NHL Free Agency: Every Team's Worst Free-Agent Signing Ever

Tab BamfordSenior Writer INovember 2, 2011

NHL Free Agency: Every Team's Worst Free-Agent Signing Ever

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    When teams go shopping each summer, fans and general managers hope that the money is spent wisely. Sometimes, however, it isn't.

    Every team has made a few mistakes through the years. But which players have been viewed as a potential home run that didn't even materialize into being worth the paper their contract was printed on? Following is a look back at the worst free agent signing in the history of all 30 teams in the NHL.

    I look forward to any suggestions for players I may have neglected.

Anaheim Ducks: Jean-Sebastian Giguere

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    Before the 2007-08 season, the Ducks handed the veteran netminder a four-year, $24M contract, despite Jonas Hiller signing with the organization that spring. Giguere was solid in the first season of the contract, posting a 2.12 goals-against average and a .922 save percentage, but things went south from there.

    After 66 games in almost two seasons with a goals-against in the low three's, the Ducks unloaded Giguere. He lost too many games and the starting job in Anaheim, and his cap number was just too big.

Boston Bruins: Martin Lapointe

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    How about three years and $16M for a guy that gave Boston four points in 18 postseason games in his three years with the Bruins. He had 17 goals in the first year of the deal (2001-02), but he then stepped back to 18 points and 25 points in the final two years of the deal.

Buffalo Sabres: Christian Ehrhoff

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    Ehrhoff just signed the deal that puts him on this list, and it's hard to say it's the worst deal in the organization's history based on one month's games. Indeed, Ehrhoff is worth more than the $4M cap number his deal carries; he isn't worth anywhere near the $18M he'll actually earn in the first two years of the deal, though.

    The concern with Ehrhoff's contract comes with the length, 10 years, and the fact that a no-movement clause joins a modified no-trade clause. Certainly the first four or five years of the deal will be the prime of Ehrhoff's career, but allowing a player to control his destiny into his late 30s has been problematic for teams in the past.

Calgary Flames: Jay Bouwmeester

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    Bouwmeester signed a five-year, $33.4M deal ($6.68M cap hit) before the 2009-10 season in Calgary. The signing was based on a 42-point, 15-goal season he had in Florida the prior season. Unfortunately for the Flames, Bouwmeester has produced only 53 points in 164 games over the first two years of the deal, seven of which came from goals. To say his deal has been disappointing is an understatement.

Carolina Hurricanes: Tomas Kaberle

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    After Toronto tried to give him away for a couple years, Kaberle was a nice role player on the champion Bruins in the spring. But signing a three-year, $12.75M deal at 33 years old after scoring four goals last year raised more than a few eyebrows. He hasn't started the year well for the struggling Canes, who expect and need more from a guy they're paying over $4M per.

Chicago Blackhawks: Cristobal Huet

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    There was a time, not too long ago, that the Blackhawks had to overpay players to come to Chicago. Huet was one of those players, and the organization still regrets giving him a four-year, $22.5M deal before the 2008-09 season. The expectation was that Huet would become the starter in the final year of Nikolai Khabibulin's deal, but Huet spent the first two years of his deal backing up Khabibulin and Antti Niemi before the Hawks shipped his rights—and $5.625M cap number—to Europe. If a team is willing to pay you almost $12M to play overseas, you know the paper stinks.

Colorado Avalanche: Ryan Smyth

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    Before the 2007-08 season, Colorado thought adding a 70-point forward was a good idea. So, the Avalanche gave Smyth a five-year, $31.25M contract. The $6.25M cap number was a problem for a rebuilding Avs team, especially when he only produced 37 points in the first year of the contract. He has now been dealt twice during the contract—first to LA and then to Edmonton—and is still playing out this bad deal.

Columbus Blue Jackets: Fedor Tyutin

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    In three years with the Jackets prior to signing his extension this summer, Tyutin scored 22 goals and was minus-18 in 242 games. In addition, he was held off the score sheet in the four playoff games he's played in Columbus.

