By age 30, he had secured a place in Boston Red Sox lore as the general manager who guided the franchise to its first World Series title in 86 years. There was perhaps only one higher mountain in baseball left to climb at that point, but he eventually found his way to its base, and by age 42, he had led the Chicago Cubs to their first title in 108 years.
At that point, Theo Epstein had a Hall of Fame résumé, a lifetime drink-for-free pass in two major American cities, three World Series rings and more money than he would probably ever need – but also, one can imagine, a gnawing realization that nothing else he could accomplish as the head of a baseball-operations department could ever compare to what he had already achieved.
The news Tuesday of Epstein’s resignation as president of baseball operations for Cubs following nine years with that franchise made perfect sense within the Cubs’ orbit. The franchise, like many in the sport, is facing a revenue crunch after a pandemic-shortened, fan-free season, and has indicated a roster restructuring is in the works. Epstein’s departure, one year ahead of the expiration of his contract, allows longtime protege Jed Hoyer to ascend to the top job and oversee the next phase of the Cubs’ long-range plan.
Less clear, but at least as fascinating, is what this means for Epstein, who is still only 46. Perhaps he doesn’t even know precisely himself. But a good rule of thumb for the parlor game that will ensue over Epstein’s next move might be: Whatever your guess is, think bigger.
It is difficult to overstate Epstein’s impact on baseball over the past two decades. A Yale graduate, he ascended to the Red Sox’s GM job in 2002 at the age of 28, and soon became the prototype for the wave of Ivy League-educated, Moneyball-influenced, analytics-oriented GMs that exploded after the Red Sox’s first World Series championship under him in 2004 and that endures across the game today.
He made two high-profile exits from Boston, though the first of them didn’t take. On Halloween night 2005, amid a contract spat with the Red Sox, he famously walked out of Fenway Park in a gorilla suit to avoid reporters.
The split lasted just 2½ months; he would wind up signing a new deal in Boston, leading the team to another championship in 2007 and staying on through the 2011 season before departing for the Cubs job. The timing of that move has eerie overtones of Tuesday’s news: he was entering the final year of his Red Sox contract and wanted to give successor Ben Cherington the opportunity to make the hire for Boston’s vacant managerial job.
Even that far back, there seemed to be a larger mission in life for Epstein, but adding a curse-breaking championship on the north side of Chicago to go along with the ones he earned in Boston was too tantalizing to resist.
“It resonated with me so much, because it had so much meaning and relevance to what you do,” Epstein told The Washington Post in March 2016 of the decision to take the Cubs’ job. “At that point, I kind of had Chicago in the back of my mind. Maybe someday, that would be so wonderful to do there, taking what I’ve learned [in Boston] and applying it to that situation.”
That box was checked in on Nov. 2, 2016, when the Cubs won Game 7 of the World Series in Cleveland. And while many viewed the Cubs’ youth and talent level as the ingredients for a dynasty, the catharsis of the fall of 2016 was too much to replicate, and the Cubs never again approached the dominance of that season. Hoyer, in the spring of 2019, gave voice to the human quandary, saying: “I do think everyone, if they’re honest, would admit it hasn’t felt quite the same since ’16. There were good moments, but not the same edge.”
Epstein, in a moment of self-reflection, acknowledged the possibility he isn’t as proficient at maintaining a champion as he is at building one. “I’m self-aware enough in this area to know that after awhile I need a new challenge,” he said Tuesday. “And I think the Cubs, with everything we’re facing . . . it was the right time.”
Notably, Epstein stayed on with the Cubs this year just long enough to see through a painful series of layoffs within the team’s baseball operations and business staffs – a common fate in baseball this winter, amid the losses in revenue in 2020 – rather than leaving that awful duty behind for Hoyer.
With Epstein now a free agent, his name will undoubtedly be linked to openings for head of baseball operations with other teams. There is a high-profile opening as we speak with the New York Mets, under a new owner, Steve Cohen, who seems to be itching for a large-impact move. There is another with the Philadelphia Phillies. But those teams may not want to waste their energy trying to recruit Epstein. He has already indicated he intends to spend 2021 away from the sport.
The larger question is whether he will ever return to baseball – and if so, in what role. The only position above president of baseball operations – the title he held in Chicago – is typically the owner, and it is possible Epstein forms an ownership group to purchase an existing team or perhaps an expansion team, whenever baseball gets around to that.
Epstein called himself “open-minded” about his future, saying: “I do hope and expect to have a third chapter in baseball. But in no shape or form do I expect to do it right away. I envision taking some time to pursue other pursuits . . . I do hope to stay engaged in the game. This game is my passion. I care deeply about it. So I’m going to seek out ways to serve the game in the near future, and I’ve already started to pursue a few possible avenues to do that.”
But there are is also a depth and breadth to Epstein that barely surfaced in his past baseball roles. He is a musician. He has a law degree (University of San Diego, 2000). He has shown an interest in philanthropy and nonprofit work, and serves on the executive adviser committee for the Players Alliance, the nonprofit formed by former and current Black baseball players in the wake of this summer’s social justice protests.
He will have options that go far beyond the front office or even the ownership suite of a baseball team. Could Epstein wind up working for MLB? Could he find a new pathway in another sport? In business? In law? Politics? Philanthropy? Broadcasting?
The answers are yes, yes, yes, yes, yes, yes, and yes. Just because something hasn’t been done, that doesn’t mean a transcendent figure such as Epstein can’t do it. Otherwise those curses in Boston and Chicago might still be alive.