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

Tim MeehanCorrespondent IJune 6, 2012

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

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    When the Stanley Cup Finals end in early June, hockey fans turn to the next exciting phase for hockey: free-agent signings.

    Every team in the NHL begins its quest for glory in the summer when general managers start to take action on what they feel will be a winner.

    Often times the free-agent signings over the summer are great deals, but unfortunately for some teams, that isn't always the case.

    This list will examine the worst free-agent signing in each team's history since it is always enjoyable to laugh at the dark spot of a franchise, unless, of course, that deal is still on the books.

Anaheim Ducks

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    Jean-Sebastien Giguere signed a four-year, $24 million contract with the Anaheim Ducks in the summer of of 2007.

    He certainly started off well for the Ducks, winning 35 games the first year.

    The second, however, was an absolute disaster, winning only 19 games and posting a .900 save percentage along the way.

    The third year wasn't much better as the veteran goalie found himself making only 20 starts for the Ducks, winning only four games and being shipped to Toronto.

Atlanta Thrashers/Winnipeg Jets

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    With the Winnipeg Jets having only one season in the NHL, it doesn't seem entirely fair to rip any of their deals, so we will go back to the days as the Thrashers for this one.

    Bobby Holik posted 91 points for the Rangers in two seasons and then bought out his contract. If that wasn't a warning sign enough for the Thrashers, I'm not sure what could be.

    The Thrashers still took a chance, signing Holik to a three-year, $12.75 million deal.

    In his three years in Atlanta, Holik posted 96 points in 228 games with a horrible -23 rating.

Boston Bruins

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    Martin Lapointe got a three-year, $16 million dollar contract with the Boston Bruins in the summer of 2001.

    How did he repay the franchise? With 83 points in 206 games during the regular season and four points in 18 postseason games.

    It is true that the money didn't make a big difference as the salary cap didn't exist in the NHL then, but this was still a huge deal for a player who contributed very little to the team.

Buffalo Sabres

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    This is a difficult deal to judge.

    Christian Ehrhoff signed a 10-year, $40 million contract with the Buffalo Sabres prior to the 2011 season.

    In 66 games last year he did post 32 points but had a -2 rating.

    The biggest problem with this deal is the length. It has Ehrhoff set to be a $4 million cap hit through the 2020-2021 season.

    That means in the final years of his deal he will be 37, 38 and 39 years old—an extremely long contract for a player who has played in 82 games in only one season of his career.

Calgary Flames

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    Jay Bouwmeester signed a five-year, $33.4 million deal with the Calgary Flames after six fairly productive seasons with the Florida Panthers.

    Bouwmeester must have missed the sun though, as he only has 82 points in 246 games with the Flames. He also has a -27 rating over those three seasons.

    Being paid like a top-pair defenseman, those numbers are simply unacceptable.

    He does have two years left on the deal, so maybe he can right the ship and change it from a horrible deal to simply a bad deal.

Carolina Hurricanes

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    Tomas Kaberle signed a three-year, $12.75 million deal with the Carolina Hurricanes prior to the 2011 season.

    He only played in 29 games for the Hurricanes, posting no goals and nine assists with a -12 rating.

    This was certainly a terrible deal for the Hurricanes, but fortunately they somehow managed to trade him and be rid of it.

    Sometimes there is a good thing to a horrible deal, and that is finding a buyer who will take it.

Chicago Blackhawks

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    Cristobal Huet was the answer for the Chicago Blackhawks in net. Unfortunately, no one told him that.

    He was signed to a four-year, $22.5 million contract before the start of the 2008-2009 season.

    His first season was respectable, posting 20 wins and a .909 save percent. The second year he won 26 games, but his save percent dropped down to .895.

    After the 2009-10 season, Huet was loaned to HC Fribourg-Gotteron SA to help the Blackhawks clear some salary space.

    It's clearly a bad deal when no one in the NHL will even trade for the guy.

Colorado Avalanche

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    Ryan Smyth signed a five-year, $31.25 million deal with the Colorado Avalanche before the 2007-2008 season.

    Smyth played two seasons of that deal with the Avalanche, putting up 96 points in 132 games. He also posted a -19 rating over those years.

