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Rich Hill’s wandering journey through the Major League Baseball landscape is truly unique. Over 21 seasons, Hill has pitched for 14 teams. He threw 195 innings in 2007 as a 27-year-old with the Chicago Cubs, and 158.2 innings in 2021 for the Tampa Bay Rays and New York Mets at age 41. He’s signed with the Boston Red Sox on eight discrete occasions. Times Rich Hill has signed with the Red Sox:2024, Aug 162021, Dec 12015, Aug 142014, March 262014, Feb 12011, Dec 132010, Dec 162010, June 30— Mike Petriello (@mike_petriello) August 16, 2024 In July, Hill made two starts for the Kansas City Royals, making him the oldest pitcher to start a game in the history of the American League franchise. More news: Dodgers Manager Reveals Disappointing Alex Vesia Update Before World Series Now, as the baseball offseason approaches, it’s worth wondering whether Hill will compete in 2026. If he can extend his major league career into a 22nd season, Hill will become only the second player to achieve the feat in the last decade, joining Albert Pujols. CHICAGO, ILLINOIS – JULY 22: Rich Hill #35 of the Kansas City Royals pitches during the first inning against the Chicago Cubs at Wrigley Field on July 22, 2025 in Chicago, Illinois. (Photo by Geoff Stellfox/Getty Images) If Hill can land a contract at age 45, who’s to say he can’t do the same at age 46? The only question is whether Hill is willing. More news: Red Sox Free Agent Hints at Retirement Plans Hill hasn’t made a decision, or at least not one he is not ready to announce publicly. Speaking to Rob Bradford on the Baseball Isn’t Boring podcast, Hill acknowledged the irony of revealing a retirement announcement as if it’s big news. “I have been sent out of the game enough where I didn’t know you had to actually tell everybody you were leaving,” he said. In July 2015, Hill was released by the Los Angeles Angels. Without an offer from an MLB team, Hill signed with the Long Island Ducks of the Independent Atlantic League. It proved to be a turning point in his career. The Red Sox signed Hill after he threw 11 innings for the Ducks without allowing a run. He was assigned to Triple-A, worked his way back to the majors, and effectively reinvented his career. More news: World Series Champion, Gold Glove Winner Announces Immediate Retirement At age 36, Hill signed a three-year, $48 million free agent contract with the Dodgers. After pitching for 15 seasons professionally, it was the most lucrative deal of his career. Going from the scrap heap to one of the most coveted pitchers in the game has afforded Hill a perspective on retirement that few active players enjoy. “I don’t know what I’m going to do 100 percent right now,” Hill said. “Can’t play forever, so we’ll cross that bridge when we get there. Soon enough.” For more MLB news, visit Newsweek Sports.
