BWIN Baldwin Insurance Group, Inc. Insider Trading

Non-officer stockholder Krystyn Elizabeth liquidated full position across two days, disposing of over 404k shares for $4.3M as stock trades well below highs.

Krystyn Elizabeth, who holds no officer or director role, executed a complete exit from Baldwin Insurance on May 6–7, selling 404,000 shares across four transactions totaling approximately $4.3 million while the stock trades significantly below its 52-week high. The sale came amid company fundamentals that remain pressured—Baldwin posted an annual net loss and currently trades near the lower end of its 52-week range—suggesting the shareholder was responsive to weakness rather than long-term conviction. Prior sales by Elizabeth at this company show mixed timing: her two most recent exits in March saw the stock subsequently rise modestly, indicating poor timing, but her three earlier exits in late 2024 all preceded declines, marking well-timed exits over a longer horizon. The liquidation reverses a brief return to accumulation (200,000 shares acquired via conversion in early May) before Elizabeth fully exited, a pattern that hints at portfolio consolidation rather than strategic repositioning in this particular holding.

Krystyn Elizabeth sold 119,987 shares at $21.25 on 2026-03-06 for $2,549,723.75 (derivative conversion), now 0 post-transaction

Krystyn Elizabeth executed 2 separate sales totaling 119,987 shares at $21.25 on 2026-03-06 for $2,549,723.75. This filing involves a conversion of derivative securities; the insider's derivative holdings in Form 4 Table II are not yet populated in our database, so the 0 post-transaction shares reflects only Table I and does not represent the full position. Notably, her prior 5 trades at BWIN were all well-timed at the 90-day mark, with each sale followed by declines ranging from -6.0% to -15.2% over 90 days; her cross-ticker track record shows a 90-day well-timed rate of 100.00%. The company is currently unprofitable (full-year net income was negative) and trading -54.7% from its 52-week high of $46.41, having declined -16.0% over the past 90 days. The insider's sales at $21.25 now sit above the current price of $21.03, reflecting a slight near-term margin. The timing and pattern of this transaction merit close attention given the insider's demonstrated historical accuracy on this name.

BWIN Director Sparks buys 44,200 shares for $1.0M across 2 transactions at $22.66 blended average

Director Paul Eugene Sparks completed 2 separate purchases totaling 44,200 shares for $1,001,760.00 on 2026-03-02 and 2026-03-03, increasing his holdings by 4.6% to 996,706 shares post-transaction. The company is operating at a loss (net income of $-18,727,000.00 in the most recent full fiscal year) despite 8.3% annual revenue growth, and the stock is trading at -52.5% from its 52-week high of $46.41. The purchases occurred at $22.66 blended average, below the 52-week high but within the context of significant downward price movement and recent upside momentum (+7.1% over 30 days). This substantial accumulation by a director occurs amid a loss-making period in the company's financials, creating a signal that warrants investor attention to both the underlying business fundamentals and the director's confidence assessment.

Roche James Morgan sold 240,000 shares (85.1% reduction) for $5.7M across 4 transactions in mid-December; stock down 49.0% from 52-week high, company unprofitable.

Roche James Morgan executed 4 separate sales totaling 240,000 shares for $5,743,136.56 between December 11–15, reducing holdings from 282,113 shares to 42,113 shares at a blended average price of $23.93. The timing is notable: Baldwin Insurance Group is trading at $23.67, down 49.0% from its 52-week high of $46.41 and -24.4% over the past 90 days, while the company posted a net loss of $18,727,000.00 against revenue of $365,389,000.00 (latest quarter) with full-year profitability negative. His prior trades at BWIN show 4 of 5 prior sells were well-timed at the 90-day mark, establishing a pattern of selling before subsequent declines at this ticker; however, the current transaction's timing relative to future price movement cannot yet be evaluated. The FLAG notation indicates derivative conversions are involved, meaning his Table I holdings (42,113 shares post-transaction) do not represent his complete economic position, limiting full assessment of his commitment to the company.

CFO Hale Bradford buys 10,000 shares of BWIN at $28.72 as stock down 22.3% in 30 days, company unprofitable but growing revenue 14.0%.

Hale Bradford, CFO of Baldwin Insurance Group, purchased 10,000 shares at $28.72 on 2025-08-07, increasing his holdings to 144,659 shares. The purchase occurs in a context of significant near-term price weakness: BWIN has declined 22.3% over 30 days and 20.9% over 90 days, currently trading at $30.72 versus a 52-week high of $55.29. The company reported negative net income of $-3.2M in its most recent quarter while maintaining revenue growth of 14.0% year-over-year and a market cap of $1.0B. Bradford's cross-ticker track record shows 1 prior buy with a 100.00% 90-day win rate, though this represents limited historical precedent at this specific ticker. The purchase extends existing substantial holdings rather than initiating a position, and occurs against a backdrop of depressed current valuation relative to recent peaks combined with ongoing operating losses despite strong top-line growth.

