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The Toronto Maple Leafs have finally worked their way out of the NHL’s cellar. The Leafs’ future is now bright, after building a young core of talent with players like Morgan Reilly, William Nylander, Mitch Marner, and, of course, Auston Matthews. They committed to a rebuild and finally realized that the NHL Entry Draft is their best bet at turning a team around. Leafs fans deserve this after an agonizing 11 years, where the Leafs missed the playoffs all but once, a devastating first round exit to the Bruins in 2013.

This lack of success can be greatly linked to poor managerial moves, with John Ferguson Jr., Brian Burke and Dave Nonis executing most of the damage. Feeling the pressure of having to win in Toronto, these managers attempted to take the fast-track in icing a winning team by signing and trading for players, instead of patiently waiting for talent to develop in their own system. Specifically, the Leafs’ managers performed their most awful doings throughout free agency and contract extensions. Let’s examine 15 of the worst Maple Leaf signings in the last decade.

15. Joffrey Lupul: Five Years / $26.25 Million

Matt Kartozian-USA TODAY Sports

Matt Kartozian-USA TODAY Sports

When healthy, Joffrey Lupul has been a force for the Blue and White. In his first ‘full’ (by Lupul standards) season with the Leafs, Lupul put up 67 points in 66 games, playing alongside Phil Kessel. This is what earned him his five year, $26.25 million contract extension the following year, in the midst of the lockout-shortened season. However, the oft-injured Lupul was struck by a Dion Phaneuf slap shot four days later, causing him to miss significant time. Lupul played in just 16 of the Leafs’ 48 regular season games. In the following three years of his new contract, Lupul missed a total of 76 games due to injury. Before the start of the 2016-2017 season, the Leafs announced that Lupul would be starting the season on the IR. As of January 2017, Lupul has yet to suit up for a game, with little hope of return. He is now in the fourth year of the contract, earning $5.25 million annually.

14. Hal Gill: Three Years / $6.3 Million

via sportsnet.ca

via sportsnet.ca

Hal Gill was brought to the Maple Leafs in the summer of 2006 by General Manager John Ferguson Jr. to add size and depth to the Leafs’ already weak blue line. There is no doubt that six-foot-seven Gill added size, but he certainly didn’t make the defence any stronger. Gill’s lack of speed and mobility made him a liability on the Leaf’s backend, especially with the NHL trending in the direction of quickness and skill, as the post-lockout rule changes had been in place. Gill lasted 145 games with the Leafs, managing 40 points and a +11 rating, before being traded to Pittsburgh in February of 2008, where he went on to win a Stanley Cup (amazingly) with the Penguins in 2009.

13. Michael Peca: One Year / $2.5 Million

via thestar.com

via thestar.com

Another Ferguson gem was the signing of Mike Peca in July of 2006. In Ferguson’s defence, it was a relatively cheap gamble on a one year trial. Peca, 32, had just come off a strong playoff run with the Oilers the previous spring, in which they made it to the Cup Finals before losing out to the Carolina Hurricanes. However, things did not work out for Peca in Toronto. His Leaf career was cut short by injury, lasting just 35 games, with only 15 points. Peca’s production while in the lineup was non-existent, as he managed just fours goals in a Leafs jersey. Peca went on to play two more seasons in the NHL with Columbus, before retiring from the league after the 2008-09 season.

12. Francois Beauchemin: Three Years / $11.4 Million

via nhl.com

via nhl.com

As an integral part of the Anaheim Ducks 2007 Cup win, Francois Beauchemin tested the free agent market in the summer of 2009. With rumours swirling regarding the future of Tomas Kaberle in Toronto, Leafs’ GM Brian Burke set out to acquire a puck-moving defenceman. Burke was familiar with Beauchemin from his time spent as the GM of the Ducks (including the aforementioned Cup win) and the two agreed on a near $4-million per year deal over three years. Although it’s hard to classify Beauchemin as an offensive defenceman (career high 34 points), maybe Burke added the 29-year old for his steady defensive play. Whatever the reasoning was, it failed. Beauchemin finished his first year as a Leaf with just 26 points in 82 games and a poor -13 rating. After 54 games the following season, Burke traded Beauchemin back to Anaheim in arguably his best move during his Leaf tenure, receiving Joffrey Lupul and Jake Gardiner in return. Beauchemin left Toronto with a minus-17 rating and 38 points in 136 games.

