Toronto Maple Leafs: 10 Best And 10 Worst Management Moves In Team History

It is well known around the hockey world that the Toronto Maple Leafs have not won a Stanley Cup since 1967. The Maple Leafs have arguably been one of the worst professional sports franchises during this time. There have been countless years of not making the playoffs, strike outs in free agency, questionable hiring decisions, draft and trade mishaps. Winning a Stanley Cup is hard enough as it is, but many management decisions in Leaf Nation have definitely contributed to this struggle. It causes one to question and wonder what the management was thinking when these terrible trades, draft picks, and free agent signings were made. Despite all of this, major props should be given to Toronto fans, as somehow the Maple Leafs still have arguably the best and most loyal fan base in the NHL.

So yes, we all know the Leafs have not exactly been a model franchise for the last few decades. However, it would be unfair to disregard the fact that some in Maple Leaf management over the years have made their fair share of good moves.  Now obviously, these moves did not help the Leafs win a Stanley Cup, but there have been some under the radar moves that have been disregarded mainly due to the fact we live in, or so it seems, a "prisoner of the moment" type world (or in the Leafs case, years).

It is also important to note, the Maple Leafs have a long and rich history. Therefore, this article will try to focus on more of the "modern" era, but at the same time there are some moves from the past that cannot be ignored. With all of that being said, let us go back into time and look at the 10 best and 10 worst management move's by the Toronto Maple Leafs.

21 10. Best: Getting Rid of the David Clarkson Contract

Jerome Miron-USA TODAY Sports

On February 26, 2015 the Maple Leafs did the unthinkable by somehow trading  David Clarkson and his terrible contract (7 years, $36.75 million) to the Columbus Blue Jackets in exchange for Nathan Horton.  Not only did they get rid of Clarkson, but they acquired cap space in doing so, because Horton has not played an NHL game since 2014. Thus, the Maple Leafs are able to place Horton on long term injured reserve and save $5.3 million in cap space.

The other factor that makes this trade even more shocking was that Clarkson had a no-movement clause.  After all, Toronto is his hometown and you would have thought he was going to do everything he could to stay and live up to the contract he signed.

20 10. Worst: Keeping Ron Wilson for too long


There is no denying Ron Wilson has had success as a hockey coach, but his time in Toronto was downright brutal. Many have openly wondered if Ron Wilson only lasted as long as he did in Toronto because of his close relationship with Brian Burke. Wilson was hired in 2008 and the club struggled all four years he was there. In 2008-09 the team finished last in their division and 12th in the Eastern conference, in 2009-10 the team finished last in the conference, and again, more of the same continued in 2010-11 when the team finished 10th in the East. Finally, in 2011-12 the team saw some improvement under Wilson, as they were sitting in a playoff spot with an 18-13-4 record. Somehow this was enough for Wilson to secure an extension. However, this minimal success did not last very long, as the team went through a major slump shortly afterwards and Burke had no choice but to fire his buddy.

19 9. Best: Drafting Auston Matthews 

Timothy T. Ludwig-USA TODAY Sports

Yes, I know this acquisition can be seen as common sense/luck (winning the draft lottery), acquisition by the Maple Leafs, and I know Auston Matthews has not played an NHL game yet, but he still deserves to be on this list due to the significant impact he will likely have on the Leafs. It is arguable the Maple Leafs have not had a player with franchise cornerstone potential since Mats Sundin and many scouts project Matthews to be much more than Sundin was, which is saying something.

18 9. Worst: Trading Alex Steen too soon


Steen was traded along with defenceman Carlo Colaiacovo to the St. Louis Blues in exchange for Lee Stempniak. What makes this trade even harder to understand is that Steen had two very respected people in the hockey world, Alexander Mogilny and Pat Quinn, raving about his skills and his potential when he was just a rookie. Clearly, someone in management did not value their opinions on Steen.