CEO Baldwin Trevor sold 175,000 shares ($6.9M) in 3 transactions at $38.48-$39.99 (June 11-12); holding reduced 86.3%

Baldwin Trevor (Chief Executive Officer) executed 3 separate sales totaling 175,000 shares for $6,892,106.00 between June 11-12, selling at prices ranging from $38.48 to $39.99 (blended average $39.38). The scale of this transaction is material: his post-transaction holding of 27,676 shares represents an 86.3% reduction from his prior stake of 202,676 shares. This is a substantial portfolio adjustment by the company's top executive. The stock currently trades at $39.12, within the 52-week range of $32.68–$55.29 and down 29.2% from the 52-week high. At the same ticker (BWIN), his prior 5 sales show a 60% well-timed rate at the 90-day mark, suggesting some historical pattern of favorable timing around decision points. However, the derivative-conversion FLAG indicates this sale may involve conversion mechanics; the insider's actual total position extends beyond the Table I shares and warrants independent verification of the full economic exposure post-filing.

Roche James Morgan sold 37.6K BWIN shares for $1.5M (blended avg $40.06) in 2 transactions, cutting holdings by 47.2%.

Roche James Morgan executed two separate sales totaling 37,573 shares on June 12–13, 2025, at prices averaging $40.06 per share, reducing his holdings from 79,686 to 42,113 shares (a 47.2% reduction). The sales came when BWIN is trading 29.2% below its 52-week high, suggesting the timing relative to recent price weakness is not unfavorable. His prior 5 trades at BWIN (dating back to August 2024) show mixed outcomes: his three earliest 2024 trades achieved positive 30-day returns (15.1% to 18.2%), while his two most recent May 2025 sales turned negative (−1.6% and −3.6% at 30 days), and none of his prior BWIN sales achieved positive 90-day returns. Cross-ticker, his track record of 14 prior sells shows a 0.00% well-timed rate at the 90-day horizon—meaning he sold and the stock subsequently rose in all measurable cases, indicating poor timing at the 90-day mark. The company is unprofitable on a full-year basis despite posting recent quarterly revenue of $413.4M and annual growth of +14.0%, adding operational complexity to the signal.

Director Baldwin Lowry sells 50,000 BWIN shares ($1.9M) at $38.98; now holds zero common shares via conversion.

Baldwin Lowry sold 50,000 shares of BWIN for $1,949,000.00 on 2025-06-09 at $38.98, reducing his common share holdings to zero. This sale comes following a pattern of five prior transactions at BWIN within two weeks (three on May 12, two on May 28), all sells. The company has generated $413.4M in quarterly revenue with +14.0% annual growth, though it reported negative full-year net income, which may be a context for recent insider activity. The stock currently trades at $39.60, -28.4% from its 52-week high of $55.29, reflecting a significant correction from earlier 2025 valuations. The flag indicating derivative holdings means Lowry retains a position in convertible securities not yet visible in this filing's Form 4 Table II, so this represents a conversion of equity rather than a complete portfolio exit.

Director Baldwin Lowry sold 62,500 shares for $2,395,000.00 at BWIN, reducing equity stake to 0.

On 2025-05-28, Baldwin Lowry (Director) executed two separate sales totaling 62,500 shares for $2,395,000.00 at a blended average price of $38.32. This eliminates his equity position at Baldwin Insurance Group, Inc. (BWIN). The sale occurs within a volatile window: the current price of $38.53 is only 0.3% above the transaction price, but the stock has declined 7.4% in the past 30 days and 6.3% over 90 days from a 52-week high of $55.29. Notably, Lowry executed three prior sales at BWIN on 2025-05-12 (16 days earlier), indicating a consecutive sell pattern in May. Although the company shows positive quarterly fundamentals (revenue $413.4M, annual growth +14.0%), it was unprofitable on a full-year basis, which may warrant monitoring. The filing contains a derivative-conversion flag, meaning the Table I position does not capture the insider's full derivative holdings, and this trade should not be characterized as a complete liquidation.

Galbraith Daniel sold 39,207 shares (91.1% of holdings) at $40.00 on 2025-05-13 for $1,568,280; stock down 30.7% from 52-week high.

Galbraith Daniel executed a substantial liquidation of his BWIN position, selling 39,207 shares (-91.1% vs pre-transaction holdings) for $1,568,280.00, reducing his stake to 3,849 shares. The transaction occurred at $40.00 per share; since then the stock has declined to $38.30, down 30.7% from its 52-week high of $55.29 and down 11.8% over the past 30 days. His cross-ticker track record shows 7 prior sales with an average 90-day return of +2.2% and a well-timed rate of 14.29%, indicating mixed execution; his prior BWIN sale on 2024-08-29 achieved a 90-day return of +5.2% but was not well-timed at the 90-day mark. The company reported $413.4M quarterly revenue with +14.0% annual growth but was unprofitable over its most recent full fiscal year, creating a backdrop where a near-complete exit by this insider warrants investor attention to whether he perceives deteriorating fundamentals or value realization.