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11 Worst Moments in Toronto Maple Leafs History

by: Esteban On  Tuesday, January 15, 2013

worst moments maple leafs history

Last week, just about 10 days before the hurried start of the shortened and condensed 48-game 2013 NHL season, the richest and most valuable team in the league did a very strange thing: the Toronto Maple Leafs threw their entire organizational structure into disarray by firing loudmouth GM Brian Burke.

In fairness, Burke had been a gruff, polarizing character from day one in Toronto. Moreover, his big moves haven’t done anything to help the team win more games. He traded two first round draft picks to Boston for Phil Kessel prior to the 2009 season, and the Bruins used one of those picks to select Tyler Seguin…who helped Boston win the Stanley Cup as a rookie.

However, the timing of the firing is terrible. It could have been done at any point in the prolonged offseason, but no. The Maple Leafs do it right before the start of the season when the team ought to be gearing up for action. It’s just downright comical—unless you’re a Leafs fan, of course.

So today I thought it would be fun to take a look at the worst moments in Leafs history. And I’m not talking about tough or embarrassing losses. Every team has those. I’m talking about those types of not-quite-game-related embarrassments that only the Toronto Maples Leafs (or maybe the New York Islanders) could bring upon themselves.

And why, you ask, does any of this matter to people outside Southern Ontario? I’m not a Leafs-hater. I sympathize with their fans, who deserve better. But I find the Leafs’s ineptitude interesting because they are worth more than a billion dollars. They’re the Yankees, Cowboys, and Lakers of hockey. And they’re ridiculous. So have a look.

11. The Great Poaching

11 Toronto Blueshirts - worst moments in maple leafs history

The Toronto Maple Leafs and the NHL were founded by the Toronto Arenas Company in 1917. The reason they were founded? Because the four other team owners in the old National Hockey Association hated the owner of the Toronto Blueshirts, Eddie Livingstone. So these other teams got together and formed a new league, the National Hockey League, and invited the Toronto Arena Company to form a franchise. And guess where the Toronto Arena Company got its players? You bet: the Toronto Blueshirts.

At first the new Toronto NHL team just “leased” the players from Livingstone’s team. The agreement was that they would go back to the But after the first season. But then the Arena Company had second thoughts and decided to keep these players—which is to say, they stole them.

Nice, huh? If the Leafs were a baseball team they’d have a legendary curse named after their origin.

10. The Great Fire (Sale) of 1919

10 Toronto Arenas hockey club - worst moments in maple leafs history

As you can imagine, when you form a pro sports team by poaching another team’s players, legal disputes arise. And in the case of the Toronto Arenas, this legal dispute created a truly sizable debt. So in 1919, to pay down this debt, the owners sold off all their good players.

Basically the Toronto Maple Leafs were the original Miami Marlins.

Anyway, the result of this fire sale was a horrendous 1918-19 season in which they won just 5 of their first 18 games, had trouble getting enough qualified players to take the ice, and ended up just ceasing operations before the season was over. Their .278 winning percentage is the worst in franchise history.

9. Great Moments in Bad Grammar

9 toronto maple leafs logo - worst moments in maple leafs history

After the Toronto Arenas era, the team was sold to a group of investors who owned a junior team called the Toronto St. Patricks. Then they were sold to another group of investors headed by Conn Smythe (the guy after whom the trophy was named), and that’s when they decided to change the name to the Toronto Maple Leafs—much to the chagrin of hockey-loving grammarians the world over.

So why “Leafs” and not the proper “Leaves”? Well, there are conflicting explanations for this, but the one the team prefers to give is that Conn Smythe named them after the Canadian Maple Leaf Regiment from World War I, and that since “Maple Leaf” in this case is a proper noun, the correct pluralization is “Maple Leafs.”

Maybe that is the real reason. Maybe not. If so, it’s nice that the team was named after a band of selfless Canadian heroes and whatnot, but “Maple Leafs” still sounds pretty silly.

8. Harold Ballard Buys the Maples Leafs

8 harold-ballard - worst moments in maple leafs history

Despite their acrimonious and ultimately illegal founding (as adjudicated by a court of law), the Maples Leafs did quite well for themselves up through 1967. They won the Stanley Cup a solid 13 times through the ’67 NHL season, second only to the mighty Montreal Canadiens. Of course, whereas the Canadiens kept on winning the Cup in the 70s, 80s, and even the 90s, the Leafs just quit the winning cold turkey.

Why? Because they were owned by Harold Ballard, the 7th worst owner in the history of North American pro sports (according to one, ahem, very authoritative source.)

Why was Harold Ballard’s purchase of the Maple Leafs to disastrous? Because he was a crook who stole from the team to pay for (a) renovations on his homes, (b) his daughter’s wedding, and (c) motorcycles for his sons. Then we was convicted of doing these things and sentenced to 9 years in prison, actually serving 3 of those years. And all the while he still owned the Leafs.

