It’s one thing to win one championship, but it is entirely another to win two, three or even four. Epstein’s legacy hinges on his ability to restore a winning tradition to Wrigley, and turn the awful 100-plus year stretch the team endured into a distant memory for Cubs fans, just as he did for the Fenway Faithful.
The Cubs have an extremely talented roster, which was mostly put together by a brilliant front office, lead by executives Theo Epstein, Jed Hoyer, Jason McLeod and others. The crux of the roster was built by strong drafting, under the radar trades and international free agency.
On Nov. 25, 2002, the Boston Red Sox hired 28-year-old Theo Epstein as general manager. The young man who had lived in New England for much of his life — he grew up in Brookline and graduated from Yale University, where he was the sports editor for the Yale Daily News — was the youngest G.M. in baseball history. The last time the Red Sox had won the World Series before Epstein was hired, the season was cut short because of World War I. That was 1918. The next eight decades became a nightmare for Sox fans.