Flavin Media

Theo Epstein is working behind the scenes for the Red Sox.

Ideal scenario.

Per: @jcmccaffrey

“Theo was really, really helpful and provided counsel along the way that helped us think about different deal structures and also ripping up different deal structures when they… pic.twitter.com/ezm6K7xm46

— Savage (@SavageSports_) February 17, 2025

Off an offseason in which the Red Sox finally opened their pocketbook at least halfway, some credit needs to be given to those who could have been pushing for a different look this winter. With Theo Epstein now part of Fenway Sports Group (FSG), it’s not hard to imagine he has a say in team decisions.

The fact that Theo Epstein is back around the Red Sox proves his desire for the city’s success, and Breslow’s inexperience prompts him to provide what he can. As Epstein’s influence becomes a mainstay, the willingness to offer bigger contracts—like real big-market teams should—could come back into the fold.

As if Epstein hasn’t done enough for this city, it’s beyond exciting to see him around the facilities in a reduced but impactful role for round two. Breslow learns from someone who’s done it before, and Henry has another voice in his ear pushing for title success.