Theo Epstein (General Manager and Executive Vice President): Boston Red Sox

Epstein was the golden boy in Boston. Hailed as a wunderkind, the Yale alum became the youngest General Manager in MLB history in 2002. It took him only two years to end the Red Sox 86-year “World Series curse”. He put an exclamation point on his career by orchestrating the Red Sox’s second title in 2007. Epstein successfully blended “Big Market” Baseball with the statistical savvy portrayed in “Moneyball,” to win honors as a top sports executive of the decade from both Sporting News and Sports Illustrated in 2009. Just two years later, following a late season collapse and numerous internal issues and resignations, Epstein announced his own departure. He left the Sox without their most stable figure in the last decade when they needed him most. Shortly after walking, Epstein joined competing Chicago Cubs as President of Baseball Operations, giving him the unique opportunity to end the Cubs’103-year World Series drought and to create a legacy as the greatest baseball executive of all time.