Red Sox Insider Declares Where Alex Bregman Won't Sign In Free Agency

Ruling out a bunch of teams right off the bat...

Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

Buckle up, Boston Red Sox fans.

Alex Bregman is headed back to free agency this winter, which could mean several more months of waiting as an encore to last offseason. Bregman eventually signed with the Red Sox just as spring training was opening in February, and most Bostonians are hoping it wasn't just a one-year tenure.

There will certainly be numerous suitors for the three-time All-Star, but it's too early to know exactly what his market will look like. However, on Saturday, an insider delivered one extremely confident statement about where Bregman would not be playing in 2026.

What Bregman values most of all

Jul 25, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) hits a RBI against the Los Angeles Dodgers during the third inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images | Brian Fluharty-Imagn Images

On Saturday, Ian Browne of MLB.com asserted that Bregman would value signing with a team that had a chance to win championships above all else, which certainly seems in line with everything we heard about Bregman throughout his first trip to free agency.

"This is likely to be (Bregman's) last, best chance to get a long-term contract, so he has to weigh all the options," Browne wrote.

"The one thing I’m sure about is that he won’t sign with a non-contender. This is a guy who has winning in his blood. He has never missed the playoffs. The Red Sox have certainly positioned themselves as a contender in the coming years."

Bregman saw that the Red Sox were building something with a lot of potential this year. He also saw that if he wasn't carrying the offense, there wasn't a ton of support behind him in the lineup bu the time the playoffs rolled around.

Certainly, having a full season of Roman Anthony -- who Bregman played an important role in mentoring this season -- should help Bregman feel more protected at the top of the order if he chooses to stay.

Bregman seemed at least mildly nervous about the Houston Astros' closing championship window when he left last offseason, so the hope from the Red Sox's perspective is that he's both feeling picky about the potential suitors that come calling and retaining his positive outlook on Boston's own future.

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