The Red Sox have a winter problem that goes way beyond the usual roster tinkering: Adley Rutschman.
Boston’s offseason figures to be a long one after another early playoff exit, even if the club looks better on paper than it did a year ago. There are still decisions to sort through before the 2027 campaign, and one of the biggest is tied to the catcher the Red Sox paid heavily to land from the Baltimore Orioles ahead of the 2026 trade deadline.
That deal brought in an All-Star backstop who made an immediate impact in different ways. Rutschman’s bat didn’t click right away after he was activated from the Injured List, but he gave Boston strong work behind the plate and then found his rhythm in September.
The catch is simple: he is only under team control for one more season. After the 2027 season, he’ll be a free agent. For a team that gave up so much to acquire him, letting that window close after just a little over one full season would be a brutal outcome.
That’s why Boston should be getting ready to push for an extension this winter. The 28-year-old is the kind of player the Red Sox need to keep around, especially because he can still fit with the core moving forward. And if a deal gets done, it won’t come cheap, which could shape the rest of the club’s offseason plans.
The Red Sox do have another notable contract situation to monitor in Sonny Gray, whose $30 million mutual option is expected to be declined. A new deal could still be worked out after that, but it remains too early to know whether that happens.
Still, Rutschman stands out as the priority. When he’s healthy and rolling, he changes the game. With the free-agent market described as very weak, Boston should be treating him like the next major piece to lock up, right alongside players such as Garrett Crochet and Roman Anthony.
In Other News...
Red Sox Offseason Depth Faces One Big Test After Likely Departures
The Red Sox are heading into the offseason with a familiar kind of roster question, one that starts with the players they may be losing before it gets to who can fill the gaps. Patrick Sandoval, Isiah Kiner-Falefa and Sonny Gray are all in line to test free agency, and Boston already has some internal answers to lean on, including Anthony Seigler as a possible replacement for Kiner-Falefa and a handful of left-handed arms that could help cover for Sandoval.
Sonny Gray is the one situation that may carry the most long-term weight for Bostons depth chart. His mutual option for 2027 is unlikely to be picked up, which adds another layer to a right-handed pitching picture the Red Sox will have to sort out carefully. Even with some stopgap options in-house, the real test this winter may be whether the organization can keep its pitching depth balanced without leaning too heavily on short-term fixes. [Read more 🡒]
Red Sox Could Be Headed For A Major Outfield Reset
The Red Sox are again staring at an offseason that could reshape the balance of their roster, and this one starts in the outfield. Bostons current mix still leaves questions about depth and fit, so the idea on the table is to add a more established presence there while also protecting the bullpen, a department that could use help if the club wants to tighten up late-game innings next season.
One proposed path would have Boston pursuing Seattles Randy Arozarena in free agency while moving Jarren Duran to San Diego for reliever Jeremiah Estrada, with Tyrone Taylor mentioned as another option to bolster defense and give the lineup more flexibility. It is the kind of aggressive reset that would signal real urgency from the Red Sox, but it also comes with the kind of roster tradeoffs that make the rest of the winter worth watching closely. [Read more 🡒]
Red Sox Just Locked In A Big Bullpen Question For 2027
Aroldis Chapmans season ended the way the Red Sox needed it to, with the left-hander healthy enough to get through his end-of-season physical and keep his status intact for the future. Chapman had already done the work on the field to get the vesting language in motion, reaching the innings threshold and returning from a late-season lat issue in time to appear in the Wild Card Series.
The bigger takeaway for Boston is that the bullpen picture for 2027 just got a lot clearer. Chapmans option is now fully guaranteed, giving the Red Sox a major late-inning arm under contract as they look ahead, with his salary locked in at a minimum of $13 million and room for additional bonus money tied to reliever award voting. [Read more 🡒]