Monday morning at 11 a.m. three of the top Red Sox’s top decision-makers — president and CEO Sam Kennedy, chief baseball officer Craig Breslow and manager Chad Tracy — will speak to the media in their year-end press conference.
The annual gathering typically serves to put a bow on the year while also offering the Red Sox a chance to explain what may have gone wrong and how the club plans to improve going forward.
Beyond the usual message about how the organization fell short of its championship goals but how the future is bright, there are a number of specific questions the Red Sox need to answer heading into the offseason. Here are a few the club’s leaders will hopefully address.
How can injury communication improve?
If there was one overarching storyline throughout the 2026 season, it was the club’s communication of injuries that often sounded like no big deal at first but wound up being season-long setbacks.
With both Roman Anthony and Garrett Crochet, the initial prognosis sounded encouraging. Both players were described as day-to-day and Tracy expressed encouragement that both might avoid stints on the injured list. As it turned out, Anthony’s sprained hand and Crochet’s shoulder inflammation were much more serious, and the mismatch between expectations and reality prompted a lot of blowback upon both the players and the club that could have been avoided if the severity of the injuries were laid out clearly up front.
Did the club really think the injuries were no big deal at first, only to learn later they were serious? If that’s the case, that’s a problem in and of itself. The alternative is the club knew both were looking at long IL stints all along, in which case the club owes its fans an explanation for why the messaging was so off base.
Why didn’t Anthony get imaging before return?
Speaking to reporters after being ruled out for Game 2 on Wednesday, Anthony spoke at length about his hand injury and how it was never 100% even after his return in late August.
But one record scratch moment came when Anthony was asked when the last time he’d underwent imaging was prior to his visit to the hospital earlier that morning.
“It was before I was in Fort Myers,” Anthony said. “So it’s been a while.”
Anthony’s rehab was transferred from Boston to Fort Myers in early July, around which point he also flew to Atlanta to see a hand specialist. If that was the last time his hand was imaged, that means more than a month passed before he began his rehab assignment in Portland on Aug. 18. He then spent almost two weeks ramping up before returning to the big league club on Aug. 30.
Time was of the essence, yes, but with a player as important as Anthony, wouldn’t it make sense to have all the information possible before putting him back on the field and risking a recurrence?
What’s done is done and Anthony will now have somewhere in the ballpark of five months (possibly more) to get his hand right, but it will be interesting to hear the club’s perspective on this.
Roman Anthony of the Boston Red Sox stands on deck in the first inning against the Cleveland Guardians at Fenway Park on Sept. 23, 2026, in Boston. (Jaiden Tripi/Getty Images)
What is status of coaching staff?
The Red Sox provided needed clarity about their future just prior to the postseason when they announced the interim tag was removed from Tracy’s title and that Breslow’s options were picked up, ensuring the two men will be leading the organization through the remainder of the decade.
But the rest of Tracy’s coaching staff remains in flux.
When Breslow first cleared house, firing former manager Alex Cora and a wide swath of his staff, the Red Sox scrambled to fill all the vacancies midseason. The hitting staff in particular saw wholesale changes. Newly elevated hitting coach John Soteropulos was only a month into his first season on a big league staff and several of his new assistants had limited experience at any level.
Obviously the group made the most of an extremely difficult situation and helped the Red Sox engineer a remarkable turnaround, but should everybody return? A case could be made that the organization would benefit from a proper offseason hiring process, and Tracy and Breslow will hopefully shed light on how they plan to proceed this offseason.
What is club’s top offseason priority?
It should go without saying that the Red Sox’s offense needs to improve, but how?
Will the Red Sox favor a right or left-handed bat? Will the focus be on the infield? The outfield? Would the club consider a full-time designated hitter? How might that impact some of the incumbent players, some of whom the club will inevitably have to move?
And will free agency be the preferred avenue this winter? Or will Breslow continue his trend of aggressively working the trade market?
Don’t expect Breslow to show his whole hand on Monday, but what he does say should be illuminating.
Message to frustrated fans
Right now the Red Sox are in a weird place. They pulled themselves out of a deep hole, gave fans an exciting summer of baseball and fought their way back to the playoffs. But then once the postseason began they got boat-raced by the Yankees in the wild card round, leaving them effectively right back where they left off last year.
This season wasn’t a failure, but it certainly wasn’t a success, and it’s hard to blame fans who feel like the club effectively spent the whole year spinning its wheels.
With a lockout looming and uncertainty hovering over the sport as a whole, those fans deserve real assurances from the Red Sox that better days lie ahead, and concrete reasons why.