Before he guided the Cubs to their first World Series title in 108 years, Theo Epstein also ended another famous title drought by building a pair of championship clubs with the Red Sox. As Boston's general manager, he assembled an impressive array of talent not only on the field but also in the front office, with Josh Byrnes, Ben Cherington, Jerry Dipoto, Mike Hazen and Jed Hoyer going on to become GMs themselves.
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