With the NHL’s Christmas roster freeze in the rear-view mirror and the trade deadline less than two months away, the number of players switching teams has started to pick up. There has been a flurry of deals since the freeze endedand there promises to be many more before the deadline arrives on February 29th. One of those most high profile deals to go down saw Vincent Lecavalier and Luke Schenn go from Philadelphia to Los Angeles in exchange for Jordan Weal and a third round draft pick, with the Flyers retaining half of both players’ salaries.

The deal was able to come about after Lecavalier agreed that he would retire at the end of the season and forego the final two years of his contract. He’ll have one last shot to pick up his second Stanley Cup victory before he hangs up his skates for good. It’s a sad end to the career of a once great player who can barely play in the league anymore.

Vincent Lecavalier’s career will last 17 seasons, having won a Rocket Richard Trophy, King Clancy Trophy and a Stanley Cup, and he’ll be remembered as one of the greatest players to ever player for the Tampa Bay Lightning. His legacy will also forever be tied to two of the worst contracts in NHL history. His swift fall from grace and failure to live up to expectations during his final years in Tampa Bay and his two plus years in Philadelphia may forever tarnish his legacy. In honor of Lecavalier’s career coming to an end and the millions of dollars he’s made along the way, we’ve decided to look at some of the other bad contracts that have been handed out over the years.

This list will only be comprised of contracts the teams themselves handed out, not contracts that a team picked up via trade midway through a deal.

 

Here’s a team by team look at each franchise’s worst deal.

Anaheim Ducks – Ryan Kesler – 6 years, $41.25 million

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

It’s never a good sign when your worst contract is one that hasn’t even begun yet. Last summer, the Ducks felt the need to lock up Kelser to a six year, $41.25 million contract despite the fact that he was a full year away from free agency and clearly on the decline. Kesler hasn’t reached the 50 point mark since 2010-11 and he’s on pace to have the worst statistical full season of his career since his sophomore campaign. Yet he can look forward to making $6.875 million per season beginning in 2016-17.

Arizona Coyotes – Mike Smith – 6 years, $34 million

Christopher Hanewinckel-USA TODAY Sports

Christopher Hanewinckel-USA TODAY Sports

Mike Smith had one good season and one less than stellar lockout shortened season under his belt with the Coyotes when they locked him up to a six year, $34 million deal in the summer of 2013. Since then, Smith has had more downs than ups and has done very little to justify being paid like a top tier goaltender. He’s still under contract for a while as the Coyotes find themselves in rebuilding mode.

Boston Bruins – Zdeno Chara – 7 years, $45.5 million

Winslow Townson-USA TODAY Sports

Winslow Townson-USA TODAY Sports

Zdeno Chara’s signing with the Boston Bruins in the summer of 2006 may go down in history as the best free agent signing of all time, but the extension they gave him in October of 2010 is the team’s worst. The Bruins signed the 33-year-old to a seven year, $45.5 million deal and although he helped them to a Stanley Cup victory that spring, the big defenseman’s play has declined since. By the time his contract expires in 2018, it will likely be more of a liability than anything.

Buffalo Sabres – Ville Leino – 6 years, $27 million

Timothy T. Ludwig-USA TODAY Sports

Timothy T. Ludwig-USA TODAY Sports

Ville Leino made the jump from Europe to the NHL as a 25-year-old with the Red Wings in 2008-09, but after failing to produce much for Detroit, he was dealt to the Philadelphia. Leino broke out during the Flyers run to the 2010 Stanley Cup Final, scoring 21 points in 19 playoff games, and followed that up with 53 points in 2010-11. As a result, he was awarded with a six year, $27 million deal from the Sabres. To say Leino underachieved in Buffalo would me a massive understatement. Over the course of three seasons, Leino produced just 10 goals and 46 points in 137 games, including zero goals in 58 games in 2013-14. Following Leino’s goalless season, the Sabres bought out the final three years of his deal and he returned to Europe.

Calgary Flames – Jay Bouwmeester – 5 years, $33.4 million

via nhl.com

via nhl.com

The Flames traded for Jay Bouwmeester’s rights at the 2009 draft and signed him to a five-year, $33.4 million deal. Bouwmeester never lived up to expectations on a bad Flames team and never posted more than 29 points during three plus seasons in Calgary. During the 2012-13 season he was dealt to the St. Louis Blues and has seemed to found a suitable role on a team where he’s not required to be the number one defenseman.

