Theo Epstein discusses his Red Sox legacy ← Related Article Visit The Boston Globe Share on Twitter Share on Facebook Comment on this Scroll to top of page Bizuayehu Tesfaye/AP Theo Epstein, who held the job of Red Sox general manager for 9 years, has been the most successful man ever to hold that position. Ezra Shaw/Getty Images Epstein won two World Series during his tenure, and assembled the roster that ended the Red Sox' 86-year title drought in 2004. Jim Davis/Globe Staff Epstein was just 28 when he started as GM on Nov. 25, 2002. At that point he was the youngest GM in baseball history. Jim Davis/Globe Staff The Red Sox lost to the Yankees in Game 7 of the ALCS in his first year and Epstein would part ways with manager Grady Little, right, after the season. Globe Staff Photo With his first managerial hire, Epstein chose Terry Francona, with whom he would form an eight-year partnership. Jeff Topping/REUTERS Epstein spent Thanksgiving at the Arizona home of Curt Schilling in 2003 as he tried to convince the pitcher to accept a trade to the Red Sox. Globe Staff Photo Epstein also courted free-agent closer Keith Foulke during a trip to a Celtics game as he assembled a new cast for the 2004 Red Sox. Minneapolis Star Tribune/AP Perhaps Epstein's biggest gamble was trading disgruntled All-Star shortstop Nomar Garciaparra at the 2004 trading deadline. Jim Davis/Globe Staff The moves panned out for Epstein and Francona when the Red Sox closed out a World Series sweep of the Cardinals. Michael Dwyer/AP Epstein celebrated at the victory parade as hundreds of thousands of fans saluted the Red Sox in Boston. Handout The Boston Globe Magazine named Epstein "Bostonian of the Year" for 2004. Globe Staff Photo Epstein's magic touch in 2004 didn't last, however. His signing of Edgar Renteria in December 2004 was a dud. The Red Sox would trade the shortstop a year later. Chris Trotman/Getty Images Epstein's decision not to re-sign Red Sox icon Pedro Martinez to a long-term deal after the 2004 season was validated when the pitcher tore his rotator cuff with the Mets in 2006. David L Ryan/Globe Staff Epstein shocked many observers, including team owner John Henry, when he left the Red Sox after the 2005 season when his contract expired. Barry Chin/Globe Staff By the next spring, Epstein had rejoined the Red Sox as GM and said his concerns about the vision of the organization had been addressed. David L Ryan/Globe Staff In December 2006, Epstein made a splash when he signed Japanese pitcher Daisuke Matsuzaka to a six-year deal. Barry Chin/Globe Staff Epstein and the Red Sox celebrated their second World Series title in four years in 2007. Globe Staff Photo Epstein (shown at a Jimmy Fund benefit on Jan. 15, 2003) grew from a Pearl Jam-loving bachelor into a seasoned baseball executive during his time with the Red Sox. Jim Davis/Globe Staff During his Boston tenure, Epstein married, Marie Whitney (left), with whom he had a son, Jack. Lara Callahan Photo Epstein joined with baseball reporter Peter Gammons, left, and musicians Dicky Barrett, Kay Hanley, and Tim "Johnny Vegas" Burton in benefits for his charitable foundation. Chris Carlson/AP In 2008, Epstein traded Manny Ramirez, whose off-field antics had been problematic for almost all of the GM's tenure, to the Dodgers at the trading deadline. Jim Davis/Globe Staff In 2010, Epstein loaded the Red Sox with free agents such as John Lackey, Mike Cameron and Marco Scutaro, only to see the team slump to an 89-73 third-place finish. John Tlumacki/Globe Staff In December 2010, Epstein made his most expensive foray into the free-agent market when he signed outfielder Carl Crawford to a seven-year, $142 million deal. Brian Snyder/Reuters Epstein also welcomed first baseman Adrian Gonzalez in a trade from San Diego. He later signed Gonzalez to a seven-year, $154 million deal. Brian Snyder/REUTERS The 2011 team was projected as a World Series contender by many analysts, and the Red Sox were on pace for 100 wins as late as August. Elise Amendola/AP But the season unraveled during a 7-20 stretch in September. The Red Sox missed the playoffs, and Epstein watched Francona depart as manager, just two weeks before he would decide to join the Cubs.