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    Tom Carroll
    Tom Carroll
    Oct 7, 2025, 16:00
    Updated at: Oct 7, 2025, 16:00

    On Monday, the Red Sox (89-73) held their annual end of season press conference, with manager Alex Cora, chief baseball officer Craig Breslow and team president Sam Kennedy all on stage to answer questions from the assembled local media.

    After a disappointing exit in the Wild Card round at the hands of the Yankees (94-68) - a team now with +1500 odds to win the World Series down 2-0 in the ALDS - Boston’s front office is faced with a bevy of questions as they look ahead to 2026.

    The organization was finally able to get over the hump and return to postseason play for the first time since 2021. That’s great! But now it’s time for one of the only real name-brands in all of baseball to start competing like the blue blood they are again.

    The Red Sox have all the ability in the world to field a World Series-caliber team every single year.

    What will they do this offseason to get themselves back into that echelon for 2026?

    According to Breslow, the answer is, apparently, ‘Just about anything.’

    Here’s the full question an answer from Breslow on Monday, accompanied by a follow-up answer from Kennedy, that played like a Rorschach test to Red Sox Twitter in the aftermath:

    Question: How much does the financial room created by the [Rafael Devers] trade change what you can do this offseason, compared to what you could do if he was on the roster?”

    Craig Breslow: “Yeah, I think about this from a baseball perspective, and that is trying to build this kind of athletic, dynamic team, and giving ourselves and the baseball operation as much flexibility as we possibly can to do that.

    “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 you know, I think we've talked a lot about how this window of contention is upon us.”

    Sam Kennedy: “I would just add that what was rewarding to see this year was these two guys to my right [Breslow and Cora], acting with urgency, starting with our [opening series against Texas] and then all the way through.

    “You know, we didn't get where we wanted to go. We all know that, but we acted with urgency and certainty and aggression, and we plan to continue to do that as we go forward, so we'll see where that takes us when we get to Orlando [for Winter Meetings].

    The large majority of Red Sox fans either read those words or saw the social clips, and their eyes immediately rolled into the back of their head. This team has lost everyone in its fanbase’s trust after trading Mookie Betts ahead of the 2020 season to avoid tax penalties. All he’s done since then is help the Dodgers win two World Series (2020 and 2024) after the franchise had been held title-less since 1988.

    Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings. (Jerome Miron/Imagn Images)

    The Betts move wasn’t the only example of this, as the trade of Devers just this season had shades of the Mookie trade, with the “best” return on the deal for Boston being San Francisco’s willingness to pick-up the entirety of the remainder of Devers’ deal - $250 million running through the 2033 season.

    The was a faction of Sox fans that heard these words from Breslow and got excited. I would please ask that they refrain from holding their breath.

    Even with the Red Sox earning all sorts of brownie points last offseason with the acquisitions of Alex Bregman, Garrett Crochet and Aroldis Chapman, the roster still needs more help.

    A No. 2 starter. Another consistent bat or two in the lineup. Potentially a new back-up catcher (the latter is more of a me thing than anything else, I think - different topic for a different day).

    If we’re to believe Breslow, Boston will be opening the wallet in a big way this offseason as they look to maximize this window in a wide-open American League.

    I’m just not ready to trust this team again. Not yet.


    Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.