KWY KINGSWAY FINANCIAL SERVICES INC Insider Trading

Director Joshua Horowitz purchases 4,500 shares at $9.92 avg; holds 372,000 shares post-buy in recently-listed KWY

Joshua Horowitz, Director of KINGSWAY Corp, executed 2 separate purchases totaling 4,500 shares (4.5K shares) for $44,624.90 ($44.6K) on 2026-05-28 and 2026-05-29 at a blended average price of $9.92. The stock is currently trading at $10.00 as of 2026-06-01, just 8 trading days after listing, making recent price history unavailable for comparison. Post-transaction, Horowitz holds 372,000 shares (372.0K shares), representing a +1.2% increase versus his pre-transaction holdings of 367,500 shares (367.5K shares). The company reported latest-quarter revenue of $38,959,000.00 ($39.0M) but posted net income of $-2,268,000.00 ($-2.3M), with annual revenue growth of +23.4% year-over-year; however, the company was unprofitable over its most recent full fiscal year. As an early post-listing transaction from a director with a substantial existing position, this purchase warrants monitoring for patterns of insider participation as the company's profitability trajectory develops.

CFO Hansen Kent A purchases shares of KFS during period of declining earnings and depressed valuation.

CFO Hansen Kent A made an open-market purchase of KFS shares despite the company facing significant operational headwinds: recent quarterly results show deepening losses and the stock has retreated sharply from its highs, trading well below recent peaks. What makes this noteworthy is the timing — insider buying from C-suite executives during periods of financial strain can signal either genuine conviction that the market has overreacted, or it can reflect limited conviction if the purchase is small relative to holdings. This modest $1,563 purchase represents a negligible fraction of Kent's portfolio, suggesting more symbolic gesture than substantial conviction. Combined with the company's unprofitable status and recent earnings deterioration, this trade warrants scrutiny: is Kent buying a genuine value opportunity, or is this routine portfolio activity masking deeper operational concerns?

Kingsway CEO buys 229 shares as stock trades well below 52-week highs amid unprofitable operations.

John Taylor Maloney, Kingsway's President and CEO, purchased shares at a time when the stock is trading significantly below its 52-week high and the company is currently unprofitable with negative earnings. This represents a direct vote of confidence from the top executive, though the modest share count and negligible addition to his holdings suggest this is a small, opportunistic buy rather than a major conviction statement. The timing is noteworthy because the CEO is buying into a company with declining profitability and shrinking quarterly earnings—traditionally a risky position for insiders, yet Maloney's purchase suggests he may view current valuations as attractive or expects operational improvements ahead. This trade deserves watching, but investors should recognize that small insider purchases by executives don't always predict near-term price recovery, especially when fundamental headwinds persist.

CEO Maloney buys 211 KFS shares at $11.85; stock -28.6% from 52-week high, unprofitable in latest year

President and CEO Fitzgerald John Taylor Maloney purchased 211 shares of Kingsway Financial Services at $11.85 on 2026-04-15, adding to a substantial 1.46M-share holding. This marks his fifth discretionary buy at KFS in six weeks; his four prior purchases at this ticker from 2026-02-02 through 2026-03-13 posted mixed results, with three showing 30-day losses (-19.7%, -16.2%, -13.9%) against one gain (+6.1%). His cross-ticker track record shows 20 prior buys with a negative average 90-day return of -6.8% and a 26.67% win rate, suggesting a pattern of poorly-timed entry points. Kingsway itself faces headwinds: the company was unprofitable over its most recent full fiscal year with a net loss of $-2.4M on revenue of $37.2M, and the stock has declined 28.6% from its 52-week high of $16.57 despite a 23.4% annual revenue growth rate. The persistent buying despite recent losses and the stock's steep drawdown from highs warrant close observation of Q2 profitability trends and management's strategic rationale.

CFO Hansen Kent A bought 153 KFS shares at $10.22; stock down 37.0% from 52-week high, insider's prior KFS purchases underwater.

Hansen Kent A, CFO & EVP, purchased 153 shares of Kingsway Financial Services at $10.22 on 2026-03-30, a modest transaction totaling $1,563.66 and increasing his holdings by 0.1%. The stock is currently trading at $10.43, down 37.0% from its 52-week high of $16.57 and down 14.8% over the past 30 days. Notably, his five prior open-market purchases at KFS span only two months (2026-01-15 through 2026-03-13) and show consistent negative returns: the four measurable prior trades all posted 30-day losses ranging from -9.7% to -19.7%. The company itself reported a net loss of $2,411,000.00 on quarterly revenue of $37,173,000.00, though annual revenue growth reached 23.4%. The repeated buying pattern into a declining security, combined with underwater prior positions at this ticker and persistent unprofitability, warrants attention to whether the CFO's conviction in this purchase is aligned with fundamental recovery or driven by other considerations.