11. Phil Kessel: Eight Years / $64 Million

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

I know there is still a Phil Kessel-sized void in some Leaf fans’ hearts, but keep in mind this list is not about the worst players, but rather the worst signings. Phil Kessel is not a terrible hockey player, but he does have one terrible contract. After four productive seasons with the Leafs, Kessel was entering the  final year of a five year, $27 million deal. Leafs’ GM Dave Nonis was under pressure to reach a deal with Kessel before the season started to avoid the risk of losing the winger through free agency the following summer. Perhaps the pressure blurred Nonis’ thinking because just days before the season opener, Kessel and the Leafs agreed to a whopping eight year, $64 million deal. The Leafs felt they had a franchise player in Kessel, but they were wrong. Sure, they had an elite goal scorer and point-producer, but Phil Kessel is in no way a franchise player. During his six-year stay in Toronto, Kessel scored an impressive 181 goals and 394 points in 446 games. However, during that period, he was a miserable -79, highlighted by a -34 campaign in 2014-15. After his first season of the eight-year deal and with new management in place, Kessel was dealt to the Pittsburgh Penguins in July 2015, a deal where the Leafs agreed to retain $1.2 million of Kessel’s annual salary, for the duration of the contract.

10. Vesa Toskala: Two Years / $8 Million

via thestar.com

via thestar.com

Leafs’ GM John Ferguson Jr. acquired goaltender Vesa Toskala from the San Jose Sharks at the 2007 NHL Entry Draft. Entering the final year of a contract with a $1.375 million annual salary, Toskala was set to become the Leafs’ number one goalie or, at the very least, create competition with Andrew Raycroft for the starting job. However, it seemed apparent that the job was all Toskala’s, after Ferguson re-signed the 30-year old to a two-year, $8 million deal, three months before Toskala would even make his Leaf debut, a substantial raise for a goalie that had been a career back-up to this point. Ferguson’s gamble did not pay out in the end, as Toskala only managed one season with a save % and GAA above .900 and below 3.00, respectively.

9. Colby Armstrong: Three Years / $9 Million

via nhl.com

via nhl.com

During the 2010 offseason, Toronto GM Brian Burke was looking to add grit and toughness to his team and he wasn’t afraid to overpay when doing so. He did just that, when he signed Colby Armstrong to a three-year, $9 million deal on July 1st. Armstrong was coming off a 29-point, 61-PIM season with the Atlanta Thrashers. If he had to match these numbers for the next three seasons in Toronto, he still would have been overpaid. But instead, he did much worse. In his first two seasons with the Leafs, Armstrong managed just 79 games combined, scoring 26 points and adding 47 PIMS. On top of that, he was a liability in his own end, ending his Leafs tenure with a -9 rating. Before starting his third year of the deal, Armstrong was bought out by Toronto, putting an end to another abysmal summer signing.

8. John-Michael Liles: Four Years / $15.5 Million

via dalje.com

via dalje.com

In his first season with the Leafs, John-Michael Liles had impressed GM Brian Burke enough that the two agreed on a four year, $15.5 million contract extension in January of 2012. In his first year of the deal, which happened to be the lockout-shortened 2013 campaign, Liles managed 11 points in 32 games, while sitting as a healthy scratch towards the end of the season and playoffs, which is the last thing you’d want from a defenseman who you just signed to a multi-year deal. The following year, Liles suited up in just six games for the Leaf, before he was traded to the Hurricanes in exchange for Tim Gleason. With two years left on a $4-million annual deal, Gleason was bought out by Toronto in the following offseason.

7. Jonathan Bernier: Two Years/ $8.3 Million

Eric Hartline-USA TODAY Sports

Eric Hartline-USA TODAY Sports

After James Reimer almost single-handedly stole the Leafs a playoff series against the Bruins in 2013, Maple Leaf management thanked him by bringing in Jonathan Bernier to take over the starting job. Bernier, who was acquired via trade from the Kings, was given every chance by the coaching staff and management to become the Leafs’ number one goaltender. However, inconsistency prevented this from happening, as Bernier could not cement himself in the starting role. After two seasons of up and down play, the Leafs were not willing to give up yet. They re-signed Bernier in the summer of 2015 to a two-year, $8.3 million deal, still without knowing what kind of player they really had. Following another disappointing season, the Leafs finally gave up on Bernier and dealt him to Anaheim for a conditional draft pick in 2017. After three seasons in Toronto, Bernier managed just 59 wins.

6. Tim Connolly: Two Years / $9.5 Million

via predlines.com

via predlines.com

After losing out on the Brad Richards sweepstakes in July of 2011, Leafs’ GM Brian Burke went after the next best centre he could find. He came up with Tim Connolly and signed him to a two-year, $9.5 million deal. The injury-prone Connolly was coming off a 42-point season with the Sabres after playing 68 games, while putting up 65 points the season before in 73 games. He managed to suit up for 70 games in his first season with the Leafs, but produced just 13 goals, 36 points and a terrible -14 rating. This turned out to be all that Connolly would experience in Toronto, as he cleared waivers prior to the following season and played out the rest of his contract in the minors.

