CB Chubb Ltd Insider Trading

EVP Ortega sold 3,886 CB shares at $322.08; retains 28,858 shares plus 60,234 derivative holdings

Juan Luis Ortega, Executive Vice President, sold 3,886 shares (3.9K shares) of Chubb Ltd at $322.08 on 2026-06-08 for $1,251,602.88, reducing his non-derivative holdings by 11.9% to 28,858 shares. However, this partial sale does not represent a material exit: Ortega retains a substantial non-derivative position and maintains an additional 60,234 shares in derivative holdings (options to acquire), preserving meaningful economic exposure to the company. His cross-ticker track record shows 4 prior sells with an average 90-day return of +6.7%, indicating historically poorly-timed sales on a cross-ticker basis, though at Chubb specifically only 1 of 4 prior sales at this ticker were well-timed at the 90-day mark. The sale price of $322.08 falls 4.4% below the 52-week high of $345.67 and represents a transaction on a stock trading near historical strength (30-day change: +3.2%), offering limited evidence of conviction-driven selling or concern.

Chubb President & COO Keogh sells 23,000 shares for $7,394,740.13; holdings drop 14.0% to 141.0K shares

John W Keogh executed 2 separate sales totaling 23,000 shares for $7,394,740.13 at a blended average price of $321.51 on 2026-05-27. This represents a 14.0% reduction from his pre-transaction holdings of 163,969 shares. At the cross-ticker level, his prior 7 sells showed a 90d well-timed rate of 66.67%, though at Chubb specifically, 4 of 5 prior trades were well-timed at the 90-day mark, suggesting a pattern of disciplined execution at this ticker. The stock currently trades at $311.71, down 4.3% over 30 days and 8.6% over 90 days, positioning this sale within the insider's established timing pattern on Chubb.

Chubb SVP Johns Bryce L. sold 1,500 shares at $336.62 on 2026-03-04; retains 24.8K shares

Johns Bryce L., Senior Vice President, liquidated 1,500 shares (5.7% of pre-transaction holdings) at $336.62, realizing $504,925.05. Post-transaction holdings of 24,770 shares remain substantial within the context of a $128.0B market-cap insurer with $16.1B quarterly revenue and a P/E of 11.94. The sale occurred at a price 2.5% above the current market price of $328.00 and near the 52-week high of $342.76, suggesting favorable market conditions. No FLAGS or TRACK RECORD context is provided; the transaction stands as a discrete open-market activity. For a mid-level executive, a partial position reduction of this scale and timing merits routine monitoring but does not signal unusual strategic repositioning.

EVP Wayland sells 7,645 shares of Chubb (CB) for $2.6M at $336.44; holds 56.2K post-sale

Wayland Joseph F, Executive Vice President, sold 7,645 shares at $336.44 on 2026-03-03, reducing his holdings by 12.0% to 56,212 shares and raising $2.6M. The sale occurred near Chubb's 52-week high of $342.76 (-3.0%), and the stock has appreciated 6.1% over the prior 30 days and 12.7% over the prior 90 days. Across his same-ticker history at CB, Wayland has completed 5 prior trades with a 60% success rate at the 90-day mark (3 of 5 were well-timed, meaning the stock declined after those sales), though the two most recent CB sales in late 2025 did not precede declines. At the company level, Chubb operates with solid fundamentals: $16.1B in annual revenue, $2.8B net income, a P/E of 12.11, and 6.5% annual revenue growth, suggesting operational stability rather than distress driving the sale decision.

CEO Evan Greenberg sold 14,925 shares of Chubb at $335.09 on 2026-02-12 ($5.0M); stock rallying +10.4% in 30 days.

CEO Evan G. Greenberg sold 14,925 shares at $335.09, reducing his stake from 511,576 to 496,651 shares, a -2.9% reduction. The sale occurred near the stock's 52-week high of $332.51 (within 0.2%), coinciding with strong short-term momentum: the stock has gained +10.4% over 30 days and +12.9% over 90 days. Greenberg's prior trades at Chubb show consistent 90-day well-timing with 4 of 4 prior sales registering negative 90-day returns, though his cross-ticker track record shows mixed results with an 80.00% 90d well-timed rate and average 90d return of -0.4%. The timing and magnitude warrant observation given the rapid appreciation context, but the company remains fundamentally strong with P/E of 13.50, +12.1% annual revenue growth, and $2.8B net income on $16.1B quarterly revenue.

