R RYDER SYSTEM INC Insider Trading

EVP/CLO Robert D Fatovic sold 5,000 shares of R at $249.85 for $1,249,250.00; stock now at $253.83, up 19.2% in 90 days vs mixed prior R timing.

Robert D Fatovic, EVP, CLO & Corp. Secretary, sold 5,000 shares (5.0K shares) of RYDER SYSTEM INC at $249.85, reducing his holdings from 93,826 to 88,826 shares. The stock has since risen to $253.83, up 19.2% over 90 days—a move that occurred after the sale. His prior trades at R show mixed timing: 4 of 5 prior sells resulted in positive 90-day returns (the stock rose after he sold), while only 1 was well-timed with a negative 90-day return. At the cross-ticker level, his 90d well-timed rate is 25.00%, suggesting limited predictive timing. With R trading near its 52-week high of $259.00, the transaction occurred in the upper range of recent valuations.

President and COO Diez sold 9,632 shares of R at $222.20; holdings down 5.0% to 183,810 shares

Diez John J., President and COO, sold 9,632 shares on 2026-02-25 at $222.20, reducing his holdings by 5.0% to 183,810 shares post-transaction. At the time of sale, the stock was near its 52-week high of $224.06 and up 17.3% over the prior 30 days and 28.8% over 90 days. However, his prior three measurable sales at this ticker were not well-timed: post-sale returns averaged +16.0%, +3.8%, and +3.3% at the 90-day mark, meaning the stock rose after each sale rather than declining. This pattern at the company does not demonstrate consistent success in exiting before weakness. The sale occurred as the company reported $3.2B in revenue with net income of $138.0M and annual growth of only +0.2%, reflecting modest business momentum alongside a valuation of 17.18 P/E.

CEO Robert E. Sanchez sold 41,779 shares for $9.3M at near-52-week highs; stock up 28.8% in 90 days.

Robert E. Sanchez, Chair and CEO of Ryder System Inc., executed 3 separate sales totaling 41,779 shares for $9,329,289.28 at prices of $223.28, $223.86, and $225.12—all near the 52-week high of $224.06. This represents a -50.6% reduction in his holdings, from 82,607 to 40,828 shares. The sales occurred during a strong market backdrop: the stock is up 28.8% over 90 days and up 17.3% over 30 days, with the company reporting $3.2B in quarterly revenue and a P/E of 17.18. His prior trading pattern at Ryder is noteworthy: in 5 prior sales on this ticker (all on 2025-07-28 and 2025-07-29), 100% were followed by negative 90-day returns, ranging from -5.8% to -11.8%, indicating consistent downside capture. While the blended transaction price of $223.30 is essentially flat to current price ($223.13), the magnitude of the reduction and the historical pattern of well-timed downside exits at this ticker merit investor attention.

EVP/CLO Robert D Fatovic sold 11,640 shares of Ryder System at $222.30 for $2,587,572.00

Robert D Fatovic, EVP, CLO & Corp. Secretary, sold 11,640 shares at $222.30 on 2026-02-20, reducing his holdings by 11.0% to 93,737 shares and generating $2,587,572.00 in proceeds. The sale occurred near the 52-week high of $224.06, with the stock currently at $223.46. At the same-ticker level, Fatovic has completed 2 measured prior sales: one in May 2025 posted a +15.4% 90-day return (poorly timed, as the stock rose after), while two November 2024 sales each posted negative 90-day returns around -5.8% to -6.0% (well-timed). His cross-ticker track record shows a 40.00% well-timed rate on 12 prior sells with an average 90-day return of +2.2%, indicating mixed execution. Ryder's fundamentals show moderate valuation (P/E 17.20, net income $138,000,000.00) against flat year-over-year revenue growth of +0.2%. The context does not signal material concern, but the magnitude and timing relative to recent price appreciation warrant monitoring of subsequent insider activity and fundamentals.

EVP & CIO Ravindran Rajeev sold 2,696 shares at $221.36–$223.03 on 2026-02-19 for $597,454.56 total.

Ravindran Rajeev, EVP & CIO of Ryder System Inc, executed 2 separate sales totaling 2,696 shares for $597,454.56, reducing his post-transaction holdings to 18,136 shares, a -12.9% reduction from his pre-transaction position of 20,832 shares. The sales occurred at prices ($221.36 and $223.03) near the current market price of $224.06 and within 0.0% of the 52-week high, during a period of strong upward momentum (90-day change: +33.2%). His prior same-ticker transaction history shows 2 recent sales on 2026-02-13 and 1 sale on 2024-02-26; outcomes on those trades are not yet measurable. With the stock near its 52-week peak and given his limited measured timing success history, this sale warrants monitoring to track whether the near-peak execution reflects an objective market opportunity or broader strategic intent.

