The Boston Red Sox face an offseason of difficult choices after Wednesday’s 9-2 loss to the Yankees ended their American League Wild Card Series. The next question is how much of this roster returns.
Expiring contracts, crowded positions and uncertain health create different paths out of Boston. These six players have identifiable reasons to depart before Opening Day 2027, although none of those exits is confirmed.
Expiring Contracts Put Three Veterans in Focus
Sonny Gray presents the biggest decision. His contract includes a $30 million mutual option for 2027, when he will be 37. As Heavy reported, he answered, “I don’t know,” when asked about returning. Retirement is also a possibility, adding another complication to Boston’s rotation planning. Boston should want reliable innings, but both sides must accept the option or negotiate another deal. His age makes a longer commitment harder to justify.
Patrick Sandoval’s two-year contract expires this offseason. His return from elbow surgery makes the next agreement a fresh bet on his health and role. His September 27 appearance came in relief, illustrating why a more clearly defined role matters. With Garrett Crochet, Ranger Suárez and younger rotation candidates in the organization, Boston should avoid paying starter money for someone it might use primarily in relief. A team offering a clearer starting opportunity could be a better match.
Isiah Kiner-Falefa also reaches free agency after a one-year, $6 million deal. His versatility has value, although Caleb Durbin, Curtis Mead and Andruw Monasterio provide infield alternatives. Unless Boston needs another veteran backup, allocating those at-bats and dollars elsewhere makes more sense than automatically bringing him back. His departure would preserve room to evaluate the younger infielders.
Trades and a Non-Tender Could Clear Roster Space
Jarren Duran is among MLB.com’s offseason trade candidates. Roman Anthony, Ceddanne Rafaela and Wilyer Abreu give Boston other outfield options. Trading Duran could convert overlapping personnel into help elsewhere, particularly if the return addresses a more pressing lineup need. However, Anthony’s hand injury means Boston should confirm its depth before sacrificing an established alternative. A useful return matters more than simply clearing the logjam.
Masataka Yoshida is another awkward roster fit. He is owed $18.6 million for 2027. Limited defensive flexibility and competition for designated hitter at-bats make his role difficult to guarantee. His hamstring injury also complicates any effort to rebuild his trade value. Boston might need to absorb salary to facilitate a trade. Releasing him would create roster space without eliminating the financial obligation, so finding even a modest trade return is preferable.
Kutter Crawford is the non-tender possibility. His injury-interrupted comeback leaves Boston weighing his health against another arbitration contract. A non-tender would make him a free agent, potentially allowing a cheaper reunion. Keeping him makes sense only if the Red Sox can reasonably project useful major league innings and a role worth protecting through the winter.
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