CAO Ohsiek sells 5,140 shares at blended $325.43 for $1.7M, reducing stake 23.2%; stock up 10.4% in 30 days

Ohsiek George F., Chief Accounting Officer of Chubb Ltd, executed 2 separate sales totaling 5,140 shares for $1,672,698.26 between February 12–13, 2026, at prices of $328.97 and $324.30, reducing his holdings from 22,156 shares to 17,016 shares. The transactions occurred as Chubb stock has appreciated 10.4% over the prior 30 days and trades near its 52-week high of $332.51, though no scheduled trading plan (10b5-1) is indicated in the filing. The company's fundamentals remain solid with revenue of $16,148,000,000 (latest quarter), net income of $2,801,000,000, and annual revenue growth of 12.1%, supporting a valuation of 13.50 P/E. The sale's magnitude—23.2% of prior holdings—is material but does not eliminate Ohsiek's remaining equity stake of 17,016 shares.

EVP Boroughs sells 27,817 shares ($9.2M) at $331.98; post-transaction holds 11,810 shares (-70.2% reduction)

Timothy Alan Boroughs, Executive Vice President at Chubb Ltd, executed two separate sales totaling 27,817 shares for $9,234,687.66 on 2026-02-06 at a blended average price of $331.98. This represents a -70.2% reduction in his holdings, leaving him with 11,810 shares post-transaction. The sales were executed near the 52-week high (current price $326.25 is -1.5% from the $331.28 high), and his prior transactions at this ticker show a strong pattern: 3 of 3 measurable sells were well-timed, with 90-day returns of -3.0%, -3.4%, and -3.6% respectively. While cross-ticker timing (30% well-timed rate) is modest, his ticker-specific execution history at CB demonstrates consistent ability to sell before subsequent declines. The timing context—sales at near-peak prices following a +6.3% 30-day run and a +10.6% 90-day move—combined with his established track record at this specific security warrants attention to the directional signal this large, concentrated reduction may portend.

CEO Greenberg sold 15.1K CB shares at $331.47 (2026-02-05); post-transaction holdings 511.6K; 80% historical sell timing accuracy

Chairman & CEO Evan G Greenberg sold 15,060 shares at $331.47 on 2026-02-05, reducing his stake by 2.9% to 511.6K shares and generating $5.0M in proceeds. The sale occurred at a price 1.5% below the 52-week high of $331.28, with CB trading recently at $326.17 (down slightly from transaction price). Greenberg's cross-ticker track record shows a 80.00% well-timed rate across 5 prior sells, and at this ticker specifically, 4 of 5 prior sells demonstrated negative 90-day returns, suggesting a pattern of exiting before declines. The company's fundamentals remain solid—$16.1B in revenue, $2.8B in net income, 12.1% annual growth, and a 13.27 P/E multiple—indicating the sale reflects portfolio positioning rather than company-specific distress. The recent stock strength (up 6.3% in 30 days and 11.5% in 90 days) and timing near the 52-week high are contextual factors for observing whether this sale continues Greenberg's established sell-timing pattern.

EVP Juan Luis Ortega sold 4,357 shares of CB at $295.04 (Dec 2); stock trading near 52-week high despite prior mixed timing record

Juan Luis Ortega, Executive Vice President, sold 4,357 shares of Chubb Ltd at $295.04 on 2025-12-02, reducing his post-transaction holdings to 36,092 shares (-10.8% vs pre-transaction). The sale occurred near the upper end of the stock's 52-week range ($257.71–$302.46), at a price 2.6% below the 52-week high. However, his cross-ticker track record shows 3 prior sells with an average 90-day return of +3.6% and a 90-day well-timed rate of 33.33%—modest performance. At CB specifically, his timing has been inconsistent: 1 of 3 prior sales achieved a negative 90-day return (well-timed, as the stock subsequently declined). Fundamentals remain solid with annual revenue growth of +12.1%, a P/E of 11.99, and latest-quarter net income of $2,801,000,000.00. The sale size represents a moderate reduction in holdings and lacks the clear conviction signal of a substantial single-ticker commitment.

EVP Boroughs sells 11,430 shares at $296.10 avg ($3.4M), reducing CB stake 87.8% to 1,585 shares on 11/24.

Timothy Alan Boroughs, Executive Vice President at Chubb Ltd, executed 2 separate sales totaling 11,430 shares for $3,384,390.10, liquidating 87.8% of his pre-transaction holdings and leaving only 1,585 shares post-trade. The stock was trading at $296.17 and $295.19 on the transaction date, near the 52-week high of $302.46, and has since moved 1.5% below that peak. His prior sales at Chubb (5 trades on record) showed mixed timing: 3 of 5 were well-timed at the 90-day mark (stock fell after), while 2 resulted in negative returns; his cross-ticker track record over 10 prior sells averaged only 0.6% 90-day return with a 30% well-timed rate, suggesting limited predictive value in prior transaction patterns. The near-complete liquidation of a substantial equity position by a senior officer warrants attention given the magnitude and the reduction in post-transaction skin in the game.