17 8. Best: Hiring Mike Babcock 

Dan Hamilton-USA TODAY Sports

Everyone knows Babcock has had major success throughout his coaching career. In the NHL, Babcock has also coached the Anaheim Ducks and Detroit Red Wings. He coached the Ducks for two seasons, leading them to one Stanley Cup Final berth. Babcock then coached the Red Wings for 10 seasons, registering a playoff berth every season, including a Stanley Cup championship in 2008. He also holds the record for most wins by a coach in Red Wings history. An interesting fact to to sum up how great of a coach Babcock is: he is the only coach to win five distinct national or international titles, winning a gold medal at the World Junior Championship, as well as two gold medals at the Winter Olympics in 2010 and 2014, a gold at the World Championship, and a CIS national cup.

16 8. Worst: Firing Pat Quinn


The late Pat Quinn was loved by many people in Toronto. Too bad management at the time did not seem to see Quinn in the same way. Quinn took over the Leafs in 1998 and the team improved significantly. The Leafs made the playoffs for six straight seasons. Overall, in seven seasons with the team, Quinn had a very respectable record of 300-196-52-26 in 574 games. He was let go after his seventh season when the team narrowly missed the playoffs.

Many rumors flew regarding the real reason for Quinn's firing. There was speculation around the league that Quinn and then GM John Ferguson Jr. did not see eye to eye. Many of the Maple Leafs players were not happy with this firing, and this can be seen by the public support Quinn received from players like Mats Sundin and Darcy Tucker.

15 7. Best: Acquiring Dave Ellett


In the middle of the 1990-91 season The Maple Leafs traded Ed Olczyk and Mark Osborne  to the Winnipeg Jets for Dave Ellett and Paul Fenton. Fenton did not have a successful tenure with the Maple Leafs and was traded quickly, but the same cannot be said for Ellett.  Ellett's career took off in Toronto, where he became known as a reliable two way defenceman. As a result, many fans consider him the best defenceman to don the blue and white in the 1990s. In his first four seasons with Toronto, he registered 38, 51, 40, and 43 points. Additionally, he is remembered as being an integral part of the 1993 and 1994 conference finalist teams. In total, he registered 30 points in 39 games during these deep playoff runs. After playing in Toronto for parts of seven seasons, Ellett was traded to the New Jersey Devils.

14 7. Worst: Signing Mike Komisarek for 5 years, $22.5 million 


It is always a bad sign when a team pays a player not to play for them. This was exactly the case for Mike Komisarek after signing a hefty $22.5 million deal with the Leafs. Komisarek had a couple of good years playing in Montreal alongside Andrei Markov, but could not find the same type of success in the blue and white. His addition was supposed to provide grit, leadership and solid defence. However, this was not the case, as Komisarek battled through injuries and constant benchings by then Leaf coaches Ron Wilson and Randy Carlyle.

13 6. Best: Acquiring Dave Andreychuk, Darren Puppa and 1st Round Pick



One of the first moves then general manager Cliff Fletcher made was trading for Grant Fuhr. With Fuhr, Fletcher thought he had acquired a solution for Toronto's goaltending situation. However, the sudden emergence of goalie Felix Potvin made Fuhr expendable and a piece that that could be packaged for other assets.  As a result, Fletcher addressed a weakness of the Leafs team: goal-scoring. Fletcher traded Fuhr, and a 5th round pick to the Buffalo Sabres for Dave Andreychuk, Darren Puppa, and a 1st round pick. This was an overall great move by Fletcher. He managed his goaltending assets perfectly, acquired an elite center, and used the 1st round draft pick for a great prospect (Kevin Popp).

11 6. Worst: Signing David Clarkson for 7 years, $36.75 million

Tom Szczerbowski-USA TODAY Sports

This was one of the defining moves in the Nonis era and it was a disaster right from the get-go. Clarkson was nowhere close to the 30 goal scorer he was in New Jersey. He did not bring the grit or passion that Maple Leafs management promised. Alternatively, he was arguably the biggest free agent bust of all time. To start his Leafs career, Clarkson got himself suspended 10 games for leaving the bench on an illegal line change to join an altercation during an NHL preseason game. Yes, he did this during a preseason game. When he did actually play, Clarkson only managed 15 goals and 11 assists in parts of two seasons with the team.

