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What Worlds Are Left for Theo Epstein to Conquer?

The famed architect of Red Sox and Cubs championship teams announced Tuesday that he’s leaving Chicago. Now comes the wait to find out his next position—and the effect it could have on the baseball world.

Getty Images/Ringer illustration

Eighteen years ago, the Boston Red Sox promoted a 28-year-old lawyer with no professional playing experience into their vacant general manager role. Since then, the Theo Epstein–built clubs have won three World Series titles, made the playoffs 11 times, and posted 15 winning seasons. They’ve broken the two most legendary title droughts in North American sports, and inspired almost every other team in the league to remake their leadership in Epstein’s image. Baseball’s Hall of Fame has just 36 members classified primarily as executives, of whom only two—Pat Gillick and John Schuerholz—were GMs within the past 50 years. Based on what he’s accomplished already, the 46-year-old Epstein seems poised to join that exclusive club; the rest of his career, he’ll just be running up the score.

What, exactly, he’ll do in the future became an issue of urgent importance on Tuesday as Epstein announced that he’s stepping down as the Chicago Cubs’ president of baseball operations, a post he’d held for nine years. Epstein had one year left on his contract, and has stated his intention to take a sabbatical in 2021. It’s unlikely that he’d seek out a job in another organization for next season, and even less likely that the Cubs would allow him to accept such a position if he did.

Epstein now not only has options, but the luxury of time to consider them. He reportedly told friends that he plans to have a “third chapter” in baseball—and considering what he did with his first two, it’s understandable why there’s so much anticipation. In Boston, Epstein employed empirical analysis in concert with the Red Sox’s immense financial might, rather than as a way to overcome financial disadvantages. In the wake of the team’s success, almost every MLB club overhauled its baseball ops department to be run by businessmen, rather than ex-players and scouts.

With the Cubs, Epstein remade himself not as a GM, but as a baseball operations executive with the title of team president. This established a new level to which the head of a front office could climb, and a model that the Dodgers, Red Sox, Twins, Phillies, and numerous other teams coopted in order to attract or retain the most successful executives.

We don’t yet know what Epstein’s third chapter will entail, but we can be almost certain that he will attempt to blaze some new territory—and that others will try to copy it if he’s successful.

It is notable that Epstein specified he would return to baseball, because his success in MLB has been so great, and so conspicuous, that he has options open to him in other industries. Moreover, after breaking title droughts in Boston and Chicago, there really aren’t any worlds left for him to conquer within the sport.

Billy Beane is probably the only baseball executive since Branch Rickey who’s more famous than Epstein, and in many respects is Epstein’s narrative and philosophical predecessor. The former A’s GM has made his way out of baseball altogether, carrying on a longtime flirtation with European soccer—he’s a consultant with Dutch club AZ Alkmaar and a part owner of English second-division club Barnsley—and getting into investment banking as one of the leaders of RedBall Acquisition Corp, a company flush with more than half a billion dollars in capital earmarked for use in sports. Epstein’s connections and cachet would make him an enticing frontman for a similar venture. His reputation for intelligence, problem-solving, and consensus-building could also make him an attractive political candidate. (Though if Epstein’s half as smart as people say he is, he’ll know better than to actually run for such an arduous and thankless job.)

Left unexamined is the very reasonable option that he could retire. Though Epstein is only 46, he’s financially secure enough to have left a reported $10 million on the table by dropping out of his Cubs contract early. He could kick back and enjoy the spoils of his success, spend time with his family, jam with Eddie Vedder, and oversee his charitable foundation. If he gets bored or needs money, he could write a book, sit on corporate boards, or tour the lecture circuit, like a retired cabinet secretary. He doesn’t have to go back to work.

But it seems like he will, eventually, and he’s already generating buzz about his next landing spot. The next-longest title drought in MLB is Cleveland’s, though Epstein has only ever helmed well-heeled teams and would probably have little interest in a club that’s jettisoning its biggest stars as its owner puts on the pretenses of poverty.

