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.

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21 Best: Getting Rid of the David Clarkson Contract

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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.

In total, Clarkson played parts of two seasons for the Leafs.  He recorded just 15 goals and 11 assists in 118 games played. Overall, then Leafs GM, Dave Nonis has to be given credit for this trade, even if it was completed to cover his own mistake (he signed Clarkson to that large contract).  Still, we do not know how the Leafs got out of that one.

20 Worst: Keeping Ron Wilson for too long

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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.

Overall, Wilson only won 130 of the 310 games he coached with the Leafs. The team never made the playoffs once under his watch. In today's NHL, coaches are on such short leashes, as results are expected almost immediately. It makes one wonder how Wilson lasted so long and secured a contract extension.

19 Best: Drafting Auston Matthews 

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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.

Think back to some of the recent 1st overall draft picks and the impact they have had and you will see why Matthews deserves to be on this list. Even during his draft year, Matthews went to the Swiss league and he dominated adult men as a teenager. Matthews had 46 points in 36 games for the ZSC Lions, good for 10th in league scoring and 2nd in points-per-game behind former NHLer Pierre-Marc Bouchard. Furthermore, Matthews benefited by being coached by a man with significant experince in the NHL, Marc Crawford. Crawford has raved about Matthews, stating that Matthews will be a superstar in the NHL. Maybe Matthews can finally be the guy Leafs fans have been waiting for.

18 Worst: Trading Alex Steen too soon

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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.

Stempniak was defined by a 27 goal season in 2006-07 with St. Louis, but never came close to that same production in his 128 games with the Leafs. Stempniak was eventually dealt to the Coyotes. Meanwhile, Steen has gone on to be a very good player on a very good team in St Louis. He recorded back to back seasons of 60 plus points in 2013-14 and 2014-15 before missing time due to injury in 2015-16 (still had over 50 points). This was a lopsided trade for the Blues, and also turned out to be another example of a professional sports team giving up on a player too soon, as Steen never really had the greatest opportunity in Toronto.

17 Best: Hiring Mike Babcock 

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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.

Based on all of Babcock's success, it is easy to conclude the Leafs struck gold with this hiring. They are also lucky that Babcock wanted to leave Detroit and help turn things around in Toronto. If there is any coach that is going to complete this difficult task, it is Babcock.

16 Worst: Firing Pat Quinn

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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.

One can argue that Quinn never took the Leafs to the Stanley Cup Final, but at least they were consistently making the playoffs under his coaching, unlike many other coaches before and after him. For a little perspective, remember the fact that Quinn ended up being sixth on the NHL's all time win list. No doubt this was a mistake by the Leafs, as they have been hard-pressed to find any of the sustained success they saw under Quinn.

15 Best: Acquiring Dave Ellett

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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.

It is important to note that Olczyk did have a more than respectable NHL career. However, his time with the Jets was short and he ended up playing for several different teams over the course of his career. Similarly, Osborne did not last long with the Jets either. He spent parts of two seasons in the 'Peg, before ending up back in Toronto. Safe to say this trade worked out for the Leafs.

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

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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.

Eventually, Komisarek accepted a demotion to the AHL in an attempt to gain confidence and revive his career. Unfortunately for Komisarek, this was not the case and he was bought out by the team. Luckily for the Leafs, the newly negotiated CBA allowed for two compliance buy-outs. Thus, the Leafs were able to save cap space.

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


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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).

The centerpiece of the deal, Andreychuk was a great player for the Maple Leafs. In his first season, he recorded 38 points in 31 games.  Additionally, he added 19 points in 21 playoff games. Andreychuk went on to play 3 more seasons with the Leafs before being traded.  He put up solid point totals throughout his time and provided veteran leadership. On the other hand, Fuhr did not have the best statistics with Buffalo, but to be fair he did help mentor the great Dominik Hasek.

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

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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.