7. Bernie Parent for Bob Neely

7 bernie_parent_cover-of-time-magazine - worst moments in maple leafs history

If you’re a hockey fan, you probably recognize Bernie Parent as the guy who won two Stanley Cups with the Philadelphia Flyers and later was elected to the Hockey Hall of Fame. Well, in between stints with Flyers, the Leafs had Parent for two years from 1970 to 1972. And they traded him for some guy named Bob Neely, who scored just 39 goals in 283 career games.

Solid hockey move, wouldn’t you say?

6. What's in a name? (Money.)

6 leafs jerseys no names - worst moments in maple leafs history

The NHL passed a rule in 1976 officially requiring teams to put players’ names on the back of their jerseys so that fans—particularly those watching on television—could more easily identify them. But Harold Ballard? He thought that rule would hurt program sales at Maple Leaf Gardens. So he complied with the letter of the law but not the intent—they stitched the names in blue letters on the blue road jerseys and white letters on the home white jerseys.

If people didn’t already think the team was a laughing stock, they did now.

5. The Imlach-Sittler Feud

5 lanny mcdonals leafs - worst moments in maple leafs history

In 1979, Harold Ballard brought his buddy, Punch Imlich (yep, Punch Imlich) to be the GM of the team. And obviously Imlich immediately begins feuding with the team’s captain, Darryl Sittler. And when Sittler refused to waive his no-trade clause, Imlich did one of the most ridiculous things any GM has ever done: he started trading away Darryl Sittler’s friends—simply out of spite. First it was some future Hall of Famer and future memeber of the 500 goal club named Lanny McDonald. Then is was defenseman Joel Quenneville.

As for Sittler, he eventually gave in and let Imlach win the feud, agreeing to waive his no-trade clause in 1982. Then the Leafs traded their captain and all-time leading scorer…just 84 points shy of becoming the first player to score 1,000 points in a Leafs jersey. Cause that’s how they roll in Toronto.

4. The Tale of Tom Kurvers

4 scott niedermayer devils stanley cup - worst moments in maple leafs history

This one is just hilarious.

In 1989, the Leafs traded their first round pick in the 1991 draft to New Jersey for zero-time All-Star and non-Hall of Fame defenseman Tom Kurvers. Okay, whatever. But then when 1991 rolled around the Leafs found themselves in the league basement, and if they finished that way the Devils would have gotten the #1 pick in the draft and, therefore, the highly touted Eric Lindros.

Why did the Maple Leafs care if the Devils (and not some other team) got Eric Lindros, even though they were in the Patrick Division and the Leafs were in the Norris Division? Who knows. But they did, so they engineered a couple of late-season trades just to make sure they didn’t finish in last place overall in the NHL.

The strategy worked. The Leafs finished third-last instead of last, and with the #3 pick in the draft the Devils had to settle for…Hall of Fame defenseman Scott Niedermayer, with whom they won three Stanley Cups.

Good work, Buds.

3. Larry "Scapegoat" Murphy

3 larry murphy leafs red wings stanely cup

In 1995, the Maple Leafs acquired two-time Stanely Cup winner Larry Murphy from the Penguins. Great deal, right? Hometown guy, top player in the league—a real no-brainer. The only problem was that the Leafs were absolutely atrocious and no one player could change that. So the fans took out their frustrations on the team’s highest paid player, booing Murphy (again, the hometown guy) every time he touched the puck. And it’s not like he didn’t play well. In his first full season in Toronto, Murphy recorded 61 points. But the fans wouldn’t stop, and so they Leafs had to trade him.

Murphy’s destination, of course, was Detroit, where he won two more Stanley Cups.

2. The Squirt

2 tie domi fights fan - worst moments in maple leafs history

For a tough guy, Leafs fan favorite Tie Domi apparently had pretty thin skin. During a game in Philadelphia in 2001, Domi was sitting in the sin bin when something a fan said really ticked him off—so his squirted his gatorade at him. The fan then went after Domi, fell into the box, and got his clock cleaned. And while it was the fan who got punched in the face, it was the Maple Leafs who got the black eye.

1. The Post-Lockout Depression

1 leafs fan bag on head - worst moments in leafs history

Without a doubt the worst period in Maple Leafs history is the one they are currently in. Since the 2004-05 NHL lockout that cancelled the entire season, the Toronto Maples Leafs—the richest team in hockey in the most hockey-mad city on earth—have not even made the playoffs. Seriously, not once.

Do you know who has made the playoffs since the lockout? EVERYBODY. The Coyotes, the Thrashers (now Jets), the Lightning, the Panthers, the Bluejackets, and even the Islanders. THE ISLANDERS!

But not the Leafs. And that pretty much says it all.