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5 Funny Stanley Cup Stories in Hockey History (Part 1)

Updated on July 31, 2016

A Player's Day with the Stanley Cup

One of the most illustrious and beautiful trophies in all of sports, the Stanley Cup, has a number of unbelievably wacky stories in its long dramatic history. Traditionally, every player on the team that wins the trophy is entitled to 24-hours of personal time with the Cup. Players will typically take it to their hometown, family house, a pub, or a local charity event to celebrate. During their occasions with the Stanley Cup, there certainly have been some strange incidents along the way.

The Original Stanley Cup (1893)
The Original Stanley Cup (1893) | Source

Rideau Canal

The funny tales of the Cup started more than a century ago in 1905 in Ottawa, Canada. At that time, the Cup was only a fraction of the size that it is now, so it was much lighter and easier to handle. After getting raging drunk and celebrating their recent championship against Yukon’s Dawson City Nuggets, the members of the Ottawa Silver Seven hockey team decided it was a good idea to try and kick the Cup across the Rideau Canal. One of the members of the team attempted to dropkick the Cup to the other side of the canal and unfortunately he fell a bit short of the target. The Cup didn’t make it across and ended up splashing into the canal to swim with the fish. It remained in the water overnight until it was eventually rescued from the murky depths the next day.

Flower Pot

A few years after the canal incident in Ottawa, the strange tales of the Stanley Cup continued to make news headlines. In 1907, the Montreal Wanderers won the Cup against the Kenora Thistles and during their quest for the Cup they had their victory documented by a photographer. The team left the Cup at the photographer’s house after a group photo shoot and the photographer’s mother had a keen affixiation with floral arrangements. Perhaps running short on vases, she had decided to fill up the Cup with a fresh assortment of carefully selected geraniums and turned the holy grail of hockey into a shiny silver flower pot. It remained in the house for several months until a member of the team returned to save it from the next watering. Perhaps it was the incident that lead to the inspiration of the famous white gloves for future Cup carriers.

MSG Mortgage

New York City’s original Madison Square Garden had been built in 1925 and demolished in 1968. When the mortgage of the arena was paid off in 1940, it was the same year that the New York Rangers had won the Stanley Cup defeating the Toronto Maple Leafs. To celebrate both the victory and the finalization of the last mortgage payment, the management of the arena decided to burn the mortgage papers in the Cup. It seemed to be an appropriate victory celebration at the time; however, some people believe it was the cause for the longest Stanley Cup drought in team history. Ever since the mortgage was burned, the Rangers weren’t able to win another championship until 54 years later. In 1994, the curse was finally broken when Mark Messier guaranteed victory in game 6 of the Stanley Cup Finals against the Vancouver Canucks. The Rangers went on to win game 7 in dramatic fashion in front of the hometown fans.

Interior of the original Madison Square Garden (1940)
Interior of the original Madison Square Garden (1940) | Source


In 1962, the Montreal Canadiens were playing a regular season game versus the Chicago Blackhawks at the old Chicago Stadium. The Stanley Cup was on display in an enclosed glass area in the arena since the Hawks had won the Cup the previous season. During the game, a passionate Montreal Canadiens fan named Kenneth Kilander decided to break into the enclosed area, steal the Cup, and bring it back to the hotel where he was staying. With security being quite slack at the arena, all Kilander had to do was bribe the security officer at the door and walk out with the Cup. The daring scheme was intended to be an April Fool’s Joke and documented by Montreal sportswriters as the plot was carried out. Eventually the Cup’s thief was arrested, imprisoned, and released from jail shortly after paying a $10 dollar fine.


The Cup has been through a number of battles and physical toil throughout its existence, though in 2007 it made its first trip to an actual warzone. Several ex-NHLers flew to Afghanistan with the Stanley Cup to support Canadian military troops who were stationed there at the time. Everyone making the trip over with the Cup was flown in on a giant Hercules transport aircraft and landed safely in the area where the soldiers were located in Kandahar. Famous retired NHL stars Bob Probert and Dave Williams were among the players in the group going over to boost the soldiers’ spirits. During their time in the warzone, they played a few ball hockey games and got a tour of the region. Fortunately, the camp didn’t suffer any artillery attacks or heavy gunfire and the Stanley Cup returned home to become an honorary war veteran.

Want to read more funny stories about the Cup? Check out 5 Funny Stanley Cup Stories in Hockey History (Part 2). Remember to cast your vote on your favorite story in the poll at the bottom of this article.

The Stanley Cup and Members of The Hall of Fame
The Stanley Cup and Members of The Hall of Fame | Source

Stanley Cup Stories from The Wall Street Journal (Video)

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