Top 10 Longest Stanley Cup Droughts in the NHL

The Stanley Cup is the nicest looking trophy in sports. What's not to like about it? It's big, shiny, and perfectly shaped for consumption of celebratory beverages. It's also an extremely grueling process to even get a chance to play for it. The argument can be made that it's the same for any sport, but a 7 game series is the longest in any professional sport, along with basketball. You also have to consider that they have to win four of these series, and that it's a full contact sport that allows bare knuckle brawling. There's players that invest so much mentally and physically in the Stanley Cup playoffs, that when they finally get to the big dance and come up a little short, it simply breaks them. Ryan Kesler of the Vancouver Canucks is the perfect example of this. He has not even been close to the same player he was back in 2011 when they lost to the Bruins in 7. Kesler is not the only one from that group that is reeling. The Sedin twins' game has slowly regressed every season since then. We even saw Alex Burrows doing his best Scott Gomez impression for most of this season as he simply could not find the back of the net for 35 games.

Okay, that's about it for the Canucks bashing (for now). They do have their problems in Van City, and probably will miss the playoffs, but there are other teams that have equally bad droughts, or even worse. One particular team comes to everyone's mind when the topic of Stanley Cup droughts is brought up, and we will certainly get to them in due time. For now, lets take a look-see at the top 10 longest Stanley Cup droughts in the National Hockey League.

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10 Edmonton Oilers, 22 Seasons (1989-1990)

The Oilers came so close in the 2005-2006 season, when they lost in 7 games to the Carolina Hurricanes. They experienced a fatal blow in game 1 of the finals when their goaltender Dwayne Roloson went down with a knee injury. At the time, Roloson was the best goalie in the playoffs and had basically put the team on his back. Craig MacTavish has gone on record saying: "I maintain, that if Roloson didn't get injured, we would have won the cup". Mac-T may be right, but boy has it been tough times for that franchise since then, as they haven't seen the post season since then (7 seasons). The Oilers managed to pick first overall 3 years in a row, drafting Taylor Hall, Ryan Nugent Hopkins and Nail Yakupov. There was so much positivity surrounding the franchise as Oilers fans started to think back to the glory days of Gretzky, Messier and Kurri. Unfortunately, the Oilers have still produced abysmal results. Management refuses to address their organizational needs on defence, and they will be in the basement until they do.

9 Calgary Flames, 23 seasons (1988-1989)

The Flames played in the Stanley Cup finals against the Tampa Bay Lightning in the 2003-2004 season and came pretty much as close as possible without ultimately winning. It's still a bitter pill to swallow to this day for Flames fans because there was a call in game 6 that was disputable. It appeared that Tampa goalie Nikolai Khabibulin kicked out a Martin Gelinas shot, and the play carried on. But on the overhead camera angle, it looked like the puck was fully over the line. This probably would have sealed it for the Flames, but instead the game went to OT and the rest is history.

The Flames waited way too long before they finally went into "rebuild mode". They were content patching up their issues, but you can only do that for so long before the bottom falls out. They appear to be on the right track now and are going with lots of youth in their lineup. Sean Monahan was a pleasant surprise for them this year in terms of his productivity and also has tremendous upside. It will be interesting to see if Brian Burke remains the GM or if he passes it off like he says he will. Burke took a lot of flak for the job he did in Toronto, and a lot of it was warranted. Considering how brash he was, it took too long before the team saw results. But ultimately, the current Leafs core was constructed by Burke, with a few exceptions, though it remains to be seen if they can get over the hump.

8 New York Islanders, 29 seasons (1982-1983)

Where to start? The word limit's here are too low to do their story of incompetence any justice. It's easy to forget that the New York Islanders were once a well respected, established franchise. They were an absolute juggernaut in the late 70's and early 80's as they won four cups in a row, led by the likes of Mike Bossy, Bryan Trottier, Denis Potvin and the infamous Billy "I'll hack your ankles" Smith in goal.

