Top 15 Reasons The Montreal Canadiens Haven't Won A Stanley Cup Since 1993

It was June 1993, on a cool summer night, when a Canadian team last hoisted the Stanley Cup. Game 5 between the Montreal Canadiens and the Los Angeles Kings, and Montreal was leading the series 3-1, on the brink of winning their 24th Stanley Cup. Imagine yourself as a fly in the Montreal Forum that day, the eruption after that final whistle, the incredulous buzz in and around the building when that beautiful Cup was lifted high by the Montreal Canadiens.

Little did we know that would be the last time the Canadiens, or any Canadian team for that matter, would lift the Stanley Cup.

Over 23 years after that glorious night, Canadiens fans really don’t have much to cheer for. Bad trades, mediocre management, and horrifying coaching are just a few of the things we had in store for us over the years. Gone are the days where the Montreal Canadiens were the team to play for, unstoppable in their attack and determined to win the Cup each year. Today, we expect mediocrity at best, and continue to cheer for it without a second’s pause.

What explains this Canadiens Stanley Cup drought? Many factors unfortunately, ranging from talent, management, coaching, and even politics. Our particular problem has many reasons for it, and this article will look to explore why the Canadiens haven’t hoisted the Cup since 1993.

15 Language


The Montreal Canadiens are an enormous part of Quebec culture. They’re the only professional sports team with that size a market in the entire province, and sports fans in Quebec live and breathe the Montreal Canadiens. The fact that the Habs represent an entire French-speaking nation means that the fans expect the team to keep a certain level of their “frenchness” even though other NHL teams don’t have to deal with this type of issue.

Now how can this make them worse or deter them from winning? Well imagine having to hire management that is always French-speaking, for one. The choice for important positions such as coach or general manager becomes a much more limited one, and more often than not they don’t get the best man for the job, but the best bilingual man for the job.

14 Fans

Eric Bolte-USA TODAY Sports

If there was a way to determine which fans care the most out of all the professional sports teams in the entire world, I’d have to figure the Canadiens fans would be somewhere near the top of that list. Their fiery passion and love of the game is intoxicating and exhilarating, and creates an unforgettable atmosphere for any player in a Canadiens uniform.

But with undying passion may also come the harshest of criticisms, sometimes for no apparent reason. For a player, this could be a major deterrent to coming and playing for the Montreal Canadiens. Signing here long-term means accepting that your private life won’t be like it used to. In Montreal, your every move is analyzed, everything you say is broken down and looked at, and one bad game means harsh criticism from every corner of the city, whether it’s on the radio, in the papers, or anywhere around town where hockey is being talked about.

13 Location and Weather

Greg M. Cooper-USA TODAY Sports

Although this may not be as much of a factor as some of the others point on the list, I do think it’s an important one nonetheless because of the things it could entail. Montreal is in the Great White North, and it gets seriously cold in Canada in the winter. Although weather and climate aren’t huge factors when it comes to hockey, free agents looking to sign for another team might hesitate when they turn on the Weather Network and see it's -45 degrees for the whole month of January. Whereas January in Florida you’re heading to the beach after practice and sipping on refreshing drinks by a beach side bar, instead of hot chocolate by your fireplace because only snowmen can live outside.

12 Profits keep rising – people get lazy

Bob DeChiara-USA TODAY Sports

Let’s not sugar coat it, the Canadiens are well off, and can boast being one of the richest hockey teams in the NHL behind only the Maple Leafs. So as the team has remained somewhat stagnant since 1993, their profits rose ridiculously quick. To give you an idea, the Canadiens were bought for $275 million in 2001 by George Gillett. The Geoff Molson group bought them from Gillett for $575 million in 2009, and last fall Forbes estimated that they were worth $1.18 billion. They’ve increased in value by over $800 million in 15 years.

11 Patrick Roy


Although Roy also falls in the bad trades category without a doubt, this trade was the most cataclysmic in Habs history. After coach Mario Tremblay refused to pull Roy during an embarrassing 11-1 loss to the Red Wings, Roy passed by the bench, right by a glaring Tremblay, and told then president Ronald Corey that this would be his last game in Montreal. Four days later, he was traded to the Colorado Avalanche, and Montreal went through their biggest sports mourning in the history of the city.

10 Star players

Joshua Dahl-USA TODAY Sports

Stanley Cup winning teams need star caliber players – and for a multitude of reasons star players rarely trade from other teams to come to Montreal. No matter how good your team is as a whole, Stanley Cups are won on the backs of players with extreme talent and above all, heart and character. There’s been a lack of that since Patrick Roy left, and therefore a lack of cups.

