The Montreal Canadiens are anything but strangers when it comes to the Stanley Cup. As we all know well, the Habs have won Lord Stanley’s Holy Grail 24 times, winning it once when they were part of the National Hockey Association, and 23 times as part of the National Hockey League. How did all this fascination with winning the beloved trophy come into play?

Well, when the Montreal Canadiens first began their quest for the silver cup they were known as Le Club De Hockey Canadien. The Habs were founded in 1909, the same year as the National Hockey Association, which was the league that the Habs played in at the time. Le Club De Hockey Canadien played their first game in January of 1910, celebrating their first ever Stanley Cup win in 1916. Le Club De Hockey Canadien played in the National Hockey Association from 1909 until 1917.

Then in 1917 came the birth of the National Hockey League, which the Habs were instrumental in helping to create. From that moment on they were known as the Montreal Canadiens, and they played in the NHL.

In 1919, just two years into their tenure in the NHL, the Canadiens were on their way to another Stanley Cup Final, but their dream for that year was cut short because of a flu epidemic, therefore there was no Stanley Cup champion in 1919.

The Canadiens then endured the loss of two arenas which were completely destroyed by fire. The Montreal Arena was lost in 1918 and the Jubilee Arena burned just a year later. The new home of the Montreal Canadiens became the Mount Royal Arena for the better part of the next decade.

In 1926, the Canadiens found what would turn out to be their next home for the next 72 years: the Montreal Forum.

The Great Depression, or The Dirty Thirties as some historians call it, was a very challenging time for everyone, to say the least and the Canadiens were no exception.
In 1935 the Canadiens were ready to pull up stakes and move to Cleveland. Worse still, the team was on the verge of folding entirely in 1939.

However, after World War II our beloved Habs started to see brighter days ahead. They reached the Stanley Cup Final each and every year from 1951 to 1960 and proceeded to win the Cup five straight times from 1956-1960.

In later years, select Canadiens players were actually appointed as Ambassadors Of The Cup. Names such as Jean Claude Tremblay, Maurice “Rocket”Richard, Elmer Lach, and Georges Vezina have been given this honour. There are three players, all of them Montreal Canadiens, who have won the Stanley Cup as both a player and a coach. They are Hector “Toe” Blake, Jacques Lemaire, and The “Pocket Rocket” Henri Richard. The Canadiens fascination doesn’t stop there.

In 1924, the Canadiens players were on their way to a victory celebration, when they realized they had a flat tire. While changing the tire they had to remove the Stanley Cup so they could get to the spare.

Tire changed, they sped off, leaving the Cup behind in a snow bank. Hours later the players realized that the Cup was missing. They drove back and found it exactly where they had left it, unharmed and covered with snow.

In 1974, when Guy Lafleur took the Stanley Cup to his parents home in Quebec to celebrate with family and friends he proudly displayed it on his parents front lawn so that everyone could enjoy the moment as well as take photographs.

Not only are the Montreal Canadiens the oldest professional organization in the hockey world, but they are also the most successful.

With 24 Stanley Cups to their credit, their obsession with Stanley and all that it represents will live on forever.