    He's posted nice numbers on the power play, but he hasn't been a special player. However, the Jackets gave Tyutin a special player contract this summer, when they rewarded the 28-year-old with a six-year, $27M deal. What's more, the deal includes a no-movement clause and a modified no-trade clause. The deal they gave James Wisniewski might not have been very good, but this one is worse.

Dallas Stars: Sean Avery

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    Whenever a bankrupt team pays someone to go away, you know it's an epic disaster. The Stars bought out Sean Avery, preferring he go away than be part of their organization.

Detroit Red Wings: Uwe Krupp

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    For a franchise that has hit so many home runs, Krupp was a disaster. He got four years and $16.4M from the Wings, and then he hurt his back in a dogsled race.

    Yes, I said dogsled race.

    This deal didn't work out for the Wings, but they've done a nice job of giving writers like me limited options for most "worst of" lists.

Edmonton Oilers: Sheldon Souray

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    Before the 2007-08 season, Souray signed a five-year, $27M deal with the Oilers. After he was limited to 26 games the first year of the deal, he rewarded Edmonton with 23 goals and 30 assists in the 2008-09 season. However, another injury-plagued season sealed his fate with the Oilers. After spending the 2010-11 season in the AHL, the un-tradeable Souray was bought out by Edmonton this summer.

Florida Panthers: Rostislav Olesz

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    After posting 26 points in the 2007-08 season for Florida, the Panthers rewarded Olesz with a six-year, $18.75M deal. In three seasons since, Olesz gave Florida 57 points before GM Dale Tallon finally, somehow, found a way to dump the final three years of his deal on another team. How did he do it? By taking back Brian Campbell's astronomical cap number. The trade has worked out well on the ice for the Panthers, and Olesz's deal will now haunt Chicago for the next three years.

Los Angeles Kings: Rob Blake

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    LA wanted to bring back the magic and it paid Blake $12M over two years to, in theory, bring it back. However, over the two years of this deal (2006-08), Blake gave the Kings only 65 points and he wasn't able to impact the postseason. In fact, Blake was better in two years after this deal with the rival Sharks than he was in LA.

Minnesota Wild: Martin Havlat

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    After a couple nice years for the Blackhawks, Chicago decided to upgrade Havlat's roster spot with Marian Hossa. Left to find work on the open market, Havlat must have been thrilled to receive a six-year, $30 million offer from Minnesota. And while Wild fans didn't get much production in the two years of Havlat they had, the trade for Dany Heatley and Devin Setoguchi could make Havlat a name remembered more fondly than his contract would have otherwise indicated.

Montreal Canadiens: Scott Gomez

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    Before the 2007-08 season, the Habs made Gomez one of the highest-paid forwards in the NHL with a seven-year, $51.5M deal ($7,357,143 cap number). While not many people will hate Gomez as a player, he falls into the same "hate the contract, not the man" category as Brian Campbell. Montreal has been accepting trade offers for Gomez for two years now... they just haven't received any.

Nashville Predators: Shea Weber

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    This is more about the implications to a financially failing franchise than it is about Weber's value. The one-year, $7.5M deal he was awarded this summer by a third party now places a rope around Nashville's neck; it now has to decide the futures of Weber, Ryan Suter and Pekka Rinne simultaneously when the bell tolls this summer.

    By not getting a long-term deal done with Weber, the Preds effectively started the countdown to Armageddon.

New Jersey Devils: Ilya Kovalchuk

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    He's a special, elite player. Nobody's questioning his ability. But 15 years? $100M? He'll be 42 when the deal ends, which means either the Devils are paying him to go away at some point while still eating the cap number or he's sticking around Chelios-style. Either way, it's up to the Devils to get as much as they can out of this guy while they can, because he's going to hang around like a fart in an elevator.

New York Islanders: Rick DiPietro

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    If 15 years for a forward is stupid, let's talk about the same term for a goalie that has injury issues. DiPietro's cap number is $4.5M, and he's already five-plus years into the paper, but looking at seasons in which he's played five and eight games under this deal makes you wonder if they'll have to buy him out.

    NOTE: It was really, really hard to not mention the name Yashin here, but handing 15 years to a goalie is just stupid.

