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.”
Says Kennedy: “I think people that have known him a long time, you quickly remind him of his shortcomings when he wasn’t the rock star baseball executive, world’s greatest leader. You harken back to 1987, 1988 when we were struggling to make the JV baseball team at Brookline High, or the lack of playing time that he may have had in high school, or the silly things we did together. I do remember him spending a lot of time as our third-base coach.”
And over the past few days, Kennedy has had ample time to remind Epstein of it.
EPSTEIN WOULD HAVE returned to Fenway Park sooner, but let’s just say he had a good excuse. When the Cubs played here in 2014, his wife Marie was about to give birth to their second child, Andrew.
“I was so bummed at the timing,” Epstein says.
So, from the moment he touched down in Boston last week, Epstein’s schedule has been packed.
On Thursday, he went for a midday run along the Charles River (and promptly got “an unsolicited high-five from a jogger going the opposite direction”), had dinner with his family, then got Kennedy to sneak him into Fenway for the last few innings of the Chris Sale-Masahiro Tanaka duel that wound up as a 3-0 New York Yankees win, after which he hung out and had a few drinks with a few former baseball operations co-workers. On Friday, Epstein co-hosted a lunchtime panel discussion with Hall of Famer Pedro Martinez, former Red Sox catcher Jason Varitek, ex-Yankees center fielder Bernie Williams and former pitcher Ryan Dempster to benefit the Foundation To Be Named Later, the charity the Epstein brothers started with venerable baseball writer Peter Gammons.
And on Saturday night, Epstein joined Vedder and three ensemble bands for a benefit concert, the second half of the foundation’s annual Hot Stove Cool Music charity event. The goal for the weekend: raise close to $1 million to benefit youth organizations in Boston and Chicago.
“One thing I can say for certain is Red Sox fans and Cubs fans are very, very generous and community-minded,” Epstein says, “and this is just a mechanism to help redirect some of those dollars toward nonprofits that are going to be doing great work.”
Oh, and in between, the Cubs played two games against the Red Sox, with the series finale set for Sunday night (ESPN, 8:05 p.m. ET).
Say this for Epstein: He makes the most of his homecoming. It’s little wonder he says he was “not planning on sleeping much this weekend.”
“I’m really happy,” Epstein says. “I’ve been looking forward to this weekend a long time. I’m kind of on cloud nine, really loving it.”
WANT TO GET a rise out of Kennedy? Ask where he thinks Epstein rates among the most influential world leaders.
In March, Fortune magazine ranked the “50 greatest leaders in the world,” a list that included Canadian prime minister Justin Trudeau (No. 31), former U.S. vice president Joe Biden (No. 23), Supreme Court Chief Justice John Roberts (No. 21), Federal Reserve chair Janet Yellin (No. 17), German chancellor Angela Merkel (No. 10), U.S. Senator John McCain (No. 9), U.S. National Security Advisor H.R. McMaster (No. 7), Amazon CEO Jeff Bezos (No. 5), billionaire philanthropist Melinda Gates (No. 4) and the aforementioned Pope (No. 3).
The notion that a baseball executive would even be considered among them?
“It’s been a little bit otherworldly when you have magazines — legitimate publications on planet Earth — referring to him as the greatest leader,” Kennedy says. “When you’ve known someone since they were a kid and you read these things and you hear these things, it becomes laughable because there are so many more important issues and causes and people in the world. I mean, we’re working in baseball, and he’s been portrayed as this world leader. I think he said it best — it’s patently ridiculous.
“That said, I think it acknowledges how important a place that sports — and especially the Red Sox and the Cubs — has in American society.”
Indeed, it’s a measure of the magnitude of Epstein’s accomplishment as the architect of championship teams for two historic franchises that doubted they would ever win again. Combine that with his admittedly unrelenting need to tackle new challenges and folks like Axelrod are reasonably speculating about his next move. Last week, Axelrod told Politico that he believes Epstein could make a successful Senate bid in Illinois.
“Ridiculous,” Epstein insists.
OK, maybe in his home state of Massachusetts?
“I think I need to go do something really ill-advised or commit a felony or something. I can put a stop to it in a hurry,” says Epstein, who last September signed a five-year contract extension to stay with the Cubs through 2021. “But people who know me would just laugh at that. I barely can get out of bed and get my job done the right way in the morning most of the time. It’s a group effort.”
THOSE CLOSEST TO Epstein insist his successes and celebrity status haven’t changed him. As much as ever, he’s quick to give credit to his baseball operations compatriots, including Cubs general manager Jed Hoyer and player development chief Jason McLeod.
If anything, Epstein has grown up since his days as the boy wonder GM of the Red Sox. These days, as he approaches middle age with a wife and two sons, his idea of horsing around is a pickup basketball game with colleagues on the morning of a playoff game. Back in the day, though, he ran a baseball ops department that resembled a frat house.
“I was so young and immature and over my head, and as I think back on that whole saga, getting the job and the heartbreak in ’03 and then winning it in ’04, I went through that whole thing with this great group of friends who I work with and we just rode the wave,” Epstein says. “We didn’t come up for air or get perspective on everything. We couldn’t process it in real time. It just felt like one big wild ride, ending with a parade.”
Accent on “wild.” Even now, Paul Epstein often jokes with Red Sox chief marketing officer Adam Grossman about the abuse he took as an intern early in Theo’s administration.
“They used to just have all-out brawls and violence towards the interns,” Paul Epstein says. “I always tell Adam, he should write a memoir and the title should be ‘Stapled’ because one time they threw a stapler at him. ‘Stapled: My Life As A Red Sox Intern.’”
File it under stories that only Epstein’s family and closest friends can tell, the tales that come up only when he comes home, the only place where the greatest leader in the world (or at least baseball) is still just Theo from Brookline.