Boston Red Sox Urged To Reunite With 3-Time All-Star Pitcher This Offseason

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BOSTON, MA - SEPTEMBER 7: Craig Breslow the chief baseball officer of the Boston Red Sox in the dugout before the game between the Boston Red Sox and the Los Angeles Angels at Fenway Park on September 7, 2026 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)

Now that the Milwaukee Brewers won the World Series in five games over the Tampa Bay Rays, an interesting offseason begins for the Boston Red Sox and the rest of MLB. There are a lot of questions about what it might look like with a potential lockout looming on December 1.

As for Red Sox Chief Baseball Officer Craig Breslow, it’s going to be another offseason with decisions about some key players. Last winter, he lost third baseman Alex Bregman to the Chicago Cubs in free agency. Now, another Boston player who can opt out of his current deal is starting pitcher Sonny Gray. Tim Kelly of Bleacher Report urged Gray and the Red Sox to find a way for the soon-to-be 37-year-old to return in 2027.


Boston Red Sox and Sonny Gray Urged To Reunite in 2027

Gray can decline a $30 million club option this offseason and hit the open market. The problem is, he might not come close to making that much in free agency. However, a decision based on how things ended in the American League Wild Card round against the New York Yankees might not be the best for Gray.

“Given that he was unhappy with being pulled after 4.2 innings in Game 2 of the ALWCS, Gray might decline his $30 million club option for 2027. Even if he loved his season in Boston, opting out and returning to the open market this offseason might be the best business decision for Gray. He may not make $30 million in 2027 if he opts out,” wrote Kelly.

Gray went 18-5 with a 2.72 ERA in 169 innings in 2026 for the Red Sox. Acquired from the St. Louis Cardinals, he had a 4.3 WAR and had a 149-46 walk-to-strikeout ratio. He was the ace of Boston’s staff after Garrett Crochet went down with an injury early in the season.

“After going 18-5 with a 2.72 ERA in 169 innings this past year, Gray can get a larger overall guarantee. Gray is better than Merrill Kelly, who landed a two-year, $40 million deal last winter as he entered his age-37 season. Gray will be 37 in November,” Kelly wrote.


Can Sonny Gray Put Playoff Frustration Aside and Return To the Boston Red Sox?

Gray was unhappy when manager Chad Tracy pulled him from his Game 2 wild-card start in the Bronx in the fifth inning. He didn’t hide his feelings after the game and the season came to an end.

“I’m the best pitcher in the American League, third time through the order. I think that’s a fact. I would have liked to have been trusted in that moment,” said Gray, NESN.

On paper, the Red Sox have a rotation that looks like Ranger Suárez, Garrett Crochet, Payton Tolle, and Brayan Bello right now. Slotting Gray into that rotation is something that Breslow should try to do. It’ll be easier said than done.

There are a lot of questions this offseason. Will there be a lockout? Will there be a salary cap? It’ll be business as usual until December 1. If a lockout occurs, it could be a long offseason for MLB. However, a decision on Gray feels like it’s going to come sooner rather than later.

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Boston Red Sox Urged To Reunite With 3-Time All-Star Pitcher This Offseason

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