Carolina Hurricanes – Jordan Staal – 10 years, $60 million

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

The Hurricanes traded for Jordan Staal at the 2012 draft with the assumption that getting him out from the shadows of Sidney Crosby and Evgeni Malkin in Pittsburgh would allow him to blossom into a top line centre alongside his brother Eric. After the trade, Staal was signed to a 10 year, $60 million deal.

During Staal’s four seasons in Carolina, he has yet to improve upon or even replicate the 25 goals and 50 points he scored during his final season with the Penguins. Staal’s best season with the Hurricanes came in 2013-14 when he scored just 15 goals and 40 points and he doesn’t look likely to improve upon those numbers anytime soon.

Chicago Blackhawks – Jonathan Toews and Patrick Kane – 8 years, $84 million

Rob Grabowski-USA TODAY Sports

Rob Grabowski-USA TODAY Sports

In the summer of 2014 the Blackhawks locked up both Jonathan Toews and Patrick Kane to identical eight year, $84 million contracts. Yes, they’ve led the Blackhawks to three Stanley Cup victories in six years, but salary cap restraints have forced the team to dump quality depth players after each one. The Blackhawks didn’t have much choice but to give the pair extensions, but within a few years both players will start to decline and those contracts will become albatrosses around the neck of the Blackhawks as their lack of depth catches up to them.

Colorado Avalanche – Ryan Smyth – 5 years, $31.2 million

via zimbio.com

via zimbio.com

After Ryan Smyth’s tear feared departure from the Edmonton Oilers at the 2007 trade deadline, the highly touted free agent joined the Avalanche on a five-year, $31.2 million contract. Smyth battled through injuries and posted 37 points in 55 games in his first season in Colorado. He rebounded the following year with 59 points in 77 games, but it wasn’t enough to justify his contract and with the Avalanche beginning their rebuild they traded him to the Los Angeles Kings in the summer of 2009.

Columbus Blue Jackets – Nathan Horton – 7 years , $37.1 million

Greg Bartram-USA TODAY Sports

Greg Bartram-USA TODAY Sports

After helping the Boston Bruins to their second Stanley Cup Final appearance in three years in 2013, Nathan Horton signed a seven year, $37.1 million contract with the Blue Jackets. Offseason shoulder surgery delayed Horton’s Columbus debut until January of 2014 and he played just 36 games that season finishing with 19 points. The following fall Horton was diagnosed with a degenerative back injury that meant he would likely never play again.

With no return in sight and the Blue Jackets needing to spend their money on someone who could play, they dealt Horton to the Toronto Maple Leafs for David Clarkson in February of 2015.

Dallas Stars – Sean Avery – 4 years, $15.5 million

via dallasnews.com

via dallasnews.com

After causing a disturbance for Martin Brodeur and helping the New York Rangers to eliminate the New Jersey Devils in the 2008 playoffs, Sean Avery signed a four-year, $15.5 million deal with the Dallas Stars during the weird, short lived era in which Brett Hull and Les Jackson served as co-general managers. Avery played just 23 games with the Stars and was suspended for comments he made about an ex-girlfriend before he was waived and loaned to the Rangers AHL affiliate, the Hartford Wolf Pack. Avery was eventually placed on re-entry waivers and claimed by the Rangers at half his salary.

Detroit Red Wings – Johan Franzen – 11 years, $43.5 million

Raj Mehta-USA TODAY Sports

Raj Mehta-USA TODAY Sports

After posting 18 points in 16 playoff games during the Red Wings run to win the 2008 Stanley Cup, Johan Franzen followed that up with a career high 34 goals and 59 points in 2008-09 and was rewarded with an 11 year, $43.5 million contract. The Mule hasn’t played more than 54 games in a season since 2011-12 and has only played two games in 2015-16 due to post-concussion syndrome. His career is all but finished, but his contract doesn’t expire until the end of the 2019-20 season. As long as Franzen remains on the long-term injury reserve, the Red Wings will be allowed to exceed the cap by his cap hit amount if they need to, but it’s not an ideal situation and if he does get healthy, it could make for a difficult cap situation in Detroit.

