How Craig Breslow Plans To Tackle First Trade Deadline As Red Sox CBO

The Red Sox have a new voice leading their baseball operations department this season, but the conversation surrounding the franchise is very familiar.

Will Boston buy or sell before the MLB trade deadline?

Teams across the league still have plenty of time to plot their paths forward. The deadline isn’t until July 30. Even then, there could be a number of clubs that look to toe the line, both buying and selling, with an eye toward improving for the short-term without mortgaging the future.

But the Red Sox’s approach — whatever it may be — will be magnified more than most. They’re a historic, big-market team with a new front-office boss. And now, they’re playing excellent baseball, potentially rewriting expectations for 2024 in the process.

“It’s difficult and one thing that I’ve pointed to is it’s extraordinarily difficult to try to accomplish both.” Red Sox chief baseball officer Craig Breslow told The Athletic’s Jen McCaffrey this week in Toronto of trying to strike a balance between adding pieces this season and building for the future. “So there are meaningful games to play between now and the deadline. Every time we set foot on the field, we’ll learn something new. I think what we have to be careful of is trying to straddle the line. But I think the most important thing to come out of our play last week is that there’s a really exciting group of players that are taking the field every night. So I think we can all see the reasons for optimism. Exactly how that materializes over the next five weeks or so, six weeks, remains to be seen. But I think, irrespective of that, it’s an exciting time to be in this organization. I think it’s an exciting time to be a fan of the organization. And we’re going to learn more and be realistic and also be decisive.”

The Red Sox enter this weekend with a 40-35 record. They won five in a row, including a three-game sweep of the Blue Jays at Rogers Centre.

Boston more than held its own last week against the Philadelphia Phillies and New York Yankees, the best teams in the National League and American League, respectively. An AL wild-card spot is well within reach, which must be tantalizing after back-to-back last-place finishes.

Of course, this isn’t uncharted territory. Former Red Sox chief baseball officer Chaim Bloom faced a similar predicament the last two seasons, trying to determine whether Boston was good enough to add pieces before the MLB trade deadline.

But this is Breslow’s first time pulling the strings. He’s cognizant of all the competing variables, and it’s perhaps incumbent upon the players to leave him with no choice but to invest in this year’s team.

“I don’t know that it makes sense to say anything is off the table or anything is off-limits,” Breslow told McCaffrey of when he could seek out moves. “If we have an opportunity potentially to improve the organization in the short term, in the long term, like we always have to be able to have those conversations. I’ve been on the other side of this. Like I’ve been in the clubhouse and the job of the 26 guys on the team and the coaching staff is to make it as hard as possible to do anything other than add to this team. I respect the heck out of that. And my decision is to try to balance all of the competing interests and do what I believe is best for the organization.”

Outside expectations for the Red Sox were tempered this season. They’re starting to change the narrative with their performance between the lines.

We’ll see if it’s a driving force behind which lane Breslow chooses over the next month and a half.