Theo Epstein was the President of Baseball Operations for the Chicago Cubs until 2020. In 2002, he became the youngest GM in the history of Major League Baseball when the Boston Red Sox hired him at the age of 28. In 2004, the Red Sox won their first World Series championship in 86 years and won another championship in the 2007 season. On October 21, 2011 he resigned from his job in Boston to become President of Baseball Operations for the Chicago Cubs.

Epstein re-signed with the club on September 28, 2016, with a five-year contract estimated to be worth up to $50 million. The Cubs finished the 2016 season with a 103–58 record, the best in the MLB and their best since the 1910 season. In the playoffs, they defeated the San Francisco Giants in the NLDS. The Cubs proceeded to beat the Los Angeles Dodgers in the NLCS, winning their first pennant since the 1945 season and sending them to the World Series. The Cubs then won their first World Series championship since 1908 when they defeated the Cleveland Indians in 7 games.

In April 2017, Time Magazine named Epstein one of the the world's 100 most influential people.

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