BOSTON — It was 1997, and the New England Patriots — before Belichick and Brady, mind you — were playing in the Super Bowl. Amid the crowd on Bourbon Street in New Orleans, 23-year-old Theo Epstein sat on his best friend’s shoulders and annoyed Green Bay Packers fans by reaching for their Cheeseheads.
“Unfortunately,” says Sam Kennedy, the best friend, recalling the events of the night to the best of his ability, “my massive, muscular build did not hold up. I went down like a sack of potatoes. Theo went down and hit his head. I think if it was 2017 versus 1997, he would’ve been diagnosed with a major concussion. It was not good. He had a migraine for about five days after that. Our parents wouldn’t have been very proud of that moment.”
Kennedy, now the Boston Red Sox team president, laughs at the memory. He knows it might embarrass Epstein, but if anyone has license to share that story, it’s Kennedy. And what better time than on the occasion of the prodigal son’s return to Fenway Park?
You see, when Epstein left the Red Sox in 2011, with the ashes of a historic September collapse still smoldering, he had already surpassed Oakland Athletics general manager Billy Beane as baseball’s most well-known executive. That’s what happens when you assemble the first World Series-winning Red Sox team in 86 years, then another one three years later.
But now, after leveling the Chicago Cubs organization down to its studs, overseeing a four-year rebuild, and last fall winning the franchise’s first World Series since 1908, Epstein has achieved full-on celebrity status. Fortune magazine recently named him the “world’s greatest leader,” ahead of even Pope Francis. And David Axelrod, a chief strategist to former president Barack Obama and die-hard Cubs fan, suggested last week that Epstein could have a future in politics, perhaps even as a savior for the Democratic Party.
Around here though, he’s still just Theo, the kid who grew up a mile from Fenway Park in Brookline, Massachusetts, dreaming of a career — any career — in baseball. He’s the son of a creative writing professor at Boston University and a clothing store owner and the twin brother of a social worker and guidance counselor at Brookline High.
Epstein, 43, hasn’t forgotten his roots, at least according to his brother, Paul. But if he has a momentary lapse — like, say, whenever he’s invited on stage to play guitar alongside Pearl Jam frontman Eddie Vedder, something that happens frequently, including Saturday night at the Paradise Rock Club in Boston — there’s a line of people at the ready to keep him in check.
“There is kind of an apotheosis thing going on right now. I’m aware of that,” Paul Epstein says. “But I think it’s good for him to be around family who can just knock him down a few pegs and bring him back down to earth. Not that he needs that because, trust me, none of this goes to his head at all.”