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Top 20 Worst Contracts in NHL History

When July 1st comes, all 30 NHL teams will be lining up to sign free agents to big money contracts, most of which they will immediately regret, in an attempt to bolster their lineup for a Stanley Cup

When July 1st comes, all 30 NHL teams will be lining up to sign free agents to big money contracts, most of which they will immediately regret, in an attempt to bolster their lineup for a Stanley Cup run in 2015-16. It happens every year, yet teams continue to do it. Often times the prospect of adding a player that could put your team over the top or re-signing a player who was a key contributor to your team's success seems to justify the overspending. More often than not, it does not.

Not every large contract ends in disaster. Zdeno Chara worked out pretty well for the Boston Bruins. Ryan Suter and Zach Parise are doing alright in Minnesota so far. The Nashville Predators have to be happy with the Shea Weber extension. And you can say what you want about the term of the Marian Hossa contract in Chicago, but he's looking to win his third Stanley Cup Championship since 2010 with the Blackhawks this year. NHL teams signing superstar players to large contracts has never been a huge problem. The problems come when teams sign second tier players - or in some cases, third or fourth tier players - and players on the downside of their careers to massive contracts that they couldn't possibly live up to.

In a salary cap world these mistakes are magnified. Every dollar counts and needs to be spent wisely. For every million being spent on a bad contract, that's one million that could be used elsewhere. On July 1st many fans will be watching in anticipation to see who their favourite team signs and hoping that their team is smart enough not to repeat any of the mistakes on this list. Here are the 20 worst contracts in NHL history:

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20 Martin Havlat: 6 years, $30 million

Sergei Belski-USA TODAY Sports

After losing Marian Gaborik to free agency in the summer of 2009, the Minnesota Wild attempted to replace some of his offence by signing Martin Havlat to a six year, $30 million deal . Havlat was coming off a career high 77-point season with the Chicago Blackhawks. Havlat's production dipped in Minnesota, as he recorded 54 points in 2009-10 and 62 points in 2010-11. During the 2011 offseason the Wild shipped Havlat to San Jose for Dany Heatley in a swap of struggling stars. Havlat played three injury plagued seasons with the Sharks and never recorded more than 27 points before his contract expired at the end of the 2013-14 season.

19 Mark Messier: 3 years, $20 million

Kellie Landis /Allsport

In the summer of 1997 the Vancouver Canucks signed the Hall of Fame centreman to a three year contract for roughly $20 million with some of that money being deferred. The contract also included clauses for fourth and fifth years that would put the total over $30 million. In three seasons with the Canucks, Messier's 60, 48, and 54 point totals were among the worst of his career and the Canucks failed to make the playoffs in all three seasons.

After the 1999-00 season, the Canucks exercised an option to buy out the remaining years for $2 million. In 2012 Messier won a $6 million arbitration case against the Canucks for money he was owed due to a clause that stated he would be compensated if the value of the franchise increased during his tenure.

18 Chris Drury - 5 years, $35.25 million

via blueshirtbulletin.com

After helping the Buffalo Sabres to to back to back Eastern Conference Final appearances in 2005-06 and 2006-07 and recording a career high 69 points in the 2006-07 season, Chris Drury signed a five year, $35.25 million deal with the New York Rangers. Drury's production dropped off on Broadway, putting up 58 points in 2007-08, 56 points in 2008-09, and just 32 points in 2009-10. After injuries limited Drury to 24 games in 2010-11, the Rangers bought out his contract and he subsequently retired.

17 Jeff Finger: 4 years, $14 million

via bleacherreport.net

After playing just 94 games for the Colorado Avalanche, interim Maple Leafs general manager Cliff Fletcher signed the defenceman to a four year, $14 million contract in 2008. Many, including Jeff Finger himself, were surprised by the contract and some believed that comments from Fletcher suggested that he had accidentally signed the wrong defenceman, meaning to sign Kurt Sauer instead. After two disappointing seasons with the Maple Leafs, Finger played out the final two seasons of his contract with the AHL's Toronto Marlies.

16 Mike Komisarek: 5 years, $22.5 million

DAVID COOPER/TORONTO STAR

The Toronto Maple Leafs signed the stay at home defenceman away from the rival Montreal Canadiens in 2009, agreeing to a five year, $22.5 million contract, believing he would vastly improve the team's defence. Mike Komisarek never lived up to expectations in Toronto, battling injuries and finding himself in and out of the lineup due to his bad play on some awful Maple Leaf teams. Komisarek was unable to crack the lineup for most of the 2012-13 season and was eventually sent to the minors. The Maple Leafs bought out the final year of Komisarek's contract that summer.

15 Ville Leino: 6 years, $27 million

Timothy T. Ludwig-USA TODAY Sports

After the Buffalo Sabres were purchased by Terry Pegula, the team made a point of becoming spenders and signed Ville Leino to a six year, $27 million deal in the summer of 2011. Leino had registered a career high 53 points in the 2010-11 season with the Philadelphia Flyers, after putting up 21 points in 19 games in the Flyers' run to the 2010 Stanley Cup Final. Leino disappointed in Buffalo, posting just 25 points in 71 games in 2011-12 and being limited to just eight games in the lockout shortened 2012-13 season. In 2013-14 Leino was goalless with 15 assists in 58 games and was subsequently bought out of the final three years of his contract.