10 5. Best: Acquiring Ian Turnbull 


Toronto made out very well when trading 42-year-old Jacques Plante, along with Doug Gibson to the Boston Bruins for a 1st round pick  that turned out to be Ian Turnbull. Plante was no doubt a marvelous goaltender with an outstanding career, but again he was 42 years old. He only played eight regular season games and two playoff games for the Bruins, his last games in the NHL. Again, this is an example of Leaf management being able to acquire assets for someone that they knew was not going to be around much longer.

9 5. Worst: Trading Darryl Sittler


In 1982, Toronto traded their best player, captain, fan favourite and future Hall of Famer to the Philadelphia Flyers in exchange for Rich Costello, Peter Ihnacak, and Ken Strong. Sittler has the second most points in Leaf history with 916, only trailing Mats Sundin. In 2003, the Leafs retired his number 27, showing how important he was to the franchise.

So why did the Leafs trade him? The main reason suggested by many is that Sittler did not get along too well with then owner Harold Ballard. As a result, Sittler waived his no trade-clause and was traded to the aforementioned Flyers. With the Flyers in 1982-83, Sittler earned his 4th all star appearance.

8 4. Best: Acquiring Rick Vaive and Bill Derlago


In 1980, the Maple Leafs traded Dave "Tiger" Williams and Jerry Butler to the Canucks in exchange for Rick Vaive and Bill Derlago. Even though Toronto was trading a fan favorite, this trade helped Toronto establish a legitimate first line for many years to come, as Vaive and Derlago formed a trio with Pat Hickey. Derlago had a few very effective years in Toronto, serving as the play-maker on the aforementioned first line. In total, Derlago played parts of seven seasons with the Leafs, recording as high as 84 points in one season.

7 4. Worst: Trading Bernie Parent


In May 1973, Toronto traded Bernie Parent's rights to the Philadelphia Flyers for Bob Neely, and Doug Favell. Unfortunately for the Leafs, the next two seasons were the best of Parent's career and have him enshrined as a goaltending legend. In his first two years with Philly, Parent won two Stanley Cups, two Vezina Trophies, and two Conn Smythe trophies. Basically, he was the best player in the league for those two seasons. He even played 73 of a possible 78 games in one season, which for the most part, is unheard of for goalies today. Unfortunately for Parent and the Flyers, the rest of Parent's career was stalled by injuries. If not, who knows what other great accomplishments Parent would have achieved.

6 3. Best: Acquiring Mats Sundin 


Undoubtedly, this was a controversial trade at the time, as it included the Leafs sending away the beloved Wendel Clark to the Quebec Nordiques. There were multiple players involved in this trade, but let us focus on Clark and Sundin, as they were the main two pieces of the trade.

At the time, it did seem like a good trade for both teams, as Quebec wanted veteran experience for the playoffs and the Leafs wanted youthful skill for the future. However, Clark only played one season for Quebec and was not the major difference maker the team had hoped for. He scored a respectable 12 goals and 30 points in 37 games, but only registered 3 points in a first round playoff exit.  Even better for Leafs fans is the fact that they got to see Clark return to the team two seasons later.

5 3. Worst: Trading for Phil Kessel

Aaron Doster-USA TODAY Sports

It was hard to put this trade higher on the list because it involves a lot of hindsight, and to be fair, this seemed like a good trade for the Leafs at the time. They sent Boston two first round picks, as well as a second round pick in exchange for Phil Kessel. In Kessel, the Leafs acquired a possible franchise player that could score 35 plus goals every season. To his credit, Kessel did put up very good statistics with the Maple Leafs before being traded to Pittsburgh (it must have hurt Toronto watching Kessel lift the Stanley Cup this past season).