9 Bad trades


The Canadiens are notorious for making some of the worst trades in the history of the modern game. A most recent example was sending the beloved Montreal defenseman P.K. Subban over to Nashville for a seasoned veteran like Shea Weber. All kidding aside, Shea Weber is a stud of a player and one hell of a defenseman, but P.K. Subban represented an elite defenseman for the modern game. He was fast, flashy, and extremely offensive. Not to mention he’s four years younger with almost the same time left on his contract.

8 Taxation

Jean-Yves Ahern-USA TODAY Sports

Taxation in Montreal and in Quebec as a whole is horrible. Especially for hockey players, who make a bigger salary than the average Joe, almost 50 percent of their paycheck goes to the government. On a $7 million salary, that narrows down to just a little over $3.5 million. Sure, it’s still a lot of money, but these are pro athletes and most of them have a high profile lifestyle.

Taxation in other cities with NHL teams are nowhere near as bad. According to a recent TSN study, Montreal is one of the worst cities to be an athlete in because of taxation. Here is an example from that study:

7 Management

Eric Bolte-USA TODAY Sports

Montreal hasn’t won since 1993, we know that. And although there are many reasons for their extreme mediocrity for the past 23 years, mediocre management should not be forgotten. Let’s start with Marc Bergevin for example. Although he seemed promising at first, it’s the same empty promises being made that Habs fans are used to. In four years as general manager, he has not signed one big time player. Not one. Bergevin is lucky enough to be the general manager of a team that has some amazing pieces in place, but he was still unable to add that extra firepower that would take this team to a whole new level. Instead, he got rid of one of his best pieces.

6 Playoff woes

Reinhold Matay-USA TODAY Sports

This may seem a little less obvious. I mean, in most recent history, the Canadiens make the playoffs pretty much every year. But all it takes is a closer look, and you’ll realize that the Canadiens are simply not very good in the postseason.

5 Coaching

Jean-Yves Ahern-USA TODAY Sports

Let’s start with Michel Therrien. For everyone wondering, I am not a fan. I’m not a fan of the way he treated P.K. Subban, of the way he blatantly ignores Montreal’s power play problem, and I’m especially not a fan of his uncaring demeanor. In a season filled with disappointments, not once did Therrien stand up at a press conference and admit that this team sucked, that their performance was dreadful, and that change was needed as soon as possible. Instead, we listened to the coach explain how hard it was without Carey, making excuse after excuse for why they Canadiens were so damn bad.

4 Lack of risks taken

Jean-Yves Ahern-USA TODAY Sports

In hockey, like in life, taking risks can be a good thing. But the Montreal Canadiens seemed more content in taking the safe route most of the time, and the results to that are not very pretty. Keeping a prospect like Ryan McDonagh could be risky if he didn’t pan out, but most people’s gut feelings were saying that he would. P.K. Subban represents risk as well. He was loud off the ice, involved in the community, and maybe a little annoying in the dressing room from what we heard. But he represents a risk worth taking because of his talent, character, and involvement in the community. But instead they traded for the more reserved, low risk defenceman which is Shea Weber.

3 Impatience

Eric Bolte-USA TODAY Sports

Montreal as a hockey organization can be a little impatient at times. Over the years, clubs around the league have realized how important it is to have all the pieces ready for a cup run, and getting all the pieces ready and in place can be a long and grueling process, especially with prospects. You need to take the time to let them get experience in the minors, bringing him up for a few games, and constantly be aware that this player is in a growing process that can take a lot of time. If this process is sped up, that players development can be flawed for a very long time.

2 Finishing in the middle of the pack – no good prospects

Steve Mitchell-USA TODAY Sports

Since 1993, despite their lack of success in the playoffs, the Canadiens have done decently well in the regular season. This isn’t a good thing – not a good thing at all. It means that unless you win the Stanley Cup, you’ll be stuck with a really low draft in the first round and nothing to show for it from the previous season. This has been the story for the Canadiens since 1993, where they’ve chosen in the top five in the first round only twice, choosing Carey Price and Alex Galchenyuk. The rest of their picks all vary between 12th and 27th, where the star players are much more sparse, and choosing players turns more into a question of the teams needs than which player is truly the best.

1 It’s hard to win

Sergei Belski-USA TODAY Sports

There might be a million more reasons why the Montreal Canadiens haven’t won a Cup since 1993, but none bigger than this one, and it’s the number one reason they haven’t either. Winning the Stanley Cup is extremely difficult. There are 30 teams competing year after year for the exact same reason. Each team has tremendous resource and use them all towards their eventual goal of winning the Cup. Even making the playoffs means nothing nowadays, because that’s where the real season truly begins and getting to the Cup becomes even more grueling.

So yes, getting all the way to the end is a difficult task, one that requires the entire organization to be on the same page at all times. For the Canadiens, unfortunately, the search for glory will still continue, probably for many more years to come. And with the NHL officially expanding in 2017, the task will only get harder.

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Top 15 Reasons The Montreal Canadiens Haven't Won A Stanley Cup Since 1993