Ben Strauss is the co-author of Indentured: The Inside Story of the Rebellion Against the NCAA, winner of the 2017 PEN/ESPN award for literary sports writing.

When Fortune magazine unveiled its annual ranking of the world’s greatest leaders last month, there was a surprise at the top of the list: Theo Epstein, the president of baseball operations for the Chicago Cubs. “Some people never heard of him,” Fortune’s Geoff Colvin said in a video introducing Epstein. (Pope Francis, a previous holder of the top spot, was third). But, Colvin added, “Baseball fans really know him well because he has done the impossible.” Indeed. In 2004, Epstein, then the 30-year-old general manager of the Boston Red Sox, presided over the team’s first championship in 86 years. Seven years—and two more titles—later, he decamped to Chicago, where he engineered the remaking of the long-suffering Cubs, and ended an impossibly longer drought, 108 years, with a World Series win last fall. (Time added to Epstein’s résumé last week when it named him one of the world’s 100 most influential people).

As Epstein has made his mark on baseball he has also been a visible figure in Democratic political circles. In 2004, he stumped for John Kerry, getting in a dig at President George W. Bush on the campaign trail. “It’s only been four years, but it sure feels like 86,” he told a crowd. Last year, Epstein attended a fundraiser for Hillary Clinton in Chicago just before the playoffs started. It is no wonder then that when the Cubs visited the White House on January 16, President Barack Obama joked of Epstein, “He takes the reins of an organization that’s wandering in the wilderness and he delivers them to the promised land. I’ve talked to him about being [Democratic National Committee] chair.”


Plenty of others have speculated about Epstein’s political future. He is telegenic, well-spoken and has a demonstrated interest in public service, having started a foundation that has donated millions of dollars to support urban youth and families. His grandfather wrote the screenplay for “Casablanca.” Epstein's father, Leslie, won a Rhodes scholarship to Oxford and is a Boston University English professor (He also happened to predict Donald Trump’s defeat of Clinton.). When Epstein was hired by the Red Sox, then the youngest general manager in baseball history, his father quipped, “At Theo’s age, Alexander the Great was already general manager of the world.” More recently, Leslie Epstein has mentioned that his son could run anything from the United Nations to the Ford Foundation after his baseball career.

Last fall, when ESPN the Magazine convened a roundtable to discuss Epstein’s place in history among baseball executives, the conversation turned to politics. “If Theo ever went into politics, I'd see him as more of an executive-branch type—a governor, rather than a congressman ... ,” wrote Buster Olney. And when Epstein earned the mantle of World’s Greatest Leader, the chatter continued. “I’ve often said that someday Theo Epstein will be a Democratic senator from Massachusetts or Illinois, and he’ll one day run for president and win,” wrote the longtime Boston Globe baseball writer Nick Cafardo.

Curious what the political pros think of Epstein, and with Democrats on the lookout for a new generation of talent, I turned to Chicago’s most notable kingmaker—and Cubs fan—David Axelrod. We discussed the possibility of Epstein in the Senate seat that once belonged to Obama, the similarities between the two leaders and if Axelrod expects a surge of celebrity candidates in the age of Trump.

Politico Magazine: You interviewed Theo Epstein for a piece you wrote in the New Yorker last fall, where you called the Cubs’ season the most pleasing campaign of 2016, and noted how similar the feel around the team was to President Obama’s 2008 campaign. Do you see similarities between Epstein and President Obama?

David Axelrod: They both have two kinds of intelligence: emotional intelligence and a more linear intelligence. They both have the self-confidence to surround themselves with very smart people. Theo’s had a core group around him (general manager Jed Hoyer and head of amateur scouting Jason McLeod) since the beginning in Boston. It’s striking how much he relishes smart people around him and has the confidence to be challenged ... Obama had it, too. I would add that Epstein has learned on the job. In Boston, he was a pioneer [in using statistical analysis] ... He’s told me that he used to be dismissive of the touchy-feely stuff [in evaluating baseball players], but now his scouts write five-page essays about the guys they’re going to draft. In the same way, Obama would tell you he was a better president at the end of eight years than at the beginning. He was smart enough to learn on the job, too.

Politico: Are any of the skills Epstein has exhibited in building championship baseball teams transferable to politics?

Axelrod: Baseball seasons are very much like campaigns in that you need to know going in that there are going to be ups and downs and that all of them are going to play out under the watchful eye of millions of people, all of whom think they can do this better than you … There are going to be some things that force you to change ... In baseball, it might be injuries. In politics, it’s some unforeseen event, or some gaffe. The ability to keep an even keel ... is another quality that Epstein and Obama share.

Politico: Let’s imagine the messaging of a hypothetical Epstein campaign. Could he sell himself as the ultimate turnaround artist? First, the Red Sox, then the Cubs, next the state of Illinois, for example?

