NHL Free Agency: Top 20 Contracts NHL Teams Would Like to Pretend Never Happened

The NHL is a league full of very talented and well compensated athletes but it is also the home to some of the most overpaid and overrated talents in all of sports. Sometimes this happens because players are awarded a large contract after a career year or a team executive overpays for a player because of a bidding war.

Some of these contracts were flagged because of their length, price or because of the impact it will have on a team's salary cap down the line. This is not to say that all the players didn't deserve their salary, but some of the deals can put a general manager in a bind.

The fact still remains that there are a few contracts that team executives wish they never handed out. With the new CBA likely to include an amnesty buyout, let's take a look at some of the top contracts in the league today that general managers may regret.

Ville Leino

Cap Information

$4,500,000 cap hit through 2016-17

The Buffalo Sabres drastically overpaid for Leino. Leino was coming off a solid season for the Philadelphia Flyers and Paul Holmgren wasn't going to meet Leino's demand.

Can someone please explain to me how a player with 30 regular-seasons goals earns a contract of almost $5.0 million per season?

Darcy Regier definitely  regrets some of the contracts he handed out this past offseason.

Vincent Lecavalier

Cap Information

$7,727,273 through 2019-2020

There is no doubt that Vincent Lecavalier is a talented player. He has been the captain of the Tampa Bay Lightning for quite some time and won a Stanley Cup in 2003-04.

However, signing Lecavalier to a deal with such a high cap hit for 11 years is not smart. His play is only going to decline over the length of the deal so moving his contract could become dicey. He also has a full no movement clause that complicates things a bit.

At the time the deal was signed, Lecavalier recorded 70 points. Last year he only hit the 54 point mark in an injury riddled season and he could miss the rest of this season with an injury and he would finish with 46 points.

This deal was handed out before Steve Yzerman became general manager, so look for Yzerman to avoid the mistakes of his predecessor.

Brian Campbell

Cap Information

$7,142,875 through 2015-2016

Brian Campbell is a talented defenseman and won a Stanley Cup with the Chicago Blackhawks. However, the salary cap situation in Chicago forced them to deal Campbell.

This deal is viewed to be a bit high because there isn't much consistency. Campbell hovers around the 40-45 point mark with a career best in 2008-09 with 52 points.

Since then, Campbell has slipped to 38 and 27 points. However, this season he has rebounded quite nicely in Florida but one wonders how long this could last.

Campbell will be 36 at the end of his current contract and possesses a limited no-trade clause in his contract.

To have a defenseman making over $7 million dollars a year is quite exorbitant considering his lack of consistency at a high rate of play.

Brandon Dubinsky

Cap Information

$ 4,200,000 through 2014-15 season

Brandon Dubinsky is another player on this list who capitalized on a career year. He led an injury ridden New York Rangers team with 54 points last season. Dubinsky, who is a penalty kill specialist by nature, went from making $1.85 million last year to making $4.2 million for the next four years.

This contract was viewed as a bit much for a player who has never scored more than 60 points. Dubinsky's down year ultimately played himself into trade rumors as the Rangers sought to acquire Rick Nash at the trade deadline.

Don't be surprised if the Rangers attempt to move him this offseason in a trade for Nash or in a secondary trade in order to gain the necessary summer cap space to pursue Zach Parise.

Ilya Bryzgalov

Cap Information

$5,666,667 through 2019-2020

Ilya Bryzgalov, better known as Mr Universe, signed a humongous contract this offseason. He may only make $5,666,667 million per year but it is for the next nine seasons.

It is never wise to sign a goaltender for an extended period of time due to the nature of the position. Goalies can get hurt and it becomes hard to replace them unless you have the necessary space. Philadelphia has been plagued with unstable goaltending for the past few seasons.

Instead of investing the future in young goalie Sergei Bobrovsky, the Flyers inked Bryzgalov to a huge deal.

If the amnesty clause is included with a new CBA, I would not be surprised if the Flyers bought him out since the team looked to acquire another starter at the deadline.

Rick Nash

Cap Information

$7,800,000 through 2017-18

Rick Nash is a top 20 player in the NHL but his contract makes him almost un-tradeable. This is the case because the limited teams that are looking to add a player of his caliber likely don't have the necessary cap space. If they don't have the space then to acquire Nash they would have to deal many valuable assets.

