Inside The Red Sox

Red Sox Predicted To Finally Sign Most Coveted Free Agent

Will it happen within the next 10 days?
Apr 19, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) throws to first base for an out against the Chicago White Sox during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
Apr 19, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) throws to first base for an out against the Chicago White Sox during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

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Decision time could be approaching for Alex Bregman, which should leave Boston Red Sox fans equally excited and nervous at this point.

Bregman's free agency has already drawn out longer than many would have liked, though it's not yet close to approaching last year's timeline. The three-time All-Star has been linked to the Chicago Cubs, Arizona Diamondbacks, and Toronto Blue Jays on top of a potential return to Boston.

If a resolution comes within a week to 10 days, should Red Sox fans feel optimistic about the team getting a deal hammered out for their biggest offensive pickup from a year ago?

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Bregman returning? Insider gives his take

On Tuesday, Jon Heyman of the New York Post gave the nervous types among the fan base some positive reinforcement.

Though Heyman didn't guarantee anything, he predicted on the Bleacher Report livestream that Bregman would return to the Red Sox for a second year and several more.

"Bregman, I mean, you've got to think it worked out so well with Boston (that) they'll figure it out," Heyman said. "They've got the one righty bat. They need another one. I think that one makes sense.

"We know that the Cubs are in on Bregman, as is Toronto, as is Arizona. ... I could see Arizona potentially stealing him, but I gotta think Boston's probably the team."

Heyman also indicated that he believed Bregman's free agency would likely be decided by Jan. 2, when Japanese corner infielder Kazuma Okamoto's posting window closes, so teams that are in on Bregman can attempt to pivot to the 29-year-old slugger.

Bregman was a picture-perfect fit in Boston, especially for what he meant to the young position players on the roster, but money always talks loudest in free agency. Last year, the Red Sox showed Bregman the money, but only on a short-term deal. We've heard repeatedly that he's their "Plan A" this time around, but that doesn't mean they're keen on paying him for five or six years.

It's pretty simple at this point. If the Red Sox match the offers Bregman gets, he's probably staying. If not, he's probably going. And as much as it's nice to hear that it might come to a close soon, the reality is that no one on the outside truly knows if that's the case, and Bregman may not yet even know himself.

More MLB: Red Sox's Possible Alex Bregman Pivot Revealed With Decision Expected Soon


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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org