Hired by the Boston Red Sox at 28, he became the youngest GM in Major League history at the time. In 2011, he became the President of Baseball Operations for the Chicago Cubs.
He attended Yale University, where he was the sports editor for the campus newspaper. He also worked for the San Diego Padres in the PR department.
He signed a five-year contract with the Chicago Cubs in 2011 to take over as the team's president.
His grandfather Philip G. Epstein and great-uncle Julius J. Epstein wrote Casablanca for which they won Academy Awards. He married Marie Whitney in January 2007; they have a son named Jack.
He was mentioned in the Mitchell Report on steroid use in baseball, which was brought on by allegations against Barry Bonds.