New York Rangers: Wade Redden

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    Worst ever? Redden signed a six-year, $39M deal with the Rangers in the summer of 2008 and has given them 40 points in the first three years of the deal. In fact, he had more points int he AHL last year (42) than he did in two years with the Rangers to start this deal.

Ottawa Senators: Alexei Kovalev

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    Who honestly gives a 36-year-old a two-year deal with a $5M cap number? Apparently Ottawa does, and the Senators regretted it with Kovalev until they were able to tade him to Pittsburgh last year. He's back in the KHL this year.

Philadelphia Flyers: Ilya Bryzgalov

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    If DiPietro's 15-year contract was stupid, what do you call handing a nine-year, $51M deal with a no-movement clause to a 31-year-old goalie? That's what Philly did this summer, hoping Bryzgalov would be good enough in the first few years of the deal to make it worth its while. Well, he hasn't been as good to begin the deal as the Flyers would have hoped... and they have him for eight more years after this.

Phoenix Coyotes: Brett Hull

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    Five games. One assist. $4.5M.

    Hull signed a two-year deal with the Coyotes in 2004, and all they got out of the future Hall of Famer was a nice photo moment when the artist-formerly-known-as-the-Jets "un-retired" his father's sweater.

Pittsburgh Penguins: Ziggy Palffy

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    After putting his signature on a three-year, $13.5M deal with the Pens, Palffy played 42 games and retired.

    Not exactly what they were hoping for.

St. Louis Blues: Paul Kariya

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    The Blues paid Kariya to be the 80-100 point player he was in Anaheim with a three-year, $18M deal before the 2007-08 season, but they wound up with a player that was aging and, unfortunately, was forced into retirement by injury.

    Over three years in St. Louis, Kariya only gave the Blues 36 goals.

San Jose Sharks: Antero Niittymaki

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    Niittymaki may just be a case of overpaying in a soft market, and he might be the worst example of making the most of a mediocre situation. However, he was signed to push Thomas Greiss for the starting job in San Jose with a two-year, $4M deal in the summer of 2010, and he had his hands on the starting job—for about a month.

    When Chicago declined the arbitration award given to Antti Niemi, the Sharks stepped in and signed the Cup here to a deal identical to Niittymaki's. Niemi won the starting job, and now Greiss has jumped ahead of an injured Niittymaki on the depth chart.

Tampa Bay Lightning: Vinny Lecavalier

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    Lecavalier is playing in the third year of an 11-year, $85M deal as a 31-year-old forward on a young team. When his contract expires in 2020, he'll be 40 and the Lightning will have worried about keeping Steven Stamkos twice. Is Vinny a top-tier forward? Maybe. Is he worth a cap number in the mid-$7M range? Not now, and especially not in five or eight more years.

Toronto Maple Leafs: Jeff Finger

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    Finger is (finally) in the final season of a four-year, $14M deal with the Leafs that he signed in the summer of 2008. How bad has he been for the money? He only registered five points last year... in the AHL. He gave the Leafs 33 points in 105 games over two years before finding his way to the AHL. He is still skating with the Marlies this year, and Toronto can't get rid of him fast enough.

Vancouver Canucks: Keith Ballard

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    Before the 2009-10 season, Ballard signed a six-year, $25.2M deal with the Canucks to help rebuild their blue line. In his first season with the Canucks, Ballard posted 28 points, a decent number. But worth $4.2M per? Not really. Last year, he had seven points in 65 postseason games and was scratched from most of the Canucks' run to the Cup Finals. He has eight points in his last 76 games with the Canucks, but he has three more years after the 2011-12 campaign ends on the Canucks payroll.

Washington Capitals: Ron Low

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    The first goalie in the history of the Caps, Low signed a three-year deal after the 1974-75 season. In the next two years, he went 22-58-7 and allowed 396 goals in 97 games.

Winnipeg Jets: Dustin Byfuglien

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    Though we cannot fully blame Winnipeg for Byfuglien's paper, there is no denying that he hasn't done much to earn his paycheck since putting his autograph on a five-year, $26M deal. At $5.2M per, his cap number is among the largest among all NHL defensemen right now.