Andy F Bessette

EVP Andy F Bessette sells 4,255 TRV shares at $308.11; retains 24,284 shares post-transaction.

Andy F Bessette, EVP and Chief Admin Officer of Travelers Companies, sold 4,255 shares at $308.11 on 2026-05-22, retaining 24,284 shares (24.3K shares) afterward. This represents a -14.9% reduction from his pre-transaction holdings of 28,539 shares (28.5K shares). His prior sells at TRV show mixed timing outcomes: 1 of 5 prior sales were well-timed at the 90-day mark, with most recent TRV sales in February 2026 posting near-flat 30-day returns (-0.1% to -0.7%) followed by modest 90-day gains (2.3% to 2.9%), while his cross-ticker track record across 8 prior open-market sales averaged a 90-day return of +3.5% with a well-timed rate of 28.57% — indicating his sells have historically occurred before stock appreciation rather than declines. The company reported revenue of $11.9B (latest quarter), net income of $1.7B, and annual revenue growth of +5.2%, providing a stable fundamental backdrop against which to assess this partial reduction in holdings.

EVP Andy Bessette sold 6,000 shares of Travelers at avg $297.65 for $1.8M, reducing holdings by 19.8%

Andy F. Bessette, EVP and Chief Admin Officer, executed 3 separate sales totaling 6,000 shares for $1,785,925.19 on 2026-02-17, with prices ranging from $297.25 to $299.03. This represents a 19.8% reduction in his holdings from 30,284 shares to 24,284 shares, occurring as the stock trades at $299.90, near its 52-week high of $301.49. At the same-ticker level, his prior 5 sells at TRV show mixed timing outcomes: 2 of 5 achieved negative 90-day returns (well-timed), while his cross-ticker track record shows a 62.50% well-timed rate across 8 prior sells with average 90-day returns of +1.6%. The company fundamentals remain solid with $12.5B quarterly revenue, $1.9B net income, and a P/E of 9.05, with the stock up 11.2% over 30 days, suggesting the sale occurred during a period of positive momentum rather than distress.

EVP Bessette sells 7,742 TRV shares at $264.90; stock -4.2% from 52-week high.

Bessette sold 7,742 shares (27.2% of pre-transaction holdings) on 2025-08-07 at $264.90, reducing his stake from 28,433 to 20,691 shares. The stock is currently trading at $264.87, approximately -4.2% from its 52-week high of $276.34 and has gained +3.7% over the past 30 days. At the same-ticker level, Bessette's prior five sales at TRV show mixed timing outcomes: his 2024-08-16 and 2024-02-09 sales were followed by positive 90-day returns (+18.1% and +2.2% respectively), while his 2024-10-28 sale showed a negative 90-day return of -4.6%. The transaction occurs in a company with solid fundamentals—$12.1B in quarterly revenue, net income of $1.5B, and annual revenue growth of +12.2%—trading at a P/E of 11.37.

EVP Andy F Bessette sold 5,000 TRV shares at $272.76 for $1,363,800; retains 20,691 shares

Andy F Bessette, EVP and Chief Admin Officer, sold 5,000 shares (19.5% reduction of his pre-transaction holdings) at $272.76, near the 52-week high of $274.54. At his same-ticker history of 5 prior TRV sales, 3 proved well-timed at the 90-day mark; his most recent TRV sale on 2024-10-28 saw a +5.2% 30-day return before turning negative at 90 days (-4.6%). His cross-ticker track record shows a 66.67% well-timed rate on 6 prior sales, with modest positive returns (avg 30d +1.4%, avg 90d +1.6%). The sale occurs after TRV has risen 7.3% in 30 days and 15.2% in 90 days, positioning the transaction at the upper end of recent price movement. No scheduled trading plan (10b5-1) is flagged, indicating this was a discretionary decision.

EVP Andy F. Bessette sold 4,520 TRV shares at $253.46; holds 16,975 post-sale. 90-day track record 75% well-timed across tickers.

Bessette sold 4,520 shares (21.0% of pre-transaction holdings) at $253.46 on 2024-10-28, reducing his stake from 21,495 to 16,975 shares. TRV is trading at $250.09, only 1.3% below the sale price and near strength (+6.8% in 30 days, +17.9% in 90 days). Across his open-market transaction history, Bessette has demonstrated a 75% well-timed rate on prior sells (3 of 4 same-ticker sales showed negative 90-day returns), though his cross-ticker sell average 90d return was -1.0%, suggesting modest timing discipline overall. The sale occurs in a strong price environment and represents a reduction but not an exit; he retains substantial TRV holdings at an equity-challenged company valuation (P/E 12.50, $11.9B revenue, $1.3B net income).

EVP Andy F Bessette sold 5,000 TRV shares at $217.20; holdings drop to 16,975 shares post-sale

Bessette, EVP and Chief Admin Officer, sold 5,000 shares for $1,086,025.00 on 2024-08-16, reducing his position by 22.8%. His cross-ticker track record shows a 75.00% 90-day well-timed rate across 4 prior sells, with an average 90d return of -1.0%, indicating his sales have generally preceded or coincided with share price declines. At TRV specifically, his prior 4 trades show mixed timing: 3 of 4 prior sells were well-timed at the 90-day mark, though the most recent TRV sale on 2024-02-09 showed positive returns (+1.7% at 30d, +2.2% at 90d). The stock has recovered 7.6% over 30 days and trades 5.2% below its 52-week high of $230.89, suggesting the company remains in an uptrend despite the recent sale. Travelers' fundamentals are solid—annual revenue growth of +12.2%, a P/E of 13.53, and strong recent quarterly net income of $534,000,000.00—providing limited fundamental context for concern, though the magnitude of this reduction (one-fifth of his holdings) warrants noting.