Theo Epstein - Boston Red Sox

Boston Red Sox

Former Padres President Larry Lucchino became president and CEO of the Red Sox on November 25, 2002, and hired Epstein to work under him. At the end of the 2002 season, Lucchino appointed Epstein to replace interim GM Mike Port. Epstein is credited with making several key acquisitions, including David Ortiz, Kevin Millar, and Curt Schilling, during his first tenure as Red Sox GM, who were regarded as instrumental in breaking the so-called "Curse of the Bambino" and winning the Red Sox their first World Series Championship since 1918.

On October 31, 2005, Epstein resigned, rejecting a three-year, $1.5-million-per-year contract for personal reasons. According to The Boston Globe, "This is a job you have to give your whole heart and soul to," he said. "In the end, after a long period of reflection about myself and the program, I decided I could no longer put my whole heart and soul into it." Because it was Halloween the night he resigned from the Red Sox, Epstein left Fenway Park wearing a gorilla suit in an attempt to avoid reporters. A witness reported spotting a person wearing a gorilla suit driving a Volvo similar to Epstein's that night. The suit was loaned to him and was later auctioned for $11,000. The money raised was given to The Jimmy Fund and Epstein's Foundation to be Named Later.

Epstein remained in contact with the team's front office and on January 19, 2006, Epstein and Red Sox management announced his return. Five days later, the team announced that he would resume the title of General Manager and add the title of Executive Vice President. In November 2008, Epstein announced, at the annual General Manager meeting, that he had signed a new contract with the Red Sox but declined to disclose the terms of the deal.