Theo Epstein and his historic journey back to Fenway Park: Jayson Stark


Can we take a moment to try to grasp the unique and magical journey of Theo Epstein?

Has there ever been anything like it in sports? Let’s go with no. Or more like no chance.

He’s walking through the gates of Fenway again – this time as a part owner and senior advisor of Fenway Sports Group. So now he’ll have not just the Red Sox, but hockey, golf and the English Premier League on his plate — among other things. And why do we think those other things will never be the same after this guy gets his hands on them?

But let’s reflect first about how Theo Epstein got here. Try to come up with anyone in the vast sporting universe who ever followed a path anything like this:

· He was once an 18-year-old hot-shot ‘Whoah, watch out for this kid’ intern in Baltimore. That was 1992.

· He was once the assistant public relations guy in San Diego, typing up the daily press notes chronicling Doug Bochtler’s 13 straight appearances without an earned run. That was 1995 and ’96.

· He was once the youngest general manager in baseball history, the 28-year-old bound-for-greatness front-office phenom who took over in Boston in November 2002, when that whole Brad Pitt/Billy Beane thing didn’t work out.

· Then Theo took that fabled spin as baseball’s all-time curse-buster — Curse Crusher 1.0 in Boston, Curse Crusher 2.0 in Chicago. That’s 194 years worth of droughts and torment vanquished, all by the time he was 43 years old.

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Epstein celebrates with Derek Lowe after the Red Sox won the 2004 World Series. (Jed Jacobsohn / Getty Images)

· Next came those three years in the commissioner’s office, from 2021 until this week. Epstein’s official job title there was “consultant,” but he’s a consultant who will be looked back on as one of the driving forces behind what we think we can safely describe as oh, just the most impactful rule changes in his sport in the last half-century.

And now this: The step that completes his journey, by age 50, from internship to ownership — with a two-decade run as arguably the greatest GM ever sandwiched into the middle. So let’s ask this again: Has there ever been anyone in the history of sports with a career path quite like this?

Who? How?

“There are people in sports who work their way up the ladder,” said Charles Steinberg, the president of the Worcester Red Sox, a man who has worked with Theo on three different franchises. “But they rarely climb the ladder from management to ownership.”

Right. Let alone from summer intern to ownership. And Steinberg would know, since he was there, literally, the day this all began.

Back in 1992, Charles Steinberg was the public relations director of the Orioles when Calvin Hill — yes, that Calvin Hill, the former Cowboys/Yale running back who was then an Orioles executive — knocked on his door one day.

“He came into my office,” Steinberg reminisced Friday, “and handed me a resume and a cover letter. And he said, ‘I wanted you to see this. It looks pretty good. There’s no pressure. But you’ll want to see it.’”

What he read was such a beautifully written letter from a Yale freshman named Theo Epstein that they immediately invited him to Baltimore for an interview – where he blew everyone away with his astonishing baseball knowledge and the eloquent ways he found to express it.

Needless to say, he got the gig. There’s a first chapter in every story. This was Theo’s.

Steinberg has spent the last 32 years witnessing the rest of that story — including up-close views in Baltimore, San Diego and Boston. It hasn’t been lost on him that he has been watching a man who was always different from everyone else.

“Of all the people I’ve known in the game over 40 years,” Steinberg said, “he is clearly one of the most extraordinary minds I’ve ever come across. I couldn’t be happier for him. Everything he has, he’s earned with his intellect.”

The crazy thing is, Theo so easily could have wound up as a writer or an actor or a lawyer. His grandfather wrote the screenplay to Casablanca. His father was the director of creative writing at Boston University for more than three decades. His sister is a screenwriter in Hollywood. And there was that time, in his mid-20s, when he went to law school at the University of San Diego, while he was still working for the Padres.

But sports had a bigger pull on him than any of that. And that pull led him down the baseball highway, even though you could argue that he has actually spent the last 20 years acting in the real-life sequel to Moneyball.

Curse-busting in Boston would have been Billy Beane’s niche if the longtime A’s architect hadn’t turned down Red Sox owner John Henry’s courtship to hire him as GM in the fall of 2002. Epstein was less than a year into life as an assistant GM in Boston back then. So friends say he was actively rooting for Beane’s hiring to happen.

“I remember vividly, at the time, when Theo himself told me that Billy Beane was going to be the next GM of the Red Sox,” said Ben Cherington, now the general manager of the Pirates, then another young rising exec in the Red Sox front office. “And he was excited about that. And he was getting us excited about that.”

But then … well, something else happened. Billy Beane said no. And …

“Theo didn’t say it,” Cherington said. “But I think we all kind of thought: OK, well, there’s really nowhere else they’re going to turn at this point.”

So poof. On Thanksgiving week, the Red Sox turned around and hired Theo. You know how that worked out. What you don’t know is the sense of excitement that hiring set off inside the Boston front office, where it had already become clear, in Epstein’s brief time with this team, that this was a guy with a chance not only to win, but to inspire everyone around him.

