Although the Toronto Maple Leafs are out of the playoffs, the team and its fans are excited to see what will come next for this team that has an especially bright future. The young Leafs are on an upswing and while seriously challenging for a Stanley Cup is still in the distance, it’s something that, for once, seems achievable in the future with the Auston Matthews-led core.
That idea of the Leafs together with the Stanley Cup wasn’t always so unfathomable. In the 22 years from 1945-1967, Toronto won nine Cups, included two stretches when they won it three times in a row. As we all know, they’ve been cursed since that ’67 win.
Over the years the Leafs have certainly had some highs, but far more lows. On May 2, the 50th anniversary of the last time the Leafs lifted Lord Stanley’s Cup, we look at some of the worst moments from the past half-century.
We won’t rank them. They’re all awful.
LONG LIST OF REALLY BAD TRADES
The Leafs have a long history of some pretty poor player swaps and your opinion on which one is the worst may relate to how old you are.
We’ll start with the recent past and perhaps the one that stands out most today: Brian Burke’s decision to trade two first-round picks and second-rounder to the Boston Bruins for Phil Kessel.
At the time, Burke thought Kessel could help the Leafs back towards the playoffs. Instead, they ended the year as one of the worst teams in the league and the Bruins picked Tyler Seguin with the second-overall pick. The next season Toronto improved, but still handed the ninth-overall pick to Boston, which they used to take Dougie Hamilton. The second-rounder became Jared Knight, who played in Denmark this season.
Also in the recent past: Andrew Raycroft for Tuukka Rask. Raycroft was two seasons removed from winning the Calder Trophy and Rask had been drafted 21st overall the year before the trade.
But you know Toronto’s trade problems go back much further than that.
We’ll also note the Tom Kurvers trade from 1989 with New Jersey, perhaps the most disastrous swap in team history. Acquiring the defenceman for a 1991 first-round pick, Toronto bottomed out and actually had to make some trades just to stay out of the basement and hand super prospect Eric Lindros to the Devils. Instead, they ended up with the third-overall pick, which actually made the trade even worse since New Jersey took Scott Niedermayer.
There’s also the Russ Courtnall trade in 1988, when the Leafs sent him to rival Montreal for John Kordic. Courtnall went on to play 11 more NHL seasons, hitting at least 60 points on five occasions. Kordic played just 104 games for Toronto.
DARRYL SITTLER CUTS THE CAPTAINCY OFF
The current Maple Leafs don’t have a captain yet (hello Auston Matthews) but that’s better than having your captain be so angry that he literally cuts the ‘C’ off his jersey.
This happened with Sittler in the 1979-80 season. 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.
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.
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.
1993, 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 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.
1994, THE CANUCKS, AND ANOTHER BLOWN OPPORTUNITY
The Leafs had another golden opportunity to reach the Stanley Cup Final in 1994 and we’re not going to let you forget about this disappointing finish.
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.
So 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. But, 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.
2000, 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 on the scoreboard, with four of the first five games being decided by one goal. But let’s be honest, the Leafs weren’t exactly running up their Corsi totals. 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 Devils went on to win their second Stanley Cup and started a stretch where they made the Cup final in three of four years.
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 and nine of their 10 losses came in regulation, so they didn’t even get a point. The bad stretch pushed the Leafs all the way to 12th in the conference and they now had a minus-9 goal differential. 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 times.
“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.”
Toronto went 5-17-3 to finish and ended up with the fifth-overall pick in the draft, which they used to take Morgan Rielly.
Bonus item: In 2013-14, the Leafs again were in the running for the playoffs, but the 18-wheeler appeared again as the team went 2-12-0 in their last 14 games.
IT WAS 4-1
TIM LEIWEKE PLANNING THE PARADE
When the Leafs brought in 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.
“I have it planned out, and it’s going to be fantastic,” Leiweke said in a Bloomberg interview. “If you can all dream about that and get that in your mind, we’ll have something we’re all driven toward.”
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 Leafs, unless in jest.
The Leafs were pretty close to hitting their lowest point in 2014-15 and a rough start to the season set a miserable tone. Fans were fairly regularly tossing jerseys on the ice in protest of the sub-par product, a fan in Buffalo had tossed a beer on to their bench that exploded on some players, and two days after an embarrassing 9-2 loss to Nashville, the Leafs players answered back with what was translated as a protest of their own.
Following a 5-2 win over Tampa Bay, which snapped a three-game losing streak, the team bucked tradition by not raising their sticks to salute the home crowd. Some of the players said it wasn’t intended to slight the fans, but was planned in advance as a “shake up” of the norm. But others, such as Cody Franson, were surprised by the move and had started skating towards centre to do the salute, when he noticed his teammates leaving the ice.
“We have great respect for our fans. We’ve got unbelievable fans, and we know how much support we have. This by no means was an attack on our fans or anything personal,” Dion Phaneuf said. “This was about our team and changing up our routine.”
The jerseys continued to fly through most of the season that ended with their lowest full-season point total since 1991-92. The fan protest became so well-known around the league that Canadiens goalie Carey Price made a joke about it at the All-Star Game.
ONE LOTTERY BALL AWAY FROM LANDING CONNOR MCDAVID
When the 2014-15 season mercilessly ended, the Maple Leafs had the fourth-best odds of winning the draft lottery and the right to choose Connor McDavid first overall. It would have immediately changed the fortunes of the franchise.
First, the way the lottery works is each team is assigned a random collection of four numbers and the teams with the best odds get the most number of combinations. While drawing for the first-overall pick, Toronto had hit on each of the first three numbers. At that point, they had the best odds to have the next number drawn as well.
As we know, the last number completed Edmonton’s combination, and the rest is history.
Toronto got Mitch Marner fourth overall that year and were again terrible the next season, when they won the lottery and took Auston Matthews.
So that last one isn’t all bad.