When I was a boy, the Toronto Maple Leafs were an important part of my life. I knew every player’s stats, bio and background. When they won the Stanley Cup in 1967, the schools were closed early to attend the victory parade. I was there hours before. It was their 4th Cup in 6 years. I thought they good times would never end. But it did. 54 years have passed, and they haven’t returned to the Cup finals let alone winning Lord Stanley’s fabled trophy.

The franchise is over 100 years old having been established in 1917. Conn Smythe purchased the team in 1927 and it was a dominant franchise is the original NHL six-team league that didn’t expand until 1967. By then the Leafs had won 13 Stanley Cup championships. But in 1961, Conn Smythe decided to cash out and sold the team to a partnership of sone Stafford Smythe, John Bassett and Harold Ballard. By 1971, Ballard was the sole owner after Bassett sold out after a dispute and Stafford Smythe had passed away. That’s when the franchise went into a death spiral that it has never fully recovered despite new owners and a parade of general managers, coaches, failed saviours, bad trades, and horrible draft picks. There have been seasons that have look promising that ended in failure and frustration. It’s been hard on Leafs fans. Meanwhile the owners rake in the money with season after season of sell outs along with the highest ticket prices in the NHl.

I’ve compiled a list of the worst moments in the franchise’s history.

ROGER NEILSON AND THE PAPER BAG

In 1978-79, Neilson’s second behind Toronto’s bench, Ballard fired his head coach after a bad stretch of games. However, he was unable to find a new coach in time to get behind the bench for Toronto’s next game, so he re-hired Neilson. Trying to take advantage of the publicity, Ballard wanted Neilson to return with a bag over his head as The Mystery Coach. Neilson refused. He didn’t last the rest of the season anyway.

DARRYL SITTLER RIPS THE “C” OFF HIS JERSEY

In the 1979-80 owner Harold Ballard had brought Punch Imlach back as general manager, his third go-around with the team, and he immediately went to war on his players, more notably his star player Darryl Sittler. Since Imlach couldn’t get rid of Sittler due to the captain’s no-trade clause, he instead traded Sittler’s friend Lanny McDonald. In response, Sittler took scissors to his jersey and cut the ‘C’ right out. Citing the stand-off with his GM, Sittler resigned the captaincy.

WAYNE GRETZKY, AND THE HIGH STICK THAT WASN’T CALLED

It’s the play that has made Kerry Fraser an embedded piece of Leafs Lore. In 1993 we nearly got a Leafs-Canadiens Stanley Cup Final, which of course under the modern league alignment can never happen. With Doug Gilmour, Wendel Clark, Dave Andreychuk, Glenn Anderson, etc., the Leafs had one hurdle between them and their first Cup final appearance since 1967: Gretzky’s Los Angeles Kings.

With the Leafs leading the series 3-2 and Game 6 tied in overtime, Gretzky high-sticked Leafs captain Doug Gilmour, which went uncalled by referee Fraser. Toronto should have been put on the man advantage and a goal would have clinched a berth in the final. Instead, the unpenalized Gretzky scored the game-winning goal shortly after. Los Angeles went on to win Game 7 in Toronto 5-4…Gretzky scored three times and added an assist.

THE CANUCKS, AND ANOTHER BLOWN OPPORTUNITY

The Leafs had another golden opportunity to reach the Stanley Cup Final in 1994. Toronto finished third in the Western Conference with 98 points but didn’t face either of the conference’s top two seeds because both Detroit and Calgary were upset in the first round. In the conference final, Toronto faced the seventh-seeded Vancouver Canucks, who Toronto accumulated 13 more points than in the regular season. Toronto won Game 1 in overtime but scored just three goals over the next three games to fall behind the Canucks 3-1 in the series. In Game 5, Toronto took a 3-0 lead and seemed poised to head home for the last two games of the series. The Leafs being cursed and all, they coughed up the lead and lost 4-3 in overtime. The team wouldn’t win a playoff series for another five years.

