Rank
1

Theo Epstein

Theo Epstein
Chicago Cubs new president for baseball operations Theo Epstein walks across Wrigley Field after a news conference Tuesday, Oct. 25, 2011, in Chicago. (AP Photo/Charles Rex Arbogast)Charles Rex Arbogast—AP
  • Title
    President, Baseball Operations
  • Affiliation
    Chicago Cubs

In the fall of 2016, as partisan distrust and division reached abysmal depths, fascination with the Chicago Cubs became that all-too-rare phenomenon that united America. As the Cubs fought to end a 108-year championship drought, television ratings for the World Series soared by almost 50%. Even casual fans who didn’t know a bunt from a beanball stayed up late to watch the excruciating extra-inning Game 7 that turned baseball’s most famous lovable losers into winners at last.

 

The Cubs owe their success to a five-year rebuilding program that featured a concatenation of different leadership styles. The team thrived under the affable patience of owner Tom Ricketts, and, later, under the innovative eccentricity of manager Joe Maddon. But most important of all was the evolution of the club’s president for baseball operations, Theo Epstein, the wunderkind executive who realized he would need to grow as a leader in order to replicate in Chicago the success he’d had with the Boston Red Sox.

 

In his book The Cubs Way, Sports Illustrated senior baseball writer Tom Verducci describes that evolution, showing how a deeper understanding of important human qualities among his players—the character, discipline and chemistry that turn skilled athletes into leaders—enabled Epstein to engineer one of the most remarkable turnarounds in sports. Click here to read more about the transformation.