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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.

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Epstein won two World Series during his tenure, and assembled the roster that ended the Red Sox' 86-year title drought in 2004.

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Epstein was just 28 when he started as GM on Nov. 25, 2002. At that point he was the youngest GM in baseball history.

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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.

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With his first managerial hire, Epstein chose Terry Francona, with whom he would form an eight-year partnership.

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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.

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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.

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Perhaps Epstein's biggest gamble was trading disgruntled All-Star shortstop Nomar Garciaparra at the 2004 trading deadline.

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The moves panned out for Epstein and Francona when the Red Sox closed out a World Series sweep of the Cardinals.

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Epstein celebrated at the victory parade as hundreds of thousands of fans saluted the Red Sox in Boston.

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The Boston Globe Magazine named Epstein "Bostonian of the Year" for 2004.

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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.

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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.

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Epstein shocked many observers, including team owner John Henry, when he left the Red Sox after the 2005 season when his contract expired.

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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.

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In December 2006, Epstein made a splash when he signed Japanese pitcher Daisuke Matsuzaka to a six-year deal.

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Epstein and the Red Sox celebrated their second World Series title in four years in 2007.

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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.

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During his Boston tenure, Epstein married, Marie Whitney (left), with whom he had a son, Jack.

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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.

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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.

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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.

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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.

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Epstein also welcomed first baseman Adrian Gonzalez in a trade from San Diego. He later signed Gonzalez to a seven-year, $154 million deal.

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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.

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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.