Aug 26, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) singles during the eighth inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images James A. Pittman-Imagn Images

Red Sox Fans Will Be Ecstatic About Insider's Latest Alex Bregman Prediction

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Sep 9, 2025 8:00 AM ET

Alex Bregman staying or leaving has a high probability of definiting the mood around the Boston Red Sox this winter.

Bregman was one of the two marquee additions of this past offseason, and he's become the most respected veteran in the lineup and in the clubhouse for Boston. He's playing a crucial mentoring role for all of the young players on the team, particularly locker neighbor and rookie sensation Roman Anthony.

However, Bregman signed a deal with opt-outs for a reason, and even after a three-week slump, his season statistics are excellent. It's highly unlikely the Red Sox will get to keep him without testing the open market first, but nearly every voice around the game seems to agree that his fit in Boston is spectacular.

Insider can't see Red Sox losing Bregman

On Monday, FanSided's Robert Murray wrote an article on "juiciest fits" for upcoming free agents, but felt so convicted that Bregman would stay with the Red Sox that he couldn't bring himself to speculate on any other team signing him.

"When this story was first pitched to me, it had Bregman’s fit with the New York Yankees. And yes, while I can see the logic behind that, I just can’t see it happening," wrote Murray. "Bregman just seems to belong with the Red Sox, and I have a hard time putting him elsewhere. Especially in the Bronx.

"Don’t take the lack of a midseason extension for Bregman as a sign that he’s leaving the Red Sox. Really, an extension during the season was never happening. His agent, Scott Boras, prefers his players go to the open market to establish their values. He rarely does extensions, especially for a player like Bregman who will land a lucrative long-term contract in the offseason."

Yes, Bregman and Boras opening up the bidding to the other 29 teams is somewhat intimidating, and beyond the Yankees, there are big-market clubs (especially the Philadelphia Phillies) who stand out as potential fits.

However, the pressure on Boston to keep the 31-year-old after displaying how perfect a fit he is for this team and city is going to be immense. Hopefully, that pressure proves to be a positive.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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