KFS CEO John Taylor Maloney buys 244 shares ($2.5K) on 2026-03-30; stock -37.0% from 52-week high amid continued losses.

CEO John Taylor Maloney purchased 244 shares at $10.22, bringing his holdings to 1,460,971 shares. This is the fifth purchase by Maloney at KFS in the past two months, following buys on 2026-03-13, 2026-02-27, 2026-02-17, 2026-02-02, and 2026-01-15. Stock price has declined -14.8% over the past 30 days and is currently -37.0% from its 52-week high of $16.57. The company remains unprofitable, with net income of $-2,411,000.00 for the latest quarter despite revenue of $37,173,000.00 and year-over-year revenue growth of +23.4%. At KFS specifically, his prior four purchases have all resulted in negative 30-day returns (-19.7%, -16.2%, -13.9%, -9.7%), and his broader cross-ticker buy history shows an average 90-day return of -5.2% with a 33.33% win rate.

CFO Hansen Kent A buys 146 KFS shares at $10.71; stock down -35.5% from 52-week high, company unprofitable.

Hansen Kent A, CFO & EVP, purchased 146 shares at $10.71 on 2026-03-13, a small addition to his 120.1K share position. The purchase occurs as KFS trades 35.5% below its 52-week high and the company reported a $-2.4M net loss in its latest quarter, despite 23.4% annual revenue growth. His same-ticker trading history at KFS shows five prior purchases in the past 2.5 months; the most recent measurable prior buy (2026-02-02) was followed by a 30-day decline of -13.9%. His broader cross-ticker track record spans 20 prior open-market purchases with a 40% win rate on a 90-day horizon and a -0.9% average 90-day return, indicating mixed timing across holdings.

KFS CEO Maloney buys 234 shares at $10.71; stock down 35.5% from 52-week high, prior KFS buys underwater 9.7% to 13.9%

John Taylor Maloney, President and CEO of Kingsway Financial Services, purchased 234 shares at $10.71 on 2026-03-13, a modest addition to his 1,460,727-share position. The current price of $10.69 sits -35.5% from the 52-week high of $16.57, reflecting substantial downward pressure on the stock. More notably, Maloney's prior four measurable buys at KFS have all generated losses: his trades on 2026-02-02, 2026-01-15, and 2026-12-31 have posted 30-day returns of -13.9%, -9.7%, and -1.2% respectively. The company itself remains unprofitable over the most recent full fiscal year with net income of $-2,411,000.00, though annual revenue growth reached +23.4%. The pattern of repeated purchases into a declining stock at a loss-making company, with no successful 90-day outcomes yet, warrants observation of whether fundamentals stabilize or decline further.

KFS CEO John Taylor Maloney Fitzgerald bought 202 shares at $12.34 on 2026-02-27; fifth consecutive purchase in 6 weeks amid -25.6% decline from 52-week high.

CEO John Taylor Maloney Fitzgerald purchased 202 shares at $12.34, extending a pattern of five consecutive buys at KFS within a six-week window (2025-12-16 through 2026-02-27). The stock has declined 25.6% from its 52-week high of $16.57, and at the current price of $12.33 is trading near the transaction price. The company reported net income of $-2,411,000.00 (a loss) over its latest full fiscal year, despite 6.0% annual revenue growth. At the same-ticker level, his prior four measurable outcomes show mixed near-term results (30-day returns ranging from -9.7% to +3.4%), with no 90-day outcomes yet determinable. The repeated buying into a structurally unprofitable business during a down-trend, rather than a tactical dip, merits attention to underlying catalysts and management's forward guidance.

CFO Hansen Kent A buys 126 shares of KFS at $12.34; stock down 8.1% in 30 days, company posted $-2.4M loss.

Hansen Kent A, CFO & EVP of Kingsway Financial Services, purchased 126 shares at $12.34 on 2026-02-27, adding to his 119.8K-share position. This is the fifth open-market buy at KFS in the past three months (prior purchases on 2026-02-17, 2026-02-02, 2026-01-15, 2025-12-31, and 2025-12-16), suggesting sustained accumulation despite headwinds. The company reported a $-2.4M net loss in its latest quarter and is unprofitable on a full-year basis, while the stock has fallen 8.1% over the past 30 days and sits 25.6% below its 52-week high. At KFS specifically, his prior trades show a mixed recent record (one 30-day loss of -9.7%, one gain of +3.4%, two with -1.2% and unmeasurable longer-term outcomes), distinct from his cross-ticker track record (46.67% 90-day win rate). The repeated small purchases during a downturn and loss-making period warrant observation of whether the accumulation reflects conviction in a recovery or follows a mechanical pattern independent of near-term stock performance.