Alex Bregman’s free agency is shaping up to be one of the most intriguing storylines of the offseason, but there’s a twist that could complicate things for the Red Sox. In a candid conversation back in June, I sat down with the Red Sox third baseman in the Fenway Park dugout to discuss his future, contract status, and long-term fit in Boston. Amid the usual sports clichés, one response stood out like a home run in the bottom of the ninth: Bregman’s unwavering desire for stability. When asked if his next deal would be about finding a permanent home, his answer was emphatic: ‘For sure. For sure. That’s definitely a very high priority.’
But here’s where it gets controversial: Bregman’s first foray into free agency wasn’t exactly a slam dunk. He turned down massive, long-term deals from the Tigers ($171.5 million over six years) and the Cubs ($120 million over four years with opt-outs) in favor of a short-term, high-value contract with Boston. That deal, worth $40 million with heavy deferrals for one season, included player options that could extend it to $120 million over three years. Now, with Bregman opting out, it’s clear he and his agent, Scott Boras, viewed this as a ‘bridge’ contract—a calculated risk to re-enter the market after proving his worth. As Boras put it, ‘This agreement allows for everyone to get to know one another,’ hinting at the strategic nature of the move.
And this is the part most people miss: This time around, Bregman’s free agency landscape is vastly different. At 32 in March, he’s seeking a long-term deal—likely six or seven years—that would provide the stability he craves as a father of two. Unlike last year, when teams had to forfeit a draft pick to sign him after he rejected a qualifying offer, Bregman is now free from that burden. This levels the playing field, potentially boosting his value and attracting more suitors. But will it be enough to secure the multi-year deal he desires?
Here’s the kicker: While Bregman’s leadership, championship pedigree, and high floor make him an attractive asset, his age and injury history could scare off some teams. Soft-tissue injuries have sidelined him significantly in two of the last five seasons, and his hard-nosed playing style might raise durability concerns. On the flip side, there are teams willing to overpay for his intangibles—the kind of qualities that helped the Red Sox thrive in 2025. Boston must now decide how far they’re willing to go in terms of both dollars and years to retain him.
With big-market powerhouses like the Yankees, Phillies, and Cubs, as well as smaller-market teams like Detroit, Kansas City, and Seattle potentially in the mix, Bregman’s offers will vary widely. A short-term deal likely won’t cut it this time. But will the Red Sox step up, or will another team swoop in to secure his services?
What do you think? Is Bregman worth a long-term, high-dollar commitment, or should teams be cautious given his age and injury history? Let’s hear your thoughts in the comments—this debate is far from over.
