CBC archival footage documenting the events of the celebratory 1967 Stanley Cup parade held by the Toronto Maple Leafs (Source: YouTube).

He was a wide-eyed rookie on a team of aging veterans when the Toronto Maple Leafs last paraded down Bay Street amidst rows of horses, Stanley Cup in hand. Brian Conacher, now 75, says that the past five decades have been defined by false hope for generations of Leafs fans.

However, Conacher thinks that this year can be different for the Leafs, who entered this season tied with the St. Louis Blues for the longest-active Stanley Cup drought in National Hockey League history at 50 years.

“The Leafs as we see them today are the most hopeful we’ve seen in years,” Conacher said.

“You flip a coin and they have as good a chance of winning in the playoffs as anybody else. The key is to get there.”

The Leafs won their 13th Stanley Cup in 1967 in a six-game series against the Montreal Canadiens. It was the team’s fourth cup in six years, and their most recent to date – a distinction that Toronto fans are reminded of yearly.

David Shoalts has covered the Leafs for The Globe and Mail since 1990. Shoalts attributed decades of mediocrity to the trades made by the team  following their last championship.

“That cup win was actually the worst thing that could have happened to the team because it fooled the managers into thinking that they had a pretty good team,” Shoalts said. “What they actually had was a really old bunch of guys who were on their last gasp.”

Over the next few seasons Leafs head coach and general manager Punch Imlach parted ways with some of team’s best young players – Mike Walton, Pete Stemkowski, Frank Mahovlich and Jim Pappin.

Conacher believes that decades of Leafs management committed the same mistake made by Imlach in the years after 1967.

“They really decimated the organization. The Leafs went into the wilderness and got rid of a lot of good young players,” Conacher said. “Up until now, the Leafs have been notorious for devouring their young.”

Born and raised in Toronto, Conacher knows what winning a Stanley Cup would mean to Toronto – a city often used as the punchline of jokes made by fans of the Montreal Canadiens, who in comparison boast a league leading 24 Stanley Cups to their name.

The Leafs currently sit in eighth place in the Eastern Conference, clinging to the final playoff spot.

This is a picture Leafs fans have seen before. The team made the playoffs six times in both the 1990s and the first decade of the 2000s, but failed to make it to the Stanley Cup Finals once during either span.

“They’ve had spurts of respectability, but the psyche as a group of Leafs fans has never been healthier – just because the team is overachieving right now,” Shoalts said.

That over-achievement is thanks  to the performance of the Leafs’ top rookies: Auston Matthews, Mitchell Marner and William Nylander. Together, they occupy three of the top four rankings in points by a rookie in the league.

Lance Hornby, a reporter who has covered the Leafs since 1992, senses optimism from the fan base, despite the team’s precarious position.

“They’re starting to see hope at the end of the tunnel,” Hornby said.

Entering Saturday night, the Leafs have 18 games left to secure a playoff spot. The Westgate Las Vegas SuperBook currently has the Leafs as 50-1 favourites to win the Stanley Cup, behind 17 other teams.

Although a Stanley Cup is unlikely this year, Conacher can imagine the impact of what a Stanley Cup win half a century in the making would mean to Toronto.

“It would be the fulfillment of a lot of hope and expectations over 50 years. I think the city would go crazy. It would make the Blue Jays or the Argonauts or the Raptors look like a pittance,” Conacher said.

“Maple Leaf Square would be full 50 times over.”