PGR PROGRESSIVE CORP/OH/ Insider Trading

Director Jeffrey D Kelly sold 7,000 PGR shares at $216.33; post-transaction holdings 22,546 shares; -18.7% from 52-week high

Jeffrey D Kelly sold 7,000 shares (22.5K shares) of Progressive at $216.33 on 2026-06-24, reducing his stake by 23.7% to 22,546 shares. The sale occurred at a price 18.7% below the 52-week high of $267.92, though the stock has gained 9.6% over both the 30-day and 90-day periods. His prior two sales at PGR both resulted in positive returns over 90 days (10.5% and 12.0%), suggesting a pattern where the stock has risen after his previous sales at this ticker. With PGR trading at an 11.01 P/E and posting 16.3% annual revenue growth on $22.2B in quarterly revenue, the company shows fundamental strength, making the timing and magnitude of this director-level sale the primary investor consideration.

John Jo Murphy (Claims President) sold 5,916 shares of PGR at $200.00 on 2026-06-05 under 10b5-1 plan; stock now -30.5% from 52-week high.

Murphy executed a $1,183,200.00 sale of 5.9K shares under a pre-arranged 10b5-1 trading plan adopted 2026-02-19, reducing his stake by 12.5% to 41.3K shares. The sale occurred at $200.00 per share while the stock currently trades at $201.57, down -30.5% from the 52-week high of $289.96. Examining his same-ticker history at PGR, four of his five prior sales saw negative 90-day returns (-7.1%, -9.9%, -12.1%, and -7.1%), with only the 2025-01-22 sale followed by positive 90-day returns (+9.0%). Since this transaction is governed by a scheduled 10b5-1 plan rather than discretionary timing, it does not reflect real-time trading decisions; however, the consistent pattern of post-sale declines in his PGR transaction history merits monitoring.

Commercial Lines President Bailo Karen sold 3,517 shares of PGR at $212.00 on 2026-03-05 for $745,604.00

Karen Bailo, Commercial Lines President at Progressive Corp, sold 3,517 shares at $212.00, reducing her holdings by 9.8% to 32,347 shares. The sale occurred well above the current price of $206.80 and near the bottom of the 52-week range, with the stock down 29.0% from its 52-week high of $291.22. Her prior trading at PGR shows mixed timing outcomes: 1 of 4 prior sells resulted in positive 90-day returns, with her most recent sale at this ticker (2025-07-28) followed by a 90-day decline of 12.1%, while her cross-ticker sales have averaged a 90d return of 6.2%, suggesting a 25.00% well-timed rate across holdings. The company remains well-positioned fundamentally with $22.5B in revenue, $2.6B net income, and a P/E of 8.95, though the recent price momentum is negative over 90 days (-8.6%).

PGR CFO John P Sauerland sold 5,000 shares at $228.48 on 2025-11-28 under 10b5-1 plan

Sauerland sold 5,000 shares at $228.48 on 2025-11-28 as part of a pre-arranged 10b5-1 trading plan adopted on 2025-08-21, reducing his holdings from 228,024 shares to 223,024 shares. The sale is purely scheduled and discretionary trading is absent. Post-transaction holdings of 223,024 shares remain substantial relative to the reduction of -2.2%, which is routine portfolio activity for a senior executive with significant equity stakes.

Progressive's Claims President Murphy sold 2,218 shares of PGR at $242.10 on 2025-09-19 for $536,977.80 total, holding 43.5K shares post-sale

Murphy John Jo sold 2,218 shares (4.9% of pre-transaction holdings) at $242.10, reducing his stake to 43,505 shares. Across his same-ticker history at PGR, only 1 of 3 measurable prior sells has demonstrated well-timed exits (negative 90-day return), with the most recent two sales in August and July occurring before price declines of -3.4% and -1.8% respectively at the 30-day mark. His cross-ticker track record shows 5 prior open-market sales with an average 90-day return of +4.0%, indicating historically poor timing as the stock has risen after his exits (33.33% well-timed rate). PGR's fundamentals remain strong with $22.0B quarterly revenue, $3.2B net income, +21.4% annual growth, and a P/E of 13.55, though the stock has declined -17.2% from its 52-week high and -9.4% over 90 days, providing context for recent selling pressure.

Callahan sold 6,420 PGR shares at $242.22 (−29.7% of holdings); stock down 17.2% from 52-week high, prior trades mixed at this ticker.

