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A Yankees–Red Sox Deadline Deal Insiders Say Could Happen

Originally posted on Athlon Sports | By Kristie Ackert | Last updated Jun 24, 2025 2:29 PM ET

Alex Bregman in pinstripes? It still sounds far-fetched. It probably is a long shot, but insiders are buzzing about the Boston Red Sox using the third baseman as a trade chip.

And the Yankees were named as the perfect landing spot.

According to ESPN’s Kiley McDaniel and Jeff Passan, Bregman is the most impactful player who could be dealt at this year’s deadline. They only give it a 10 percent chance, but hey, they are saying there's a chance.

Bregman’s name is also starting to surface more often among league insiders as Boston’s most likely trade chip.

Bregman was slashing .299/.385/.553 before landing on the injured list with a quad strain. He’s still owed the bulk of a 3-year, $120 million deal—but that includes opt-outs after 2025 and 2026. That makes him both expensive and flexible, which could appeal to a contender looking for short-term impact without a long-term commitment.

For the Yankees, the fit is clear. Third base remains a revolving door. Bregman brings postseason experience, right-handed power, and a playoff mindset. He knows what October feels like, and he can still hit.

Of course, there’s history here.

Yankees–Red Sox trades are rare, but not unheard of. Boston would have to be willing to deal inside the division, and New York would need to part with real pieces to make it happen.

Bregman isn't exactly beloved in the Bronx because of his ties to the Houston Astros' cheating scandal, but he isn't exactly treated like Jose Altuve either. The Yankees kicked the tires on Bregman last winter but weren't interested in a long-term deal. The opt-outs in his contract could be attractive.

Another connected insider, Jim Bowden, suggested the Yankees would revisit a deal with Bregman this winter if he opted out.

It’s a long shot. But the Yankees are in a win-now window, and Bregman fits the kind of profile they’ve chased before—productive, proven, and playoff-tested.

If Boston continues to struggle, Brian Cashman should be calling.

This article first appeared on Athlon Sports and was syndicated with permission.

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