Theo Epstein ... for president?

Theo Epstein might have earned a place on the Mount Rushmore of baseball executives. How about, someday, the actual Mount Rushmore? Illustration by Elias Stein

Editor's Note: In light of Fortune magazine naming Theo Epstein the world's greatest leader (no joke), we've decided to bring back this panel discussion, originally published on Election Day in November.

Now that Theo Epstein has broken curses in both Boston and Chicago, is he the greatest MLB executive of all time? What can he do as an encore? Could he be a hit beyond sports?

This Election Day, our panel -- featuring ESPN Insider Buster Olney, ESPN analyst Tim Kurkjian, SweetSpot Blog Network/ESPN.com's David Schoenfield, ESPN.com Chicago Cubs beat writer Jesse Rogers and FiveThirtyEight.com's Neil Paine -- takes a swing at Theo's third act.

From the Goat to the G.O.A.T.: Is Theo Epstein the greatest baseball executive of all time? If not, why not, and who is? Where does Theo rank?

Olney: Branch Rickey has a legacy distinct from any other executive in any sport, as he was the leader who had the courage and integrity to sign and promote Jackie Robinson. But if the criterion is success on the field, nobody can match Theo Epstein's track record. That's because he has been able to climb both baseball's K2 -- Boston's 86-year championship drought -- and its Mount Everest, the Cubs' 108 years without a title. That success will be the standard against which all elite executives will be judged, and while history remembers that Sir Edmund Hillary and Tenzing Norgay were the first to climb Everest, almost nobody can recall the names of the next to follow. Some of those among Theo's peers who aren't necessarily fond of him regarded him as the sport's best executive before the Cubs' World Series title.

Kurkjian: It is difficult to put any executive ahead of Rickey, who, along with integrating the sport, was the father of the farm system in baseball. Hall of Famer Pat Gillick and perhaps soon-to-be Hall of Famer John Schuerholz are executives of the highest order, but Epstein is in another category after his wins with the Red Sox and the Cubs. Those successes will make him the most famous executive and most decorated after Rickey. Epstein is the best executive in the game today, and his intelligence, vision and determination likely will keep him as the best for a long time. We sometimes forget that he is only 42 years old.

Schoenfield: There's no doubt Theo is climbing the ranks of the best ever. Heck, the fact that he needs only his first name referenced says a lot. Still, let's keep in mind that he has run two deep-pocketed franchises, a huge advantage. Yes, he ended The Curse in Boston, but he also took over a team that had just won 93 games and included Pedro Martinez, Manny Ramirez, Jason Varitek, Nomar Garciaparra, Johnny Damon and others. He added the finishing touches with David Ortiz in 2003 and Curt Schilling in 2004. The Cubs, even with a core of young, inexpensive stars, had the fifth-highest payroll in 2016. Not every franchise can go out and sign Jon Lester, Jason Heyward, John Lackey and Ben Zobrist as free agents.

Rickey is the best ever. Gillick has matched Theo's three World Series wins while also guiding the Orioles to the playoffs and building the 116-win Mariners of 2001. Ed Barrow and George Weiss built dynasties with the Yankees. Bob Howsam built a World Series champion in St. Louis and the Big Red Machine in Cincinnati, while Schuerholz won World Series with Kansas City and Atlanta. Theo is right in that group.

Rogers: One factor I use in rating managers over the course of their careers is their ability to win for more than one franchise. The more they do, the fewer people can claim they were simply "in a good situation." The same can be said of executives. Not only is winning titles in two cities rare, but the fact that Epstein won in Boston and Chicago, after both franchises experienced historic droughts, only adds to his legacy.

Paine: He certainly is by far the most accomplished of the modern wave of young, sabermetrically savvy GMs who entered baseball in the post-Moneyball era. It's a little difficult to compare him to earlier GMs such as Rickey, if not simply because Rickey transformed the entire role of the GM. Theo has also stood on the shoulders of more modern GMs such as Sandy Alderson and Billy Beane, who helped introduce the sabermetric team-building approach Epstein has used to great effect. Even so, Theo should definitely be in the conversation with those guys. He's already probably the analytics era's answer to Gillick, in terms of building great teams in multiple locations.

Theo's third act: What would you like to see Theo do next in baseball? How does he top breaking both the Red Sox's and Cubs' curses?

Olney: The Yankees of 1996 to 2001 were baseball's last dynasty -- and the only dynasty since the advent of free agency after 1976. Theo's next challenge will be to continue building something that will last, around an extraordinary group of young position players: Kris Bryant, Anthony Rizzo, Addison Russell, Javier Baez and Willson Contreras. There will be significant obstacles along the way, particularly in the challenge of building the next wave of pitching, because Jake Arrieta and John Lackey are free agents after next season, and Jon Lester is on the downward slope of his career. Rival officials say the Cubs don't have a lot of pitching in their farm system, and Theo and his staff will have to figure out a way to fill that gap while the club is losing financial flexibility -- because some of the position players will become more expensive. Also, look, even the best executives make mistakes, with Heyward's deal seemingly destined for that definition.

