It is now 53 years since Jim Pappin fired the Toronto Maple Leafs to a thrilling Stanley Cup Finals victory over Montreal. The Vietnam War was raging on, The Doors had just released their debut album and NASA was still two years away from putting a man on the moon.

Long-suffering Maple Leafs fans have since endured the longest trophy drought in the NHL. Some have speculated that it will never end, so will they ever win a 14th Stanley Cup?

A Litany of Disappointment

The Brendan Shanahan era has been a source of great disappointment for Maple Leafs fans thus far. The Leafs had a winning record before firing Randy Carlyle as head coach in 2015, which sparked the collapse of their season.

Shanahan set about a “scorched earth” rebuild of the club following a record-breaking 11-game losing streak, but it is yet to bear fruit. They did not qualify for the playoffs in 2015-16, and they have suffered three consecutive first round defeats since then, with the Boston Bruins frequently tormenting them.

There have been green shoots of recovery this season, and they were sitting comfortably in second place in the Atlantic Division before season was suspended as a result of the COVID-19 outbreak. However, if you check out the NHL odds in some emerging markets, you will see that they are considerable underdogs for Stanley Cup glory if and when the season resumes.

The Bruins are 5/1 (+500) favorites, while the Leafs are 25/1 (+2500) outsiders, behind 10 rivals in the betting. It would take a significant upturn in performance levels for the Leafs to lift the famous trophy.

Feb 29, 2020; Toronto, Ontario, CAN; Toronto Maple Leafs goaltender Frederik Andersen (31) takes warmup against the Vancouver Canucks at Scotiabank Arena. Mandatory Credit: Nick Turchiaro-USA TODAY Sports

Blind Optimism

Every year, an optimistic Toronto fan pens a rousing article declaring that they will finally win their first Stanley Cup since 1967. “This is the year that the Toronto Maple Leafs will finally do it, for the first time since 1967,” roared this article before the current season, following a long trend of Leads supporters daring to dream and ultimately ending up crushed.

Why are they such perennial underachievers? After all, the Leafs are among the most valuable sports franchises on the planet. The franchise is worth $1.5 billion, according to Forbes, making them the second most valuable team in the NHL, behind only the New York Rangers.

The Leafs have millions of passionate fans and the Scotiabank Arena is regularly packed, despite having the highest ticket prices in the league. In most sports, this level of financial clout usually translates into trophies.

Yet that has not been the case for the Maple Leafs, for several reasons. First, it must be noted that it is very difficult to win the Stanley Cup in the modern era. Toronto had two great dynasties in the past and racked up 13 triumphs, but that sort of dominance is now unprecedented.

Secondly, they have been poorly run for half a century. They remain hugely profitable due to the passion and blind optimism of the fans, and you could argue that there is little incentive for the owners to strive for on-ice success, as financial success is guaranteed anyway.

There is also a great deal of pressure heaped on the coach and the players. That long trophy drought acts as an albatross around their necks, and they are subject to hyper-criticism from their own fans and from rivals.

You need a bit of luck to win the Stanley Cup, and that has proved elusive for Toronto in recent times. Had a few contentious referee calls gone their way, the drought might have been ended.

Mar 5, 2020; Los Angeles, California, USA; Toronto Maple Leafs right wing Kasperi Kapanen (24) takes the puck down ice in the first period of the game against the Los Angeles Kings at Staples Center. Mandatory Credit: Jayne Kamin-Oncea-USA TODAY Sports

The Need for True Grit

You could also argue that the current Maple Leafs lack the mental fortitude to win the Stanley Cup. They are a young, talented bunch, blessed with some extremely talented stars, but they often wilt under pressure.

Auston Matthews, Mitch Marner and John Tavares are three of the best players in the league. Their presence gives the Leafs a chance in every game. Yet they regularly lose to weaker teams after making far too many inexcusable mistakes, and they fall apart in big playoff games.

Mike Babcock is trying to build a team that is all about speed and skill, but they need to toughen up in big games. They need stronger leaders on the ice. They must improve when it comes to shutting down the opposition.

They have a lot of the necessary ingredients to go on and break their trophy drought. The average age of the team is 26.5 years, which is the fourth youngest in the league. It is a considerably younger group than the last five Cup winners. There is time for this team to grow into champions, if the management can keep them together and find a way to blend speed and skill with the requisite grit, resilience, backbone and discipline.

Long Cup droughts are by no means uncommon in the NHL. It took the Rangers 54 years to win another Cup in 1994. The Blues needed 51 years and it took the Kings 45 years. It will become even more difficult when the league expands to 32 teams, but Toronto certainly has the foundations in place to end its winless streak one day.

There will not be any action for the foreseeable future, and that gives the management plenty of time to plot a route back to the top, so fans can only hope that the Leafs emerge rejuvenated after a lengthy layoff.