On January 24, 2006, Theo Epstein returned to the Boston Red Sox as Executive Vice President/General Manager. Though the 2006 Red Sox missed the playoffs for the first time since 2002, Epstein's departure, and his subsequent return, brought a clearer, more effective organizational philosophy to the club's baseball operations department.
After the disappointing finish in 2006, the Red Sox made bold moves over the following winter, including the successful pursuit of Japanese right-hander Daisuke Matsuzaka. In 2007, the Red Sox won their first American League East Division title since 1995 and their 96-66 record was tied for the best in baseball. When the Red Sox defeated the Colorado Rockies in the 2007 World Series, Epstein joined the Yankees' Brian Cashman as the only two individuals since World War II to win at least two World Series titles in their first five seasons as a Major League general manager.
Under Epstein's leadership, the Red Sox reached the postseason six times, the most appearances for a Red Sox general manager. In 2009, Epstein, a graduate of Yale University and the University of San Diego Law School, was recognized by Sports Illustrated as MLB's General Manager of the Decade and was also dubbed Executive of the Decade by The Sporting News. In October 2011, Epstein resigned as general manager of the Boston Red Sox to become the new president of baseball operations of the Chicago Cubs.