Kim Klement-USA TODAY Sports

With exactly one week left until the free agency period begins, the Toronto Maple Leafs clearly have several holes and have almost $49-million dollars already spent on only 12 players. With over $22-million left to spend on the roster, fans can hope for the Leafs to make a play for at least one major unrestricted free agent, but should they?

The sad reality is probably not. In fact in the last decade, the Maple Leafs have a history of free agent busts. Here’s a list of the major signings since the 2004-05 lockout and how they ended up being colossal busts.

2013

Last year on the first day of free agency GM Dave Nonis signed David Clarkson to perhaps the worst contract in the history of the league. While that may sound harsh, Clarkson got $36.75-million over seven years with almost all of it paid out in bonuses, including a no movement clause and a modified no trade clause. There’s a reason Clarkson has been the most searched buyout option on Capgeek. James Mirtle also explained how Clarkson can’t be bought out.

Suffice to say that Clarkson has thus far been a total bust in Toronto. Last year he earned $477,272.73 per point. Phil Kessel earned $67,500 per point. Clarkson enters this season as the second highest paid Maple Leaf and his only chance to not become the most hated Maple Leaf in history will be to start producing at somewhere near his career high levels.

Honourable Mention: Tyler Bozak. While his $4.2-million salary this year wasn’t terrible, he could easily be the third centre on the Leafs depth chart before his contract comes to an end after the 2017-18 season.

2012

The Leafs went for cheap and low risk in 2012 free agents, signing Jay McClement and Mike Kostka to low priced and short term contracts. While Jay McClement has been brutally overused during his Leafs tenure, his contract of only $1.5-million a year is hardly going to break the bank. Kostka signed for $600,000.

That being said, the Maple Leafs actually went over the cap last year due to bonuses and McClement was certainly overpaid at $1.5-million. While primarily a defensive forward, McClement had shown flashes of offense before arriving in Toronto, having five straight season over 20 points. That didn’t happen here though, as in two seasons McClement managed only 27 points in 129 games for the blue and white.

All that being said, this may be the year of the best free agent signings Toronto has had in the last decade. You got a centre who missed only one game in two years and a low risk defenceman. Compared to other years, that’s not that bad.

Honourable Mention: Remember how Toronto did well in 2012? Well maybe they did well in the summer because they had seen earlier that year what happens when you give a four year extension to a defencemen you then decide you don’t like. John-Michael Liles never really found his footing after that extension and has since been shipped out for a worse contract belonging to a less mobile defender. They also signed Grabovski to his massive contract in March.

2011

The Toronto Maple Leafs signed Tim Connolly on the second day of free agency in 2011 for two years at $4.75-million per year. That $9.5-million total got the Leafs 70 games out of Connolly, and 36 points. He never came close to being the player he was in Buffalo and spent the second year getting paid millions to play in the minors. Despite still being only 33-years-old, Connolly’s career came to an end in Toronto as no other team wanted to touch him after his stint here.

Honourable Mention: Philippe Dupuis also had his career die in Toronto. He hasn’t played an NHL game since scoring exactly zero points in 30 games for the Maple Leafs in 2011-12. That’s even more impressive when you consider he had 17 points in Colorado the year before.

2010

Colby Armstrong led the 2010 class for the Leafs when he signed a three year $9-million contract. He played so well in Toronto that they bought out his final year, preferring to let him play for the rival Montreal Canadiens. Armstrong’s stint ended in Toronto after three points in 29 games in 2011-12 and after his poor year in Montreal he couldn’t find a team in the NHL. He played last season in Sweden. Considering the Leafs signed him for three years, and he played the last year in Montreal, this would be yet another contract where once the full term was done the player never played in the NHL again. The good news is his buyout is finally off the books next season.

Honourable Mentions: This is one of those occasions where the honourable mention may be just as bad as the contract talked about above. The Maple Leafs thought Brett Lebda was worth a two year $2.9-million contract in 2010. He played only one season for the Leafs (or rather parts of one season) before being part of the trade with Nashville that brought over Cody Franson. The highlight of Lebda’s tenure in Toronto was undoubtedly when the Toronto Maple Leafs beat the Atlanta Thrasher 9-3 and Lebda somehow managed to finish the game as a -3. You have to actively try to be that bad. Of course Nashville traded for him, never let him play a game, then bought him out at season end so it’s reassuring to see the Leafs aren’t the only team that makes terrible decisions.

2009

Mike Komisarek was a disaster in Toronto. His five year $22.5-million contract was an albatross from the very beginning as Komisarek looked old and slow from day one. Despite his poor defensive play, Komisarek was even worse offensively. He managed 19 points in 158 games before the Leafs finally gave up and sent him to the minors. To make matters worse the Leafs brass decided to buyout the last year of Komisarek’s deal ($4.5-million) rather than buy out the three years left on John-Michael Liles at $3.875-million per year. Liles was eventually traded for Tim Gleason, who still has two more years left at $4-million and like Komisarek is old and slow. So instead of buying out Liles and eating Komisarek’s contract last year (total cost $4.5-million) the Leafs thought it smarter to buy him out and eat three years of Liles ($11.625-million). They then traded him for Gleason ($12-million). I assume they did this because math is hard.

