Top 25 Worst Management Mistakes in Toronto Maple Leafs History

The bottom line about the Toronto Maple Leafs is that they have not won a Stanley Cup since 1967 and this has been the result of several terrible mistakes by management. There have only been a few years of success when they moved deep into the playoffs as recent as the 1990s but the majority of the decade of the 2000s and 1980s were epic failures. This is highlighted by the Leafs not even making the playoffs nine of the past ten years and ten of the last eleven if you count this year.

Losing is a part of being a fan of any team, but it is just how the Leafs have lost that really hurts. During the past decade the Leafs would tease their fans by missing the playoffs by only a couple of points and the one year the team did make the playoffs was the ultimate in heart ache. The Leafs came back from being down 3-1 in the series against the Bruins in 2013 to tie the series only to lose the series in seven games in overtime. If that was not bad enough the Leafs led the game 4-1 with less than ten minutes left and imploded in a way I have never seen in a hockey game before.

With all these failures management has decided to take a rebuilding approach and gut the team and start from the very bottom. The team might not experience any success for a few years but the Leafs are finally catching up to the rest of the successful teams in the NHL. Only time will tell if this works out in the long run. It can't be much worse!

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25  25. Tim Connolly Signing


The only reason this move is not higher on the list was that it was only for two years. In those two years Tim Connolly would accumulate a grand total of 36 points in 70 games for the Maple Leafs and in one of those years he spent the entire year on the Leafs minor league affiliate. Not exactly the best way to spend $9.5 million on a player that had a career high of 65 points during the 2009-10 season. It's a cautionary tale of signing a guy after one great year.

24 Mike Komisarek Signing


The signing of Mike Komisarek is another move in the long list of awful moves by the Maple Leafs that come off a career season of a player. Komisarek was voted to the January 2009 All Star game and in July of that year he signed a five-year contract with the Leaf’s averaging $4.5 million a year. Four very uneventful years later Komisarek was waived and has not been able to stick with an NHL team playing a grand total of 32 NHL games since then.

23 Re-signing Joffrey Lupul

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The ironic thing about Joffrey Lupul is that he is a good player and an All Star when playing with the right players and also part of one of the best trades in Maple Leafs history. Unfortunately signing a player to a five-year, $26.25 million contract who has a history of injury issues is just not wise. I feel for Lupul because he is talented and a lot of his injuries with the Leafs are of the freak variety, but he is just another wasted contract on this team with him being stuck with mediocre players.

22 John Kordic Trade

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This move is on the list because it was something that was talked about during the entire decade of the 1990s and continues to be talked about as one of the worst trades in Maple Leafs history. Kordic did not much play much for the Leafs and had a history of alcohol and drug abuse which ultimately led to his death in 1992. Gord Stellick traded Russ Courtnall who was part of the infamous “Hound Line” with Wendel Clark and Gary Leeman for Kordic. Courtnall would have a nice career in the NHL amassing a total of 744 points in 1,029 games.

21 David Clarkson Signing

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Not much to say about this signing other than that it was another knee jerk reaction to a player coming off a career year. During the 2011-12 season, Clarkson scored 30 goals and the Leafs rewarded him with a ridiculous seven-year contract worth $36.75 million. Since then Clarkson has been traded to the Columbus Blue Jackets and has come nowhere close to matching the play his enormous contract would entail. His time with the Leafs was a complete disaster, one that everyone saw coming given his ridiculous contract.

20 Dmitri Khristich Trade

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The reason this trade was bad was not because of the move itself but the following release of Steve Sullivan that resulted from the move. Khristich only played two years for the Leafs and was ultimately traded back to the team that originally drafted him. Sullivan last played in the NHL during the 2012-13 season and since then has retired. He accumulated over 700 points during his career which is similar to what Russ Courtnall achieved and which is odd because they are of the same build and played the same style of game and were fan favorites during their stays in Toronto.

19 Naming Dion Phaneuf Captain

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This is another item on this list that has a double edged sword. Acquiring Dion Phaneuf in 2010 was a steal as no one of substance was given up to acquire his services but naming him as captain the following summer was a terrible mistake. Phaneuf is a solid number two or three defenceman on most NHL teams but naming him captain after less than a season with the team put unnecessary pressure on Phaneuf and he was never able to play to his potential.

18 The Departure of Mats Sundin

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Mats Sundin's departure from the Leafs is on this list because despite being one of the most successful and popular captains in their history he left the team in 2008 like he was not here at all. This was largely due to the management not doing anything to appreciate Sundin during his stay here and since then only a short tribute has been given since he has left. Upsetting for a player that is now a Hall of Famer and one of the greatest ever to play in the NHL.