If Epstein takes another job like the one he left, the two most likely destinations (at least at the moment) seem to be the Mets and Phillies, two NL East clubs with first-place economic resources but fourth-place vibes. Both would be able to endow Epstein with the kind of competitive infrastructure he enjoyed in his first two stops, and both clubs are in periods of transition: The Mets have just been bought by billionaire Steve Cohen, who’s promised to liberate the club from the scandal and mismanagement of the Wilpon years. The Phillies are without a GM, and president Andy MacPhail is planning to retire after the 2021 season.

But both of those jobs are smaller than what Epstein’s already done.

There’s only one way to get bigger and stay in baseball operations. Ken Rosenthal and Jayson Stark of The Athletic postulated that Epstein’s next venture might be as part of an ownership group that attempts to either buy an existing team or land an expansion franchise. Epstein, for all the power and money and prestige he’s accumulated over the past 18 years, was still an employee when he resigned from the Cubs. Other people—the Ricketts family, who owns the team—paid him to perform a service and reaped the resulting financial windfall. He could jump to the other side of that barrier by holding a stake in the next team he works for.

A few particularly successful athletes—Derek Jeter, Mario Lemieux, Michael Jordan—have accumulated enough money to buy a stake in a team, sometimes even a majority interest. But Epstein has never made the kind of money Jeter and Jordan made, and never will—unless he becomes an owner.

At his exit press conference Tuesday, Epstein made an interesting comment about the direction of baseball under what’s broadly defined as the analytics movement: “[E]xecutives like me, who have spent a lot of time using analytics and other measures to try to optimize individual and team performance, have unwittingly had a negative impact on the aesthetic value of the game, and the entertainment value of the game.” Fans, Epstein says, would be more interested in a game that rewarded athleticism more and featured fewer strikeouts.

Epstein called the modern style of play a “threat” to the game, and in this I agree with him 100 percent. Contemporary baseball too frequently lacks action and rhythm, and while modern ballplayers are capable of physical acts Alexander Cartwright could not have comprehended in his wildest imaginations, they aren’t afforded enough opportunities to showcase that athleticism.

But while it is a threat to the game, it is not an existential one. Fan interest in baseball has survived 150 years of tactical evolution and will survive the juiced ball era and bullpen games. The greater threat comes not from a sabermetrically informed front office, but from the people who sign the paychecks.

Consider the state of the Cubs team Epstein is leaving. Perhaps it was never reasonable to expect Chicago to parlay its 2016 World Series title into a half-decade of outright dominance, but the competitive window Epstein and his subordinates forced open in 2015 is coming to an end. Jon Lester is leaving. Kris Bryant and Javy Báez are a year from free agency. Anthony Rizzo, José Quintana, and Kyle Hendricks are all on the wrong side of 30. This team is on the verge of atrophying back into a perennial third-place finisher as ownership withholds the resources necessary to keep the good times rolling.

Playing winning baseball, or entertaining baseball, is no longer the primary economic function of an MLB team. Franchises have become tech companies, media conglomerates, and real estate developers. As the Cubs have backslid on the field over the past five years, the Ricketts family has poured hundreds of millions of dollars into redeveloping the area around Wrigley Field and starting a team-owned cable TV channel. That—not gate receipts or jersey sales—is where the real money is, and the team is merely a branding anchor and asset to be borrowed against.

Even if most fans don’t know the financial details of these enterprises, they can sense their effects. When there’s a curious leaguewide refusal to spend in free agency; when, as revenue growth and franchise values far outstrip player and front office wage growth, teams pinch pennies on talent; when the goal is to build a cheap playoff contender, rather than even a moderately expensive favorite.

Epstein must know this too, and if his next job comes with an ownership stake and a new position above baseball operations, this will be why. His ability to construct winning teams became less valuable to the Cubs than building the team’s real estate and media interests. The time has come for him to move on to something bigger than constructing a roster. That’s where the money is, and that’s increasingly what MLB’s bigwigs value above all.