The Toronto Maple Leafs. I am born and raised 40 minutes away from the big city, and have been a fan for almost 16 years now, since 8 years old. However, the team's much, much older than I am. An Original 6 team with close to 100 years of history, the wealthiest team in the game, and arguably the most well-known worldwide.
However, they share the longest drought without a Stanley Cup (1967). They have not even appeared in the finals since then. No Maple Leafs player has even led the league in points since 1938, and in goals since 1946. Currently, the Leafs are on route to missing the playoffs again for the 10th time since 2003-04. They have not made the playoffs after a full 82 game schedule in over a decade. When they finally did make it in the shortened season in 2013, they were able to pull off one of the most epic collapses in recent memory, and were sent home in the first round.
The seasons since they last made the playoffs in 2004 has included very similar themes. Heart-breaking finishes where they barely miss the playoffs, ~8 game losing streaks (to begin the season, early season, or mid-season) which puts the team out of playoff contention, and lackluster performances from players brought in to help the team improve. To make things better, we currently have a coach, general manager, and president who have no real previous experience holding their role.
To sum up, most real Maple Leaf Fans are clinically depressed, break shit in frustration when watching games, and yell at the TV. The lucky ones who can afford the most expensive ticket in the league to watch them play have been able to put brown paper bags on their heads in the stands, or throw their jersey (and the rare Eggo waffle) on the ice during play to show their disgust.
So, they sound like a TERRIBLE team to root for. That's why they say Maple Leaf fans are either the stupidest people around, or the most loyal. It may be a mix, who knows, but growing up here I can say that when the team is competitive, winning games, consistently making the playoffs, and winning rounds, EVERYTHING I said above goes out the window. It's forgotten once April hits. The atmosphere in the city, and in the cities surrounding Toronto is INSANE. Hockey is a religion here, year-round. The players that have been lucky enough to experience it have said there's nothing that compares to playoff hockey in Toronto.
So yeah, the team might not be in a good situation right now, but hey it's already been 10 years, so how much longer can it last? Many fans of other teams might joke that it will never end, but that's not likely. The team has it's 100th anniversary season coming up in 2017. If they are able to put together a competitive team by then, the hype would be through the roof. If you're looking for an exciting team to cheer for right now, I wouldn't suggest my beloved Maple Leafs. But, in the long run, it may turn out to be a great investment ;)