Since dominating the 40s and 60s with nine combined Cups, the Leafs have been on a horrendous downswing.
Although they sell tickets like crazy, the fans have come to know much hardship. Horrendous trades, bad signings, and terrible management have haunted the team and tortured fans. Trading the pick that became Scott Niedermayer for average defender Tom Kurvers is right at the top of that list. Trading the picks that became Tyler Sequin and Dougie Hamilton for Phil Kessel is an eerily similar lowlight.
A city like Toronto is wonderful to play in when you're winning but equally uncomfortable when losing. And this franchise has lost a lot. The Sundin/Quinn era brought about some strong regular seasons but never getting close to a Cup stings. This pain breeds negativity and hatred towards players. Players that make mistakes are scapegoated for the franchise's woes. A defender blowing coverage, a forward missing an empty net, or a goalie who just can't cut it, all earn the revulsion of a passionate yet unlucky fanbase.
The fans have kept this team financially successful throughout years of mediocrity. They show up no matter how bad the on-ice product is. They might be wearing paper bags and throwing their jerseys on the ice but they're still there. And that gives them the right to hate. They love this team dearly and to see it in such a poor state over the years hurts deeply.
So let's take a look at the biggest magnets for decades of Leaf self-loathing.
15 David Clarkson
July 1st hits, you're a free agent and your childhood team comes knocking on the door offering you a deal worth about triple you are as a player. Do you flat out refuse it? Hell no. Anybody would have taken the seven-year, $36.75 million deal David Clarkson was given by Toronto in the 2013 offseason. That contract is the sole reason he was loathed by his hometown fans.
Clarkson was once a 30-goalscorer and even though it was ridiculous to think a third liner would do that again, the contract raised expectations and Clarkson was a total bust as a Maple Leaf. They traded him to Colombus in just his second year for Nathan Horton, who will likely never play again.
14 Mike Komisarek
Similar to David Clarkson, Mike Komisarek was hated by Leafs fans due to getting a huge free agent contract, being signed away from the rival Montreal Canadiens. The LEafs signed him for five years at $4.5 million a season in 2009. Komisarek's slow skating was always masked by the work of Andrei Markov in Montreal, but without that security blanket, Komisarek's weaknesses were exposed. He was prone to taking dumb penalties and constantly being beaten on rushes. Komisarek was eventually sent to the minors and subsequently bought out.
13 Shayne Corson
Shayne Corson's on this list really because well, every fanbase hated Corson. Whether he was fighting with a young Jason Arnott in Edmonton over a credited assist or he was getting in bar fights in Montreal, Corson never really endeared himself to fanbases. Coming off a run in Montreal, it's safe to say Leafs fans were less than enthused about an aging Corson coming to don the blue and white. Corson would last three years in Toronto becoming injury prone and putting up subpar numbers.
Corson infamously 'resigned' from the club after he was scratched for a playoff game in 2003.
12 Bryan McCabe
McCabe's exciting brand of 'defense' endeared him to fans for his first few years in Toronto. He skated well, made big hits, and played with emotion. Perfect for the big city.
But defensemen that skate fast, go for big hits, and play with emotion also give up the puck and cause odd-man rushes. Fans grew tired of this and with an underperforming team (they were really tired of that) McCabe became an easy target.
Couple this with a giant contract that included a no-movement clause and the fanbase really began to hate this guy.
Toronto has lacked a legitimate No.1 defenseman for years. This has put unfair pressure on everyone from McCabe, to Kaberle, to Phaneuf.
11 Scott Clemmensen
Mostly known for backing up workaholic Martin Broduer, Clemmensen managed to piss off Leaf fans playing for and against Toronto.
At the end of the 2006-07 season, the New Jersey Devils could put Toronto in the playoffs with a win over the Islanders. The game came down to a shootout, where Leaf fans watched helplessly as Devils goaltender Clemmensen played like hot garbage, destroying their playoff dreams.
Terrible Leaf GM John Ferguson Jr actually signed him to a minor-league contract after this. Fans were livid to see Clemmensen take the AHL starting position away from their (at the time) highly touted prospect Justin Pogge, playing every AHL playoff game.
10 Andrew Raycroft
It seems a lifetime ago that Raycroft won the Calder for rookie of the year. It was all downhill from there.
In one of the more recent terrible Leaf trades, Toronto dealt Boston their future franchise goaltender Tukka Rask for the one-season wonder.
Raycroft crumbled under the pressure, never matching his previous game, as Rask went on to win a Stanley Cup.
Impressive that it's not the franchise's worst ever trade.
9 Larry Murphy
This is why you can't have nice things.