THE DEVILS, AND THE PUTRID OFFENCE

The Leafs won their division with a 100-point season in 1999-2000, and after getting past Ottawa in the Battle of Ontario in Round 1, they faced the Dead Puck Devils, a defensively stout team with one of the all-time greatest goalies in Martin Brodeur behind it all. It was a close series, with four of the first five games being decided by one goal. But Toronto had managed just 21, 20, 23, 22 and 25 shots against Brodeur in the first five games, but were still in it, down 3-2 in the series heading back to New Jersey. Game 6 is where it all fell apart though, and it really distinguished how far apart these teams actually were. Toronto was embarrassed and put only six shots on goal all game, ultimately falling 3-0.

THE 18-WHEELER

On Feb. 1, 2012, things weren’t so bad for the Leafs. Their 28-20-6 record was good enough for sixth place in the Eastern Conference and, unlike all the teams chasing them, they had a positive goal differential.

But, of course, it didn’t finish so smoothly. Toronto won just once over its next 11 games. The bad stretch pushed the Leafs all the way to 12th in the conference. Head coach Ron Wilson was fired, and then-GM Brian Burke uttered these now-famous words, which you’ll commonly see referred to in Leaf Land in nervous.

“I’ve never had a team fall off a cliff like this before, I’ve had dips, slumps, rough patches, but this is akin to an 18-wheeler going right off a cliff, I don’t know what happened.”

4-1 LEAD AGAINST THE BRUINS

After missing the playoffs for several years, in 2013, the Maple Leafs were back and up against the Boston Bruins. The Leafs had a 4-1 lead in Game 7 with five minutes to go. After a nine-year post-season hiatus, it looked like Toronto was set for a playoff run. The fans in Boston were streaming into the exists.

But then, an epic collapse. The Bruins scored three goals in quick succession to tie the game 4-4. The game went to overtime, and Boston centre Patrice Bergeron, who had the game-tying goal, scored 6:05 into OT to leave the Leafs and their fans stunned.

TIM LEIWEKE PLANNING THE PARADE

When the Leafs brought in Tim Leiweke as the new CEO of MLSE, he came with bold ideas of where to take the company and he had special plans for the Maple Leafs. Just a couple months after blowing that 4-1 lead mentioned above, Leiweke mentioned that he already had a parade route planned out for when the team did win the Stanley Cup. Leiweke had great success leading the Los Angeles Kings to Stanley Cup glory, so he came in full of confidence. And while he should be considered a success overall in his time with MLSE, he, obviously, wasn’t able to get that Cup. The parade route is something that just shouldn’t be mentioned with the Leaf fans, not even as a joke.

IT HAPPENS AGAIN AGAINST THE CANADIENS

It happened again. The Maple Leafs run roughshod in the Canadian Division formed during the Covid-shortened 2021 season. It was their best chance at a Stanley Cup in decades. After a 3-1 series lead and all the momentum to boot, the Toronto Maple Leafs’ path to a deep playoff run never seemed so clear. But Toronto’s history repeated itself in a cruel manner as they dropped three consecutive games to the bottom-ranked Montreal Canadiens to bow out of the opening round of the 2021 playoffs. It was the Habs who seemingly figured out how to stop Toronto’s potent offense dead in its tracks in a 3-1 victory on Monday to take Game 7.

SEX ABUSE

The worst event Maple Leaf history emerged in 1997, when it was learned that some employees of the Maple Leaf Gardens had sexually abused young boys in the 1970s and 1980s. Martin Kruze was the first victim to come forward. His story of abuses beginning in 1975 prompted dozens of other victims to come forward. In October 1997, Gordon Stuckless pleaded guilty to sexually abusing 24 boys dating back to 1969 and was sentenced to a jail term of two years less a day. Three days later, Kruze committed suicide. In 1999, former usher John Paul Roby was convicted of sexually molesting 26 boys and one girl. He was subsequently declared a dangerous offender and could have been kept in prison for the rest of his life. Roby died in Kingston Penitentiary from an apparent heart attack in 2001. In 2002, former Gardens security guard Dennis Morin was found guilty of sexual assault, indecent assault and gross indecency for incidents involving teenage boys.