Former GM Is Wrong About Alex Bregman, Red Sox

There arguably isn't a better fit out there right now for free agent third baseman Alex Bregman than the Boston Red Sox.

Bregman spent the 2025 season with the Red Sox and slashed .273/.360/.462 with 18 homers and 62 RBIs. If Bregman didn't hurt his quad in May, this probably wouldn't even be a discussion. Before the injury, Bregman slashed .299/.385/.553 with 11 homers, 35 RBIs, and 17 doubles in 51 games played while looking like an American League Most Valuable Player candidate.

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Despite a second half slump, he was one of the biggest reasons why Boston won 89 games and made it back to the playoffs. After the season, he opted out of his deal and became a free agent and now can sign anywhere.

On Wednesday, former big league general manager and current insider for The Athletic, Jim Bowden, shared a column in which he picked the best matches for the top remaining free agents. For Bregman, Bowden had the Chicago Cubs at No. 1, followed by the Detroit Tigers at No. 2, and Boston at No. 3.

The Red Sox are the best fit for Alex Bregman

"Best matches: 1. Cubs 2. Tigers 3. Red Sox," Bowden wrote. "Bregman is looking for a long-term commitment like Schwarber and Pete Alonso just received. His best shot to get that at this point would be with the Cubs, who will be trying to replace Tucker in the lineup. The Cubs covet Bregman’s leadership and mentorship of younger players. If they were to sign him, they could move Matt Shaw to second base and trade impending free agent Nico Hoerner or just move Shaw to the outfield.

"The Tigers offered Bregman a long-term deal last offseason, and if it’s still on the table he might grab it this year. The Red Sox want him back, but I’m not sure they’re going to meet his contractual demands."

This, arguably, is wrong. Last offseason, Bregman picked Boston over both of these two organizations. At the time, Boston was trending upwards. With Bregman, Boston won 89 games in comparison to the Tigers' 87 wins and the Cubs' 92 wins. Chicago had more wins, but it very well could lose Kyle Tucker this offseason. Then you take into account that the club already has Shaw and Hoerner. Sure, you could move them around or trade guys, but is their long-term future better than Boston? Arguably not.

Then, you look at the Tigers. Detroit offered Bregman a large deal last offseason but he still chose Boston. Detroit very well could contend in 2026 and has a lot of young talent, but this is also a team that has had trade rumors swirling around its best player (Tarik Skubal) all offseason. Again, are they in a better long-term position than Boston? Arguably not.

Boston has an opening at third base, it should have enough money to match or beat any offer, and boasts an exciting, young core and farm system that few other teams come close to. Where else are you going to find a young player as talented as Roman Anthony or Garrett Crochet on long-term extensions already? There are few places.

From a pure fit perspective, Boston's window is just opening and it has the resources to keep it open for a while if Bregman stays.

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