When was the last time the Toronto Maple Leafs won the Stanley Cup?

The Stanley Cup is the greatest trophy in sports. It's been awarded since the 1800s, and since the NHA ceased operations giving the NHL sole possession of the Cup, it's been awarded a total of 107 times to 26 different franchises. One of those franchises is the Toronto Maple Leafs.

The Maple Leafs are either the most popular team in the NHL or second to the New York Rangers. There are 6.37 million people in the Greater Toronto Metropolitan Area. We'd guess that about 80% of them claim to be Leafs fans. It's an iconic franchise that has the pride of the city. Toronto needs a championship in the sport of hockey.

Just look at how the city celebrated when the Toronto Raptors won the title in 2019. The parade brought as many as 2 million people to downtown Toronto. Imagine if it was the Leafs? One could imagine the city would be prepared to double that and possibly triple it. That's because it's been so long since the Leafs won it all.

The Maple Leafs were one of the Original Six teams. They had this 25-year era where the teams that contracted due to the Great Depression and World War II never got replaced and expansion had not started. In 1942, the New York Americans closed up shop and the league was left with six teams. The Maple Leafs won that 1942 Stanley Cup, their fourth Stanley Cup.

The Maple Leafs would go on to win 10 Stanley Cups during this 25-year era. They were dominant among the six teams. It was the Maple Leafs and the Montreal Canadiens, the team currently with 24 Stanley Cup Championships, the most all-time. The Leafs are second with 13.

In 1967, the NHL decided it was time to give more cities a chance to see hockey. They added teams in Los Angeles, Pittsburgh, Philadelphia, St. Louis, a second California team, and Minnesota. St. Louis actually made it to the Stanley Cup Final in their first season. The Maple Leafs, a team once dominant, never made it to the mountaintop again.

That's right, the Maple Leafs haven't won a Stanley Cup since the league grew from six teams to 12. 1967 was their last championship. It's been so bad, the Maple Leafs haven't even made it to the Final. They haven't been one of the two best teams in 57 years. Out of 2.8 million people in the city of Toronto, only about 800,000 people have been alive for a Maple Leafs championship.

It's pretty famous how bad the Leafs have been in the playoffs. Prior to last season, the Maple Leafs couldn't win a playoff series. They lost eight series in a row before beating the Tampa Bay Lightning in 2023. Right after that, they lost to the Florida Panthers in five games. The last time the Leafs appeared in the Eastern Conference Finals was before the 2004 NHL Lockout.

This is a team with constant championship aspirations. They have more stars than anyone, but they haven't been able to get that team to win. Maybe it will change one day, but with so many players on the team now making over $10 million, they are running out of excuses and the fanbase has been out of patience.