5. Dion Phaneuf: Seven Years / $49 Million

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Most reasonable hockey fans would agree that Dion Phaneuf is not a number one defencemen, but thanks to Leafs’ former GM Dave Nonis, he is certainly paid like one. On New Year’s Eve 2013, Nonis and Phaneuf agreed to one of the worst deals in Leafs’ history. Phaneuf, who was already greatly criticized by Leaf fans and media around the hockey world, made things exponentially worse when he signed a seven year, $49 million contract extension. As previously mentioned, it’s clear that Phaneuf is not a number one defenceman, but when you are paid like one, people expect you to play like one. Phaneuf could not live up to these standards. In his first season under the new contract, Phaneuf finished -11 on the season and scored just three goals in 70 games. As the situation worsened in the second year and with the Leafs under new management, Phanuef was traded to the Ottawa Senators in a nine-player blockbuster deal. Amazingly, Leafs’ GM Lou Lamoriello balanced the salaries involved and the Leafs parted ways with Phaneuf, without having to retain any of his remaining salary.

4. Mike Komisarek: Five Years / $22.5 Million

via thestar.com

via thestar.com

As the better teams in the NHL were focused on adding finesse and speed, Leafs’ GM, Brian Burke was stuck in the 90s, still trying to add size and toughness. Therefore, in July 2009, Burke immediately overpaid Mike Komisarek by signing him to a five year, $22.5 million deal. Komisarek was big, slow, and made terrible decisions with the puck. During his first three seasons with the Leafs, Komisarek played in just 154 games, missing time through several injures and eventually becoming a healthy scratch. He did manage to score twice in those three years and compiled a nasty -30 rating. In his fourth year of the contract, Komisarek cleared waivers and was sent down to play with the Leafs’ AHL affiliate. In July 2013, the Leafs bought out the remaining year on Komisarek’s contract, ending his career in the blue and white.

3. Stephane Robidas: Three Years / $9 Million

John E. Sokolowski-USA TODAY Sports

John E. Sokolowski-USA TODAY Sports

A head-scratcher from the beginning, on July 1st, 2014, Leafs’ GM Dave Nonis signed 37-year old, Stephane Robidas to a three year, $9 million deal. If this term and amount for a 37-year old defencemen didn’t already grab your attention, let me throw you some more bait. The previous season, Robidas broke his right leg, not once, but twice. He first broke his leg while playing with Dallas and later fractured it again while playing with Anaheim in the playoffs. How Nonis justified signing a 37-year old, with one leg, to a three-year deal, for $3 million per season, is certainly a question for the ages. Robidas actually played 52 games with the Leafs in the first year of his deal, notching one goal and six assists. He was unable to start the second season of his deal, due to a leg injury (go figure) and hasn’t played since.

2. Jeff Finger: Four Years / $14 Million

via thestar.com

via thestar.com

Definitely the strangest Leaf signing in the last decade, on July 1st, 2008, Leafs’ GM Cliff Fletcher signed the unknown, Jeff Finger to a four year, $14 million deal. Appearing in just 94 NHL games at this point, Finger, 28, left the Colorado Avalanche after his first full season, in which he collected 8 goals and 19 points. In his first season in Toronto, Finger had a mediocre year with 26 points and finished with a -7 rating. It was already clear that Fletcher had made a mistake and that Finger was highly overpaid. In his second season, Finger played just 39 games, finishing with a -11 rating, along with 10 points. That was the last of the NHL for Finger, who finished the final two seasons of his contract in the minors, playing with the Leafs’ AHL affiliate. Finger has not played professional hockey since.

1. David Clarkson: Seven Years/ $36.75 Million

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Although former GM Dave Nonis made some terrible moves in his tenure with the Leafs, nothing can compare to the catastrophic signing of David Clarkson. Heading into the 2013 offseason, Clarkson had not surpassed 46 points in a season, although he did score 30 goals that same year. Either way, the contract he would sign with the Leafs in July 2013 was far more overpriced than his actual worth. Clarkson, 29, agreed to a monstrous seven year deal worth $36.75 million. He began his disastrous career in Toronto with a ten-game suspension, after jumping the bench during a preseason line-brawl against the Sabres. It did not get any better from there. Clarkson finished his first season as a Leaf with just 5 goals and 11 points in 60 games, including a -14 rating. His second season wasn’t going any better and, with such an enormous, overpriced contract, Clarkson was untradeable, or so we thought. Ironically, Nonis made his best move as Leafs’ GM when he remarkably found a taker for Clarkson. Through a savvy financial move, Nonis dealt Clarkson to the Blue Jackets for the contract of the long-term injured Nathan Horton. Clarkson played 26 games with the Blue Jackets in the following two years, before failing his physical at the beginning of the 2016-2017 season.

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