In the modern era, this once revered franchise has entered the depths of darkness in the (Mike) Milbury era. He dug them into a hole that they may never get out of. Making trades such as; Brad Isbister and Raffi Torres for Janne Niinimaa, JP Dumont and a 5th for Dmitri Nabokov, Bryan McCabe and Todd Bertuzzi plus a 3rd for Trevor Linden, Zdeno Chara and Bill Muckalt plus a 2nd overall pick (Jason Spezza), for Alexei Yashin. Last but not last, quite possibly the worst trade in NHL history; Olli Jokinen and Roberto Luongo for Mark Parrish and Oleg Kvasha. Once Milbury was relieved of his duties, Garth Snow (former backup goalie) was hired as GM and promptly signed injury plagued goaltender Rick Di Pietro to an unprecedented 15 year contract.

The team hasn't been out of the first round of the playoffs in 20 years and the future looks rather bleak. Unfortunately for the Isles, it's impossible for them to attract any suitors in terms of UFA's in the off season due to their past reputation. Expect John Tavares to bolt in the very near future.

7 Winnipeg Jets/Phoenix Coyotes, 33 seasons (never won)

Of course, the old Winnipeg Jets franchise got run out of town and moved to Phoenix in 1996. Thankfully, the reeling Atlanta Thrashers franchise was relocated to Winnipeg two years ago. Winnipeg absolutely deserves an NHL franchise, as despite their lackluster results since the team moved back, the building is still packed and fan support is unwavering.

Unfortunately the same cannot be said for the Coyotes, as hockey never seemed to take off in the desert. The lack of interest definitely attributes to the team's struggles. An empty building translates to cash strapped owners, which leads to a handcuffed GM who never has the funds to make a splash on the UFA market. For years, the team didn't even have ownership as the NHL took over. This led to the joke: "If Phoenix ever won the cup, would Gary Bettman congratulate himself as the owner?"

6 Philadelphia Flyers, 37 seasons (1974-1975)

The Philadelphia Flyers are the closest thing to the NHL's version of the Buffalo Bills. They've gotten plenty of sniffs at the Stanley Cup but constantly come up short. They did win in the 1974-1975 season, but since then they have made the finals on six occasions and have lost every single time. They're a franchise who simply can never get it right in regards to their goaltending.

Since Bernie Parent and Pelle Lindbergh (who tragically died in a car accident at 26), they've constantly had issues between the pipes. When they made the finals in 1997, they were rotating games between Ron Hextall and Garth Snow as they got swept by the Red Wings. The two goaltenders allowed 16 goals in 4 games. In the 2010 finals, the 7th seeded Flyers gave it a good go, but Michael Leighton simply wasn't good enough. Even when they did accidentally develop a capable goalie in Sergei Bobrovsky, they ultimately shipped him away and signed Ilya Bryzgalov, who was bought out within two years due to poor performance and eerie infatuation with talking about the universe.

5 Washington Capitals, 38 seasons (never won)

The Caps have only made the finals once since they entered the league in 1974. That is a lot of years without much success. They did however make the finals in the 1997-1998 season, but were outgunned in 4 games by an insanely powerful Detroit Red Wings team. Hopes have been high in recent history as they have put together some extremely strong teams, but just can't get it together in the playoffs. Hopes were particularly high in the 2009-2010 season when they won the Presidents Trophy and it seemed like all the stars were finally aligned for a Cup run. Ovechkin was having a career year, Backstrom and Semin were humming, and they had a great supporting cast with guys like Brooks Laich, Eric Fehr and Mike Green. Jose Theodore was also enjoying a career resurgence. Sadly for them, they ran into the Montreal Canadiens and Jaroslav Halak, who put on one of the most impressive goaltending performances of all time, ousting them in the first round.

4 T3. Vancouver Canucks, 42 seasons, (never won)

Yes, after that brief pause, we're back to talking about the Canucks. Upon talking to members of their fan base, it's very clear that there's some deep rooted frustration, and it makes them walk around with a chip on their shoulder. They came so close in 1994 and more recently in 2011. Against the Bruins in 2011, it just wasn't meant to be. It seemed like every game another player would drop due to injury. It's easy to say: "injuries are no excuse," but the fact of the matter is, that injuries do impact a team, especially playing at the highest level in the Stanley Cup finals. There always seems to be some ugliness after these heart breaking losses occur, which attributes to the overall frustration. In 1994, there was a rumor circulating that Pavel Bure demanded $6 million dollars as blackmail, or else he would not play in game 7 vs. the Rangers, which led to some very fiery interviews. Then of course in 2011, an extremely nasty riot broke out after the Canucks dropped game 7 to the Bruins.

