Who's the greatest leader in the world? Chicago Cubs's Theo Epstein

Surpassing the Pope, Jeff Bezos, and LeBron James, the Cubs's team president is ranked No.1 on Fortune's list of 'the world's greatest leaders.'

First Look

Who is the world's greatest leader? Not German Chancellor Angela Merkel, Canadian Prime Minister Justin Trudeau, or Amazon founder Jeff Bezos, but the Chicago Cubs's Theo Epstein. 

The club's team president and former general manager of the Boston Red Sox claimed the top spot on Fortune’s list of “The World’s Greatest 50 Leaders?” 

For readers who don’t follow the Sox or the Cubs – which both recently claimed their first World Series wins in living memory under Mr. Epstein’s watch – Fortune’s decision will likely come as a surprise. But the business magazine also chose to honor Epstein's leadership principle in Chicago, one that prioritized character and connections in a game dominated by numbers and statistics:

“If we can’t find the next technological breakthrough, well, maybe we can be better than anyone else with how we treat our players and how we connect with players and the relationships we develop and how we put them in positions to succeed.”

In leading the 2016 Cubs to their first title since 1908, Epstein showed that focusing on the “soft,” non-quantifiable aspects of an organization – its interpersonal relationships, member enthusiasm – can help yield success. Now, it appears Fortune’s editors are endorsing this approach.

Since the late 1990s, Major League Baseball teams have increasingly relied on statistics and data to guide their player development systems and gain an edge over their rivals, a trend popularized in the book and movie “Moneyball.”

Epstein brought this approach to the Red Sox in 2002, when he became the MLB’s youngest-ever general manager at the age of 28 and proceeded to make several risky, high-profile trades and acquisitions.

That approach paid off with a World Series win in 2004 and another in 2007. But in 2011, the Red Sox faced an end-of-season collapse, and players’ attitudes towards the franchise and each other soured. One unidentified player wondered aloud, “Why do we want to play in October anyway? We don’t get paid for that.”

It was then that the Sox and Epstein parted ways. He left for the Chicago Cubs.

At the time, The Christian Science Monitor’s Mark Sappenfield observed that “the Cubs' new owner [Tom Ricketts] openly talks about replicating the Boston model – smart moves bolstered by big money. He's there to break the Cubs' 103-year World Series drought just as he helped end the Sox' 86-year drought in 2004.”

But to repeat that magic, Epstein recognized that he would have to tweak the “Boston model.” He directed his talent scouts to study players’ character traits, like their responses to adversity and family situations. As explained by sports writer Tom Verducci, Epstein took this approach “not to replace the edge in analytics he once wielded in Boston, but to enhance it.”

“Maybe our environment will be the best in the game,” he reflected, “maybe our vibe will be the best in the game, maybe our players will be the loosest, and maybe they’ll have the most fun, and maybe they’ll care the most. It’s impossible to quantify.”

But in the wake of the Cubs’ historic victory, Fortune has recognized this strategy as one other leaders would do well to follow. As for Epstein's response to the honor? 

"Um, I can't even get my dog to stop peeing in the house,” he told ESPN. “That [world’s greatest leader] designation is ridiculous.”

"It's baseball – a pastime involving a lot of chance," he continued in a text message. "If [Ben] Zobrist's ball is three inches farther off the line, I'm on the hot seat for a failed five-year plan. And I'm not even the best leader in our organization; our players are."