Theo Epstein

Epstein then moved with Larry Lucchino to the San Diego Padres as director of player development. While working for the Padres, he also studied at the University of San Diego School of Law and earned a Juris Doctor degree at Lucchino's suggestion.[6] Epstein based his class selection on which professors seemed to be the most lenient with attendance policies given the Padres' often-late work hours. By studying law Epstein was invited to take part in high-level negotiations and discussions by then-GM Kevin Towers since few in the Padres' small operations division had a legal background to understand contract language.[5] Epstein worked his way up to become the team's Director of Baseball Operations.[7]

Epstein at the 2007 World Series victory parade

After leaving the position as the Padres' President, Lucchino became president and chief executive officer (CEO) of the Red Sox on November 15, 2001[8] and hired Epstein to work under him. At the end of the 2002 season, Lucchino appointed Epstein to replace interim general manager (GM) Mike Port. Epstein is credited with initiating the trade of Nomar Garciaparra[7] and making key contract acquisitions including those of Bill Mueller and Curt Schilling during his first tenure as Red Sox GM.[7] The new players were regarded as instrumental in breaking the so-called "Curse of the Bambino" when the Red Sox defeated the St. Louis Cardinals in the 2004 World Series. It was the Red Sox' first World Series championship since 1918, ending what remains the third longest championship drought in the history of any Major League team, after the Chicago White Sox (1917–2005) and the Chicago Cubs (1908–2016).[9][10]

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.[11] 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 the Foundation to be Named Later (FTBNL).[12]

Epstein remained in contact with the team's front office and on January 12, 2006, he and Red Sox management announced his return. Six days later, the team announced that he would resume the title of general manager and add the title of executive vice president. In November 2007, 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.[13]

In December 2007, Epstein was mentioned in the Mitchell Report regarding a November 2006 email exchange he had had with Red Sox scout Marc DelPiano on the possible acquisition of closer Éric Gagné. In the email, Epstein asked DelPiano, "Have you done any digging on Gagné? I know the Dodgers think he was a steroid guy. Maybe so. What do you hear on his medical?" DelPiano replied that "steroids IS the issue" with Gagné, questioned his "poise and commitment" and expressed questions about his durability "without steroid help."[14] Despite DelPiano's reservations about Gagné, Epstein traded Kason Gabbard and minor league outfielders David Murphy and Engel Beltré to the Texas Rangers for Gagné on July 31, 2007.[15]

On October 12, 2011, Epstein agreed to a five-year contract worth $18.5 million with the Chicago Cubs.[16] On October 19, 2011, it was reported that Epstein's official title with the Cubs would be President and that San Diego Padres general manager Jed Hoyer would take the GM position with the Cubs.[17]

Epstein talks to reporters before the 2016 NLCS Game 6.

On October 23, 2011, he took out a full-page ad in The Boston Globe, thanking Red Sox fans and the team's owners for their support.[18] Two days later, the Cubs officially introduced Epstein as president of baseball operations.[19] While the Red Sox were already a winning team when Epstein was hired in Boston, the Cubs were coming off a fifth-place finish in the National League Central and had a depleted farm system.[20] The Cubs finished in last place in the National League Central for the first three years of Epstein's presidency, as the focus was to acquire young talent rather than maximize short-term competitiveness.[21] After a three-year, top-to-bottom rebuild, the Cubs clinched a playoff berth in 2015; their first since 2008. They advanced to the National League Championship Series, where they were swept by the New York Mets.[22]

Epstein re-signed with the club on September 28, 2016, with a five-year contract estimated to be worth up to $25 million.[23] The Cubs finished the 2016 season with a 103–58 record, the best in MLB and their best since the 1910 season. In the playoffs, they defeated the San Francisco Giants in the NLDS.[24] The Cubs proceeded to beat the Los Angeles Dodgers in the NLCS, winning their first pennant since the 1945 season breaking the so-called "Curse of the Billy Goat" and sending them to the World Series.[25] The Cubs then won their first World Series championship since 1908 when they defeated the Cleveland Indians in 7 games.[26]

Epstein's "Hot Stove Cool Music" are biannual Boston and Chicago benefit concerts that have raised millions of dollars for the "disadvantaged youth and families" of the respective cities. Epstein said in advance of the 2015 event, "We've collectively raised more than $6 million and look forward to increasing that total this year through another great night of music, baseball and giving back."[35]