The Boston Red Sox have yet to make a splash this MLB offseason. While all signs indicate Alex Bregman will receive the biggest check from chief baseball officer (CBO) Craig Breslow, a new report has cast doubt over what seemed obvious just days ago.
Out of every player still unsigned in free agency, Bregman is among those with the most suitors yet the fewest certainties about his future. The third baseman is leaving no stone unturned, which has only fueled speculation that the Red Sox might be left in the dust ahead of the 2026 MLB season.
According to several reports around the league, Bregman is seeking a long-term deal valued at around—or over—$170 million. However, that essentially sets up a conflict of interest for Breslow and the Red Sox, who aren’t particularly fond of handing that level of job security to veteran MLB players. Thus, the 30-year-old baseman’s fate may already be written on the wall.
“The [Red Sox] organization has long been questioned about this,” as reported by The Athletic. “Yet it has still made large investments in free agents 30 or older in years past. Under Breslow, that tune has changed starkly with almost exclusively one- and two-year deals in free agency.“
As it stands, Bregman and the Red Sox appear to be further apart than ever from reaching an agreement. One side will have to give in to the other’s demands. If not, Bregman’s stay in the Hub will be short-lived.
Red Sox may have learned their lesson
As a matter of fact, Breslow—appointed CBO in October 2023—handed Bregman a three-year, $120 million deal prior to the 2025 MLB season. That was the biggest deal his administration in Boston has given to a free agent.
Needless to say, watching Bregman opt out of the final two seasons just months into his new deal has been far from exciting for the Red Sox front office. In more ways than one, Boston may have learned its lesson. Whether that means steering away from Bregman or retaining him under a bigger contract—preferably with no opt-outs—remains unknown.
What’s next?
There is only one way to find out—or rather, two: the Red Sox either dive into the pool or stay idle while Bregman completes his free-agency tour and comes to a decision. Fans in Beantown should be advised, though, the latter may come back to bite them.