On Monday night, Boston Red Sox Chief Baseball Officer Craig Breslow met with the Boston media, who made the trip to Las Vegas for the annual GM Meetings. During the nearly 30-minute availability, Breslow spent much of his time discussing roster construction and where the team will look to improve. However, it was comments made about shortstop Trevor Story that showed the third-year CBO is learning from his past mistakes and growing into his role. 

One of the biggest themes of Breslow’s availability was that the team is going to explore all possible avenues to improve the team. Among the questions stemming from that discussion was whether or not veteran shortstop Trevor Story would be the team’s starting shortstop on opening day. 

“We know what [Story] is capable of doing when he’s healthy and performing. This year was disrupted for a number of reasons… I think we’re always evaluating these things,” Breslow said. “We still have a ton of confidence in [Story], but any decisions like that are going to take place between [Story] and me before I speak to anything,” he continued. 

Breslow’s answer on Story starkly contrasts with the tone he struck last offseason, when Story was quickly named the team’s starter at short. 

The biggest error Breslow made during his tenure as Red Sox CBO was how he and the team handled the events leading up to the trade that sent Rafael Devers to the San Francisco Giants. 

Throughout the 2024-25 offseason, both Breslow and former manager Alex Cora discussed bringing in Alex Bregman at second base, with Devers remaining at third base. However, shortly after Bregman signed, the team declared him the third baseman, catching Devers off guard and fracturing his relationship with the organization. 

In the aftermath of the Devers trade, both Cora and Breslow were open about the fact that there were plenty of things they could have and should have done differently in the way they handled moving Devers off of his position, including the way they communicated with him.

Story is not immune to outside noise, the Red Sox were very openly searching for a long-term solution at shortstop at the deadline and will reportedly continue to explore that market throughout the offseason. Now, there is no perfect match for the Red Sox to target in free agency or on the trade market to take over shortstop the way Bregman did two years ago, making these discussions somewhat premature, as Breslow acknowledged. 

There are also, of course, major differences between Story and Devers. Story enters the final year of his contract with the Red Sox, while Devers was only in year two of the 10-year, $313.5 million extension signed with the team. Devers was the face of the franchise and the undisputed best hitter. Story has struggled to stay on the field and has done little to produce when he has been. However, unlike Devers, Story has become a key veteran voice in the clubhouse as one of the longest-tenured players on the roster, despite being limited to only 384 games over five years. 

The situation with Devers is just the biggest in what has become a long line of communication blunders by Red Sox management, most of which have involved injury categorizations and timelines. Despite those key differences between the two situations, particularly in the two's performance and contract status, the fact that Breslow is striking a different chord and making a more intentional effort to improve his communication before he or the manager makes declarative statements in the media about what the roster might look like shows he is truly learning from his mistakes. 

When the Red Sox hired Breslow from the Chicago Cubs, there was always going to be a bit of a learning curve. During his time in Chicago, he worked remotely from his home in Connecticut, rather than in the front office or with players. He also worked mostly in the pitching development department, rather than overseeing the inner workings of the entire organization. That learning curve was why people were so excited to see future Hall of Fame executive Theo Epstein be in the organization to help show Breslow the ropes. 

Whether the conversation is premature or not, Breslow's clear signs of growth in his position are a welcome sign.