Alex Bregman was a last-minute add to the Boston Red Sox last offseason. His first foray into free agency ended up being very drawn out. He didn't receive the types of offers he had hoped for, and instead opted for the high AAV deal with the Sox that allowed him to hit free agency again this year.
It came as a bit of a shock to Red Sox fans after the deal was signed when reports emerged that the Cubs had offered Bregman a four-year contract and the Tigers had offered him a six-year contract. Those were the types of deals that he had been looking for, especially Detroit's, but he apparently wasn't happy with the overall value.
Fast forward to this offseason, and Bregman is back on the market after opting out of his contract, and it's the same suitors once again. The Red Sox, Tigers, and Cubs are all vying for the third baseman's services.
This time around, the Red Sox are going to need to up their offer. Just like last year, the righty, who will be 32 by Opening Day, is looking for a long-term commitment. Unlike last year, it seems like he will get the long-term deal he wants, with the money being closer to what he desired. If the Sox are serious, they are going to need to commit to Bregman for the time he wants.
Red Sox, Tigers and Cubs running last offseason back as top competition in Alex Bregman chase
The interest the Tigers have shown in Alex Bregman so far is “lukewarm”, per @EvanPetzold.
— Tyler Milliken (@tylermilliken_) December 8, 2025
“The Tigers' interest in Bregman has been lukewarm so far, according to a person with knowledge of the situation, but it could heat up with the MLB Winter Meetings underway.”
I like that. pic.twitter.com/1T0G0xYaSb
Red Sox Nation is hoping that Bregman proved his worth to Craig Breslow this season. The Red Sox CBO was hesitant to give Bregman the long-term deal he had hoped for last winter, which is why they gave him the three-year deal with opt-outs. Bregman ended up being an integral part of the Red Sox's successes with his presence on and off the field.
With the Winter Meetings underway, there are reports coming out about all the teams. Two nuggets of information have come out about Bregman that should ease the minds of Red Sox fans. The first was ESPN insider Buster Olney predicting on an episode of The Just Baseball Show podcast released December 6th that Bregman will return to the Red Sox this winter. The other was a report from The Detroit Free Press' Evan Petzold that the Tigers' current interest in the third baseman is "lukewarm".
While that is good news for Red Sox Nation, the biggest thing for them to hope for right now is that Breslow is pushing hard for him. Ultimately, it will come down to Breslow and the Red Sox outbidding the other teams, and Bregman wanting to come back and finish what he started in Boston.