Luckily, Dave Nonis pulled off a mini miracle and traded Clarkson, and more importantly his contract at the first opportunity. So, we do have to give some props to Nonis for recognizing his mistake, otherwise this would be much higher on the list.

10 Best: Acquiring Ian Turnbull 

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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.

What did that asset management lead to? It led to the Maple Leafs drafting a great defenceman that would be the cornerstone of their blueline for many years to come. Turnbull played nearly 10 seasons and 580 games for Toronto. He recorded 414 points including a career high 79 points in  the 1976-77 season. He also performed exceptionally during the playoffs, recording 45 points in 55 total games. Remember, the Leafs were able to acquire this tremendous defenceman with a 42-year-old goalie being the centerpiece of the trade.

9 Worst: Trading Darryl Sittler

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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.

Overall, this trade would have been more justified if the Leafs received adequate pieces in return. However, Costello played only 12 games in his NHL career. Strong only played 15 career games in the NHL. Ihnacak did have more success than the prior two players, recording 28 goals and 66 points in his first season in Toronto. Unfortunately for Toronto, this success was not sustained and Ihnacak never reached 20 goals or 50 points again.

8 Best: Acquiring Rick Vaive and Bill Derlago

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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.

Meanwhile, Vaive went onto become the first 50 goal scorer in Maple Leaf history, surpassing the mark on three separate occasions. Vaive also recorded as high as 94 points in one total season during his seven year tenure with the Leafs. He also went on to serve as the team captain from 1982 to 1986. Overall, the Leafs did trade a fan favorite in Williams, (he also had success in Vancouver) but at the same time they acquired two productive point producers for many years.

7 Worst: Trading Bernie Parent

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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.

How about the players Toronto acquired? Neely was a first round pick, but only put average numbers in his 4 seasons with the team. Doug Favell was a backup goalie for the Leafs for two seasons. Eventually, both Neely and Favell were traded to Colorado. Talk about a trade that backfired.

6 Best: Acquiring Mats Sundin 

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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.

Meanwhile, Sundin established a Hall of Fame worthy career in Toronto.  He played 13 seasons for the team totaling 981 games, which is 6th all time in Maple Leafs history Toronto.  He also scored 987 points which is good for 1st all time. He was captain of the team and as Leafs fans will remember, one of the most consistent players to ever lace up skates for the blue and white.

5 Worst: Trading for Phil Kessel

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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.

If it makes the Leafs fans feel any better, the Bruins have now lost both Seguin (another terrible trade) and Hamilton to other teams.

4 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.

Meanwhile, Gilmour essentially became a legend in Toronto after two unreal seasons. In 1992-93 Gilmour scored 32 goals and 95 assists for 127 points. He also led the Leafs within one win of the Stanley Cup Finals that same season with 35 points in 21 playoff games. The following season he scored 111 points and again, led the Leafs to the Conference Finals with 28 points in 18 playoff games. Afterwards, Gilmour did see a decline in his statistics, but still provided solid leadership. Eventually, after parts of six seasons with the team, he was traded when the Leafs decided it was time to rebuild and start in a new direction.

3 Worst: Losing out on Scott Niedermayer

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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.

Meanwhile, Niedermayer went on to be one of the greatest defenceman of all time. He recorded 476 points in 892 games with the Devils, winning three Stanley Cups. He then went on to record another 157 points in 209 games for the Anaheim Ducks, winning a fourth Cup in 2007. He also won a Norris Trophy as the NHL's top defenceman in 2004, and the Conne Smythe Trophy in 2007 as the MVP of the playoffs. Niedermayer also won Olympic Gold Medals in 2002 and 2010, gold in the World Junior Championship in 1991, World Championship Gold, and he won in the 2004 World Cup of Hockey. Basically, Niedermayer was a winner at all levels. Oh, what could have been for Toronto.

1. Best: Acquiring Ted Kennedy

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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 Worst: Trading Tuukka Rask 

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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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