Having owned a Coonhound named “Karma” for 13 years, I’m well familiar of the idea that what goes around comes around.
Even the dog who would stare at the wall during thunderstorms would join us in being amused by veteran Boston Red Sox pitcher Sonny Gray’s upcoming predicament. As things stand entering the regular season’s final week, the 36-year-old right-hander would likely start next Wednesday’s second game of the Wild Card Series.
Fittingly, Gray would make his Red Sox playoff debut against a Yankees team he’s 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.
“It feels good to me to go to a place where it’s easy to hate the Yankees,” Gray said this past offseason. “I never wanted to go there in the first place.”
Good news, Sonny: Your next trip to the Bronx could also mark the last start of your impressive 14-year career.
Could Boston Red Sox pitcher Sonny Gray retire after the 2026 season?
We’ve done plenty of speculating about players’ futures lately, but this isn’t one of those instances. Gray recently told the Boston Globe that he’d retire in a “heartbeat” if his family wanted him to, and the organization is reportedly preparing for the possibility that he won’t return in 2027.
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’s difficult to envision the Red Sox passing on his option given his performance and his outspoken love of pitching in Boston.
Garrett Crochet gets all of the attention, but don’t sleep on Gray’s impact. He climbed the 2,000-strikeout threshold earlier this year, and he's already recorded a career-high 17 wins. The journeyman starter’s 2.82 ERA and 4.0 bWAR both mark his best since 2023, his final year with the Twins.
The only thing left on Gray’s to-do list is pitching in the World Series, which is far easier said than done. Boston is all but locked into the AL’s 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, the Red Sox would start the ALDS away from Fenway Park, and the only way they’d have home-field advantage in the ALCS is if the No. 6 seed — currently the White Sox — embarks on a miracle run.
Hey, we’ve 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’s like poetry.
And what would be more poetic than Gray either exacting revenge on the Yankees or seeing his career end against that same team?
"We’ll 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."
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