3 Players Red Sox Could Lose In Offseason After Heartbreaking Loss

The Boston Red Sox had a very productive season this year. They had one of the best pitchers in the sport, Aroldis Chapman, emerge, despite many in the game not believing in him. The Red Sox have also seen multiple top prospects come up to the big leagues and dominate.

Still, injuries and poor roster management led to the Red Sox's downfall. Boston made the postseason and matched up against the rival New York Yankees. After taking a 1-0 series lead backed by a dominant showing from Garrett Crochet, the Red Sox lost back-to-back games and were bounced from the postseason.

After such a disappointing end to the season, there are bound to be some roster shake up. Which players could leave the Red Sox in the offseason?

RHP Dustin May

The Red Sox acquired pitcher Dustin May in a trade deadline deal, but not many Red Sox fans understood the reasoning behind the deal. May didn't move the needle for the Red Sox and he's set to enter free agency when the season ends.

With the Red Sox looking to add pitching in the offseason, it's hard to imagine they'll look to reunite with May. May hasn't been great since returning from injuries and the Red Sox need to add pitchers who move the needle.

3B Alex Bregman

Boston Red Sox infielder Alex Bregma — Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) celebrates his RBI double against the New York Yankees during the ninth inning of game one of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Alex Bregman is the biggest storyline of Boston's offseason. He has an opt out clause in his contract and will almost certainly activate it to enter free agency.

When Bregman lands in free agency, it's fair game for every team.

Boston could be looked at as the favorite to land him, but it's going to be tough to win the sweepstakes twice. Teams like the Detroit Tigers, Seattle Mariners, and Philadelphia Phillies could end up in the hunt for Bregman, which would only complicate things for the Red Sox.

LHP Steven Matz

Matz is in the same boat as May, but Matz was impressive with Boston. There's real reason the Red Sox would want to retain the lefty in free agency. In fact, he would be a huge boost for their bullpen going forward.

But other teams also saw his dominance down the stretch. There will likely be over a dozen suitors for Matz this winter. He could land a solid deal in free agency, and the Red Sox might not be the favorites.

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