Alex Bregman was supposed to be the stabilizing force in the Boston Red Sox's clubhouse for years to come, which has made his free agency so ironic: it's been a fluctuating, stomach-turning, mysterious cocktail of worry for Red Sox fans who were once cozy and comfortable with the assumption that Bregman would re-sign.
Bregman opted out of his deal on Nov. 3. Six weeks later, he's still unsigned, and there are ominous signals everywhere indicating that a return to Boston is very far from guaranteed. For one, Boston's reported pursuit of All-Star infielder Ketel Marte suggests that they are preparing for a 2026 roster that doesn't feature Bregman on it.
Are the Red Sox really going to let Bregman slip through their grasp after trading superstar third baseman Rafael Devers six months ago (due to chemistry issues caused somewhat by Boston accommodating Bregman over Raffy)?!
Alex Bregman's return to the Red Sox is completely up in the air
Most Red Sox fans assumed a deal was going to get finalized shortly after he opted out. "Oh, maybe the Red Sox are waiting to see what happens with Kyle Schwarber and Pete Alonso first," some fans logically surmised. Schwarber gone, Alonso gone ... and Bregman remains unclaimed. He's also changed his profile picture on Instagram to remind us all that he's not beholden to the Red Sox.
The strangest rumors surrounding Bregman for much of the offseason — as it relates to Boston having failed to take care of business — have been that Bregman doesn't have that many teams interested in him; that his market isn't as voluminous as one would assume. The Detroit Tigers have been continually linked to Bregman since last offseason, but even they've been deemed an unlikely landing spot by ESPN's Buster Olney, due to what Olney described as "nasty" negotiations that took place between Tigers POB Scott Harris and Bregman's camp last winter.
The Chicago Cubs have been floated in rumors as a Bregman destination, but they're more than okay with Matt Shaw at the hot corner in 2026. They're certainly not going to get into any type of bidding war for Bregman.
On Dec. 16, as the clouds surrounding Bregman's market reached their darkest hue of the offseason, another suitor for the third baseman appeared out of thin air: the Arizona Diamondbacks. Funny timing, wasn't it?
Are we to believe that the D-Backs are truly in on Breggy, or is this a media tactic/leverage play from Scott Boras? While the Arizona buzz is something, the overall gut-feeling inside everyone observing Bregman's free agency is that he's not going to get a huge contract. ESPN's Alden Gonzalez recently asserted during Olney's Baseball Tonight podcast that Bregman's probably going to end up with a similar deal to the one he signed with Boston a year ago — short-term, high AAV-type stuff.
Even if Bregman was holding out for a long-term deal, reports indicate that the Red Sox aren't that interested in giving out those kind of contracts to ... anyone. But hey, maybe this is why Bregman and Boston actually aren't going to work out.
Of course, all of this unexpected wishy-washiness with Bregman's free agency has given opportunities to non-Red Sox teams to swoop in and steal away the two-time World Series champ. Maybe it'll be Arizona, and the buzz is real. But here's another idea: why shouldn't it be the New York Yankees?
Yankees have obvious opportunity to sign Alex Bregman and make life miserable for the Red Sox
The Yankees have a real need for Bregman, and it's not like Brian Cashman has already emptied out his wallet this winter. They're already setting themselves up for a platoon situation at third base (Amed Rosario will chip in) despite trading for Ryan McMahon, who is set to make $32 million over the next two seasons.
How about this: ditch the McMahon experiment and sign Bregman! You'd be addressing multiple team needs with Bregman and simultaneously plunging a dagger into the collective psyche and sanity of Red Sox Nation. Bregman would sort out your third base situation and give you a superstar-level right-handed bat in a lineup that we all know is too left-handed.
Cashman bagging Bregman would be explosively good for the Yankees in so many ways. The Red Sox would obviously pivot and overpay for Marte, and this rivalry would be on fire once again. Make it happen, or at least try!
