How Theo Epstein Helped Red Sox Land Marquee Free Agent Alex Bregman

The Fenway Sports Group brought in former Boston Red Sox general manager Theo Epstein as a senior advisor a year ago.

Epstein’s work since then has been almost exclusively done in the shadows. But how Epstein was an integral part in helping the Red Sox land marquee free agent Alex Bregman came to light Monday in a story written by The Athletic’s Jen McCaffrey.

Epstein did exactly as his title says: he advised Red Sox chief baseball officer Craig Breslow throughout the three-month process, which ended with Boston signing Bregman to a three-year, $120 million contract with two player opt-outs. Breslow certainly was better off having Epstein’s guidance.

“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 don’t work,” Red Sox president and CEO Sam Kennedy told reporters, per McCaffrey. “I really think it helped Bres in terms of, you’re talking about perhaps the best negotiator in the history of baseball agents, and Bres is still a year and a half, two years on the job.”

Epstein brought a different perspective and years more of experience to the table than Breslow, who was hired by Epstein to join the baseball operations team with the Chicago Cubs in 2019. Epstein served as the Red Sox general manager and Cubs president of baseball operations for 18 seasons, while Boston just hired Breslow for his first leading front office role in October 2023.

Epstein made sure to give advice to Breslow when it came to the negotiations with Bregman. And Epstein didn’t appear to step on any toes during the process as Breslow handed out the largest contract since becoming the Red Sox CBO.

“He was incredibly helpful,” Breslow said. “From everything from, ‘Let’s make sure that we zoom out and see and appreciate the big picture’ to here is maybe the right way to communicate. How are we thinking about this or that. Also, he was very respectful of the reality that, ultimately, this had to be my decision. And while his opinion may be something, I needed to do what I felt like I was comfortable with.”