The Boston Red Sox head into the offseason without many players coming off their books. The front office has done well acquiring players with multiple years of team control and getting its young players to sign long-term, guaranteed contracts.
While that is nice for roster continuity purposes, it does mean they will have fewer spots available to new free agents this offseason without making trades or non-tendering players. Before they have to think about that, though, they will have to make decisions on the players who are no longer under contract or have options that need to be exercised (or not).
A complete list of 2026 Red Sox free agents and their outlooks
Sonny Gray
The veteran pitcher had an incredible late-career resurgent season for the Red Sox. After the Sox traded for him from the St. Louis Cardinals last offseason, Gray had a full-season career-low ERA of 2.72 while leading the AL in wins with 18. The unfortunate part for the Sox is that he only had one guaranteed year left.
Gray heads into the offseason with a $30 million mutual option that is very unlikely to be picked up. He will almost certainly earn a multi-year deal on the open market unless he decides to retire, which he has already hinted at this season.
If he does decide to keep playing, it's unlikely he'll be back in Boston after what happened. The Red Sox aren't likely to give the righty a multi-year contract, plus what happened in the Wild Card game might have soured him on the organization, even if they say they talked it out.
Patrick Sandoval
The Red Sox signed Sandoval two offseasons ago, but it took him almost a year and a half to make his team debut. Once he did, he looked sharp. His first six starts, even though shortened because they were still building him back up, saw him have a 3.30 ERA.
It went downhill from there. The lefty had an unsightly 6.47 ERA in starts seven through 15 with the Sox. Sandoval is now an unrestricted free agent, and the chances the Red Sox re-sign him after that must be close to zero.
Isiah Kiner-Falefa
Boston signed the utilityman to a one-year deal last offseason. He didn't get a lot of playing time in April; in May and June, he was one of the few players who was actually hitting for the Sox. From May 1 until his last game before he got injured on June 18, Kiner-Falefa hit .298 with a .789 OPS in 33 games. Unfortunately, his injury cost him two and a half months, and he didn't return until September.
While the infielder was injured, multiple other utility infielders stepped up in his absence. Those players, like Andruw Monasterio, Nick Sogard, and Anthony Seigler, are all under team control for a few more seasons. It just doesn't make sense to bring Kiner-Falefa back this offseason.
Garrett Whitlock
The elite reliever is nearing the end of the pre-arbitration contract he signed with the Red Sox, but that doesn't mean he's going anywhere yet. Boston has two years of club options on Whitlock, the first one being this season for only $8.25 million.
Whitlock has been one of the best relievers in baseball since switching back to a full-time reliever in 2025. His 4.2 fWAR ranks sixth among qualified relievers in the last two years, and his 2.03 ERA is ninth. While $8.25 million may seem expensive for a relief pitcher, it wouldn't have been top 25 highest AAV for relievers this season. It's a no-brainer to exercise that option.
Aroldis Chapman
It is a foregone conclusion that Chapman will be back next season. When the Red Sox signed the flamethrowing lefty to an extension during the 2025, their was a conditional option for 2027. That option automatically vested into a guaranteed contract if Chapman pitched 40 innings in 2026 and he passed an end-of-year physical. He pitched 40 innings this season, and reporter Francys Romero reported on October 3 that he passed his physical, vesting the contract option.
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