Secrets of Leadership Success of Theo Epstein

Hot on the heels of leading the Boston Red Sox to their first Major League Baseball World Series in 86 years, baseball executive Theo Epstein moved to the Chicago Cubs to engineer their first World Series win in 108 years.

What are the secrets to his success?

In 2017, Fortune named Theo Epstein the greatest leader in the world. Epstein’s path to this title has been relatively short – but focused and determined.

Born in New York City in 1973, Epstein played baseball in his Massachusetts high school and dreamed of working for the Red Sox. His love of baseball continued during his time at Yale, where he was sports editor of the Yale Daily News. As a Yale undergraduate, he sent several letters to baseball teams expressing his desire to work for them.

When one of his letters landed on the desk of Calvin Hill, head of personnel at the Baltimore Orioles and Yale alumni, Epstein was invited to make his first steps into the world of sports management; interning for three consecutive summers with the Orioles before becoming their public relations assistant after graduation.

Even in these early years, Epstein took a strategic approach to build his career; telling David Axelrod on his podcast, The Axe Files: “Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like. So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll make them really happy, improve their quality of life and their work experience.”

When president of the Baltimore Orioles, Larry Lucchino, moved to the San Diego Padres he took Epstein with him.

At Lucchino’s suggestion, Epstein studied law at the University of San Diego before working his way up to the Padres’ Director of Baseball Operations. In 2002, Epstein followed Lucchino to the Red Sox, where Epstein’s record tale of success began to play out.

The “Moneyball” approach

At Boston, Epstein followed a “Moneyball” approach; using data-driven analysis to identify and sign players with little-noticed but crucial strengths.

Using this approach, in his nine seasons as general manager, Epstein led the team to six playoff appearances and two World Series titles – the first, in 2004, was the Red Sox’s first in 86 years.

The feat was repeated in 2007 but, by 2011, the shortcomings of Epstein’s data-driven approach were becoming apparent – and the Red Sox experienced a late-season collapse.

Writing in Fortune, Tom Verducci explains: “The egos that had created cracks in the clubhouse while they were winning caused deep fissures as they lost.”

The arrival at Chicago Cubs

For Epstein, who had already announced his departure from the club once before in 2006 before being convinced to stay, it was time to move on. In October 2011, he resigned from the Red Sox to become President of Baseball Operations for the Chicago Cubs.

At Chicago, Epstein enhanced his data-driven approach to team building with detailed qualitative data about personal character: how players responded to adversity on and off the field.

After Epstein’s arrival, the Cubs finished in last place in the National League Central for three years running. But this was part of the plan; the focus of these three years was long-term teambuilding and the reinvigoration of the Cub’s much-depleted farm system.

By 2015, the Cubs made it to their first playoff since 2008. By 2016, there had their best season in MLB since 1910 – and went on to win the World Series for the first time since 1908.

The combination of data-driven analysis and detailed character assessments promoted by Epstein at the Cubs had created a long-term, sustainable winning formula for Epstein once again – gaining him international plaudits for his leadership as well as his team’s success on the field.