Axelrod: [laughs] It would work if he were running for alderman on the North Side of Chicago, but I suspect voters might resist the idea that turning around a baseball team is commensurate with turning around a city, a state or a country … A good example would be Bill Bradley (a former New York Knicks star who became a Democratic senator from New Jersey). When he ran he did very little referencing of basketball. He was actually even self-conscious about being a jock, so I think you have to separate yourself a little bit from sports ... One thing that is transferable is the notion of building a team and getting people to work together. You could use that as a bridge to say what we need in this country is to regain the sense that we’re all on the same team and that we’re only going to prosper if we work together and find a way to build that bridge. That would be a winning message.

Politico: He could also say he’s worked across the aisle because his bosses, the Ricketts family, own the Cubs. (Pete Ricketts is the Republican governor of Nebraska and Joe Ricketts, the family patriarch, has been a prodigious funder of Republican candidates.).

Axelrod: You could certainly say that. Your next call should be to them to ask would you support him for office [laughs] ... Obviously, the Ricketts family was not particularly supportive of President Obama, but to the credit of the Ricketts family and to Theo, they’ve teamed up on one endeavor and that’s to build the best baseball team they can. I don’t think anyone gives a rat’s ass about the politics of folks involved.

Politico: Could Epstein win a statewide race in Illinois—either for governor or Senate?

Axelrod: Yeah, he could. He’s got a positive image here and he’s a very bright, elegant thinker. Very public spirited. His ego is in check. He’s got a lot of the requisite qualities except one: the desire to hold public office.

Politico: I want to come back to his desire shortly, but, first, would you enjoy working on a Theo Epstein campaign?

Axelrod: I’m sort of done with campaigns, but I would be an avid supporter of his ... He would find the whole thing amusing that we’re even discussing it, but he seems like a really, really good guy to work with. One of the reasons I retired from politics is after Barack Obama I didn’t think I would find a better candidate. I think Theo would be that kind of client.

Politico: So if you’re the Democratic Party and you’re looking for an infusion of new leadership, would you be calling Epstein to recruit him?

Axelrod: He’s an attractive guy, he’s got a lot of great qualities ... He does well when he’s in public, he’s incredibly articulate. Take a look at his speech at the White House. It’s Obama’s last event—Obama being a very, very prominent White Sox fan—and Theo couldn’t have handled it better. His remarks were graceful, funny, disarming and yet inspiring. So he has those abilities and he is by the way, like Obama, a very fine writer ... but he genuinely is an introvert ... He doesn’t like the spotlight, he doesn’t thrive on the attention. And I’m not sure he would like the constant personal exposure that one has in that job. My doubts, again, are not about him as a candidate, but his desire to do such a thing. I’m sure there are people who will talk to him about [running]. I don’t think there’s any doubt about it. It’s not like there’s a long line of superstars out there.

Politico: But you don’t think he’ll take the bait?

Axelrod: I think as soon as he gets that call, he’s immediately changing his number ... I think Theo would be frustrated in public office because of the situation he’s in now. He basically has free rein to do what he needs to do for the success of the organization. That is not the case in politics—you’re seeing that with the governor in Illinois (Bruce Rauner) right now. You have to deal with legislatures and all kinds of public stakeholders. And if you’re used to making things happen, I’m not sure the Senate would be a particularly satisfying job for you. When I talked to him on my podcast ... about what he might want to do next ... he allowed that he might want to own a team sometime and use that team or use that platform to try to impact on a community. He clearly cares about the larger world and wants to make an impact ... But there are many, many reasons I think Cubs fans can relax and enjoy the benefits of his leadership for many years to come.

Politico: Let’s take this beyond Epstein for a moment. Given the success of Donald Trump, do you expect to see a spike in celebrity candidates—including sports figures—with no government experience? Tommy Tuberville, for example, the former football coach at Auburn is mulling a run for governor in Alabama.

Axelrod: Yes, Marc Cuban has talked about running for president, too. We live in a celebrity culture and that has been amplified by social media and Trump has proven that it can be done. But I also think there is a pendulum quality to our politics, relative to presidential politics. People never look for the replica of what they have; they look for the remedy. Barack Obama was the anti-George Bush in many ways. Certainly Donald Trump is the anti-Barack Obama. And Barack Obama left as a popular president. Trump may have spoiled it for the wealthy celebrity outsider, at least for the short run.

Politico: Will Trump’s performance impact future candidates who want to run on their business records?

Axelrod: Trump built his brand through 14 years on television. So, yes, he has this patina of a can-do businessman. Especially for people who had grievances about the economy, that was useful. But how much of [his success] was [due to] that? How much of it was his celebrity and personality? I can’t really parse.

Politico: I have to ask: Can a baseball executive really be the world’s greatest leader?

Axelrod: I was a little taken aback by that ... Theo is an extraordinary leader, there’s no question about that … He really understands how to build both a culture of an organization and how to push for constant innovation. While I’m not sure that I would have nudged the pope out of the way, I certainly think there’s a lot to be learned by the way he’s run that organization.

This interview has been edited for length and clarity.