The Boston Red Sox’s 2026 season came to a disappointing conclusion on Wednesday, as they lasted just two games against the rival New York Yankees in a best-of-three American League Wild Card series.

“Regardless of all the special things that happened this summer, the goal was to win the World Series, that ended for us tonight,” Red Sox manager Chad Tracy said to reporters postgame, after his squad was outscored eighteen to two in a two-game sweep.

Going into this offseason, the Red Sox will have key decisions to make on several positions, but none perhaps more important than starting pitcher Sonny Gray.

Gray, 36, is due for a $30 million mutual option for the 2027 season. It’s worth noting that roughly 96 percent of mutual options are declined, per ESPN.

In a controversial decision on Wednesday, Tracy pulled the right-hander after throwing just 70 pitches through 4 2/3 innings, allowing six hits and one earned run to that point while punching out five Yankees hitters. He accrued 12 whiffs at a 32 percent clip in his start, per Baseball Savant.

“I'm the best pitcher in the American League going through the order for a third time,” Gray said to reporters at Yankee Stadium postgame.

“I think that's a fact. I would've liked to live or die with me in that moment… ask the guys in here if they felt the same way. I felt strong, confident.”

Gray's undeniable 2026 success with the Red Sox

Gray has a point, as throughout 2026, the Vanderbilt baseball product has pitched to a 1.99 earned run average (ERA) and 3.35 expected fielding independent pitching (xFIP) through 45.1 innings pitched, per FanGraphs.

It’s clear that this decision left a sour taste in the soon-to-be free agent’s mouth. Postgame, when he was asked if he would welcome a return to Boston for a second season, he told reporters “I don’t know.”

Losing Gray would be detrimental for the state of the Red Sox rotation. In 169 innings pitched this season, he was undoubtedly one of the best pitchers in the American League, pitching to a 2.72 ERA, 15.1 strikeout-minus-walk-percentage (K-BB%) while accumulating 3.4 wins above replacements.

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While the Red Sox returning pitching depth is serviceable to a degree, with the presumptive full-throttle return of 2025 American League Cy Young award candidate Garrett Crochet, and other returning pieces such as left-handers Payton Tolle and Jake Bennett, losing Gray would immediately result in their rotation becoming one of the worst in their division, with pitching-laden teams such as the New York Yankees and Tampa Bay Rays sitting atop the American League East division.

In 2026, the Red Sox rotation ranked fourth in the American League with a 3.92 ERA — becoming a true strength for the club even after missing Crochet for the vast majority of the season.

Gray could consider another direction entirely

Another roadblock that may plague Boston is Gray’s age and consideration of retirement.

“I was telling him that a second ago, whatever him and his family decide, it was a joy to watch this year,” Crochet said to reporters postgame on Wednesday, via Chris Cotillo of MassLive.com.

“I still think he’s got a lot to give the game, but there’s something to be said about going out on your own terms, I suppose. Whatever he ultimately decides, that’ll be something that as a team, we support him on. But it was a pleasure having him here in Boston.”

It’s clear that based on this information, and other sparse reports from the course of the season, retirement is truly an option for the Smyrna, Tennessee native, who currently resides in Nashville.

If Gray chooses to continue playing, the Red Sox must bring him back to remain competitive in a division that will surely be better next season, with teams like the Blue Jays and Orioles primed for bounce back seasons after disappointing 2026 campaigns, and the Yankees and Rays expected to remain formidable foes.