Just over a decade ago, Theo Epstein was the boy wonder in the world of baseball's front offices, having been named the youngest general manager in baseball history at age 28. Two years later, in 2004, the Red Sox won their first World Series since 1918. Three years after that, the Red Sox did it again.
At this point, Epstein could write his own ticket, and in 2011 that's just what he did, accepting a five-year deal worth an eye-popping $18.5 million to become the team president of the Chicago Cubs, bringing with him one of his key assistants from his earlier Boston years, Jed Hoyer, from the San Diego Padres to serve as GM. From one curse to the other, Epstein took on the challenge of turning around the Chicago Cubs, a team in far worse straits than the Red Sox were in 2001, the year before he took over.