    For a cap hit of $6.25 million, the production simply wasn't enough.

    Smyth just finished that contract, where he played for three different teams.

Columbus Blue Jackets

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    Scott Lachance got a two-year, $4 million deal with the Columbus Blue Jackets before the 2002-2003 season.

    He gave the Blue Jackets five assists and a -43 rating over two seasons.

    In the 11 seasons prior to that deal, Lachance had 31 goals and 112 assists with a -33 rating. There is no way possible the Blue Jackets could have thought giving him $2 million a year was a good idea.

    Maybe they just didn't think it would end up being as horrible as it was.

Dallas Stars

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    Sheldon Souray signed a one-year, $1.65 million dollar deal with the Dallas Stars prior to the 2011-2012 season.

    He was a free agent because the Edmonton Oilers had bought out his contract.

    While his numbers certainly weren't bad, posting 21 points on a one-year deal, it is tough for a team to justify paying someone over $1 million immediately after he is bought out by one of the worst teams in the NHL.

Detroit Red Wings

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    Uwe Krupp signed with the Detroit Red Wings prior to the 1998-1999 season and inked a four-year, $16 million contract.

    Krupp then played 30 games for the Red Wings over two seasons where he had six points and a -1 rating.

    The reason for Krupp's only playing in those 30 games over two seasons for the Red Wings was a back injury that happened to occur during a dogsled race.

    It is tough to fault a team for signing someone who happens to get hurt, but for a team that makes it difficult to find bad free-agent signings, Krupp will have to do the trick.

Edmonton Oilers

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    Yes, Sheldon Souray was the worst free-agent signing for two teams.

    When he signed with the Edmonton Oilers, it was on a five-year, $27 million contract.

    He played three seasons with the team, which were mostly injury plagued, and posted 76 points and a -25 rating.

    His contract was bought out by the Oilers after playing the 2010-2011 season with their AHL affiliate.

Florida Panthers

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    Scottie Upshall just completed the first year of a four-year, $14 million contract he signed with the Florida Panthers.

    He played in only 26 regular season games and had five points and a -2 rating to show for it.

    Another tough deal to judge since it still has three years left on it, but for a guy who has never posted more than 34 points in a season, it seems like a lot of money to throw at someone.

Los Angeles Kings

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    Rob Blake signed a two-year, $12 million contract with his former team before the 2006-2007 season.

    While his numbers weren't particularly bad, posting 65 points over two seasons, it was the fact that he had apparently forgotten he was a defenseman, posting a -45 rating during his second stint with the Kings.

    At $6 million per year, that is simply unacceptable production, and it is safe to say those were two of his worst years in the NHL.

Minnesota Wild

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    Martin Havlat signed a six-year, $30 million contract with the Wild after posting some solid numbers in his three years with the Chicago Blackhawks.

    In 151 games with the Wild, he only managed 106 points and a -29 rating. During his career, Havlat has only posted a negative plus/minus rating three times in his career, and two of those seasons came with the Wild.

    The Wild ended up trading Havlat for Dany Heatley of the San Jose Sharks after only two seasons of his massive six-year deal.

Montreal Canadiens

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    Sergei Samsonov inked himself a nice, two-year, $7.05 million deal with the Canadiens before the 2006-2007 season.

    He played in 63 games, posted 26 points and was waived by the team in February of 2007.

    For $7 million dollars, the Canadiens got 63 games and 26 points—talk about being one of the worst deals in NHL history.

Nashville Predators

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    Radek Bonk is one of the few free-agent signings that the Nashville Predators have taken on.

    He was signed to two years at $2.95 million.

    Not a very big contract, but with the hype that surrounded Bonk and the subsequent 23 goals he scored in those two years, it is a pretty bad deal.

New Jersey Devils

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    Brian Rolston found himself signing a four-year, $20.25 million deal with the New Jersey Devils after three productive seasons with the Minnesota Wild.

    Rolston's numbers over three seasons with the Devils were just pathetic considering the money he got. He posted 103 points in 209 games before being shipped out.

New York Islanders

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    Rick DiPietro.

