Fifteen years ago, Theo Epstein famously sneaked out of Fenway Park in a gorilla suit on Halloween and stepped down as general manager of the Boston Red Sox, claiming his heart was no longer in it amid a power struggle with the team president.

It took all of 80 days for Epstein to reclaim his job — and more autonomy.

The point is, Epstein craves the action. Since the Red Sox made him baseball’s youngest GM in 2002, he assembled the first World Series-winning team in his hometown in 86 years, won another title three years later, orchestrated a move to Chicago, and rebuilt the Cubs from the ground up before shepherding their first championship in 108 years. In all, he has run a team for 18 seasons. He isn’t sedentary, and he doesn’t usually take one step without knowing the next.

So, when Epstein resigned Tuesday after nine years with the Cubs and said he intends to sit out 2021, some within the game were dubious. The 46-year-old future Hall of Famer has worked in baseball every summer since high school. Short of touring with Pearl Jam, what else would stoke his professional fire?

The Phillies surely will make a phone call to find out.

It has been six weeks since the demotion of general manager Matt Klentak, three since team president Andy MacPhail pledged to "happily step aside” a year before his contract runs out if John Middleton is able to “land a big fish” to run the Phillies' baseball operations.

Epstein is a front-office whale. It would be ownership dereliction, then, to simply take him at his word about taking a gap year. But his next chapter can be just about whatever he would like, so if Middleton really wants Epstein, he will have to make a full-court press the likes of which he staged two years ago when he jetted to Las Vegas in the middle of spring training to put a personal touch on his eventual $330 million offer to Bryce Harper.

Because as much as Epstein thirsts for a challenge, he also takes on the biggest ones imaginable. Staring down World Series droughts that dated to 1918 and 1908 and helping transform the Red Sox and Cubs from cursed franchises into money-printing monoliths were monumental accomplishments.

Getting the Phillies into the playoffs for the first time since 2011, even winning only their third championship since 1883, wouldn’t be as transcendent, at least not beyond the Delaware Valley.

Phillies managing partner John Middleton (right) speaking with team president Andy MacPhail before a spring-training game in February.
YONG KIM / Staff Photographer
Phillies managing partner John Middleton (right) speaking with team president Andy MacPhail before a spring-training game in February.

At present, there isn’t a bigger challenge in baseball than averting a work stoppage after next season. Perhaps Epstein will want to lend a hand to the commissioner’s office. Helping to broker a deal between the owners and players might position him favorably to someday take over as commissioner, if that interests him.

But Epstein has many interests. He cofounded a charity to benefit disadvantaged children and might want to help his twin brother, Paul, run it. He’s involved with the Players Alliance, the nonprofit formed recently by current and former Black players in the wake of George Floyd’s killing. He’s curious about politics.

In a news conference Tuesday, Epstein said he does “hope and expect to have a third chapter in baseball, but in no shape or form do I expect to do it right away.” He also hinted his next act will go beyond running a front office. Asked about someday owning a team, his answer revealed another of his passions.

“Being part of an ownership group is something that has always appealed to me, but it can seem so unattainable that I haven’t been really realistic about it. Yet,” Epstein said. “I have seen how impactful a championship team can be in a community, and I’ve seen firsthand how baseball team owners can be transformed into forces for civic good and help a lot of people and be involved in a lot of important conversations in the city and be a solution for a lot of issues in cities. That does appeal to me.”

It will take more than money, then, to lure Epstein, who made $10 million per year with the Cubs. Middleton and the Buck family (cousins Jim and Pete) each own 48% of the Phillies, while Hall of Fame former GM Pat Gillick and the Montgomery family own the remaining shares.

Is there a slice of the pie for Epstein? Would that even satisfy his ambitions? Maybe Middleton can impress upon him what another World Series would mean to Philadelphia. Maybe not.

Regardless, if Epstein really is intent on kicking back in the Wrigley Field bleachers in 2021 while pondering his next move, his timeline won’t align with the Phillies’, who can’t waste another prime year of Harper, Aaron Nola, and Zack Wheeler. There are too many president and GM candidates (Jim Hendry, Michael Hill, Dan Duquette, and J.J. Picollo, to name a few who have drawn the Phillies’ interest) to wait for a superstar executive whose sights might be set higher.

All it takes to find out is one phone call. The Phillies will certainly make it, and then, in all likelihood, move on.