17 Jeff Finger Signing

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This was perhaps the worst move during the Cliff Fletcher era and that is saying a lot because the majority of his tenure in Toronto was a success. Finger signed a four-year, $14 million contract during a time when that kind of money was not being thrown around and was limited to the stars of the game. Finger lasted two years in Toronto and became what he always was prior to his big deal, a decent sixth or seventh NHL defenceman. He spent the final two years of his contract in the minors as no other team was interested in him due to his large salary cap hit.

16 Firing Pat Quinn

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Pat Quinn had success wherever he coached and his three Jack Adams awards as coach of the year are a testament of that. This success was repeated with the Maple Leafs and they recorded 100 points and made the playoffs in every year but his last in 2005. During his tenure with the Leafs Quinn was able to change the Leafs from a boring, checking style of play into one of the highest scoring teams in the league and that he was let go in 2005 because of a possible rift with management, which is just typical of the franchise.

15 Firing Pat Burns

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During his tenure with the Leafs, Pat Burns won a Jack Adams award and led the Leafs like Quinn to two conference finals appearances losing to the Kings and the Canucks respectively. Burns made hockey relevant again in Toronto and that is why letting him go was a hard pill to swallow. Burns would end his coaching career with one more Jack Adams award and and his only Stanley Cup ring with the New Jersey Devils and his commonly known as one of the best coaches in NHL history.

14 Phil Kessel Contract

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At the start of the 2013 season Kessel signed a contract that would make him earn $8 million a year until the 2021-22 season. This type of deal should be limited to the elite superstars of the NHL and even though Kessel has been an elite scorer through most of his career, the past two seasons of his career have clearly shown his limitations and his inability to step up his game to that elite superstar status. Subsequently, he continues to struggle in Pittsburgh where he was traded to last year and he is having one of the worst years of his career playing with the likes of Malkin and Crosby, two of the biggest names in the NHL.

13 Dion Phaneuf Contract

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Shortly after signing Kessel to his extension the Leafs brought back Phaneuf until the end of the 2021 season. His cap hit is $7 million for the duration of the contract and this is just way too much for a defenceman that could be replaced for at half the price if not more. I am not a Phaneuf hater but he did not provide anything to the team during his stay and it is a miracle that they were able to trade him to the Ottawa Senators this season. As mentioned perhaps if Phaneuf was not named captain of the Leafs he would have had more success but as it stands his nickname “pylon” Phaneuf is relevant and he should never have signed this contract in the first place.

12 Wendel Clark Trade

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There are a couple of reasons why this transaction is one of the worst in Maple Leafs history. First of all, the move was made in 1996 largely due to the pressure management received from fans to reacquire his services despite being traded for Mats Sundin, one of the most successful Leafs and best captains in their history. Secondly, after a couple of good years with the team, Clark fizzled and could have been dealt for a first round pick to Pittsburgh in 1997 but he wound up walking as a free agent to Tampa Bay following the 1996-97 season. Cliff Fletcher’s hesitance to move Clark to Pittsburgh brought about the quote “draft schmaft” which stuck with the team throughout the entire 1990s and most definitely hindered the Leafs' future development.

11 Host of Awful Draft Picks

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From Jeff Ware to Luca Cereda there are a handful of Leafs picks that never amounted to anything and played less than 100 games in the NHL. Currently all teams in the NHL try to stockpile their draft picks because in the fiscally responsible times of today, this is the only way to build a successful team. As a matter of fact, most of the successful teams in the modern NHL built their teams through the draft. The Blackhawks who are the most successful team in the decade of the 2000s with three championships drafted Jonathan Toews and Patrick Kane in the first round, the L.A Kings also drafted Drew Doughty in the first round and the arguably the most successful team in sports over the past 30 years the Detroit Red Wings drafted all of their stars. What do the Leafs have to show in their history? Nothing much.

10 1988 Draft

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The next two spots in this list will illustrate how terrible the Leafs have been in drafting prospects. In 1988 Gord Stellick picked Scott Pearson with the sixth overall pick and the likes of future hall of famers Jeremy Roenick, Teemu Selanne, Rob Blake, Mark Rechhi and Alexander Mogilny were still available. Yikes. Solid NHLers such as Rod Brind'Amour, Tony Amonte and Joe Juneau were also picked after Pearson and all had solid NHL careers. Pearson on the other hand only totaled 98 points in 292 NHL games.

9 1989 Draft

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What makes this draft worse than the 1988 draft was that Gord Stellick and the Leafs management had three first round draft picks and all of them bombed in the NHL. Their first pick was third overall and they selected Scott Thornton, but the Leafs also picked Rob Pearson and Steve Bancroft in the first round. Available after these picks were once again future hall of famers such as Pavel Bure, Sergei Federov and the best defenceman of the modern era, Nicklas Lidstrom. The draft is a crap shoot for all teams involved but the history that the Leafs have is one of the worst in pro sports.

