Originally posted by darvlaymost cups AND disrepectful fans...seems to imply the answer has to fulfil both requirements.
I have one:
Which team boasts the most Stanley Cup victories and also boasts the most foul-smelling, disrespectful Neanderthalian fans this side of the Atlantic Ocean?
Montreal has the most cups but Toronto fans are by far the most usless bunch of tits on the face of the planet but they haven't won the cup since that battle on the Plains of Abraham.
So I'll say that the New York Islanders fit both of those requirements, with Toronto a close 2nd.