In the future. Between my two favorite teams in the world:
The New York Islanders or The Chicago Cubs.
The Islanders have one of the top 3 Prospect Pools in the NHL according to HF. They have a young superstar in JT. They will probably have another high draft pick in the '12 Entry Draft and will hopefully draft a stud defenceman. However, there are real questions in the front office with team ownership and the GM.
The Cubs do not have a highly regarded farm system. Their young budding superstar shortstop has recently been implicated in some kind of sexual assault investigation. Their hockey loving #1 pitcher has seen better days. They have not won a World Series since 1908. However, they have a new owner who seems to know what he is doing and has this off-season put together a real management dream team led by Theo Epstein. Sure the cub-board is bare right now, but one of the managers built the SD Padres farm system into the best in baseball in two years and Theo has done it before and is regarded as a genius.
So who will win first...the franchise with better management, or the team currently with much better stable of prospects?