Did the Red Sox get more bad news on the Alex Bregman front?
The latest on free-agent third baseman Alex Bregman might not be what the Red Sox want to hear when it comes to a reunion.

May 16, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) runs out of the dugout before the start of a game against the Atlanta Braves at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
The Red Sox are not alone in their pursuit of Alex Bregman.
That alone, while not shocking, is not good news for Craig Breslow and the Sox. Especially with some of the market's other options of interest to the Red Sox (Pete Alonso and Kyle Schwarber, most notably) off the board. And things may have gotten even worse for the Red Sox and their hopes for a Bregman deal on Thursday night, with the forever-uncomfortable 'term' Bregman wants looking like an inevitability, courtesy of the latest update from ESPN's Jeff Passan.
"Bregman and [Cody] Bellinger have taken shorter-term deals with opt-outs in the past, so both are looking for the security of long-term deals," Passan wrote in his latest rumor roundup of the MLB offseason and what's to come. "Neither is likely to move off such an ask. Bregman figures to seek six years."
Passan was not the only insider to mention this kind of term for Bregman, either.
MLB.com's Mark Feisand wrote on Wednesday that Bregman, who will turn 32 before the start of the 2026 MLB season, was believed to be seeking a five-year contract this offseason. And with the DBacks joining the race earlier this week, the odds of Bregman ultimately getting what he wants feel higher than they may have already been. And with no shortage of potential suitors — the Tigers, Mets, Cubs, Blue Jays, and even the Yankees are among the teams linked to Bregman this offseason — the bidding may very well come down to who offers the longest deal.
Passan, like everyone else in the world, is also acutely aware of Boston's needs, noting that the club "badly" needs a big bat added to their lineup. Again, that does not help the club in talks opposite Bregman and MLB superagent Scott Boras.
This might be nothing new to anybody following this saga from the jump, really. Bregman opted out of his contract with Boston with this exact hope in mind. And the opts out were put in his Red Sox contract for this exact reason. But now that it's looking like a mere formality that Bregman will get the term he wants on his next deal, the idea of him staying with the Red Sox becomes a true mystery.
When the Sox were 'in' on Alonso, it was said that their offer was a three-year deal. That's simply not what it takes to acquire free agents of that caliber. And it's also in line with reporting from MassLive's Sean MacAdam earlier this month, with an agent telling MacAdam that the Red Sox "don't believe in long-term deals."
The Red Sox are not ones to get uncomfortable these days, and the Bregman negotiations sound like they will get uncomfortable with the term required.
And the problem is two-fold for the Red Sox in this respect, too, as any pivots away from Bregman would also require term. Toronto star and current free agent Bo Bichette isn't signing for a three-year deal, same for Kyle Tucker, though the Red Sox have yet to be linked to the latter at any point this offseason.
Even a trade for Arizona's Ketel Marte would see the Red Sox get uncomfortable by this standard, with Marte under contract through 2030 and in possession of a player option for 2031, which would be his Age-37 campaign.
If the Red Sox were looking to play a game of 'chicken' with Bregman, it appears that things are getting real uncomfortable... but only for the Red Sox.





