Red Sox Predicted to Reunite With 3-Time All-Star in Big Offseason Move

Craig Breslow, Red Sox
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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)

The Boston Red Sox saw their hopes of winning the World Series come crashing down against the rival New York Yankees this season.

Boston made the playoffs, but they were swept by New York in two games within the American League Wild-Card series. The two games weren’t very close, with the Red Sox failing to do much of anything against their longtime rivals.

But as the team now enters into a crucial offseason, there are real questions around how the roster will look next season. Boston saw a lot of inconsistency from the offense, with the starting rotation carrying them for most of the year.

The Red Sox have to address issues on the roster, including the starting rotation with a few players heading toward free agency. But how the front office plans to do this remains up in the air.

Red Sox Linked With Three-Time All-Star

One key player entering free agency for the Red Sox will be veteran right-hander Sonny Gray, whose future remains up in the air. There has been a lot of talk about what Gray will do, especially since he is 36 years old.

But given his advanced age and the success that he’s seen with the Red Sox, the fit for him to return to Boston could be there. And MLB analyst John Perrotto of FanSided is now predicting that Gray will come back to the Red Sox.

Perrotto sees the two sides coming together on a big one-year, $25 million deal to keep the veteran right-hander with the Red Sox.

“At 36, the right-hander should have a robust market after a season in which he posted an 18-5 record and a 2.72 ERA in 29 starts. Gray hinted he might retire after the Red Sox lost to the Yankees in the Wild Card Round, but he soon decided to keep playing. He also was noncommittal about returning to Boston specifically after expressing his displeasure with manager Chad Tracy pulling him early in their season-ending loss,” Perrotto wrote.

Gray was a key piece to the Red Sox’s rotation all year long, and replacing him wouldn’t be easy. So, Boston should try to retain the veteran for next season, giving the unit a boost, even for one more year.

Will Sonny Gray Return to Red Sox?

Coming into the winter, the big question is what Gray will do, especially since the Red Sox still have Chad Tracy as the team’s manager. Gray was upset with Tracy for pulling him at the end of his game against the Yankees in the playoffs, but that should easily be dealt with.

Tracy understands how important Gray is to this pitching staff, and the move was made to try to keep the Red Sox’s season alive. If the two sides were to talk about it all, it could probably get handled in no time.

But whether Gray wants to return to Boston remains a key point in all of this. In free agency, it takes two to tango, and the right-hander may want to see what else is out there.

If the two sides can agree on a number, this could be a much smoother process this winter. Both parties should want to remain a partnership, but whether that takes place remains to be seen.

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Red Sox Predicted to Reunite With 3-Time All-Star in Big Offseason Move

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