The offseason and free agency drama is just getting started, and at the centre of it again stands Scott Boras, looking to land the best deal for his clients. And this time, the focus is on finding the next home for Alex Bregman. Five teams have reportedly entered the bidding for the third baseman, and the Red Sox suddenly find themselves in a difficult position. Why? Well, Boras’ calculated strategies.

The 30-year-old spent much of his career with Houston, where he won two World Series titles. He joined the Red Sox in 2025 in $120 million deal for 3 years with opt-outs after the 2025 and 2026 seasons. After spending nine months in Boston, he has decided to test the market again in order to find the next best deal. And it looks like many teams would like to sign him.

As per the latest update on X by Mathew Crory, MLB Senior Mark Feinsand identified potential landing spots other than the BoSox. The other 5 teams are: Tigers, Phillies, Mariners, Cubs, and Mets. Feinsand also noted uncertainty about whether Bregman can secure more than five or six years, but suggested “the AAV should push his total guarantee ahead of the deals signed by Matt Chapman (6/$151M) and Willy Adames (7/$182M).” For Boston, that means competing against deep-pocketed franchises with their own third base needs.

This is a worrisome situation for the Red Sox. Boston fans have seen their club sit on the sidelines throughout the last few offseasons as other teams made big changes. The franchise needs to show that it is ready to compete again, and Bregman is the kind of established veteran who could help speed up that process. But if the Tigers offer seven years, the Mets promise more money, or the Phillies make it easier for Boston to go to October, the Red Sox lose their edge.

Boston doesn’t need all five clubs to be real competitors. They just need one opponent who is ready to pay more than they are, and that one competitor may ruin their whole plan. The Mets have the money and the drive to do well. The front office in Detroit has shown that it wants to spend more. And the Phillies? Well, if they were not able to get Schwarber back, they also got the leverage. One serious bidder can turn this from a simple negotiation into a real threat.

In between all the ifs and the buts, one thing is certain: this winter is not going to be as simple as many of us might have thought.

Will Boston pass on Alex Bregman’s extension?

Beyond questions about rival interest, another complication has emerged: Boston’s own willingness to pay. Yes, as per an insider, even the BoSox are not sure. This adds a fresh aspect to the story!

As Gordo reported on X, MLB insider Jim Bowden said, “The Red Sox loved their time with Alex Bregman and appreciated all he did on and off the field.” “That said, I’m not sure they’ll be willing to commit to Bregman on a long-term contract at his market price.” Bowden’s comment has a totally different tone than the idea that Boston would just be sitting around with an open pocketbook.

Jon Heyman, an MLB insider, said earlier this offseason that Alex Bregman might get a deal worth close to $200 million. Keith Britton of The Athletic said that a six-year deal costing roughly $171 million would be a good fit. Both numbers show that the player is making a big commitment as he will turn 31, and the Boston front office seems hesitant to sign a long-term deal that could be risky in the long run.

This doesn’t mean Boston is out. However, it does suggest that the Red Sox may not push the matter financially. If Alex Bregman’s market doesn’t reach the high sums that Boras wants, Boston might come back. The team may decide to step aside if it does. What are your thoughts?