The Boston Red Sox appeared to secure one of the biggest prizes of last offseason when they landed Alex Bregman in free agency. However, after delivering an excellent season, the star infielder chose to opt out of his deal, immediately returning to the open market. With Bregman available again, a wide range of teams are expected to show strong interest in his services.
According to The Athletic’s Jim Bowden, Bregman could command a contract worth around $182 million. While that price tag may narrow the field slightly, it is unlikely to cool demand significantly, as Bregman remains one of the most reliable and accomplished infielders in the game. His combination of experience, consistency, and postseason pedigree makes him an appealing target for clubs looking to take a meaningful step forward.
FOX Sports recently pointed to the Chicago Cubs as a team that should consider making an aggressive push for Bregman this winter. In their view, Bregman aligns well with the Cubs’ competitive window, offering a veteran presence who is still firmly in his prime. He would complement a young and improving core while also providing immediate offensive production. His established track record at the plate could ease the pressure on younger hitters, particularly Matt Shaw, who struggled offensively last season and may still need time to fully develop.
The Cubs are also facing the likely departure of Kyle Tucker via free agency, creating a clear need to add another impact bat. Signing Bregman to play third base could solve that problem while offering flexibility across the infield. Shaw could continue his growth, potentially shifting to second base long term, or Bregman himself could move there if needed. Either scenario would give Chicago another proven star with championship experience and the ability to perform in high-stakes moments.