Theo N. Epstein

On November 25, 2002, the Red Sox elevated Brookline, MA native Theo Epstein to the general manager's seat. Epstein, who had served as the team's assistant GM before the promotion, was 28 years old at the time of his appointment and became the youngest GM in Major League Baseball history. Previously, Epstein had been a member of the baseball operations department of the San Diego Padres after working in the Padres' communications department and as an intern with the Baltimore Orioles before that.

With a sabermetric-oriented focus, Epstein and the Red Sox baseball operations department immediately began to build a championship caliber team. In the winter of 2003, the Red Sox signed Kevin Millar along with free agents Mike Timlin, Bill Mueller and a left-handed slugger named David Ortiz. Though the 2003 Red Sox came within five outs of the franchise's first World Series appearance since 1986, the club looked for new managerial leadership after the season and hired Terry Francona as the team's new skipper. A little over a month later, Epstein convinced Curt Schilling, over Thanksgiving dinner, to waive his no-trade clause and come to Boston.

After adding Keith Foulke as their closer, the 2004 Red Sox started the season on a roll but leveled off a bit during the early summer months. At the trade deadline, Epstein acquired the speedy Dave Roberts and showed the courage to trade the immensely-popular Nomar Garciaparra, receiving Orlando Cabrera and Doug Mientkiewicz in return. Epstein's moves paid off as the Red Sox finished with a flurry to clinch a Wild Card playoff berth en route to winning the club's first World Series in 86 years. At the age of 30, Epstein became the youngest GM ever of a World Championship team.

In their title defense, the 2005 Red Sox reached the postseason again but couldn't recapture their October magic of the year before. After the 2005 season, Epstein and the Red Sox couldn't reach an agreement on a contract extension and the young GM stunned observers when he suddenly resigned his position on Halloween.

General Manager Eddie Collins, Owner Tom Yawkey and Manager Bucky Harris in 1934 (Credit: Leslie Jones Collection/Boston Public Library)