Red Sox CBO Craig Breslow Hints At 'Aggressive' Offseason Roster Moves

Time to see if the words lead to actions this winter...
Nov 7, 2023; Scottsdale, AZ, USA; Boston Red Six chief baseball officer Craig Breslow speaks to the media during the MLB General Manager's Meetings at Omni Scottsdale Resort & Spa. Mandatory Credit: Mark J. Rebilas-Imagn Images
Nov 7, 2023; Scottsdale, AZ, USA; Boston Red Six chief baseball officer Craig Breslow speaks to the media during the MLB General Manager's Meetings at Omni Scottsdale Resort & Spa. Mandatory Credit: Mark J. Rebilas-Imagn Images / Mark J. Rebilas-Imagn Images
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October is becoming the loneliest month to be a Boston Red Sox fan nowadays.

Though the Red Sox have always been a franchise where the playoffs were the expectation, that hasn't been the case this decade. Boston has now missed the playoffs three seasons in a row, and Chief Baseball Officer Craig Breslow knows that fans are growing weary of the club's failures.

Breslow took over the front office last November, and his first year in charge was a mixed bag. There were brilliant moves (trading for Tyler O'Neill and Justin Slaten), and there were some serious duds (trading future National League Cy Young winner Chris Sale). But with the Red Sox, the narrative has become about what the front office isn't doing.

The Red Sox have taken heat for their lack of spending in past offseasons, as they have trimmed the payroll from first in the league in 2019 to 11th in 2024. Fans have been wondering when that might change, as Boston is typically far from a small-market or even a medium-market sports town.

On a recent episode of Baseball Isn't Boring, Breslow detailed a vision for the offseason that he termed more "decisive" and "aggressive," though he avoided specifically talking about spending in free agency.

"I think we are preparing for that to be the case," Breslow said. "We are preparing to be more decisive, more aggressive. To field a team that is capable of winning the division, making a deep playoff run… That was the tone that (team president) Sam (Kennedy) struck. That is the messaging I am getting throughout the organization, that it is time to deliver to our fans the teams they have come to expect”

Boston has ample opportunity to build a playoff team in 2025. They have three returning All-Stars, a burgeoning core of young position player talent, and all the profit they could ask for to use on payroll. But no one can be certain how much they will spend until the free-agent window opens in November.

If Breslow's words prove hollow, it will be an uncomfortable, precarious 2025 season at Fenway Park. Red Sox fans crave playoff baseball, and this is the year the front office needs to deliver on that promise.

More MLB: Insider Warns Red Sox Failure To Keep Playoff Legend In Boston Was 'Obvious' Mistake


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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org