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Considering how April went, the 2026 season turned out far better than initially anticipated for the Red Sox. But for a franchise with annual title hopes, it still wasn't quite good enough.
Boston's front office and fanbase, for the most part, won't be satisfied with anything but World Series contention — and with the Red Sox's Game 2 elimination against the Yankees on Wednesday night, they now enter their offseason after an 87-win season that ended over two nights in the Bronx.
In two-straight years, the Red Sox's season has ended at the hands of their rival on the road. If any similar outcomes are going to be avoided in 2027, there's likely work to be done this offseason, especially offensively.
Here's a look at Boston's upcoming offseason.
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Red Sox free agents 2027
- SP Sonny Gray ($30 million mutual option)
- SP Patrick Sandoval
- SS Isiah Kiner-Falefa
- RP Garrett Whitlock ($8.3 million club option)
Fortunately for the Red Sox, they won't have to worry much about retaining players this offseason. They only have four players who can hit free agency, and only two were bona-fide contributors to the 2026 roster.
Sonny Gray is 36 years old, but he's coming off one of his best MLB seasons, tied for the AL lead in wins (18) with a 2.72 ERA over 29 starts. He looked resurgent in Boston after being traded by the Cardinals last offseason.
Gray has a mutual option this offseason worth $30 million, but it would be no surprise if the Red Sox look to bring him back on a shorter-term, high-AAV deal. He proved he can help lead the rotation in 2026, and there should be plenty of interest in re-upping for another few years.
The other notable free agent may be reliever Garrett Whitlock, one of the best right-handed relievers in the game. He has a $8.3 million club option that Boston may pick up.
Otherwise, Patrick Sandoval and Isiah Kiner-Falefa are the only other players set to hit the open market for Boston.
Red Sox offseason targets
According to Spotrac, the Red Sox's $177.96 million projected payroll for 2027 ranks eighth in baseball. They shouldn't be expected to go after a ton of big-name free agents — Tarik Skubal, Bo Bichette, Randy Arozarena and Michael King will headline the class — but they could be active on the trade market, or look for lower-cost moves to improve the offense.
Outside of bringing back Gray, Boston's 2027 rotation appears set. Ranger Suarez and Payton Tolle were terrific in 2026, while the team will be hopeful that the full return of Garrett Crochet will bring another ace-level arm to the top of the staff. Assuming Gray returns, the Red Sox are likely to invest in their bats.
On the free agent market, Seiya Suzuki could make sense. The Cubs outfielder has established himself as a consistent slugger, and he'd bring the kind of power the Red Sox lacked in 2026, finishing among the worst teams in MLB in home runs. Expect Suzuki to be one of the names connected to Boston.
In the infield, the Red Sox relied on a combination of Nick Sogard and Kiner-Falefa at second base this past season. They could use a better bat at the position, allowing Trevor Story to stay at shortstop and Curtis Mead at third base. Free agent Brandon Lowe, who hit 35 homers for the Pirates in 2026, would be a good fit, another slugger who could bring more pop to Chad Tracy's lineup.
The future of Jarren Duran appears to be in significant question entering the offseason as well. After peaking with a 2024 season in which he had an .834 OPS as a strong defender, he's declined in each of the last two years, leading to trade rumors. Nothing has come to fruition yet, but if Boston's going to shake things up, Duran faces the most uncertain future. It wouldn't be surprising to see Duran flipped to another contender willing to take a shot on him, with the Red Sox also hoping for a full healthy season from Roman Anthony in 2027.
The Red Sox also watched as their bullpen struggled against the Yankees in the Wild Card round; adding more leverage relievers beyond Aroldis Chapman, especially with Whitlock perhaps hitting free agency, will be key. Adrian Morejon, Raisel Iglesias and Ryan Helsley are expected to be some of the best relievers on the open market.
Bringing back Gray, finding a power bat, and adding to the bullpen look like the priorities for the Red Sox this winter.
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