14 Sean Avery: 4 years, $15 million

via dallasnews.com

In the summer of 2008, the Dallas Stars signed Avery to a four year, $15 million deal. Just 23 games into his Stars tenure, Avery was suspended for six games after making controversial remarks about an ex-girlfriend. During the suspension, the Stars made it clear that he was not welcome back to the team. Avery was eventually claimed on re-entry waivers by the New York Rangers. After two more full seasons in New York, Avery was sent to the minors before the 2011-12 season. He would play 15 more games for the Rangers, but spent most of the season in the AHL with the Conneticut Whale where he was a frequent healthy scratch. Avery officially retired in March of 2012.

13 Dany Heatley: 6 years, $45 million

via nhlsnipers.com

After back to back 50 goal seasons, the Ottawa Senators signed Heatley to a six year, $45-million extension. In the first year of the deal, Heatley put up 72 points, his lowest point total in any full season since his rookie year. Unhappy with his playing time under coach Cory Clouston, Heatley demanded a trade. The Senators agreed to trade Heatley to the Oilers prior to July 1st, but the star winger used his no trade clause to block the move, meaning the Senators would have to pay him a $4 million signing bonus on July 1st, although the team would later get some of that back through a grievance.

Heatley was eventually traded to San Jose and put up 82 points in his first season with the Sharks. Heatley's production dropped the following season to 64 points and he was traded to Minnesota. Heatley's play continued to plummet with the Wild and in the final year of his deal, Heatley recorded just 28 points in 76 games.

12 Ilya Kovalchuk: 15 years, $100 million

via zenfs.com

After acquiring Ilya Kovalchuk from the Atlanta Thrashers prior to the 2010 trade deadline, the New Jersey Devils attempted to re-sign the star winger to a massive 17 year, $102 million contract. The NHL rejected the deal, believing the structure of the contract to be cap circumvention. As a result the Devils were fined $3 million and forced to forfeit a third round draft pick in 2011 and a future first round draft pick, which they deferred until 2014.

The Devils modified the contract to a 15 year, $100 million deal. Kovalchuk had three strong seasons in New Jersey and helped the Devils reach the Stanley Cup Final in 2012. However, at the end of the 2012-13 season, Kovalchuk retired from the NHL to return to his native Russia, forfeiting the 12 years and $77 million remaining on his contract. The league then reduced the Devils' circumvention fine and restored their first round pick in 2014 at the 30th position.

11 Brad Richards: 9 years, $60 million

Kirby Lee-USA TODAY Sports

The Rangers signed the star centreman to a nine year, $60 million contract in the summer of 2011. In three seasons with the Rangers, his point production declined. He posted 66 points in 2011-12, 34 points in the brief 2012-13 season, and 51 points in 2013-14. Richards struggled in the Rangers' run to the 2014 Stanley Cup Final and was demoted to the fourth line for the fourth and fifth games of the Final. After New York's loss to the Los Angeles Kings, they bought out the final six years of the deal.

10 Sheldon Souray: 5 years, $27 million

via oilersnation.com

After posting a career high 64 points during the 2006-07 season with the Montreal Canadiens, Sheldon Souray signed a five year, $27 million deal to quarterback the Edmonton Oilers' power play. He was limited to 26 games in 2007-08 due to injury. After posting 53 points in 81 games in 2008-09, Souray's play was again derailed by injuries in 2009-10.

Concerned about his medical treatment, Souray asked for a trade the following offseason. Unable to find anyone to take Souray's contract, the Oilers waived the defenceman and sent him to the minors. Souray spent the 2010-11 season playing with the AHL's Hershey Bears and in the summer of 2011, the Oilers bought out the final year of his contract.

9 Bobby Holik: 5 years, $45 million

via bleacherreport.net

You can thank teams like the Rangers for causing the recent NHL lockouts when they're handing out contracts like this. After 10 seasons in New Jersey, Bobby Holik joined the rival Rangers on a five year, $45 million contract. Holik had never posted more than 65 points with the Devils, but in a pre salary cap era, the Rangers were willing to pay him $9 million per season if he could help their Cup chances. Holik played two seasons in the Big Apple, recording 35 points in 2002-03 and 56 points in 2003-04. After the 2004-05 lockout, the Rangers bought out the remainder of Holik's contract.

8 Roberto Luongo: 12 years, $64 million

Anne-Marie Sorvin-USA TODAY Sports

"My contract sucks." Those were the words of the Canucks goaltender following the 2013 trade deadline in regards to the 12 year, $64 million deal he signed in 2009. At the time of the extension Roberto Luongo was the Canucks number one goalie and captain. After the emergence of Cory Schneider however, Luongo told the Canucks that he would be open to a trade. After trying and finding no takers for Luongo's contract, the Canucks instead traded Schneider at the 2013 draft, only to trade Luongo to the Florida Panthers at the 2014 deadline, after agreeing to retain 15% of Luongo's salary. The contract isn't too bad for Florida, as Luongo's still a very serviceable goaltender for them, but it proved to be a disaster for the Canucks.

