Less than 24 hours after the news broke that Alex Bregman is leaving the Red Sox to sign a five-year, $175 million deal with the Cubs, Red Sox chief baseball officer Craig Breslow agreed to answer some questions about Bregman’s departure in a brief email interview with MassLive. Here are Breslow’s answer on the departure of Bregman, discussions with him before his signing and the Sox’ offer, which MassLive has confirmed to be worth $165 million over five years with heavy deferrals.
This interview has been slightly edited for clarity
Q: What was your immediate reaction to last night’s news that Alex Bregman is signing with the Cubs, and how does it change the outlook of your offseason?
A: Any time you are active in trying to bring a player in, it’s disappointing to lose out. We do this job because we are competitive and we want to deliver a championship to our fans, and falling short in a pursuit is an obstacle to that.
Q: It was pretty clear Bregman was your top priority at this stage as you look for a bat. With the need to pivot, is a free agent offensive addition the natural Plan B? Or could you pivot to a different, less obvious solution like bolstering the pitching staff to focus on run prevention?
A: It’s going to sound redundant, but we’ll be open to any way to improve our team. Free agency is an obvious path, but so are trades. We will try to continue to add offense, but leaning into pitching and defense is another way to boost our win total.
Q: Did the Red Sox approach Bregman about a contract extension during the regular season? Looking back, do you wish there was more urgency to get something done then?
A: I don’t think it’s productive at this point to get into the details of past conversations.
Q: Knowing now that you won’t have Bregman past the one year, do you view the chain of events around Rafael Devers and the eventual trade that sent him to the Giants differently? What would your reaction be if someone told you in February that neither Bregman nor Devers would be on the roster in 11 months?
A: Rather than spend a ton of time on the particulars of these cases, what is most important is 1) how we respond to improve our roster in the near term and 2) how I can learn from the experiences and allow that to inform how I approach the role going forward. Neither outcome we face right now is ideal, but both will be evaluated over a longer time horizon.
Q: Why do you feel as though your offer to Bregman fell short? Is there an organizational policy against no-trade clauses, a reported sticking point here? Why were the reported deferrals in this case part of the club’s strategy to get a deal done?
A: Without getting into the specifics of the negotiation, Alex and his family earned the right to decide where they want to spend the next 5 years of his career, and while we had hoped it would be here, we respect the right they’ve earned. It would be foolish and unfair for me to guess what was most important in their decision making.
Q: When you traded Devers, you discussed one impact being the ability to “re-package some of the resources and fill some voids in the roster.” To this point, has that been successful? Are those efforts still underway?
A: We will continue to find the best ways to exhaust our resources. Obviously, we made commitments to Roman (Anthony) and (Aroldis Chapman), we’ve traded for established players like Sonny (Gray) and Willson (Contreras), and we have the flexibility to continue to push.
Q: What does the loss of Bregman mean to the Red Sox? What would your message to the fan base be at this point?
A: I am not going to gloss over the impact that Alex had on our season. He is a great player with a strong leadership presence in our clubhouse. But this job requires balancing long and short term interests and making the best decisions for the organization, difficult as they be. It means losing out on good players sometimes. However, while we will enter the ’26 season with different personnel, there will be no less resolve to compete for the division and make a deep post season run. I believe in the group we have while we keep working to find ways to add to it. Our goal is to deliver to our fans, the season that they deserve.
