Fittingly, Gray would make his Red Sox playoff debut<\/a> against a Yankees team he\u2019s publicly admitted to despising. The three-time All-Star pitched in 41 games for the Yankees from 2017-18, a stint that resulted in him being demoted to the bullpen midway through that second season.\u00a0<\/p>\n \u201cIt feels good to me to go to a place where it\u2019s easy to hate the Yankees,\u201d Gray said<\/a> this past offseason. \u201cI never wanted to go there in the first place.\u201d<\/p>\n Good news, Sonny: Your next trip to the Bronx could also mark the last start of your impressive 14-year career.<\/p>\n Could Boston Red Sox pitcher Sonny Gray retire after the 2026 season? Boston Red Sox starting pitcher Sonny Gray | IMAGN IMAGES via Reuters Connect<\/p>\n We\u2019ve done plenty of speculating about players\u2019 futures lately, but this isn\u2019t one of those instances. Gray recently told<\/a> the Boston Globe that he\u2019d retire in a \u201cheartbeat\u201d if his family wanted him to, and the organization is reportedly preparing for the possibility that he won\u2019t return in 2027.<\/p>\n Gray turns 37 in November and has a $30 million mutual option for 2027, though he can opt out and forfeit a $5 million buyout. Assuming that he wants to return next year, it\u2019s difficult to envision the Red Sox passing on his option given his performance and his outspoken love of pitching in Boston.<\/p>\n Garrett Crochet gets all of the attention, but don\u2019t sleep on Gray\u2019s impact. He climbed the 2,000-strikeout threshold earlier this year, and he’s already recorded a career-high 17 wins. The journeyman starter\u2019s 2.82 ERA and 4.0 bWAR both mark his best since 2023, his final year with the Twins.<\/p>\n The only thing left on Gray\u2019s to-do list is pitching in the World Series, which is far easier said than done. Boston is all but locked into the AL\u2019s No. 5 seed, and the Red Sox would play the entire Wild Card Series on the road. If they were to knock off the Yankees<\/a>, the Red Sox would start the ALDS away from Fenway Park, and the only way they\u2019d have home-field advantage in the ALCS is if the No. 6 seed \u2014 currently the White Sox \u2014 embarks on a miracle run.<\/p>\n Hey, we\u2019ve seen stranger things. Who else is old enough to remember the 2007 Rockies going from a controversial Game 163 win to sweeping the NLDS and NLCS as a Wild Card team? Of course, they suffered their own sweep at the hands of the Red Sox. It\u2019s like poetry.\u00a0<\/p>\n And what would be more poetic than Gray either exacting revenge on the Yankees or seeing his career end against that same team?\u00a0<\/p>\n “We\u2019ll see what the future holds for me,” Gray said. “But if this is it, no better way to go out and try to do something special here the next couple months.”<\/p>\n![\"Boston](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/09\/01m3046pgqxmt1d2r3d6.jpg\" "\\"Boston")
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