7 Vincent Lecavalier: 11 years, $85 million

AP Photo/Chris O'Meara

After back to back 90+ point seasons, the longtime Tampa Bay Lightning superstar signed an 11-year, $85 million extension in the summer of 2008 that would begin with the 2009-10 season. Lecavalier's production immediately dropped and he posted justed 67 points in the 2008-09 season. A deal to send Lecavalier to his hometown Montreal Canadiens before the extension kicked in was discussed. The 2009-10 season would be the last 70 point season of Lecavalier's career as his production continued to decline. After the short 2012-13 season, the Lightning paid $30 million to make the final seven years of his deal disappear. The Flyers followed this up by giving Lecavalier another bad contract, at least from the team's perspective, signing him to a five-year, $22.5 million deal that they're now trying to dump off on someone else.

6 Wade Redden: 6 years, $39 million

via nhlsnipers.com

Despite Wade Redden's play dropping off during his final two seasons in Ottawa, the New York Rangers signed him to a six year, $39 million contract in the summer of 2008. Redden's production dropped further in New York, posting 26 points in 2008-09 and just 14 points in 2009-10. The Rangers buried Redden's contract in the minors for the next two seasons and bought out the final two years after the 2012-13 lockout. This contract played a key role in the implementation of a rule in the new CBA to prevent teams from burying big money contracts in the minors.

5 Alexei Yashin: 10 years, $87.5 million

via zenfs.com

After sitting out the entire 1999-00 season due to a contract dispute with the Ottawa Senators, Yashin returned for the following season and recorded 88 points in 82 games. That offseason the Senators traded Yashin to the New York Islanders for Zdeno Chara, Bill Muckalt, and a first round draft pick which the Senators used to draft Jason Spezza. The Islanders then signed Yashin to a 10 year, $87.5 million contract. Yashin recorded 75 points in his first season on Long Island, but his point production soon dropped and in 2007 the Islanders bought out the four years remaining on his contract.

4 David Clarkson: 7 years, $36.75 million

Jerome Miron-USA TODAY Sports

Convinced that a lack of grit and character - not actual hockey talent - were the main reasons for their 2013 Game 7 collapse against the Boston Bruins, the Toronto Maple Leafs signed hometown boy David Clarkson to a seven year, $36.75 million contract. Clarkson had one 30 goal season in New Jersey, but otherwise had never posted more than 32 points in an NHL season. Clarkson began his first season in Toronto by serving a 10-game suspension and finished with just five goals and 11 points in 60 games. Clarkson recorded 10 goals and 15 points in 58 games this season before he was miraculously traded to the Columbus Blue Jackets for Nathan Horton. This contract was a disaster from the start and was structured in a way that Clarkson would receive 75% of his salary in guaranteed signing bonuses, making it virtually buyout proof.

3 Scott Gomez: 7 years, $51.5 million

via exruefrontenac.com

On the same day that the New York Rangers signed Drury, they also signed Scott Gomez to a seven year, $51.5 million contract despite the fact that the centreman had only exceeded the 70 point mark once in his NHL career. Gomez recorded 70 points in 2007-08 with the Rangers, but his point total dipped to 58 the following season. After two seasons in New York, Gomez was traded to the Montreal Canadiens in a multi-player deal that brought Ryan McDonagh to New York. Gomez's play further diminished in Montreal. Gomez went into a year long goal drought from February 2011 to February 2012. Following the 2012-13 lockout, the Canadiens bought out the rest of Gomez's contract.

2 Ilya Bryzgalov: 9 years, $51 million

via thestar.com

Always looking to upgrade their goaltending, the Philadelphia Flyers acquired the rights to Ilya Bryzgalov and signed him to a nine year $51 million dollar contract in June of 2011. The Flyers also traded away Mike Richards and Jeff Carter to fit Bryzgalov's contract on the cap. In his first year in Philadelphia, the Russian goaltender became more known for his media interviews than for his play on the ice.

Bryzgalov helped the Flyers reach the postseason in 2011-12, but his play in the playoffs was abysmal, sporting a .887 SV% and 3.46 GAA in 11 games. The Flyers failed to reach the postseason in the lockout shortened 2012-13 season and decided they had enough of Bryzgalov, buying out the final seven years of his deal.

1 Rick DiPietro: 15 years, $67.5 million

via lighthousehockey.com

The Islanders didn't learn their lesson with the Yashin contract, signing goaltender Rick DiPietro to an unprecedented 15 year, $67.5 million contract in 2006. After signing the contract, DiPietro went 32-19-9 with a .919 SV% and 2.58 GAA to go along with five shutouts in 62 games in 2006-07. Unfortunately for DiPietro, that was the pinnacle of his success. A plethora of injuries soon derailed his career and after playing just 50 NHL games from 2008-09 through 2012-13, the netminder was bought out with eight years remaining on his contract. This contract seemed like a bad idea at the time and set the standard for future long term contracts, making it the worst contract in NHL history.

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Top 20 Worst Contracts in NHL History