3 T3. Buffalo Sabres, 42 seasons (never won)

When it comes to the Buffalo Sabres and their hardships, there's no riots, blackmail, goaltending blunders, or anything out of the ordinary that really stands out. They just quietly go about their business and proceed to never win the Stanley Cup, year after year. But there is the one exception...

The Sabres met the Stars in the 1999 Stanley Cup Finals. The two teams put on quite an entertaining series, but during overtime in game 6, one of the most controversial endings in NHL history transpired as the Stars were up 3-2 in the series. In the third overtime, Brett Hull scored to win the game but his foot was clearly in the crease. That particular season, they had implemented a rule that if a player's foot was in the crease, the goal would be called back, yet somehow this goal stood. The NHL defended itself by saying that they had sent out a memo before the playoffs started, stating that the goal would be allowed in instances where the goal scorer maintained control of the puck prior to entering the crease. Seems ridiculous, considering they weren't calling it like that for the entire season.

2 T1. St. Louis Blues, 45 seasons (never won)

The St. Louis Blues broke into the league in the 1967-1968 season and immediately made an impact as they made the Cup finals three seasons in a row. Unfortunately, during these trips to the finals, they didn't win a single game. The Montreal Canadiens swept them twice, despite goaltender Glen Hall playing incredible and then were swept by the Boston Bruins in 1970. They haven't been back to the big dance since then.

In the Blues history, they're a team that never seemed to have an identity. They haven't had much in terms of star power other than Brett Hull (Wayne Gretzky for 1/4th of a season does not count) and always seem to be missing that extra "little something" to make a solid push. Yes, there was Al MacInnis, Chris Pronger and Bernie Federko, but that's only three players and the franchise has been around for 45 seasons. This season the Blues are all in, and may have finally got it right with the acquisition of Ryan Miller. They look like they're "for real".

1 T1. Toronto Maple Leafs, 45 seasons (1966-1967)

It was actually enjoyable to see the Maple Leafs fans gather outside in downtown Toronto as they were up 4-1, and on their way to defeating the powerhouse Boston Bruins in the 2013 Playoffs. But the look of jubilation and euphoria on their faces slowly turned into the look of shock, despair and heartbreak as the Leafs melted down in the second half of the third period with the Bruins ultimately winning the game in OT.

This sequence of events just adds to the ever growing frustrations of Leaf Nation. It's such a shame that one of the Mecca's of hockey has not seen Lord Stanley's Mug in 45 seasons. It's not as if the franchise has been a total bust in the modern era. They had a lot of success in the early 2000's and played an exciting brand of "rock em sock em" hockey with the likes of Gary Roberts, Darcy Tucker and Tie Domi. Their 7 game slug fest of a series against the Islanders in 2002 was fantastic to watch, and their mastery of the Battle of Ontario still leaves Sens fans scratching their heads.

Unfortunately for Leaf Nation, it's been total deception since 2004. Starting with Cliff Fletcher signing Jeff Finger to a lucrative, multi year deal, thinking that he was signing someone else. Which was followed up by John Ferguson Jr. swapping Tuukka Rask for Andrew Raycroft, thinking that Justin Pogge would be the future goalie for years to come. Ferguson also signed players that were well past their prime such as Eric Lindros, Jeff O'Neill and Jason Allison. Finally when Brian Burke took over, there was some renewed hope, but he really got off to a shaky start and set them back even further as he wasted a significant amount of cap space locking up Mike Komisarek and Francois Beauchemin, neither of which panned out.

Burke's core has eventually come to fruition as the Leafs are a solid team at this time, but it unfortunately took way too long. The franchise has been constantly marred by set backs due to incompetence at the GM position for the past decade. This does not take anything away from Leafs fans, it anything it's the opposite. Their patience demonstrates their loyalty and devotion to their team.

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