#1 New Jersey Devils
Cup drought: 11 seasons
three-time cup champs
Maybe Lou Lamoriello knew what he was doing when he bailed on this organization. These Devils have a dim past (just one playoff appearance in the past five years), a painful present (the NHL’s 29th rated offense in 2014-15) and a grey, dystopian future (arguably the least promising prospect pool in the game). This is a team so bereft of hope that it can only aspire to being dull and dreary.
Um, ok. Granted, it's not all roses right now, but I'm guessing teams with ridiculous cup droughts are much more miserable than us.