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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 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:

20 Martin Havlat: 6 years, $30 million

Sergei Belski-USA TODAY Sports

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.

18 Chris Drury - 5 years, $35.25 million

via blueshirtbulletin.com

17 Jeff Finger: 4 years, $14 million

via bleacherreport.net

16 Mike Komisarek: 5 years, $22.5 million

DAVID COOPER/TORONTO STAR

15 Ville Leino: 6 years, $27 million

Timothy T. Ludwig-USA TODAY Sports

14 Sean Avery: 4 years, $15 million

via dallasnews.com

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.

12 Ilya Kovalchuk: 15 years, $100 million

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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.

11 Brad Richards: 9 years, $60 million

Kirby Lee-USA TODAY Sports

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.

9 Bobby Holik: 5 years, $45 million

via bleacherreport.net

8 Roberto Luongo: 12 years, $64 million

Anne-Marie Sorvin-USA TODAY Sports

7 Vincent Lecavalier: 11 years, $85 million

AP Photo/Chris O'Meara

6 Wade Redden: 6 years, $39 million

via nhlsnipers.com

5 Alexei Yashin: 10 years, $87.5 million

via zenfs.com

4 David Clarkson: 7 years, $36.75 million

Jerome Miron-USA TODAY Sports

3 Scott Gomez: 7 years, $51.5 million

via exruefrontenac.com

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.

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