The Boston Red Sox are expected to prioritize re-signing Alex Bregman this offseason after Bregman announced that he will be opting out of his deal. Early contract predictions for Bregman have landed in the five-year, $175 million realm, which Boston would presumably be more than okay with paying.
However, Bregman will not be without other suitors on the free-agent market, a reality that Bregman’s agent, Scott Boras, will surely use as leverage.
While Bregman may have some unexpected suitors like the Kansas City Royals, who have been mentioned recently by The New York Post’s Jon Heyman, Boston probably isn't too worried about small- or mid-market teams entering the Bregman sweepstakes.
On the other hand, the Red Sox should fear big-market teams that are in a position to contend. Bregman said back in June that he’s making it a priority to sign with a club that he can finish his career with, and you have to think he doesn't plan on doing so with a non-contender.
4 biggest threats to sign Alex Bregman and ruin Red Sox’s offseason
New York Yankees
Passan lists third base as a need in the offseason for the Yankees despite acquiring Ryan McMahon and he mentions they could spend big for Bregman. I’ll believe it when I see it but it’s something to monitor pic.twitter.com/orh0c9eRV7
— Jimmy (@L28Jimmy) September 4, 2025
We might as well get this one out of the way first, as Red Sox fans don’t want to consider for too long the pain that would come with Bregman leaving Boston to don pinstripes.
While the Yankees did recently trade for Ryan McMahon, ESPN’s Jeff Passan doesn’t believe that would deter New York from going after Bregman this offseason.
Philadelphia Phillies
Phillies GM Dave Dombrowski has never been afraid to make a big move, and Bregman would represent an upgrade for Philly over Alec Bohm, who made the All-Star team in 2024 but saw his OPS and homers drop in 2025.
Like the Yankees, Philadelphia has both the pockets and the winning culture to lure Bregman away from Boston as a viable landing spot where he could see himself contending for the rest of his career. Last offseason, ESPN’s Buster Olney pointed out that Bregman’s swing fits the Phillies’ ballpark, as does his “postseason scar tissue.”
Detroit Tigers
Detroit has been linked to Bregman since last offseason, when it reportedly offered him a six-year, $170 million deal, which Bregman turned down to sign with the Red Sox for a higher AAV.
Tigers manager A.J. Hinch managed Bregman in Houston, so there’s an obvious connection there.
Chicago Cubs
Speaking of last offseason, the Cubs were seen as one of the top favorites to land Bregman. Chicago’s GM Jed Hoyer was open about how disappointing it was not to end up with Bregman, and Hoyer might be motivated to gear back up and give it another go, especially given the very successful regular season the Cubs just had.
The Red Sox must take care of business and bring Alex Bregman back
The above four teams have the spending power and cultural allure to sign Bregman. Nonetheless, the Red Sox are still the favorites to land him as they, too, have a ton of fiscal resources, especially after trading Rafael Devers over the summer. In fact, Boston could ostensibly use the Devers money to re-sign Bregman and go after Pete Alonso.
The Sox shouldn’t get complacent or waste too much time getting a Bregman deal done, though. If they don’t handle the situation well, Bregman could end up elsewhere, leaving them with much less appealing backup plans.