“You know there are those people,” Cherington said, “that we’ve all been around in our lives that immediately strike you as (having) just a different level of energy. A thinker. And just sort of culturally additive, someone who people are immediately drawn to, where people want to be in their orbit. And Theo was just one of those people. And it was obvious right away in that office.”

So why, two decades later, is Fenway Sports Group asking Epstein to be, essentially, a leadership coach, across multiple sports? Because even looking back now, it’s clear that “Leader” was always part of his DNA.

Steinberg used the phrase, “inspiring charisma,” to describe him. But you can’t teach charisma. So it’s all those other leadership qualities that FSG is looking for him to impart.

“Some people (in leadership) can retain information, but can’t always recall it,” Steinberg said. “Some people don’t even have the knowledge because they haven’t put in years and years of devouring books to teach you what came before you. Some people may have all of that, but don’t have the perceptiveness to read the mind of the person they’re talking to. He has all of the ingredients that collectively make for an extraordinary mind.”

So why is this happening? Why did Red Sox president Sam Kennedy approach Epstein about this role late last summer? Obviously, it’s all of those leadership qualities we just described — not to mention the track record, the New England roots, the instant credibility with the fan base and the longtime connections with the people he’ll be joining in FSG ownership. None of that is a mystery.

But why did Theo himself think the time was right — and the role was right — to take this step? That’s the part that wasn’t so obvious.

For years, ever since he left the Cubs, Epstein had been saying publicly that he would someday find his way back to the team side of sports. He wasn’t sure when. He wasn’t sure where. But he sure as heck wasn’t going to come back so he could sign six minor-league free agents on New Year’s Eve, with invitations to big-league camp.

It was always the allure of ownership that intrigued him. So when Kennedy — his longtime friend and former teammate, as far back as the freshman baseball team at Brookline High School — first dangled this idea last summer, Epstein initially laughed it off, friends say.

But that, clearly, wasn’t the end of this conversation. Kennedy got his owners, Henry and Tom Werner, involved. Then they looped in FSG president Mike Gordon. They knew a potential multi-sport platform was one that Epstein has long had interest in. They laid out an array of possible roles, across all of the Fenway Sports Group holdings, that felt to Theo like a near-perfect fit, friends say. Eventually, his adrenaline started pumping.

“It took him some time,” Kennedy told The Athletic’s Jen McCaffery on Friday. “And he started to get excited about building a new skillset as an ‘executive coach’ of sorts, getting involved in multiple sports and as an owner. He became excited about it. John, Tom and Mike were ecstatic about the concept of having him.

“He told me, ‘This might be one of your worst or one of your best ideas,’” Kennedy said. “I eventually wore him down.”

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Sam Kennedy and Ben Cherington worked closely with Epstein throughout his Red Sox tenure. (AP Photo / Elise Amendola)

The other half of this equation was that Epstein’s heaviest lifting at MLB was in the rear-view mirror. The barrage of rule changes — pitch clock, shift limits, incentives to re-energize baseball’s running game — had made it from the drawing board to the field last year.

The sport was in a good place. And it was hard to imagine, as new ideas emerge and new rule changes are up for debate in the future, that the people at MLB wouldn’t dial up a guy named Theo Epstein to see what he thought. So the timing, for Epstein to take his next step, was excellent.

All of a sudden, every puzzle piece was dropping into place. The announcement came Friday morning. We’ll learn more, at a major Fenway press conference extravaganza, shortly.

But it is times like this that allow us to ponder not merely the news of the day, but all the forces that converged to make this moment possible. So one last time, let’s ask: Has it dawned on everyone yet — across New England, across baseball, across the big blue sports sky — that it’s not just an old friend who is returning to Fenway this month? It’s a one-of-a-kind figure in sports history.

“I think it has to be thought of in that way — in baseball, certainly,” Cherington said. “I mean, 20 or 30 years from now, if you think back on this era of baseball, taking out people who wear uniforms, he’d be certainly be amongst a short list of people who would be seen as transcendent in this time. And I don’t know who else who else would be on that list.”

It’s enough to make you wonder: What could possibly be next for Epstein? Once he has finished conquering ownership the way he conquered curses, what mountain could he look to climb once he turns, say, 55?

Commissioner of baseball? Ambassador for world peace? Fund-raiser to spearhead the fight to cure all the world’s most deadly diseases? How could we put anything past him?

After all, if the Curses of the Bambino and the Billy Goat were no match for Theo Epstein, what in this world couldn’t he do if he directed his fiercest will toward doing it?

“There are so many ways you can describe the qualities that make him special,” Charles Steinberg said. “The work ethic. His perceptiveness. His ability to retain information and to recall information. But it all adds up to one of the most capable minds I’ve ever come across.”

(Top photo: AP Photo / Gregory Bull)





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