8 Jason Smith Trade

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This was another one of those moves Leafs management made that had nothing to do with a player’s performance. Smith was traded away by Pat Quinn in 1999 because the two did not get along. Smith wound up playing almost 600 more games in the NHL and became the captain of the Edmonton Oilers and a very solid defenceman. What makes this trade especially terrible is that for most of the Leafs recent history they have been looking for a player just like Jason Smith and have ultimately failed in doing so.

7 Hiring of Gord Stellick

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Stellick was only the Leafs GM for over a year and this shows that it was a mistake in the first place and should not have been hired at all. At the time he was the youngest GM in NHL history and had no experience whatsoever in the NHL. After being fired he was hired as the New York Rangers assistant GM, but that only lasted until 1991. Stellick is now a successful media personality in Toronto and that is something he should have went with from the beginning.

6 Hiring of John Ferguson Jr.

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The tenure of JFJ in Toronto is known for signing over the hill free agents for big money, making bonehead trades and giving out no trade clauses to these over the hill players like no one’s business. The worst of his free agent signings was Jason Blake who signed a long-term big money deal after scoring 40 goals with the New York Islanders. He would not come close to this with Toronto. However, the worst of JFJ’s moves is higher up on this list and continues to haunt the Leafs today even though the contract was not renewed in 2008.

5 Owen Nolan Trade

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This was a bad trade made by John Ferguson Jr. but definitely not the worst. Nolan did nothing for the Leafs and Alyn Mccauley and Brad Boyes were solid NHLers for a long time and Boyes developed into a 40 goal scorer with the St. Louis Blues. If that is not bad enough the Leafs also gave up a first round pick which they could have used to select the likes of current NHL stars Shea Weber, Patrice Bergeron and Loui Eriksson. All for a guy who played a total of 79 games for the blue and white and scored 26 goals.

4 Phil Kessel Trade

Jerome Miron-USA TODAY Sports

Giving up two first round draft picks and a second round draft pick for a player that can only do one thing is just something that most franchises in pro sports would not even contemplate. However, Kessel did contribute a lot of goals for the Maple Leafs but what else did he do for the team? Nothing. He was not committed to defence at all, he was not a leader in any sense of the word and it was apparent to most that he quit on the team during his final year here which ultimately led the Leafs to trade him to the Penguins. That the picks in this trade were used to select NHL superstar Tyler Seguin and Dougie Hamilton does not even matter anymore. I am just glad that Kessel is gone and in the past and I hope the prospects the Leafs got in return from the Penguins amount to something more than one-way players in the NHL.

3 Harold Ballard

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Even though I was too young to fully understand why so many Leafs fans hated Harold Ballard during the I was aware of a couple of his policies, even as a young boy. The one thing that stood out to me during the 1980s was that he had an anti-European policy when it came to players. This is senseless in the modern era NHL with European players being almost equal to those in North America. What makes this more interesting is that one of the all time Leafs greats is Borje Salming, a Swedish born defenceman was only signed because Ballard was in jail at the time. Ballard was also an extremely stubborn owner and it was either his way or no way at all and this attitude was apparent in such things as trading all time Leaf’s great Daryl Sittler, his feud with Dave Keon and firing Roger Neilson.

2 Tuukka Rask Trade

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This trade is bad on so many levels the biggest one being that in today’s NHL you need a franchise player in net and ever since this trade was made the Leafs have not had one. Rask has developed into one of the top goalies in the league whereas Raycroft only played one full year with the Leafs. This trade also exemplifies the Leafs awful rating of talent as Justin Pogge was deemed the goalie of the future and made Rask expendable, but he played less than five games in the NHL and currently he is playing hockey in Europe. I have nothing against the likes of James Reimer, Jonas Gustavsson and Jonathan Bernier, but Rask is simply better than all of them put together and the Leafs have been dealing with a bunch of second tier goalies in net ever since trading Rask in 2006.

1 Tom Kurvers Trade

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This trade is known in Leafs circles as the worst in their history because they could have used their third selection in the 1991 draft to pick Scott Niedermayer. Niedermayer is perhaps the best defenceman of his era and has won championships on every level and during the time of trade and the majority of the 1990s, it was apparent that Floyd Smith had made an enormous mistake. This trade ranks higher than the Rask trade because Niedermayer is a hall of famer and one of the best players ever to play the game at his position and a Norris Trophy winner to boot. Kurvers actually played well with the Leafs for the one season he was here which leads one to believe that the Leafs brass knew what they did was a huge mistake and wanted to do anything in their power to undo it.

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