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Why has it Been so Long Since the Montreal Canadiens Last Won a Stanley Cup?

For long-serving fans of the Montreal Canadiens, the past three decades have been marked by a series of frustrations and disappointments. This storied NHL franchise has failed to capture hockey’s ultimate prize, the Stanley Cup, since the 1992-93 season.

Once the most dominant team in the NHL, the Canadiens are now trophy-less for 32 seasons. This is in stark contrast to their illustrious history of winning 24 Stanley Cups and divisional championships apiece. It’s gotten to the point that an entire generation of Canadiens fans have never tasted the sweet success of Stanley Cup glory.

It must be galling for Canadiens fans once again this season, as they sit and watch fierce rivals, Toronto Maple Leafs, embark on their postseason playoff bracket. However, the latest NHL odds suggest that Toronto could be dumped out in the first round as opponents, Boston Bruins, are considered the current favourites.

The Canadiens were previously talked about in the same breath as other iconic North American sports teams like the New York Yankees and the Boston Celtics, such was their dominance and competitive edge. Having been such an NHL powerhouse throughout the 20th century, what’s gone wrong for the Montreal Canadiens since the turn of the new millennium?

The team’s hierarchy has never recovered its draft skill

In the 1980s, the Montreal Canadiens were revered throughout the entire NHL for the way they did business. They leant heavily on the trading smarts of Sam Pollock, the former general manager of the Canadiens, who was often able to find a diamond in the rough. It’s hard to argue that Montreal has lacked Pollock’s innate ability to pluck high draft picks ever since.

Three of Pollock’s selections in the 1987 NHL Draft – Eric Desjardins, Mathieu Schneider and John LeClair – stuck around to help the Canadiens lift their last Stanley Cup in 1992/93. It’s quite telling that no player has been inducted into the Canadiens’ Hall of Fame since 1993.

The “Ronald Corey factor”

If you speak with any long-suffering Canadiens fan, you’ll find that they often state the 17-year era of Ronald Corey as president was the moment the franchise lost its way. Corey has often been criticized by fans for the way in which he led the team, prioritizing commercial decisions over talent-based decisions for the roster. In doing so, many fans believe Corey’s reign encouraged a poisonous working environment to ensue, which was unlikely to be conducive to success on the rink. There was a sigh of relief all around when Corey resigned in 1999, to be replaced by Pierre Boivin.

Has there been a sense of entitlement and complacency that’s crept into the team’s mindset? Quite possibly. All of which has led to a lack of urgency and accountability on the ice.

Incomparable rosters

One of the main impacts of the franchise’s poor drafts is the weakening of the Canadiens’ roster. There’s been a general lack of elite talent and depth for coaches to call upon. Of course, the team has always enjoyed standout players, including the likes of goaltender, Carey Price, and defenseman, Shea Weber, but they’ve often lacked the star power and depth necessary to compete with the top teams in the NHL.

An increasingly competitive NHL landscape

It’s no secret that the NHL has become increasingly competitive in the last couple of decades. Parity among teams makes it difficult for any franchise to develop and maintain a dynasty like the one Montreal established in the 20th century.

The rise of salary cap regulations has levelled the playing field, enabling smaller-market teams to compete with their more financially powerful counterparts. All of which has made it harder for the Canadiens to re-establish themselves as a credible force.

Last but by no means least, the passionate fan base of the Canadiens can also weigh heavily on the team. Despite being a source of unwavering support through the years, there is often immense pressure and expectation for the team to succeed. There are two generations of Canadiens fans who are used to seeing their team routinely lift major trophies, after all.

Managing these external pressures and maintaining focus will always be the number-one goal for any Montreal roster keen to write their own chapter in this franchise’s storied legacy.