Alex Bregman-Cubs Intel From Jim Bowden Is Bad News For Red Sox
Alex Bregman’s free agency has become a lot more complicated than a lot of Boston Red Sox fans expected. Bregman was Boston’s clubhouse leader last season, and he thrived in the role of mentoring guys like Roman Anthony and Marcelo Mayer. Still far from over the hill at 31 years old, Bregman’s excellence at the plate and at the hot corner for the Red Sox was also paramount to Boston’s success in 2025.
This all made a reunion feel inevitable. Even after Bregman opted out on November 3, many fans expected that a new deal returning Breggy to Fenway Park (for good this time) was pretty much in the oven.
Well, the last six weeks have revealed an entirely different reality. Bregman remains unsigned, and the Red Sox are reportedly pursuing alternative options like Ketel Marte while they continue to negotiate with Bregman and super-agent Scott Boras.
What’s weird is that the public sort of has no idea what Bregman’s market looks like. He’s been linked to the Detroit Tigers since last offseason, but some pundits — including ESPN’s Buster Olney — have basically said that Detroit’s probably not happening.
The Arizona Diamondbacks magically emerged as a new suitor on Tuesday, but no one’s sure how real that is. Then there’s the Chicago Cubs, who were hot on Bregman last offseason (like the Tigers), but have more so recently been deemed a cooler suitor due to their happiness with Matt Shaw at third base.
This is what made Jim Bowden’s new intel on Bregman (published Wednesday via The Athletic) so surprising. Bowden said that the Cubs are the team that Bregman has the best chance to get a long-term deal with.
“Bregman is looking for a long-term commitment like Schwarber and Pete Alonso just received,” Bowden wrote. “His best shot to get that at this point would be with the Cubs, who will be trying to replace (Kyle) Tucker in the lineup. The Cubs covet Bregman’s leadership and mentorship of younger players. If they were to sign him, they could move Matt Shaw to second base and trade impending free agent Nico Hoerner or just move Shaw to the outfield.”
This is all dangerous news for the Red Sox because recent rumors indicate hat Bregman’s having a harder time locking down a long-term deal than he thought he would. Negotiations with Boston clearly haven’t arrived at a happy point for he and Boras, and he remains unsigned.
Are the Cubs, as Bowden surmised, going to be the team to swoop in and give Bregman the dollar figure that he desires? That would certainly be the surprise of the offseason.