Edmonton Oilers – Sheldon Souray – 5 years, $27 million

via oilersnation.com

via oilersnation.com

Sheldon Souray posted a career high 26 goals and 64 points for the Montreal Canadiens in 2006-07 and then signed a five year, $27 million deal to join his hometown Oilers. Souray was limited by injuries to 26 games during his first season in Edmonton, rebounded with 53 points in 81 games 2008-09, and then played just 37 games the following year due to more injuries. In the summer of 2010, Souray asked for a trade out of Edmonton, citing frustration with the Oilers treatment of his ailments, but there were no takers for his contract. He was waived and spent the 2010-11 season playing 40 games with the AHL’s Hershey Bears before the Oilers bought out the remainder of his contract.

Florida Panthers – Dave Bolland – 5 years, $27.5 million

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

Dave Bolland was limited to 23 games during his one season with the Maple Leafs, but drew praise from the team and the Toronto media for his “leadership” abilities. In the summer of 2014 his contract demands ultimately proved to be too much for the Maple Leafs and he signed a five year, $27.5 million deal with the Florida Panthers were he was re-united with general manager Dale Tallon, who he had previously played for in Chicago. The injury prone Bolland was limited to 53 games in his first season in Florida and posted just 23 points. He has just five points in 25 games in 2015-16 and earlier this season he was waived and sent to the minors for a couple of games. The red hot Panthers currently sit atop the Atlantic Division, but they don’t have Bolland and his $5.5 million salary to thank.

Los Angeles Kings – Jonathan Quick – 10 years, $58 million

Kirby Lee-USA TODAY Sports

Kirby Lee-USA TODAY Sports

Following their first Stanley Cup victory in 2012, the Kings were quick (pun intended) to lock-up their netminder to a massive 10 year, $58 million deal. Since then Quick has added another Cup victory to his resume and he has the Kings atop the Pacific Division in 2015-16. Quick has played good, but not great under the deal, but regardless of his play, it’s never a great idea to sign a goaltender to a long-term deal and sooner or later that contract is going to come back to bite the Kings.

Minnesota Wild – Zach Parise & Ryan Suter – 13 years, $98 million

Brad Rempel-USA TODAY Sports

Brad Rempel-USA TODAY Sports

In the summer of 2012, Zach Parise and Ryan Suter were the top free agents on the market and both players agreed to sign with the Minnesota Wild on identical 13 year contracts at $98 million each. The pair may have helped turn the Wild into a playoff team but they haven’t exactly been Stanley Cup contenders. Thirteen years is a ridiculously long time to sign any player for. Both players are the wrong side of 30 and still have nine years left on their deals after this season.

Montreal Canadiens – Daniel Briere – 2 years, $8 million

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

When you think of the Montreal Canadiens and bad contracts, your mind immediately jumps to Scott Gomez until you remember that the Canadiens willingly traded for that contract after it was already apparent that it was an atrocious deal. In terms of contracts they handed out themselves, the Habs’ worst deal came in the summer of 2013 when they signed Daniel Briere to a two year, $8 million deal.

Briere had just been bought out by the Flyers after struggling through his final two years in Philadelphia, but the Canadiens were hopeful that he could bounce back in Montreal. That didn’t happen and Briere posted just 25 points in 69 games during his lone season with the Canadiens before being traded to Colorado.

Nashville Predators – Shea Weber – 14 years, $110 million

Christopher Hanewinckel-USA TODAY Sports

Christopher Hanewinckel-USA TODAY Sports

In the summer of 2012, Shea Weber signed a 14 year, $110 million offer sheet with the Philadelphia Flyers, with $68 million of the deal coming in signing bonuses. Having already lost Ryan Suter to free agency, the Predators couldn’t allow Weber to leave and had little choice but to match the deal. As is the case with the Parise and Suter deals, Weber may be a good player, but it’s hard to justify a contract of that size. Weber remains a productive NHL defenseman, but he’s now 30 years old and still has another 10 years left on his contract after this season.

The Predators would’ve been better suited to try move Weber rather than Seth Jones, but even if they could find someone willing to take his contract, it would be difficult to justify trading the face of the franchise to that fan base. So they may be stuck with him for another decade.