Ryder President Sensing sells 30,110 shares for $6.6M; reduces holdings 38.0% in 8 transactions

John S. Sensing, President of Global SCS & DTS at Ryder System Inc, executed 8 separate sales on 2026-02-19 totaling 30,110 shares for $6,635,009.77 at prices ranging from $219.69 to $222.52, reducing his post-transaction holdings to 49,081 shares from 79,191 shares (-38.0%). The current price of $224.06 is at the 52-week high, and the stock has gained 15.2% over 30 days and 33.2% over 90 days, placing this sale in a period of strong price momentum. His prior 5 trades at Ryder have all been sells with outcomes ranging from -8.0% to +12.2% over 30 days and -7.9% to +12.2% over 90 days; none of his same-ticker prior sales were well-timed at the 90-day mark. The scale of this transaction and the reduction of over one-third of his holdings merit investor attention, though the timing against recent upward price trajectory is a key data point to track.

President Thomas M. Havens sells 12,571 shares of Ryder at $221.65 avg for $2.8M, reducing stake by -27.5%

Thomas M. Havens, President of Global FMS at Ryder System Inc, executed two separate sales on 2026-02-18 totaling 12,571 shares for $2,786,346.79 at a blended average price of $221.65. The sale reduced his post-transaction holdings to 33,074 shares from 45,645 shares, a -27.5% reduction in his stake. The transaction occurred at 2.4% below the current price of $224.06; the stock has risen 15.2% over the past 30 days and 33.2% over the past 90 days, near its 52-week high. At Ryder, Havens' prior five transactions show a mixed record: only 1 of 5 prior sales demonstrated positive 90-day outcomes (well-timed = negative 90d return for sells), with outcomes ranging from -6.3% to +8.8% at the 90-day horizon. This sale represents a significant reduction in his equity position at the company.

EVP/CLO Robert D Fatovic sold 10,000 shares of Ryder at blended average $217.13 on 2026-02-17

Robert D Fatovic, EVP, CLO & Corp. Secretary, executed two separate sales totaling 10,000 shares for $2,171,336.65 at a blended average price of $217.13 on 2026-02-17. Post-transaction holdings stand at 93,737 shares, representing a -9.6% reduction from prior holdings of 103,737 shares. At the current price of $223.04, the insider sold below today's market level. His prior sales at Ryder (5 historical trades) show a 40.0% well-timed rate at the 90-day mark, with 2 of 5 prior sales followed by declines; however, this current sale's timing cannot yet be assessed. The stock has appreciated +16.9% over 30 days and +37.3% over 90 days, reflecting strong recent momentum that occurred after this filing date. No discernible pattern of conviction or concern is evident from the transaction alone; the sale reduced a substantial executive position without eliminating it entirely.

Karen M. Jones (EVP & CMO, Ryder) sells 6,000 shares at $208.21 avg for $1.2M; holds 12.5K post-sale

Karen M. Jones, EVP & Chief Marketing Officer, executed 3 separate sales on 2026-02-13 totaling 6,000 shares for $1,249,232.64, reducing her holdings by 32.5% to 12,473 shares. The blended average sale price of $208.21 sits 6.7% below the current price of $223.04, which sits at the 52-week high. At her same-ticker history at Ryder, prior sells show a timing pattern of 2 of 5 well-timed at the 90-day mark; her cross-ticker track record shows a 50.00% well-timed rate on prior sells with an average 90-day return of +7.9%, indicating her prior sells typically occurred before stock gains. The recent 90-day price appreciation of +37.3% suggests current valuations have moved substantially from her execution prices.

EVP & CIO Ravindran Rajeev sold 14,367 shares ($3.0M) in 2 separate transactions at $211.73–$211.94 blended average

Ravindran Rajeev, EVP & CIO of Ryder System Inc, executed 2 separate sales on 2026-02-13 totaling 14,367 shares for $3,041,943.38, reducing his holdings by 40.8% from 35,199 shares to 20,832 shares. The blended average transaction price of $211.73 reflects sales at $211.94 and $211.50, below the current price of $223.04; the stock has gained +16.9% over 30 days and +37.3% over 90 days, reaching the high end of its 52-week range ($130.14–$223.04). Notably, his cross-ticker track record shows only 1 prior sell with a 0.00% well-timed rate (stock rose 6.3% afterward), and his single prior sale at Ryder on 2024-02-26 also resulted in a +6.3% 90-day return—indicating prior sales were poorly timed. Given strong recent share price appreciation and the lack of a pattern of well-timed exits in his history, this filing does not signal conviction-aligned timing.