[1] In 2004, when he was vice president and general manager for the Red Sox, the team won their first World Series championship in 86 years.

His letter to the Baltimore Orioles reached team executive Calvin Hill, a Yale alumnus and head of personnel, who invited him for an interview.

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.

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.

Epstein is credited with trading away Nomar Garciaparra and acquiring Bill Mueller and Curt Schilling,[9] moves that helped break the "Curse of the Bambino" when the Red Sox defeated the St. Louis Cardinals in the 2004 World Series, their first championship since 1918.

As it was Halloween the night he resigned from the Red Sox, he left Fenway Park wearing a gorilla suit in an attempt to avoid reporters.

[15] 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.

[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 rebuild, the Cubs clinched a playoff berth in 2015 and advanced to the National League Championship Series, where they were swept by the New York Mets.

[23] The Cubs would proceed to break the so-called "Curse of the Billy Goat" by defeating Cleveland Indians in the 2016 World Series, their first championship since 1908.

[33] Boston Globe sportswriter Gordon Edes reported that the wedding took place at Nathan's Famous hot dog stand at Coney Island, then later published a correction, noting that he had fallen for a prank by Theo's father Leslie.

[34][35] 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.

Before the 2015 event, Epstein said, "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.