Kurkjian: Building a dynasty is harder to do now than ever, but thanks mostly to Epstein, the Cubs are at least positioned to become one. The 2016 Cubs started six players age 24 or younger in a World Series game and were the first team in history to do that. Their farm system remains a little short on pitching, but now the Cubs have so much money with which to deal and so many prospects that if there is a need, they can fill it as easily as any team. Owner Tom Ricketts trusts Epstein with his money -- as he should. That great parade won't be the last over the next 10 years.

Schoenfield: Repeating what the Yankees did from 1996 to 2000, winning four titles in five years, will be almost impossible due to the precarious nature of the postseason, but how about matching the Yankees' run of 13 straight playoff trips (including four 100-win seasons)? Or Schuerholz's leading the Braves to 14 first-place finishes in 15 years (including six 100-win seasons)?

Rogers: I'd like to see Epstein take one more moribund franchise, say the San Diego Padres (where he worked while an MLB up-and-comer) or Miami Marlins, and turn it into a winner. He has nothing left to prove, but it would be interesting. Perhaps a West Coast team without deep pockets; that would complete a trifecta from the Atlantic to the Pacific. Could he repeat his success in a smaller market? I'd like to see an attempt.

Paine: It wasn't like there weren't built-in advantages to assembling champions in Boston and Chicago, even if Theo's predecessors hadn't always made full use of them. Next, I'd like to see him win in one of baseball's oddest locations: Coors Field in Colorado. The Rockies are a relatively small market -- 19th in the U.S., with MLB's 22nd-biggest payroll -- and they always have trouble assembling a good pitching staff. Weirder still, they've never once had an above-average offense (in terms of wOBA) after adjusting for park effects. If Theo goes there, it would be a true test of his ability to adapt to strange circumstances and win.

Beyond baseball: Where might Theo thrive outside sports? What skills could he bring to the business world ... the world of academia ... politics ... even -- gasp! -- the White House?

Olney: Theo has a passion for politics and public service, and it's no secret that he leans left, having grown up in a state with a deep history of Democrats. But I'm not sure he would have the patience or the stomach for the kind of public life that is required of politicians these days, and I can't see him running for office in the legislative branch, where he would be required to schmooze in the grand tradition of Tip O'Neill. If Theo ever went into politics, I'd see him as more of an executive-branch type -- a governor, rather than a congressman -- so that he would have the power to do as he's done in baseball: surround himself with really smart and talented people and attack problems. What is often missed by reporters constructing stories about Theo is how competitive he is: He has an instinctive ambition that draws him to challenges, and underneath the polite niceties, I think he absolutely believes he can beat anybody and will find a way to beat anybody. This is part of what separates him.

Kurkjian: Cubs manager Joe Maddon described Epstein as "a real person, a real guy. He has great empathy.'' A former player, now working for the Cubs, said: "I had no idea that a front office cares so much about the lives and the careers of the players and puts in so much time to making them better. And that all starts with Theo.'' Like Maddon, Epstein loves baseball, but he is so well-rounded. He has a love for music and for helping people. Going into public service after baseball seems logical, as would doing something in the music industry. Going into politics does not. Epstein values his privacy and has no tolerance for what it takes to be a politician. That said, he is going to do something else important after baseball. His upbringing -- from an extended family of educators, intellectuals, artists and writers -- tells us that.

Schoenfield: Very few have gone from baseball and been successful in politics at the national level, with Hall of Fame pitcher Jim Bunning, a member of the U.S. House of Representatives and then a two-term senator from Kentucky, the notable exception. The thing about running a baseball team is you're responsible to only your owner. Politics is a whole different headache. Why would you want to deal with that when your office is Wrigley Field?

Rogers: Beyond baseball -- but not sports -- I'd like to see Epstein try his hand at football, basketball or even hockey. Can he apply his analytical mind, combined with an understanding that perhaps all athletes are alike, to succeed in a sport he isn't familiar with? That would truly be starting from scratch. Politics might be a difficult world for Epstein, as he has been known to speak his mind. If political correctness is on its way out, though, he might have a better chance.

Paine: Given the way our country's politics have become so polarized and toxic, asking Theo to work his miracles in politics seems like an obvious answer. But given his track record, a more realistic future for him might be in business, advising investors who are looking for underachieving companies to turn around and make profitable again. Theo has already shown a great capacity for diagnosing the problems that ail an organization and putting the right people in charge -- not just at the top but all the way down to the lower levels of the minor leagues. It isn't hard to imagine those skills translating to a corporate setting, should Theo ever want to leave the sports industry. (And if he just wants to switch sports: Please, Theo, come to New York, and fix the Knicks!)