The Toronto Maple Leafs currently hold the longest Stanley Cup drought in NHL history at 54 years and counting. They last lifted Lord Stanley’s Trophy overhead in 1967. Prior to that, the New York Rangers ended it after 53 seasons in 1994.
Over the last few years, they have gone out and added plenty of big name stars either in or past their prime. Yet, not only does the Cup elude them, but playoff success in general.
This past season, playing in a weak North Division they finished first. However, the Leafs blew a 3-1 series lead against the 4th seed Montreal Canadiens.