New Jersey Devils – Ilya Kovalchuk – 15 years, $100 million

via thecomeback.com

via thecomeback.com

After trading for Ilya Kovalchuk at the 2010 deadline, the Devils signed him the following summer to a massive 17-year, $102 million contract. Due to the small amount that was to be paid in the latter years of the deal, the NHL rejected the deal believing it to be designed to circumvent the salary cap. After an amendment to the CBA, the contract was modified to be a 15-year, $100 million deal and the Devils were fined $3 million and forced to forfeit a future first and third round draft pick for the original contract. Kovalchuk played quite well for the Devils under the first three years of the deal. He scored 83 points in 2011-12 and 19 points in 23 playoff games while helping the Devils to reach the 2012 Stanley Cup Final.

Following the 2012-13 season, Kovalchuk chose to retire from the NHL and return to Russia, foregoing the final 12 years and $77 million of his contract. As a result, the NHL returned half of the $3 million fine and reinstated the Devils first round pick, which they had yet to forfeit, at 30th overall in 2014.

New York Islanders – Rick DiPietro – 15 years, $67.5 million

via lighthousehockey.com

via lighthousehockey.com

The New York Islanders and Rick DiPietro set the bar for all of the future massive contracts when the goaltender was signed to a 15-year, $67.5 million contract in September of 2006, despite having only two full seasons with varying degrees of success on his resume. DiPietro played two more full NHL seasons after signing the deal before a run of injuries derailed his career.

DiPietro was waived after playing just three games in the lockout shortened 2012-13 season and after the season came to an end, the Islanders bought out the final eight years of his deal.

New York Rangers – Bobby Holik – 5 years, $45 million

via bleacherreport.com

via bleacherreport.com

The Rangers have signed quite a few players to bad contracts over the years, including Brad Richards, Scott Gomez, and Wade Redden, but most of them you could at least argue that the player may have been worth his salary at one point in his career. However, there’s no world in which you justify the five year, $45 million contract they handed to Bobby Holik in the summer of 2002.

Holik had never posted more than 29 goals or 65 points in a single season, yet the Rangers were willing to pay him $9 million per season. Holik played two years of the deal, scoring 35 points in 2002-03 and 56 points in 2003-04 and then had the remainder of his deal bought out following the 2004-05 lockout.

Philadelphia Flyers – Ilya Bryzgalov – 9 years, $51 million

via thestar.com

via thestar.com

The Flyers are another team that has handed out many bad contracts, but the nine year, $51 million deal they gave to Ilya Bryzgalov easily takes the cake as their worst. The Flyers had a history of bad goaltending and attempted to rectify that by bringing in Bryzgalov and they traded away both Mike Richards and Jeff Carter to accommodate his salary. Bryzgalov played two less than stellar seasons in Philadelphia, which featured a disastrous playoff performance in 2012 and no playoff appearance the following season, before the Flyers bought out the final seven years of his deal.

Pittsburgh Penguins – Zigmund Palffy – 3 years, $13.5 million

via pinterest.com

via pinterest.com

The Penguins have generally been smart with their money, mostly because for many years they couldn’t afford to spend a lot of it. They’ve also managed to dodge a few bullets, like Jordan Staal rejecting the same ten year deal from the Penguins that he accepted after being traded to the Hurricanes.

To find their worst contract signing you have to go back to 2005 when they signed Zigmund Palffy to a three year, $13.5 million deal. Palffy actually played well for the Penguins, producing 42 points in 42 games, but he abruptly retired part way through the first year of the deal due to a lingering shoulder injury, although he would later resume is his career in Europe.

Ottawa Senators – Alexandre Daigle – 5 years, $12.25 million

via windsorstar.com

via windsorstar.com

The Senators drafted Alexandre Daigle first overall in 1993 and then handed him a five year, $12.25 million deal before he had even played a game. Daigle’s deal was the largest starting salary for a player in league history at the time and led to the NHL introducing a rookie salary cap a short time later. After signing the deal, Daigle proceeded to be one of the biggest draft busts in NHL history.

San Jose Sharks – Paul Martin – 4 years, $19.4 million

Sergei Belski-USA TODAY Sports

Sergei Belski-USA TODAY Sports

The Sharks have been pretty conservative with their money over the years. In fact you’d be hard pressed to find a Sharks deal with much term that didn’t work out. Having said that, their worst deal would have to be the four year, $19.4 million contract they gave to defenseman Paul Martin this past summer. Martin is 34 years old and clearly on the decline and the Sharks would’ve been better off finding another way to spend nearly $5 million over the next four seasons.

