Age: 33
Title: General Manager, Boston Red Sox
Pro: The youngest GM in baseball history when the Red Sox hired him at 28, Epstein built the '04 curse-busting World Series winner and the team with current best record in baseball. His stats-driven success spawned a wave of youth hiring in front offices throughout.
Con: Broke up the '04 "Idiots" team disband too quickly. Post-series signings of pitcher Matt Clement and shortstop Edgar Renteria were busts, and recent signings Julio Lugo and J.D. Drew aren't much better. And did he really have to leave Fenway Park in a gorilla suit to avoid reporters after his short-lived '05 resignation?