Red Sox Could Lose 2-Time All-Star To Yankees In Free Agency

The New York Yankees could make a free agent move this offseason that would haunt Boston Red Sox fans for a long time.

New York has an obvious need at third base, something the Yankees will address either before the July 31 Major League Baseball trade deadline or in the winter.

One player who could emerge as a prime free agent target is a proven star with a track record of postseason heroics and elite production. This two-time World Series champion, who was thriving with the Boston Red Sox in 2025 before a quad injury, is slashing an impressive .299/.385/.553/.938 this year with 11 home runs, and 35 RBIs in 51 games. Moreover, his familiarity with high-stakes environments, honed through years with the Houston Astros, would align perfectly with the Yankees’ championship-or-bust mentality.

Yes, we are talking about two-time All-Star Alex Bregman.

New York Post's Jon Heyman recently discussed Bregman's contract status on MLB Central: “I mean, look, he's got an opt-out… he's gonna opt out. There's no way around that at this point.”

If Heyman's correct, Bregman will hit the free agent market this winter, giving the Yankees a golden opportunity.

Signing Bregman would be a masterstroke for the Yankees. Not only would they acquire a superstar third baseman, but they’d also weaken their bitter rival in the American League East.

Red Sox fans, already reeling from losing Rafael Devers, would be beyond demoralized to see Bregman leave for the Yankees.

The Yankees, per usual, could structure a massive offer, leveraging their financial might to outbid teams like the Red Sox, Detroit Tigers, or Chicago Cubs. By slotting Bregman at third, the Yankees could move Jazz Chisholm Jr. back to his more natural infield spot at second.

The Yankees’ hesitation to overspend after a handful of big acquisitions last offseason could be a barrier to signing Bregman, but trading Marcus Stroman’s $18 million salary and some other pieces could free up room.

Signing Bregman would be a smart baseball move and the ultimate gut punch to the Red Sox. You have to think New York's general manager Brian Cashman has grinned while thinking of the possibility.