Red Sox, in ‘window of contention,’ have ‘urgency’ — and Rafael Devers money to spend this winter

BOSTON — Four days after their season ended with a shutout loss in a die-or-die game at Yankee Stadium, the Red Sox are still performing a post-mortem on their 2025 season and dissecting what went wrong. Soon, though, it will be time to answer one of the most pressing big-picture questions when it comes to the club this offseason.

As the Red Sox look to jump from fringe playoff contention to being a real World Series threat, they have money to spend, in large part due to the cash that came off the books when the club traded Rafael Devers to the Giants in a shocking blockbuster trade in June. Even for a big-market team like the Red Sox, the commitment to Devers — who was in the second year of a 10-year, $313.5 million deal that came with a CBT (collective bargaining tax) hit of $29 million per year — was a sizable one. Having him off the books creates some financial flexibility.

The first chance to put that flexibility to use will come this winter with the Red Sox having the ability to spend big in free agency or look to take on a big contract in a trade. At Boston’s end-of-season press conference Monday, chief baseball officer Craig Breslow didn’t shy away from the fact that the after-effects of the Devers trade might help the Sox this offseason.

“I think about this from a baseball perspective, and that is trying to build this athletic, dynamic team and giving ourselves and the baseball operation as much flexibility as we possibly can to do that,” Breslow said. “What I have seen as a player and what I’ve seen over the last couple of years is that with this ownership group, when there is a chance to build a winner and a team that can contend for the postseason, resources aren’t a problem. And I think we’ve talked a lot about how this window of contention is upon us.”

The Red Sox saved about $15.4 million toward their 2025 payroll by trading Devers in June, but reliever Jordan Hicks (and his four-year, $44 million contract, worth a CBT hit of around $7 million) was involved in the deal and offset about half of that. The real financial freedom starts in 2026 — as the Sox’ Devers-related tax bill (a Devers hit based on signing bonus and Hicks’ money through 2027) is worth about $28.4 million over the next eight seasons, a mere fraction of the $232 million it would have equaled had Devers played out the rest of his contract in Boston. Simply put, the Red Sox have plenty of room to make long-term commitments with star players using the money saved by moving Devers. Roman Anthony’s eight-year, $130 million deal, which begins in 2026 and comes with a $16.25 million CBT hit, was a first effort to that end. But a Red Sox team entering a true “window of contention” can — and should — do more.

“We acted with urgency and certainty and aggression,” said team president/CEO Sam Kennedy, “and we plan to continue to do that as we go forward.”

The Red Sox, after extending a series of key young players in recent years, have some high-dollar deals on the books for 2026. Garrett Crochet ($28 million), Masataka Yoshida ($18 million), Anthony ($16.25 million), Aroldis Chapman ($13.3 million), Hicks ($12 million), Brayan Bello ($9.166 million), Patrick Sandoval ($9.125 million), Kristian Campbell ($7.5 million), Ceddanne Rafaela ($6.25 million) and Garrett Whitlock ($4.68 million) are all locked up. Jarren Duran and others will get raises in arbitration. The Red Sox will have money to spend even if Alex Bregman ($31.7 million CBT hit if he returns) and/or Trevor Story ($23.33 million) opt in and forego free agency. The Sox aren’t particularly close to the $244 competitive balance tax threshold to start the winter.

With a lot of young pieces locked up and the core of the roster intact, the Red Sox are expected to look for a No. 2 starter behind Crochet, a big bat in the middle of the order (especially if Bregman leaves) and defensive upgrades this winter. The first base and designated hitter spots remain unsettled as well. A power bat like Pete Alonso or Kyle Schwarber would fit well, especially after Breslow wasn’t shy Monday about adding power to a group that ranked ninth in the American League with 186 homers this season.

“I think it would be fair to look at some of those other teams (still playing) and say that they hit the ball in the park a little bit more than we do,” he said. “In the postseason, a lot of runs come via the home run because the pitching is so dominant. I think that’s a consideration.”

Breslow, after pulling off trades for Crochet and catcher Carlos Narváez and signing Bregman and Chapman to free agent contracts a year ago, said he expects the Red Sox to be involved on both markets again. He also preached the importance of not being “complacent” by banking on internal options to take a step forward.

“I’m going to be reluctant to make commitments about rosters or roles,” Breslow said, “just because I think we’ve got work to do ahead of us to improve the team.

“I think we approach each offseason pretty similarly in terms of trying to improve our outlook,” he continued ”Maybe the thing that changes is just how far into the future we’re, kind of, declaring that outlook. We’re certainly putting prioritizing wins forward. We’re going to pursue every opportunity to improve the team. Exactly what that means in terms of magnitude of transactions or number of transactions, I can’t really speak to yet.

“I think there are obviously the two extremes. One is where you’re thinking only about the future and you’re making decisions with the long-term in mind. The other is, you’re going kind of all-in on the season that’s in front of you. I think what we try to do as a baseball operation is to consistently make disciplined decisions that improve both. It’s really hard, but it can be done.”