How a journeyman pitcher defied the odds to become an MLB endurance legend
In short: Rich Hill’s career is a masterclass in persistence. After battling injuries, control issues, and repeated demotions, he reinvented himself from a struggling prospect into a reliable starter. By 2025, he stood as the oldest active player in Major League Baseball, having played for a record-tying fourteen different franchises.
Born in Milton, Massachusetts, in 1980, Hill was originally right-handed but learned to pitch left-handed from his brother. His path to the majors was anything but linear. Drafted three times before signing with the Chicago Cubs in 2002, he spent years moving between the minors and the big leagues, often hampered by mechanical struggles and injuries. His resilience was tested repeatedly, including a 2011 Tommy John surgery and a 2014 season marked by the tragic loss of his newborn son, Brooks.
Hill’s career trajectory shifted dramatically when he committed to becoming a starter again. After a brief stint with the independent Long Island Ducks in 2015, he returned to the majors with the Boston Red Sox, showcasing a dominant curveball that had once been his signature. His performance in the latter half of his career defied conventional aging curves for pitchers. In 2017, he achieved a rare and frustrating milestone: he became the only pitcher in MLB history to have both a perfect game ruined by a ninth-inning fielding error and a no-hitter spoiled in extra innings by a walk-off home run in the same game.
Throughout his two decades in professional baseball, Hill played for teams including the Cubs, Orioles, Red Sox, Dodgers, and Royals. His ability to adapt—transitioning to a sidewinder delivery and constantly refining his command—allowed him to remain competitive well into his forties. By the 2024 and 2025 seasons, he held the distinction of being the oldest active player in the league. His journey from a 36th-round draft pick who struggled with a 9.23 ERA as a college freshman to a seasoned veteran tied for the most teams played for in MLB history remains a testament to his enduring work ethic.
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- Summary by Intellect · source: Rich Hill
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