    There really isn't a whole lot to say about his massive 15-year, $67.5 million deal other than it is horrible.

    Since signing it prior to the 2006 season, he has appeared in only 172 games, posting 72 wins.

    The deal will keep DiPietro collecting the Islanders' money until he is 40 years old.

    This is certainly one of the worst contracts ever given by a team.

New York Rangers

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    There is no question that Wade Redden's contract with the New York Rangers is the worst in the history of the NHL.

    Redden signed a massive six-year, $39 million deal prior to the 2008-2008 season, and I'm sure he is laughing about being the highest paid AHL player.

    He played two seasons of this deal with the Rangers, posting 40 points in 156 games.

    He is currently the captain of the Connecticut Whales, the Rangers' AHL affiliate.

Ottawa Senators

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    Alexei Kovalev signed a two-year, $10 million deal with the Ottawa Senators prior to the 2009-2010 season.

    He played 131 games with the Senators, put up 76 points and was traded to the Pittsburgh Penguins.

    With as much talent as he has, the Senators thought they were getting a steal. What they got instead was a player who often times didn't feel like playing and never played any defense.

Philadelphia Flyers

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    Derian Hatcher signed a four-year, $14 million contract with the Flyers in 2004.

    He posted 33 points in 203 games with a -18 rating.

    Hatcher was at the tail end of his career, but that is no excuse for giving a player who had never put up more than 31 points in a season that type of contract.

Phoenix Coyotes

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    Brett Hull's deal with the Phoenix Coyotes was a steal at $4.5 million for two years.

    Then he only played in five games and got one assist, and the deal became a huge joke.

    It was certainly worth taking a flyer on for the Coyotes, but clearly the deal didn't work out for the franchise or the 41-year-old player they signed, and that is what makes it so bad.

Pittsburgh Penguins

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    Three years and $13.5 million isn't a bad deal for a player who is going to be a superstar. Ziggy Palffy, however, was never a superstar.

    He played in 42 games for the Penguins and then retired.

    His reason for retiring was an injury, but Palffy went on to play in Slovakia for three years after he was too hurt to play for the Penguins, and that is what makes this deal so bad.

San Jose Sharks

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    Kelly Hrudey signed a two-year, $4.8 million contract with the San Jose Sharks in 1996. He was 36 years old at the time.

    In 76 games for the Sharks, Hrudey won only 20 games, and his save percent never reached .900.

    He was a veteran goalie who was supposed to help the Sharks contend; instead he was horrible.

St. Louis Blues

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    Paul Kariya signed a three-year, $18 million contract with the St. Louis Blues before the 2007-2008 season.

    Once a star in the league, Kariya appeared to no longer have it. He put up 123 points in 168 games and retired after the contract ended because of injuries.

    Six million a year for that type of production is downright terrible.

Tampa Bay Lightning

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    Ryan Malone is not a bad player. His seven-year, $31.5 million deal is a bad deal, though.

    His 178 points in 261 games over four seasons is not what a team should take a $4.5 million cap hit for.

    Malone hasn't played in all 82 games in a single season in his career, which makes this deal even worse.

Toronto Maple Leafs

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    Jeff Finger signed a four-year, $14 million deal in 2008 with the Toronto Maple Leafs.

    He put up 33 points in 105 games over two seasons for the Leafs and then was sent to the AHL.

    That is $3.5 million for two years for a guy to play in the AHL.

    Not as bad as the Redden deal, but it is certainly up there.

Vancouver Canucks

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    Mark Messier was an absolute superstar, so when the Canucks inked him to play for $6 million a year, it was the sign of glorious times for Vancouver.

    That's not how it worked out, though. The Canucks didn't make a single postseason with Messier, and he managed 162 points in 207 games.

    It does make the deal a little less terrible when you consider that Messier was 37 years old when he signed, but nonetheless, the Messier experiment in Vancouver did not work out well.

Washington Capitals

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    Michael Nylander signed a four-year, $19.5 million deal with the Washington Capitals in 2007.

    He played two seasons with the Capitals, putting up 50 points in 112 games.

    He is currently playing in the Swiss National League A, not something the Capitals were expecting when they inked him to that deal.