tax withholding are not counted.
How did John Taylor Maloney Fitzgerald's past buys perform?
Measured from the first close after each filing, the stock trailed the S&P 500 by a median 19.9% over six months across 33 past buys, with 30% ahead of the index. Past results describe what happened; they do not predict the next trade.
Where does John Taylor Maloney Fitzgerald file Form 4?
John Taylor Maloney Fitzgerald has filed Form 4 at KWY (KINGSWAY FINANCIAL SERVICES INC) as President and CEO. A Form 4 is required of officers, directors and holders of more than 10% of a share class within two business days of a trade.
Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.