Alex Bregman’s free agency was never supposed to be this complicated-at least not for the Boston Red Sox. After all, this was the guy they brought in to be a cornerstone, a leader, a steadying force in the post-Devers era. But here we are, six weeks after Bregman opted out of his contract on November 3, and not only is he still unsigned, but the Red Sox are giving off some serious signals that they might be preparing for life without him.
The clearest sign? Boston’s reported interest in All-Star infielder Ketel Marte.
That’s not the kind of move you make if you’re confident your third baseman is coming back. It’s the kind of move you make when you’re preparing for a roster shake-up-and possibly bracing for a future without Bregman.
Let’s rewind for a second. The Red Sox traded Rafael Devers just six months ago, a move that stunned fans and sent shockwaves through the league.
Chemistry issues were cited, with whispers that part of the tension stemmed from the organization prioritizing Bregman’s presence over Devers’ long-term role. So to now be facing the very real possibility of losing Bregman too?
That’s not just a roster problem-it’s an identity crisis.
The Bregman Market: Quiet, Confusing, and Wide Open
When Bregman opted out, the assumption was simple: a new deal with Boston would come together quickly. Maybe the front office was waiting to see how the markets for Kyle Schwarber and Pete Alonso played out. But now both of those dominoes have fallen, and Bregman’s still twisting in the wind.
Even his social media seems to reflect the uncertainty-he’s changed his profile picture, a subtle reminder that he’s not tethered to Boston or anyone else at the moment.
One of the more surprising developments this offseason has been the lack of a robust market for Bregman. You’d think a two-time World Series champ with a proven bat and postseason pedigree would have teams lining up. But that hasn’t been the case.
The Detroit Tigers, long rumored to be interested, appear to be out of the running. According to ESPN’s Buster Olney, negotiations between Tigers president of baseball operations Scott Harris and Bregman’s camp last offseason were “nasty,” and that bad blood may have closed the door there.
The Chicago Cubs? They’ve been mentioned, but they seem content to roll with Matt Shaw at third base in 2026. And they’re not expected to get into a bidding war for Bregman-or anyone, really.
Then came the Arizona Diamondbacks. On December 16, just as Bregman’s market felt like it had hit rock bottom, Arizona’s name popped up.
Was it a real pursuit? Or just a classic Scott Boras leverage play to stir the pot and nudge hesitant teams into action?
Hard to say. But what we do know is that Bregman’s market hasn’t materialized the way many expected. ESPN’s Alden Gonzalez recently said on Buster Olney’s Baseball Tonight podcast that Bregman could be headed for a short-term, high-AAV deal-something similar to what he signed with Boston last year.
That fits with what we’ve heard about Boston’s current approach. The Red Sox, reportedly, aren’t enthusiastic about handing out long-term contracts right now. That might be the real reason this reunion is stalling out.
A Window Opens in the Bronx?
All of this uncertainty around Bregman’s future has created an opening-and there’s one team that makes a whole lot of sense if he’s not going back to Boston: the New York Yankees.
The Yankees have a need at third base. Yes, they traded for Ryan McMahon, who’s owed $32 million over the next two seasons, and Amed Rosario is expected to contribute in a platoon role.
But neither of those options screams long-term solution. If Brian Cashman wants to make a serious upgrade-and take a shot at the Red Sox while he’s at it-Bregman fits the bill.
This isn’t just about plugging a hole on the infield. Bregman would bring a right-handed bat to a lineup that leans heavily left.
He’d give the Yankees postseason experience, leadership, and the kind of edge that plays well in October. And let’s be honest-stealing Bregman from Boston would be a gut punch to Red Sox fans still reeling from the Devers trade.
If Cashman were to land Bregman, it would force Boston’s hand. The Red Sox would likely pivot hard toward Ketel Marte, possibly overpaying to fill the void. And just like that, the rivalry would be back in full swing.
What’s Next?
At this point, Bregman’s free agency feels like a poker game with too many players holding their cards close. Boston isn’t showing its hand.
Other teams are lurking, but not lunging. And Bregman-along with agent Scott Boras-is waiting for the right moment to strike.
Whether that moment comes in Boston, Arizona, New York, or somewhere else entirely remains to be seen. But one thing’s clear: this saga is far from over. And wherever Bregman lands, it’s going to have ripple effects across the league-especially if it’s in the Bronx.