Callahan Patrick K, Personal Lines President at Progressive, sold 6,420 shares (29.7% reduction) on 2025-09-19 at $242.22, leaving holdings at 15,191 shares. The stock is currently $241.15, down 17.2% from its 52-week high of $291.22 and off 3.2% over 30 days. His cross-ticker track record shows modest gains post-sell (avg 90d return +6.2%, 20% well-timed rate), but his same-ticker history at PGR is mixed: 1 of 5 prior sells were well-timed at the 90-day mark, with outcomes ranging from −7.9% to +8.6% over 30 days. The stock's current weakness (17.2% below 52-week high) and his material reduction in PGR holdings warrant observation of whether this trade marks a directional shift or is routine portfolio management.

Progressive CEO Susan Patricia Griffith sold 30,659 shares at $246.06 on 2025-09-02; post-sale holding remains substantial at 471,286 shares.

Susan Patricia Griffith, President and CEO of Progressive Corp, sold 30,659 shares (30.7K shares) at $246.06 for a total value of $7,543,892.22 ($7.5M), reducing her holdings by 6.1% from 501,945 to 471,286 shares. The sale occurred near the lower end of the stock's 52-week range ($235.61–$291.22), approximately 15.3% below the 52-week high, and the stock is up 2.1% over 30 days but down 12.0% over 90 days. Her prior trades at Progressive show a mixed record: of the 4 prior sales with measurable outcomes, zero generated negative 90-day returns, meaning the insider's prior sales at this ticker have been poorly-timed relative to subsequent stock performance (the stock rose after each of those sales). Despite the CEO's large remaining position of 471,286 shares and the company's strong fundamentals (revenue $22.0B, net income $3.2B, annual revenue growth +21.4%, P/E 13.86), the absence of well-timed sells in her transaction history at this ticker does not suggest prescient timing on this sale.

President Murphy John Jo sold 2,218 shares of PGR at $250.78; stock down -2.4% in 30 days, -12.4% in 90 days.

Murphy John Jo, serving as President, sold 2,218 shares (2.2K shares) at $250.78, reducing holdings from 47,941 to 45,723 shares. The stock has subsequently declined -2.4% over 30 days and -12.4% over 90 days, currently trading at $244.09, down -16.2% from the 52-week high of $291.22. His prior trades at PGR show a mixed track record: two recent sells on 2025-07-28 and 2025-06-20 with outcomes not yet measurable, while his 2025-01-22 and 2024-08-15 sales were followed by gains (+9.4% and +7.6% at 30 days, respectively), indicating his prior sell timing at this ticker has not been well-timed at the 90-day horizon. His cross-ticker track record across four prior sells shows an average 90-day return of +9.5% with a well-timed rate of 0.00%, meaning those sales preceded price increases rather than declines. Despite solid fundamentals (P/E of 13.71, annual revenue growth of +21.4%, and net income of $3.2B on $22.0B revenue), the downward price trajectory following this sale merits monitoring to understand whether it reflects broader market conditions or company-specific concerns.

Personal Lines President Patrick K Callahan sold 6,232 shares of PGR at $249.96 for $1,557,748.85

Patrick K Callahan sold 6,232 shares at $249.96 on 2025-08-22, reducing his holdings by 22.4% to 21,611 shares remaining. At the current price of $244.09, the stock is -16.2% from its 52-week high and has declined 12.4% over the past 90 days. His prior trades at PGR show mixed timing outcomes: of 4 prior measurable sells at this ticker, only 1 was well-timed at the 90-day mark, with returns ranging from -7.9% to +17.3%. His cross-ticker track record across 6 prior sells shows an average 90-day return of +6.2% with a 20.00% well-timed rate, suggesting inconsistent execution in avoiding downturns. The company fundamentals remain solid with $22.0B in quarterly revenue and 21.4% annual revenue growth, and the P/E of 13.71 is moderate, providing context that this sale occurs within a stable operating environment rather than amid obvious operational distress.

PGR President Lori A Niederst sold 8,063 shares at $250.18 for $2.0M on 2025-08-14, reducing holdings 17.1%.

Niederst sold 8,063 shares at $250.18, reducing her stake by 17.1% to 39,040 shares. At the transaction price, she was selling approximately 1.2% above the current market price of $247.15, which sits 15.1% below the 52-week high of $291.22. Reviewing her prior transaction history at Progressive, her three most recent sales occurred on 2025-01-30, 2024-07-22, and 2023-11-28, with 90-day outcomes of +14.0%, +17.3%, and +17.8% respectively—all positive returns, indicating her prior sales preceded stock appreciation. The stock is trading in a depressed state relative to its recent range, having declined 13.6% over 90 days.