When Nash was shopped at the deadline there were only a few teams on his list. When you factor in Nash's salary, his list and the demands of Scott Howson, it is hard for a team to justify taking on such a large cap hit despite the fact that he has performed without talented players in Columbus.

Christian Ehrhoff

Cap Information

$4,000,000 through 2020-21

New owner Terry Pegula wanted to make a splash in the offseason. In addition to adding forward Ville Leino, he attempted to bolster the blue-line by adding Ehrhoff, who was a vital member of the 2010-11 Western Conference Champion Canucks.

Ehrhoff was a defenseman who was a consistent 35-45-plus point performer with a career high of 50 last season. This deal is not so terrible in terms of the cap hit, but because Ehrhoff has nine years left on his deal, it makes it tough to move him.

On the right team Ehrhoff is a valuable blue-line asset but unless Buffalo adds some complimentary players, this deal could be an overall bust.

Brad Richards

Cap Information

$6,666,667 through 2019-20

This contract has the potential to be regrettable. I would be remiss if I didn't include it because Richards would turn 40 at the completion of this contract. Richards is still a top player and is still adjusting to New York but one has to wonder if his play will have a steady decline in years 2017-18 to the end.

While this isn't an issue now, it could be towards the end of the decade.

Rick DiPietro

Cap Information

$4,500,000 through 2019-20

This contract could go down as the absolute worst deal in the history of pro sports. Rick DiPietro was once a very young an promising goaltending prospect who even went No. 1 overall in the NHL Entry Draft.

However, signing DiPietro to this contract was not very wise. After appearing in 63 and 62 games in the 06-07 and 07-08 seasons, DiPietro has appeared in only 51 games when you combine seasons 08-09 to the present.

Injuries have marred his career and he can never stay healthy. This contract may not hurt the Islanders now as they need it to get to the cap floor. If this team ever gets a new arena in Long Island, it will be tough to make the team competitive when bogged down with a $4.5 million cap hit for the next nine seasons.

Ilya Kovalchuk

Cap Information

$6,666,667 through 2024-25.

Ilya Kovalchuk is a very talented hockey player with lightning speed and a booming shot, but for Lou Lamoriello to sign him to a 15 year contract was not very smart.

Kovalchuk's contract was so outrageous, an arbiter ruled that the first proposed contract as illegal because it would circumvent the salary cap. His contract forced the league to ratify the CBA to prevent teams from signing players to similar contracts.

While Kovalchuk is worth the cap hit as he is still young with a lot of years left, due to the Devils' financial woes, Kovalchuk's deal may make it impossible for the Devils to re-sign their star captain Zach Parise. It is never wise to lockup players for exorbitant amounts of time because it doesn't give a team the flexibility to reassess its needs further down the line.

Wade Redden

Cap Information

$6,500,000 through 2013-14

Glen Sather has handed out a few bad contracts in his day and this is one of the worst. Redden currently is the captain of the Connecticut Whale, the Rangers' AHL affiliate.

Redden was severely overpaid and was awarded this contract during the decline of his career. Redden is a serviceable defenseman but is not worth $6,500,000 million per season.

While he does not count against the salary cap during the regular season, Redden's contract counts against the summer cap. While the Rangers are allowed to spend to 10 percent above the cap ceiling during the offseason, Redden's deal limits to an extent the moves the team can make.

Roberto Luongo

Cap Information

$5,333,333 through 2021-22

The Vancouver Canucks won the Presidents' Trophy last season on the heels of strong goaltending by Roberto Luongo. However, come playoff time, Luongo faltered in the first round to the point that Cory Schneider was given some starts.

Luongo got it together in the second and third round but had a tough Stanley Cup Final. This contract follows suit with Bryzgalov's and DiPietro's. The cap hit is low but the length is unnecessary. 

The Canucks will likely be forced to part ways with Cory Schneider this offseason because of Luongo's long-term contract. If he is not traded, odds are Schneider could be offer sheeted at an amount the Canucks would fail to meet.

The strategy may have been to give Luongo a longer contract to dilute the annual cap hit, but in this case, it didn't make sense to extend him into the next decade.

Jeff Carter

Cap Information

$5,272,727 through 2021-22

I debated putting Carter's contract on the list due to the fact that the unmovable contract was moved twice in the past six months.

Nonetheless, this is still a deal of unimaginable length. To sign a player through the next decade isn't smart because needs of a team can certainly change as time passes. Having Carter's contract on Los Angeles' books for the next decade is either a very smart or very dumb decision.

