Toronto Maple Leafs now own the saddest stat in NHL history

When was the last time Toronto won the Stanley Cup? Maple Leafs fans are going to hear that question more times than they want to until it happens again. 

Stop me if you’ve heard this one before, but it’s a tough time to be a Maple Leafs fan.

After being the punchline of every joke since blowing a 3-1 lead to the Montreal Canadiens in the first round of the Stanley Cup Playoffs, there punches just keep on coming as today officially marks the day that they pass the New York Rangers for the longest Stanley Cup drought in NHL history at 19,786 days.

The Maple Leafs last won the Stanley Cup in 1967, when the NHL was a six team league. They haven’t even made the Stanley Cup Finals at all during that stretch, and own the current longest drought there as well. To make matters even worse, they also currently own the second longest playoff series win drought at 16 seasons since they won a playoff round. Only the Florida Panthers have a longer drought at 24 seasons.

Last time Toronto won the Stanley Cup

It’s a question that will be asked more and more now that the Maple Leafs own the streak: When was the last time Toronto won the Stanley Cup?

On May 2nd, 1967, the Toronto Maple Leafs defeated the Montreal Canadiens 3-1 in Game 6 of the Stanley Cup Final to win their 13th Stanley Cup in franchise history. The game winning goal was scored by Jim Pappin late in the second period, and Maple Leafs captain George Armstrong put the game away with an empty net goal with less than minute to go in the third period.

Just a day prior to the Maple Leafs Stanley Cup victory, Elvis Presley and Priscilla Beaulieu were married in Las Vegas. Two days later, the Lunar Orbiter 4 spacecraft was launched to orbit the moon. Later in May, the 25th amendment of the Constitution was ratified. The most popular song on the day the Leafs hoisted the Stanley Cup was “A Little Bit Me, A Little Bit You” by The Monkees.

You know you might be a cursed franchise when your team’s last modicum of success predates the moon landing by two whole years.

Could any team break this record anytime soon?

Well first and foremost, for anybody to beat this record it would obviously require the Maple Leafs to stop setting the record first. So as long as Toronto remains cursed and hapless, this record is going nowhere anytime soon. However, if the Maple Leafs were to somehow break this drought in relative short order, there are teams that could take over the top of this list before too long.

Of course there are teams that have never won the Stanley Cup before, but the two teams that are even close to the Maple Leafs drought are the Buffalo Sabres and Vancouver Canucks, who have both never won the Stanley Cup since their inception in the league in 1970. Their drought only trails the Maple Leafs by three seasons, and barring some miracles, they will also be passing the New York Rangers old record within the next few seasons.

However, both Buffalo and Vancouver have actually been to a combined five Stanley Cup Finals during that time (Buffalo 2, Vancouver 3), so they’ve at least had the opportunity to bring home the Cup. The Maple Leafs have not. In fact, the Maple Leafs drought gets even sadder when you compare to teams on similar Stanley Cup droughts.

Only two more teams have Stanley Cup droughts longer than 40 years, those being the Philadelphia Flyers and Arizona Coyotes. The Flyers have been to six Finals during their drought, and while Arizona has never been to a Final, they’ve been a Conference Final as recently as 2012.

After another heartbreaking first round defeat for the Maple Leafs at the hands of the Canadiens after an outstanding regular season, and watching that same Habs team march all the way to the Final, this is just another punch to the gut for the long suffering organization. Maybe they can channel all of that frustration into a run next season with all of the talent that they have right now, but that opportunity is still months away at minimum. They’ve a long offseason ahead of them first, and a fanbase that is understandably out of patience.