Overall, the 2025 season was a step in the right direction for the Boston Red Sox. But it ended with a massive dud with a disappointing playoff loss to the hated New York Yankees, which should fuel the Boston front office to go out and have a big offseason.
While the sting of Thursday night’s Game 3 defeat in the Bronx will carry through the winter, there is a lot to be optimistic about regarding the Red Sox. The team did indeed get better after the Rafael Devers trade, as Craig Breslow promised back in June. Boston’s window is just opening, and with the right moves this offseason, World Series contention is not far from becoming a reality.Â
The Red Sox have an stud in the front of the rotation in Garrett Crochet. Roman Anthony is a franchise player and foundational piece, and young arms Connelly Early and Payton Tolle showed a lot of promise late in the season. Others got some valuable postseason experience, and should have learned quite a bit from falling to the Yankees.
At the same time, losing the Wild Card series also showed that the Red Sox have work to do this offseason. The Boston brass cannot get complacent, like the previous regime did in 2021 after the team made a run to the ALCS. The Red Sox are close, but an aggressive offseason could push them from being in the glorified play-in round to a legitimate postseason contender.
What do the Red Sox need to do this offseason?
Alright Breslow, now it’s time to go put that money saved from shedding Devers’ contract to use. It became abundantly clear as the offense struggled after Anthony’s oblique injury and into the playoffs that Boston needs an impact bat for the middle of the lineup. But really, the Red Sox need a pair of bats for the heart of their order, especially one that adds some pop from the right side of the plate.
Alex Bregman provides valuable leadership in the clubhouse, but there’s no guarantee he’s back next season. His departure would only increase the need for more pop in the lineup. Ideally, one of the big bats would play first base, given the likelihood Tristan Casas is going to miss all of next season. Pete Alonso and Josh Naylor will be free agents and would fit nicely at first base, but both are going to cost a pretty penny. But signing either and bringing back Bregman would be a solid start for Boston. If the Red Sox want to get real aggressive, they could throw a truckload of money at Bo Bichette to pry him out of Toronto.
There are a pair of Kyles with big bats set to become free agents in Kyle Schwarber (whom we know can play in Boston) and Kyle Tucker. Both are lefties, but if Breslow trims some of the outfield excess via trade, they’d be welcome additions. Jarren Duran’s time in Boston may be coming to an end, and Wilyer Abreu could also be dangled in trade talks for pitching to help clear up the logjam in the outfield.
While Brayan Bello had a breakout regular season, he gave the team nothing in the playoffs. The Red Sox need a legit No. 2 (or better yet, a 1A) to pair with Crochet, and they have the assets and/or money to go get one. Breslow should make another run at a trade for Minnesota’s Joe Ryan, and if he strikes out on that front, Frambler Valdez, Dylan Cease, and Shane Bieber (should he opt out) are will be on the free agent market.
Early and Tolley will be rotation options if they’re not traded, and Boston should get Hunter Dobbins, Kutter Crawford, and Richard Fitts back, with Pablo Sandoval also figuring into the mix. But really, a team hoping to content for a title can never have enough pitching, especially given the number of arms coming back off injury. And it’s always a plus to have an excess of depth if an offseason addition doesn’t work out, ala Walker Buehler in 2025.
Away from the roster, a new third base coach wouldn’t be a bad idea after Kyle Hudson had an extremely chaotic season sending and holding runners. And come spring training, defense has to be a real focus after an embarrassing display in the outfield during the Wild Card round.
Red Sox free agents this offseason
The left side of the Boston infield may look different next season, as both Bregman and Trevor Story have opt-outs this winter. Both could be welcomed back at the right price, though Marcello Mayer is waiting in the wings for either position — if healthy.
Lucas Giolito had an excellent season that unfortunately ended before the playoffs. He pitched over 140 innings this year, which turned his $14 million club option into a $19 million mutual option. He’ll have the ability to opt out and hit the open market in search of a multi-year pact.
Deadline day acquisitions Dustin May and Steven Matz are both heading to free agency, as is reliever Justin Wilson. Utility outfielder and lefty-killer Rob Refsnyder will also be a free agent this winter.
The Red Sox have an $8 million option on Duran, which they will likely pick up. But the outfielder could be traded in an effort to clear some room in the outfield and bring in more pitching.
However it plays out, the Red Sox need to be aggressive in free agency and on the trade front this winter. Their window to contend is just opening, but as we saw in the three years after 2021, it’s not something Boston can take for granted. Complacency is a killer, and the Red Sox cannot afford to take any steps backwards in 2026.