What, exactly, is the role of Theo Epstein with the Red Sox and FSG?

Take a good look at that photo above and you should get the idea: that's Theo Epstein in the background as Red Sox principal owner John Henry speaks, though the photo is now 20 years old. So here we are, 20 years later, and Theo is in the background again.

But is he involved ... or isn't he?

And if so, how much?

This is all relevant now - and for obvious reasons. The Red Sox failed at yesterday's MLB trade deadline, landing only back-end starter Dustin May and left-handed reliever Steven Matz in the flurry of activity that took place throughout the sport. Breslow himself sounded defeated. The Red Sox are now 496-484 since the start of the 2019 season, during which they've fired two chief baseball executives and hired only one manager, and their win-loss record basically puts them at something close to 82-80 on an annual basis. Give them a little time, of course. They could be back to 81-81 in no time at all.

Roughly 18 months ago, the Fenway Sports Group (FSG) issued a press release indicating that Epstein joined the group as a "senior advisor," news met obvious satisfaction. The whispers surrounding the Red Sox suggested Epstein would offer some guidance in getting the Red Sox back on track, and there is evidence to suggest he has indeed been involved. In February 2025, just slightly more than a year after Epstein returned, The Athletic wrote this story outlining Epstein's involvement in the pursuit of Alex Bregman, the Red Sox most significant free-agent signing in some time.

Roughly two months before the Bregman acquisition, the Red Sox also completed a major trade, acquiring ace left-hander Garrett Crochet from the Chicago White Sox. If you try to connect the dots - and you should - you should assume he was involved in that, too.

^{Former Red Sox general manager Theo Epstein (L) shakes hands with principal owner John Henry Nov. 2, 2005 following a press conference at Fenway Park.}

Nonetheless, no one ever really seems to ask the Red Sox about Epstein and he's rarely available - at least publicly. In some ways, this is a smart move by the team because the presence of Epstein would overshadow the efforts of Breslow, who is in his second year as chief baseball officer. On the other hand, the Red Sox still have a major credibility problem with their fan base, which threw its collective hands up in frustration yet again yesterday at the news that the Red Sox - who are currently in possession of a wildcard playoff spot - once again failed at midseason to make what even Breslow cited as an "impact" acquisition.

And so, again, here's the question: is Theo helping? If so, how much? And if Epstein is involved, wouldn't it be of value to have him out there assuring people that the Red Sox are headed in the right direction?

Instead, we're to treat him like Santa Claus or the Easter Bunny.

He's there.

You just don't get to see him.

Let's remember something here: the last two hires as chief baseball executive of the Red Sox have had no experience running a franchise. Zero. Chaim Bloom came from the Tampa Bay Rays, Breslow from the Chicago Cubs, where he was originally hired by Epstein. The general belief through the Boston media (and, perhaps, baseball) is that Epstein was consulted in the hiring of both. Depending on how many names you put a checkmark next to do, the Red Sox went through 10-12 names before they hired Breslow, whose hiring took place only after a number of people withdrew from consideration or turned down the job.

Breslow himself was initially considered as a candidate to serve as the overseer of the team's pitching program, which would have allowed him time to be groomed as a chief executive. When the Red Sox struggled to find a more qualified baseball czar, Breslow skipped high school altogether and jumped right into baseball's equivalent of an Ivy League college.

The truth? Like many of the Red Sox players promoted from the minor leagues in recent years - Jarren Duran and Kristian Campbell to name a couple - he wasn't ready. He was rushed. Breslow's first offseason was a fail. Interestingly, late in that offseason, Epstein returned to FSG. (That hardly feels like a coincidence.) Breslow's 2024-25 offseason was far more successful though, again, we can't help but believe that Epstein was involved. Now another talent acquisition period has gone poof, and Breslow was left to deal with the fallout.

^{Theo Epstein, MLB consultant, looks out during a press conference at MLB Headquarters.}

If you're frustrated by the Red Sox' ability to deliver you a product you deserve in recent years, you should be. And if you want to question their willingness to extend themselves and also be financially "uncomfortable," you have every right to vent. Mookie Betts was traded. So, too, was Rafael Devers. And yet, incredibly, this isn't entirely about money, either. It's about the push-and-pull that routinely takes place between any organization and ownership with deep pockets, and with the exception of Alex Cora, the Red Sox don't really have anyone at Fenway Park who can successfully push back on ownership anymore.

Is Epstein that guy? Let's hope so. The Red Sox clearly need an experienced someone to oversee their baseball operation because minor league prospects like Bloom and Breslow weren't equipped upon their hiring. That's really not their fault. But Breslow clearly needs Epstein the same way - or more - that Epstein once needed Larry Lucchino, which is, for anyone who remembers the genesis of that 2005 photo above, the irony of all ironies.

Back then, after all, Epstein stood in the background as Henry spoke of the young executive's resignation slightly more than a year after the Red Sox won the World Series. Of course, Theo eventually came back.

And if he's back again now, even in a more clandestine manner ... well, it would certainly help if people on the outside knew what the heck is going on.