Last winter, Alex Bregman signed very late in the off-season. The third baseman couldn't find an offer to his liking, so he accepted a short-term contract with the Red Sox, giving himself exit options.
And after a fine season in 2025 (despite a long absence due to injury), he exercised his exit option. So he's as free as a bird right now.
So where will Bregman end up this time? The Red Sox may be interested in bringing him back, but they won't be alone.
And among the clubs to keep an eye on, there's one that's starting to make some noise: the Chicago Cubs.
Sahadev Sharma reports for The Athletic.
While pitching remains the focus for the Cubs, with the expected departure of Kyle Tucker, they're considering additions on the position player side. Sources tell us that there's renewed interest in Alex Bregman. Story from@PJ_Mooneyand me: https://t.co/sJu12vuB5a
– Sahadev Sharma (@sahadevsharma) December 4, 2025
We know that the Cubs, who seem ready to let Kyle Tucker leave on the free-agent market, will have some money to spend. And Bregman, in effect, is likely to sign a smaller contract than Tucker.
And for the Cubs, who have depth in terms of outfielders, Bregman fits the team's needs better.
The club is banking on Matt Shaw, a promising young player, at third cushion right now. But in light of the fact that he didn't have a huge 2025 campaign, he's not exactly untouchable if the club can convince Bregman, who could replace Tucker to some extent offensively, to come to Chicago.
Last year, the Cubs were also interested in Bregman. The club was prepared to give him a four-year, $115 million pact, and Jed Hoyer had targeted him as an important player in his plan.
In the end, Bregman chose Boston… but this winter, the Cubs will have the opportunity to convince Bregman again. Let's see if this time, it will be the right one.

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– MLB Network (@MLBNetwork) December 5, 2025
- What's next for Pittsburgh?
What's next for the Pirates after their first major transaction of the offseason? https://t.co/yOJyYyK7nG
– Ken Rosenthal (@Ken_Rosenthal) December 5, 2025
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