Red Sox Fan Favorite Starter Could Be One-and-Done in Boston

The Boston Red Sox's starting rotation may not look exactly the same in 2027.

Jun 23, 2026; Denver, Colorado, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches in the first inning against the Colorado Rockies at Coors Field. Mandatory Credit: Isaiah J. Downing-Imagn Images | IMAGN IMAGES via Reuters Connect

The Boston Red Sox made the right move bringing Sonny Gray to town last offseason, but now he is a free agent and the buzz out there hasn't been overtly positive so far this offseason when it comes to the idea of coming together on a new deal for 2027 and beyond.

On Tuesday, NESN dropped a new episode of the 310 to Left podcast with Tom Caron and Alex Speier. Throughout the conversation, Speier threw some cold water on the idea of Gray coming back.

"My guess is that the interest on the part of the Red Sox in re-upping with Sonny Gray is going to be muted, at least in the short term, and that they’re likelier to try to use any resources that they have elsewhere," Speier said.

Cold Water On A Sonny Gray Return

Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Cleveland Guardians during the first inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

Gray is going to be a hot commodity out in free agency this winter. The Athletic's Jim Bowden mentioned the Atlanta Braves, Toronto Blue Jays and the San Diego Padres as potential landing spots. The Braves already have been mentioned as a potential fit multiple times for Gray and it's just Nov. 4, as of writing.

The free agent class is very weak in general this winter. Tarik Skubal is the clear top dog, but there aren't a lot of slam dunks beyond him. Gray is somebody who is close to that, but his age is the only thing that raises question marks. He's coming off a season in which he led the league with 18 wins and logged a 2.72 ERA, but he will be 37 years old on Nov. 7. Gray is very likely going to get a multi-year deal this winter and has earned himself a nice payday. Boston has financial questions elsewhere. For example, will they find a way to get an Adley Rutschman extension done? Hopefully that is the case.

Gray gave Boston exactly what it needed in 2026. He was brought in to be a good No. 2. He outperformed expectations and was an ace. Plus, on top of his performance on the mound, Gray became a fast fan favorite in Boston. After joining the organization, he immediately got brownie points by throwing shade at the New York Yankees. From there, Boston fans grew to love Gray even more.

It would be great if the partnership wasn't just one year, but the Red Sox's rotation is loaded and there are holes elsewhere. Boston's rotation would be among the game's best right now if it simply rolled with Garrett Crochet, Payton Tolle, Ranger Suarez, Jake Bennett and Brayan Bello. Because of the competition and likely high price, Boston fans very well could have seen the last of Gray in a Red Sox uniform.