Carter has shown that he can be a perennial 30-goal scorer, so $5,272,727 is an amazing rate for a scorer of his caliber. On the flip-side, if things sour like they did for Carter in Columbus, it could become harder to trade him.

Either way, long-term contracts aren't always the smartest decision. 

Shea Weber

Cap Information

$7,500,000 through 2011-12

Don't take this the wrong way. Shea Weber is one of the league's top defenseman and deserves to be paid as such.

However, general manager David Poile wishes this deal didn't happen because in order to even retain Weber's rights as a RFA Poile will likely have to give Weber a raise.

Why?  Firstly, Poile didn't set the terms of this contract. Weber already makes $7,500,000 due to an arbiter's ruling. With Weber on pace to have a career year, odds are Weber will go to arbitration and will sign another one year deal until he becomes a UFA.

There is a lot of uncertainty because the Predators always could decided to extend Weber and could allow Ryan Suter to become a free agent.

At the end of the day Polie probably wishes Weber didn't make as much so it would be a lot easier to retain his services. 

Scott Gomez

Cap Information

$7,357,143 through 2013-14

Montreal Canadiens die-hards likely have July 1, 2014 circled on their calendars. Why is this the case? That is the day that the team would officially be rid of Gomez and his contract if the Canadiens are unable to trade him before then.

This deal is probably one of the worst that Glen Sather has handed out during his tenure as general manager of the New York Rangers. However, another general manager's gaffe is more memorable then his.

Bob Gainey foolishly dealt Ryan McDonagh and Pavel Valentenko two defensive prospects in order to acquire the once talented center. McDonagh has since emerged as one the league's top American defenseman.

Gomez recently broke his scoring drought as he went over a year without scoring a goal.

James Wisniewski

Cap Information

$5,500,000 through 2016-17

James Wisniewski is an offensive-minded defenseman but $5.5 million for a defenseman who had one 51 point season? 

This signing was not one of Scott Howson's best decisions because Wisniewski missed most of the season with an injury. The market for Wisniewski was big last summer but not big enough for him to earn a $2.25 million raise.

Ales Hemsky

Cap Information 

$5,000,000 through 2013-14

Steve Tambellini is going to end up regretting this contract. There is no logical reason why Hemsky, a talented but oft-injured forward, deserved a $5,000,000 cap hit for the next two seasons. The Edmonton Oilers have a nice youth core and could have used that money to better compliment their roster.

What makes this deal even worse is the fact that it can become a benchmark for other upcoming free agents such as P.A. Parenteau. Garth Snow is not going to be happy when Parenteau is looking for a new contract coming off a very successful career year.

Chris Pronger

Cap Information

$4,921,429 through 2016-17

Chris Pronger's career could be over due to post concussion symptoms. When Pronger signed his contract it was a 35-plus contract. What this means is if Pronger has to retire, he can't do so without costing the Flyers valuable cap space. 35-plus contracts count against a team's salary cap until the deal is completed.

If his career is in fact over, the Flyers would have to place him on LTIR if it was deemed by a doctor that he can no longer compete.

This contract really could comeback to hurt the Flyers due to the fact that Pronger was signed to a lucrative 35-plus deal.

Pronger loved playing for the Flyers, so it probably would have been smart to sign similar one-year contracts each offseason in order to allow the Flyers to maximize their cap space.

Alexander Ovechkin

Cap Information

$9,538,462 through 2020-21

This may surprise you but Alex Ovechkin is having an uncharacteristically bad season. Ovechkin is on pace for 62 points. Last year Ovechkin has 85 points and that was considered low. While Ovechkin, when on his game, may be one of the best players in the world, his cap hit and length makes it difficult to move him if things ever went sour.

I don't think that Ovechkin will remain in the 60 point range next year but to have him signed through age 35 could cause some problems if Washington ever decides to undergo a complete shakeup. 

The bottom line here, it doesn't make sense to give an athlete such a lengthy contract, especially when they are making almost $10 million a year!

Dustin Penner

Cap Information

$4,250,000 through 2011-12

Dustin Penner is an upcoming free agent and will likely receive a a major pay cut. He has failed to live up to his contract since being traded to the Los Angeles Kings. Instead of being known for his size and scoring prowess, he is known for pancakes.

Odds are Dean Lombardi is going to be thrilled once Penner's contract is off the books.

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Tom Urtz Jr. is an NHL Featured Columnist. For NHL news, updates and alerts about players: