Most of Montreal's Stanley Cups were won when there were less than 15 teams in the NHL. Montreal's never winning another Stanley Cup unless Quebec becomes a tropical paradise due to global warming and Canadian inflation goes down.
Besides, which hockey player wants to play in a French-speaking place? That was the biggest problem with the Quebec Nordiques; players like Eric Lindros couldn't stand the owner and the thought of playing in the area.
Before Maple Leaf fans start laughing, know that you face many of the same problems that Canadien fans do. Inflation, unfortunate prospects of never winning a Stanley Cup. These things are why you should never root for Toronto or Montreal.