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
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
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
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
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
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.