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Sep 2, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) hits a one run RBI during the eighth inning against the Cleveland Guardians at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images Eric Canha-Imagn Images

Alex Bregman Would 'Love' Red Sox Reunion: Insider

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Dec 3, 2025 10:56 AM ET

The 2025 Major League Baseball Winter Meetings are just a few days away at this point.

Typically, the Winter Meetings are when the action around the league begins. This offseason has been a bit different, though. Pitchers have already flown off the market left and right. The Toronto Blue Jays landed Dylan Cease and reportedly agreed to a deal with Cody Ponce on Tuesday. The reliever market has been red-hot with guys like Devin Williams, Ryan Helsley, Phil Maton, and Raisel Iglesias all reportedly agreeing to deals with different teams.

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The trade market has been hot as well. The Boston Red Sox acquired Sonny Gray from the St. Louis Cardinals and the New York Mets and Texas Rangers swapped Marcus Semien and Brandon Nimmo. All in all, it has been an active offseason. The only market that hasn't really picked up steam yet is free agent offensive players. All the top guys are still available: Alex Bregman, Kyle Tucker, Pete Alonso, Kyle Schwarber, etc. For the Red Sox, Bregman is the most interesting for obvious reasons.

Bregman shined in Boston in 2025 and it would be nice to have him back. On the bright side, The Athletic's Jim Bowden shared that Bregman would "love" to stick around, but noted it's still unclear if Boston will meet his asking price.

"Bregman, 31, opted out of his contract with the Red Sox earlier this offseason because he would like a long-term deal to finish his career with one team," Bowden wrote. "He’d love that team to be Boston, but it remains to be seen whether the Red Sox are willing to offer him the kind of long-term deal he’s seeking. Bregman was important to the Red Sox last year not just because of what he did on the field, but because of his leadership qualities and willingness to help develop their young players at the major-league level.

The Red Sox shouldn't wait around to get a deal done

"However, there are several contending teams that Bregman would be a difference-maker for if he signs with any of them, including the Tigers, Phillies, Mariners, Yankees, Mets and Blue Jays, as well as non-contending teams like the Angels and Pirates. His free agency is going to be must-watch during the Winter Meetings."

This aligns with pretty much everything else that has been said about Bregman and Boston dating back to the season itself.

This sort of quote from Bowden shouldn't come as much of a surprise. Back in August, Bregman was effusive with his praise of the city and the organization.

"I think for me, being the new guy here in Boston, just seeing how the fans have embraced me, and really welcomed me with open arms, we kind of wanted to partner with Sam Adams and give back to the Boston fans and do something super ‘Boston’ to enjoy during the games,” Bregman said when talking about a partnership with Sam Adams. "Talking with (Alex Cora) before I signed, he did a good job of telling me about Boston…since I’ve been here, my wife and I have loved every second of it. I feel like we were expecting to love it, but we have loved it even more."

This is just one of many examples from the season. The front office has been clear as well about their love for Bregman. Now, it's all just about getting together on a new deal.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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