St. Louis Blues – Jay McKee – 4 years, $16 million contract

via sikids.com

via sikids.com

The Blues are another team that doesn’t have much of a history of overspending. Their worst deal came in the summer of 2006 when they gave a four year, $16 million contract to shot-blocking defenseman Jay McKee. Injuries limited McKee to 23 games during his first season with the Blues. He then struggled through two more seasons in St. Louis before the Blues bought out the final year of his deal.

Tampa Bay Lightning – Vincent Lecavalier – 11 years, $85 million

AP Photo/Chris O'Meara, File

AP Photo/Chris O’Meara, File

As noted in the intro, Vincent Lecavalier was the recipient of one the worst contracts of all time as a member of the Tampa Bay Lightning. After posting 92 points in 2007-08, the Lightning locked up their captain to an 11-year, $85 million deal in the summer of 2008 that was set to begin in the 2009-10 season. Lecavalier’s production dipped to 67 points during the final year of his old deal and the Lightning tried to trade him before the extension began.

GM Brian Lawton agreed to a deal to send Lecavalier to the Montreal Canadiens, but the deal was squashed by ownership and Lecavalier remained in Tampa Bay. His play continued to drop off and following the 2012-13 lockout shortened season, the Lightning handed Lecavalier the largest buyout in NHL history.

Toronto Maple Leafs – David Clarkson – 7 years, $36.75 million

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

The Maple Leafs are another team whose history of contract signings isn’t great. The seven year, $36.75 million contract they handed David Clarkson in the summer of 2013 is by far the worst. Clarkson had scored 30 goals and 46 points on the 2011-12 Devils squad that made a trip to the Stanley Cup Final, but he had never scored more than 17 goals and 32 points in any other NHL season and definitely didn’t justify his $5.25 million salary.

What made the contract worse was that it was structured so that more than 75 percent of the deal would be paid in signing bonuses, essentially making it buyout proof. Clarkson began his Toronto tenure with a 10 game suspension and finished the 2013-14 season with just 11 points in 60 games. He followed that up with 10 goals and 15 points in 58 games for the Maple Leafs in 2014-15 before they miraculously rid themselves of his contract in the trade for Nathan Horton.

Vancouver Canucks – Roberto Luongo – 12 years, $64 million

Anne-Marie Sorvin-USA TODAY Sports

Anne-Marie Sorvin-USA TODAY Sports

Roberto Luongo himself said it best, “My contract sucks.” The Canucks locked up their starting goaltender to a 12 year, $64 million extension in 2009, but after he struggled in the 2011 Stanley Cup Final and Cory Schneider emerged as a capable starting goaltender, it became apparent that the deal was an albatross around the Canucks’ neck. The Canucks tried to trade Luongo, but couldn’t find any takers prior to the 2013 deadline, prompting Luongo to utter those words.

The Canucks instead opted to trade Schneider at the 2013 draft, but less than a year later they dealt Luongo to the Florida Panthers after finally agreeing to retain part of his salary in the trade.

Washington Capitals – Jaromir Jagr – 7 years, $77 million

via sikids.com

via sikids.com

Jaromir Jagr is going to go down in history as one of the greatest players to ever play the game, but his time with the Capitals were not best years of his career. After acquiring Jagr from the Penguins, the Capitals signed him to a seven year, $77 million contract that at the time was the largest in NHL history. Jagr continued to play at a point per game pace in Washington, but his numbers failed to live up to the 100 plus point seasons people had come to expect from him, making it difficult to justify his $11 million salary.

Midway through the 2003-04 season, the Capitals traded Jagr to the New York Rangers for Anson Carter. The Capitals agreed to pay $4-$4.5million per year of Jagr’s salary and he agreed to defer $1 million per year to allow the trade to go through. After the 2004-05 lockout, Jagr’s salary was reduced and with the Capitals still paying a portion of his deal, it became a much more reasonable deal for the Rangers.

Winnipeg Jets (Atlanta Thrashers) – Bobby Holik – 3 years, $12.75 million

via zimbio.com

via zimbio.com

Bobby Holik has the honor of being the recipient of two teams’ worst contracts of all time. After he was bought out by the Rangers, Holik signed a three year, $12.75 million deal with the Atlanta Thrashers. Holik played all three years of the deal with the Thrashers, but again he failed to live up to his salary and he never scored more than 34 points during his time in Atlanta.

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