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Mon, March 25

Column: Is Theo Epstein the world’s greatest leader?

When we think of a great leader, our search may instinctively turn to business or government. Fortune magazine, which publishes an annual list of the World’s 50 Greatest Leaders, includes individuals from two additional categories: philanthropy and “beyond.” This year, Fortune turned to the beyond category and selected Theo Epstein as the World’s Greatest Leader.

For those of you who need an introduction, Epstein is the president of baseball operations for the Chicago Cubs, who ended their 108-year World Series drought last fall. If that doesn’t sound like an accomplishment worthy enough to head the greatest leaders list, Epstein’s resume also includes ending the Boston Red Sox’ 86-year World Series drought in 2004. The Red Sox proceeded to win another title in 2007 and Epstein’s fingerprints were all over the team’s 2013 World Series title even though he left Boston for Chicago after the 2011 season.

If you’re conflicted on whether a sports executive should be in the discussion for the title of world’s greatest leader, you’re not alone. Epstein himself scoffed when informed of the designation. “Um, I can’t even get my dog to stop peeing in the house,” Epstein told ESPN’s Buster Olney. “That is ridiculous. The whole thing is patently ridiculous. It’s baseball — a pastime involving a lot of chance. 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.”

There are a number of characteristics great leaders possess and Theo’s response to Olney shows why he is deserving of the title. No one accomplishes much in a vacuum. Great leaders acknowledge that and deflect praise to those around them. They steer the spotlight away from themselves and don’t allow individual honors to overshadow the accomplishments of the organization as a whole. Epstein deftly did that, while acknowledging the contributions of others. He was also prepared to accept the blame if the Cubs had lost.

There were many people on Fortune’s list worthy of the highest honor. The top five included Alibaba founder Jack Ma at second, Pope Francis was third, Melinda Gates was fourth and Amazon CEO Jeff Bezos fifth. Epstein at number one was reminiscent of Babe Ruth’s response when a reporter once asked if he was worthy of a salary higher than the President’s. The Babe’s response was, “I had a better year than he did.” Perhaps no one on Fortune’s list had a better year than Epstein. But there’s more.

Epstein was the boy wonder of baseball executives when, at the age of 28, he became the general manager of the Red Sox in 2002. He proceeded to turn the sport on its traditional head by using analytics and technological advancements to mine inefficiencies in a game that over a period of 150 years had embraced advances incrementally, if at all. The results seemed to justify the approach until the Red Sox collapsed in September of 2011 and fell from contention. Epstein was taken by the lack of character and chemistry on the club, something he vowed would not be the case with the Cubs.

In Chicago, Epstein surrounded himself with smart and talented people, from the executive offices at Wrigley Field down to the lower levels of the Minor Leagues. He is a great delegator and allowed his staff to do their jobs. The executive team brought in self-motivated, high-character, disciplined players and created an environment that allowed them to flourish. To his emphasis on technology, Epstein added an emphasis on people, the most valuable asset in any organization.

Perhaps the bar for good leadership is low in the areas of government and business, but despite Epstein’s modesty, he is more than worthy of Fortune’s honor.

Although sports are games, the leadership qualities required to be successful in sports are transferable to any endeavor. The world’s leaders could learn a lot about leadership from Theo Epstein.

Jordan Kobritz is a former attorney, CPA, Minor League Baseball team owner and current investor in MiLB teams. He is a Professor in and Chair of the Sport Management Department at SUNY Cortland and maintains the blog: The opinions contained in this column are the author’s. Jordan can be reached at


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