However, the issue with this trade was that no one expected the draft picks to be as high as they were. One first round pick ended turned into the 2nd overall pick for the Bruins, and they selected Tyler Seguin. With their second first rounder from the Leafs, the Bruins drafted Dougie Hamilton 9th overall. Seguin has already established himself as a franchise player and Dougie Hamilton has the potential to be an elite defenceman for a long time.

4 2. Best: Acquiring Doug Gilmour


Poor Calgary Flames fans will never forget the day then Leafs GM Cliff Fletcher fleeced then Flames GM Doug Risebrough. Along with Gilmour, Toronto also acquired Jamie Macoun, Ric Nattress, Kent Manderville. and Rick Wamsley for Gary Leeman, Alexander Godynyuk, Jeff Reese, Michel Petit, and Craig Berube. Essentially, the trade is known as Leeman, who was a proven scorer at the time of the trade, for Gilmour. However, for unknown reasons, Leeman did not work out in Calgary like he was supposed to and registered just 11 goals and 12 assists in 59 games. Perhaps this is why most people tend to forget he was once a 50 goal scorer in Toronto.

3 2. Worst: Losing out on Scott Niedermayer


Another instance where hindsight is 20-20, and an instance where the Leafs wish they could go back in time. This notorious trade occurred in 1989, and saw the New Jersey Devils trade defenceman Tom Kurvers to Toronto in exchange for a 1st round pick in the 1991 draft. Toronto ended up being a terrible team and New Jersey was awarded the 3rd overall pick and yes, they drafted Scott Niedermayer. The rest is history.

To be clear, Kurvers was not a bad player by any means. He recorded 52 points in his first season with the Leafs before his production dipped in his second season. As a result of this dip, he was traded to the Vancouver Canucks.


Some of the younger readers may not be familiar with this trade, but Ted Kennedy was an absolute steal.  He was originally property of the Montreal Canadiens, but did not want to play for their junior club. Then came along Frank Selke, who pulled off arguably the greatest trade in Maples Leafs history by acquiring the rights to Kennedy in exchange for Frank Eddolls.  Kennedy went on to spend his entire career in Toronto, while Eddolls only played parts of three seasons in Montreal.

Meanwhile, Kennedy averaged a point per game in his first full season with Toronto. In total, Kennedy won 5 Stanley Cups during his playing days. Kennedy was also captain of the team for 8 seasons.  He is known by many as the "ultimate" leaf, a playoff performer, great face-off master, and additionally, some debate that he is the greatest player in franchise history. In total, Kennedy played 696 games, recording 560 points.  However, he was known for much more than his point producing as referred to above.  Overall, there is no debating how great of a trade this turned out to be for Toronto.


1 1. Worst: Trading Tuukka Rask 

Kim Klement-USA TODAY Sports

The reason this trade is the highest is because a lot of the other aforementioned trades involve hindsight.  In this case, Rask was already drafted by the Leafs and very highly touted by many around the league. One has to wonder how if feels for the Leafs when they watch Tuukka Rask perform as one of the elite goaltenders in the NHL year after year. Oh, what could have been. To make matters even worse, the Leafs traded Rask to the Boston Bruins, one of their division rivals. What did they get in return? They got Andrew Raycroft. Yes, he was a former Calder Cup winner, but he fell off dramatically and only ended up being a starter for one full season in Toronto.

How about Rask? Well, he has won a Stanley Cup (to be fair, as a backup) and a Vezina trophy for being the best goaltender in the league. Since becoming the starter, Rask has consistently been one of the elite goalies in the NHL. Currently, Rask is only 29 years of age and has plenty of great years ahead of him.  The justification given by the Leafs on this trade was that they already had their goaltender of the future in Justin Poggee, making Rask expendable. Safe to say this was the wrong judgement, as Poggee only played seven total games in the NHL.

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Toronto Maple Leafs: 10 Best And 10 Worst Management Moves In Team History