The Red Sox may have one fewer rotation question than most clubs heading into the winter, but the biggest one is impossible to ignore: what happens if Sonny Gray isn’t there in 2027?
Gray’s future in Boston is murky at best. He’s 36, has 14 years in the majors, and hasn’t shut the door on retirement altogether.
His mutual option for 2027 almost certainly won’t be exercised, and when he was asked after the Red Sox were eliminated whether Boston would be a place he’d want to pitch in 2027, his answer was simple: “I don't know.” That leaves the door open for a new deal, but it also means Boston has to be ready to find another right-handed arm if Gray moves on.
That possibility shapes an early look at what the Red Sox’s 2027 Opening Day rotation could look like.
Garrett Crochet looks like the easy anchor. He returned to the mound during the wild-card series out of Boston’s bullpen, and with a full healthy offseason ahead, the expectation is that his next appearance will come on Opening Day, whenever that lands. He’s the kind of arm you build around.
Payton Tolle forced his way into the picture in a hurry. The rookie posted a 3.03 ERA in 26 starts and even got the ball in Game 1 of a playoff series for Boston. That’s not just promising stuff - that’s the kind of performance that can push a pitcher into ace territory if the progression keeps going in 2027.
Brayan Bello is another name that fits near the top. Around the league, plenty of teams would be thrilled to have him as a No. 1 or No. 2 starter. In Boston, he could wind up as the No. 3, which says plenty about the group’s upside.
The back half gets trickier, especially because of the handedness issue. Crochet, Tolle and Suarez all throw left-handed, so if Boston sticks with a five-man rotation, there’s a clear need for balance. That’s why Bello gets the edge for Opening Day in this projection, even if both he and the other arms should get plenty of chances across the season.
If Gray is gone, the Red Sox will likely need a veteran right-hander to fill the gap. Shane Bieber is the name that stands out.
Boston has been linked to him repeatedly over the last two offseasons, but a deal never came together. He’ll be a free agent again after the season, so the fit is still there.
Maybe this is finally the moment.
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