Honourable Mention: Paying Colton Orr $4-million over four years isn’t horrific but who commits to an enforcer for four years? Apparently the Leafs do, because they signed him after that for another two years.

2008

Every member of the media was scratching their heads when Cliff Fletcher signed Jeff Finger to a $3.5-million contract. Making matters worse was it was a four year deal. Let’s put this into perspective, the year before Finger made $475,000. He was coming off of a solid if unspectacular season as a depth defenceman for the Colorado Avalanche, with 19 points and a plus 12 ranking. After a poor season to start his contract, Finger saw limited action in his second before spending the final two season in the minors. He hasn’t played for a team since his contract expired in 2012.

Honourable Mention: Four years and $12-million for Niklas Hagman is ridiculous. While Hagman did have a solid NHL career and was good for the two years he was with the Leafs, he had been making only $675,000 a year. He was part of the trade with the Flames for Phaneuf, and was promptly scratched in 6 of their first 14 games the following season. He then spent time in the minors before being claimed by Anaheim. He then played in the KHL for Yaroslavl Lokomotiv the year after the plane crash. He played last year in Switzerland. That’s an impressive slow dive into the ‘where are they now’ file.

2007

2007 was rough…really, really rough. The Leafs made a big splash on day one of free agency by landing Jason Blake with a five year $20-million deal. Fresh off a 40 goal season with the Islanders, Blake finished his first year in Toronto with only 15. That total is incredibly disappointing, but it should be noted that Blake 52 points that year and didn’t miss a game despite being diagnosed with a rare but very treatable form of leukemia. Blake wasn’t a complete whiff like a lot of the other free agents on this list, he scored 141 points in 216 games as a Leaf, but he was never the goal scorer the Leafs hoped he was. In his last two years on the Islanders he scored 68 goals. In three years in Toronto he managed 50. When he was traded to Anaheim for Jean-Sebastien Giguere the Ducks were forced to take Vesa Toskala, so for that we should all be thankful.

Another horrific contract that year was the re-signing of Darcy Tucker for $12-million over four years. Tucker played exactly one season for the Leafs before being bought out. How bad is that? The Leafs were still paying Darcy Tucker to not play for them LAST YEAR. This season the Leafs will officially be Tucker free which is exciting when you keep in mind that he retired in 2010. While Tucker didn’t come over from another team, the inexplicable raise combined with term is worth mentioning.

Honourable Mention: Technically nobody, but after trading for Vesa Toskala and Mark Bell from the San Jose Sharks (which cost a first and second in 2007 and fourth round pick in 2009) the Leafs re-signed Toskala, who was making $1.375-million to a two year $8-million contract. Toskala went down as one of the worst goalies in Toronto history posting an .891 and .874 sv% for those two extra years. When you’re more hated than the guy who came over in the trade with you – who missed the first 15 games in Toronto because he was suspended for a DUI – you’re impressively bad.

2006

On July 1st the Maple Leafs decided to shore up their defence by signing Hal Gill and Pavel Kubina. Gill was signed for three years at $6.225-million while Kubina got $20-million over four years. Neither player was bad for the Leafs but both were big, slow, lumbering defenceman that had dominated in the old NHL before the lockout. Kubina was traded after three years of his deal and bounced around for a few more years before retiring. Gill played two years in Toronto before being traded to Pittsburgh where he won a Stanley Cup. While neither were bad, both were overpaid for what they could deliver and found roles more suited to their talents elsewhere.

Honourable Mention: Without any real other options than Boyd Deveraux, it’s got to be Nathan Perrott. Perrott played for the Leafs both before and after the NHL lockout. He was traded early in 2005-06 to Dallas for a 5th round pick. The Leafs then re-signed him in 2006-07 where he played only four games for the Marlies. Considering his Maple Leafs career was three points in 43 games with 118 PIM’s, he was basically a waste of a roster space. His most impressive stat is 276 PIM’s in St. John’s during the lockout in only 60 games. That’s an average of 4.6 penalty minutes per game.

2005

While $1.5-million doesn’t sound like a lot for a forward who scored 60 points in 66 games, Jason Allison was horrific for the Leafs. He was old and slow. A former 95 point scorer for the Boston Bruins, Allison had incentives built into his salary which paid him an extra $3-million for a total of $4.5-million. Allison received top powerplay time to try to justify his signing, but was so bad defensively he still finished -18. Unsurprisingly he was never offered another contract by any NHL team…that is until he had a tryout with the Maple Leafs four years later. While he failed to make the team he did give the world one great last moment in a fight with Darroll Powe where he ripped his helmet in two.

Honourable Mention: Eric Lindros never found his footing in Toronto and played only 33 games due to injury. He made $1.55-million for those 33 games though, good work if you can get it.

With only a week before the free agent period begins, the Leafs look likely to make a play for Paul Stastny, Brad Richards, Dan Boyle or a host of others and while many look like good signings on paper it’s clear some high profile signings in Toronto don’t work out. The one year where the Leafs didn’t spend big on a free agent (2012) also happens to be the easiest to swallow of the last nine years. With almost one big name free agent bust in every year, do you think the Leafs should swing for the fences once again and who should they sign? Tell us in the comments below.