How Red Sox Felt About Losing Alex Bregman to Cubs in Free Agency

The Red Sox were “disappointed” after Bregman agreed to a contract with the Cubs.

Bregman on Saturday agreed to a free agent deal with the Cubs. | Kamil Krzaczynski-Imagn Images

Free agent third baseman Alex Bregman agreed to a $175 million contract with the Cubs this past weekend, helping to stabilize the National League contender's lineup while dealing a blow to the Red Sox, who had hoped to bring the four-time All-Star back to Beantown.

But it was not to be, leaving Red Sox brass, specifically chief baseball officer Craig Breslow, disappointed.

“Any time you are active in trying to bring a player in, it’s disappointing to lose out,” Breslow on Sunday told MassLive's Criag Cotillo in a Q&A via email. “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.”

While the Red Sox ultimately fell short to the Cubs, it wasn't for lack of effort.

Red Sox' contract offer to Alex Bregman revealed after he joined Cubs

According to reporting from Cotillo, Boston's best offer to Bregman was a five-year contract worth $165 million, with heavy deferrals. In terms of the total value of the contract, the Red Sox weren't far off from the Cubs' winning, five-year, $175 million deal. But the Cubs went one step further than the Red Sox did.

Bregman's deal with the Cubs includes a full no-trade clause, which the Red Sox reportedly did not include in its offer to the star third baseman, according to Cotillo and Sean McAdam of MassLive. Bregman, who is married with two young children, evidently valued the security that comes with a full no-trade clause.

“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,” Breslow said. “It would be foolish and unfair for me to guess what was most important in their decision making.”

Bregman's exit to Chicago hurt doubly, as it came less than a year after his initial signing with the Red Sox, which also set off a chain of events that angered then-franchise star Rafael Devers, ultimately resulting in his shocking departure via trade to the Giants in June of 2025.

“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,” Breslow said. “Neither outcome we face right now is ideal, but both will be evaluated over a longer time horizon.”

The Red Sox will now look to continue improving an 89-win club from 2025, with Breslow saying he's open to additions to the offense and pitching staff through all avenues.

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