At the age of 28, Epstein was thrust into the front lines of Red Sox management and found himself right at home. Barely a full year after becoming the team's GM, Epstein was sliding a World Series ring onto his finger — the Sox's first in 86 long, painful years.
Born and bred in Boston, Epstein was the Red Sox' savior — and there's very little question as to why. After bringing not one, but two world championships to a team that suffered perhaps the most noteworthy title drought in sports history, Epstein had just as much to do with snapping the "Curse of the Bambino" as most of the players on the field.
But can Epstein's wizardry in the front office carry over to the only team that has suffered a longer World Series drought in Chicago?
So far this season, things haven't looked that way. As the Sox breeze into Chicago on Friday for the start of a three game series at Wrigley Field, the Cubs find themselves at the bottom of the NL Central with a measley 21-42 record.
In his first year as the Sox GM, Epstein made a handful of key signings that ultimately led to a ring ceremony at Fenway the following April. Most notably, he picked up clutch slugger David Ortiz and bloody-sock legend Curt Schilling, both key components in the 2004 World Series victory.
So maybe Epstein just needs some time to settle before the magic really starts to accrue in the Windy City. What can we expect eventually? Will Theo Epstein duplicate his World Series success in Chicago, or will his efforts fall flat?