Although the defenseman scored 100 points in 151 games he was still viciously booed by the fans, scapegoated for their troubles on the ice.
Detroit absolutely swindled the Leafs in a trade for Murphy, giving up only 'future considerations' while leaving Toronto to pay 2/3 of his salary!
Murphy went on to win two Cups with Detroit, to go with his two from Pittsburgh. He is a Hall of Famer and proof that Toronto is arguably the toughest city to play hockey in.
8 Jason Allison
A great example of the type of player that struggled after the 2004 lockout. Allison was always a slow skater that put up points, but in a sped-up NHL he stuck out much more.
He still managed 60 points in 66 games but his ugly skating would not be ignored. He wasn't offered a contract after his lone Toronto season, retiring to run his horse farm.
A fascinating player that put up a respectable 485 points in 552 games of mostly low-scoring hockey.
7 Dmitri Khristich
After two seasons in Boston of 66 and 71 points, an arbitrator awarded Kristich a $2.8 million salary. The Bruins made history as the first NHL franchise to walk away from a player after losing an arbitration case.
He would prove Boston right with two awful seasons in Toronto, scoring 30 points the first year, and only nine the next. He was injury prone and mostly ineffective. Fans found nothing to like.
6 Andy Wozniewski
Affectionately called 'Andy WasNewToSkating'.
Although Wozniewski never played more than 48 games in a season for the Leafs, he has a surprising amount of 'low-lights' detailing his frequent defensive mistakes. One instance was so bad that Score analyst Steve Ludzik couldn't help but say "Are you sh**** me Wozniewski" on live television while reviewing the play.
I'm sure much worse was heard in the stands every time he hit the ice.
5 Aki Berg
Yet another terrible Toronto trade saw serviceable Adam Mair and the pick used to draft Mike Cammalleri go to L.A. for Berg.
Berg was drafted third overall but could never live up to the hype. He was best known for being slow and giving up the puck. Fans held their breath when he was on the ice, many passing out in the time it took him to skate back to the bench. His mistakes were extra noticeable as he performed them at the speed of sloth.
4 Jonas Hoglund
It was running joke in Toronto that Sundin rarely had linemates of his calibre. For many fans, Hoglund was the punchline for that joke.
Fans liked him at first. He scored 29 in his first year with the team, after just eight goals with rival Montreal the year before. Leaf fans loved seeing an ex-Hab perform so much better. But it quickly dropped off from there.
He would have one more 20+ goal season, but would follow up with just 26 over the next two campaigns.
Fans claim Hoglund robbed Sundin of assists and the Leafs of wins with the many empty nets missed.
3 Dion Phaneuf
Phaneuf stormed into the league, hitting and shooting like a powerhouse veteran. Toronto was ecstatic to acquire him for mostly spare parts, naming him captain just a few months later.
But he's yet to regain that initial dominance. Perhaps on a more talented team he could thrive as a great number-two but he struggles mightily in the top dog role. He also has a tough time as captain in the hockey-mad market, frequently angering fans with his bewildering responses.
Like most Toronto defensemen, Phaneuf has been pushed out of his comfort range and scapegoated as a result.
2 Phil Kessel
Kessel did not charm Toronto. He hated the media, started each season out of shape and had the leadership qualities of buttered noodles. Not the qualities you want in your highest paid player. He consistently scored points and goals but on a team guilty of playing terrible defense and lacking work ethic, he stood out to fans as a symbol of their worst symptoms.
To make matters worse, Brian Burke traded two first-rounders for him that would become Tyler Sequin (Cup winner) and Dougie Hamilton (better than Phaneuf). This deal haunted Kessel throughout his time in Toronto, constantly reminding fans of yet another terrible Toronto trade.
1 Harold Ballard
The players on this list were hated for bad plays and contracts, but there's one man that caused more grief than any of them combined.
Known as the worst owner in NHL history. Ballard tops this list because he negatively impacted the team for decades with an infamous reign of terror.
This is a man accused by the government of stealing the team's money to renovate his house and cottage, rent limos for his daughters wedding, and buy motorbikes for his sons.
Speaking of money, he fought to control the player salaries and despised the union. When his star player Darryl Sittler supported the NHLPA, Ballard took it very personally and traded Sittler's friend (and star player) Lanny MacDonald.
This trade rocked the team, and they posted a losing record for 13 straight seasons! Although the team was pathetic on the ice, the franchise was actually quite profitable. Ballard wasn't paying big money to players yet tickets were selling like crazy. The fans have to take some of the blame for rewarding this behavior.
For this list Ballard sits atop all of the players. Just the way he liked it.
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