This is quite the list. We leadoff with the Curse Breaker Theo Epstein. Epstein did more for Boston and the Cubs in a short span than everyone else 200 years combined. He brought championships to both cities. Now with Major League Baseball, it seems only time before he is the commissioner of baseball.
Red Auerbach is the only person to be on two Mount Rushmores (Coach and GM). The 1980 Executive of the Year and 7 NBA Championships easily land him on this list.
Mark Shapiro does not the championships the others have on this list. His is a two time Sporting News Executive of the Year (2005, 2007). He first found success with the Cleveland Indians and is now with the Toronto Blue Jays.
Last on the list is the controversial Jerry Krause. With all the buzz about his bad decisions, Krause was responsible for 6 NBA rings. He drafted Michael Jordan, traded for both Scottie Pippen and Dennis Rodman. He landed and was patient for Toni Kukoc and added the right supporting casts to bring the Chicago Bulls to glory.
Honorable Mentions: Andrew Friedman (Rays and Dodgers), Jed Hoyer (Padres and Cubs), Marv Levy (Bills), Al Davis (Raiders).