I like to think when the Leafs stole the Cup from the Habs in 1967 was one of the worst defeats in Habs history. The Leafs dubbed too old and too slow, lost 10 games in a row in the regular season, huge underdogs, banded together to go on a playoff run. 1967 Montreal was Canada's largest city and it was Canada's 100th year and Expo was in Montreal that summer. The Habs wanted to have the Cup displayed at Expo but the Leafs ruined that plan.