NHL Free Agents: The Worst Free Agent Signing in Each Team's History

Andrew EideCorrespondent IJuly 20, 2011

NHL Free Agents: The Worst Free Agent Signing in Each Team's History

0 of 30

    Free agency signings in the NHL, like most sports, is a hit or miss proposition.  Each year NHL teams empty out the bank to sign that one guy who will take them to the promised land.

    Each year fans across the league rush out to their team shops to buy the new guy's jersey.  They take it home and make plans for the Stanley Cup parade.

    Those free agent dreams often don't come true.

    Instead, many teams are left with a player who isn't what they thought he was going to be and are stuck with a huge contract.  It can ruin a franchise, get coaches and general mangers fired and lead to fans ripping names and numbers off those jerseys.

    This year's free agency frenzy saw some crazy contracts thrown about and again, a lot of excited fans who are convinced their team is now the league top contender (looking at you Rangers fans).

    When looking at free agency, it's buyer beware.

    Since hind sight is perfect, and fun, let's take a look at each teams biggest free agency mistake.

    As always, feel free to mention anyone missed in the comments section.

Anaheim Ducks: Todd Bertuzzi

1 of 30

    The Ducks picked up the beefy winger in 2007, signing him to a two-year $8 million contract. 

    The hope was that Bertuzzi still had some spark left. 

    Bertuzzi wasn’t terrible in Anaheim, but they only got 40 points out of Bertuzzi and had to buy out his contract after one season to relieve their salary cap.  Perhaps they wouldn’t have had cap troubles if they didn’t sign old and declining players to $4 million a year contracts.

    Bertuzzi is still kicking around in the NHL, which is surprising as his best days are long gone.  Hopefully, no other team will offer him money the way the Ducks did.

Atlanta Thrashers: Bobby Holik

2 of 30

    Since Winnipeg hasn’t made many free-agent signings yet, the focus will remain with the now defunct Thrashers.  

    In 2005, they signed maligned Rangers forward to a three-year, $12.75 million contract.  This move just makes you shake your head. 

    Holik could have been the Rangers selection on this list as he never lived up to his contract there. 

    What made Atlanta think giving him $4 million a year would be wise is beyond comprehension.  To make matters worse, they made Holik the team captain.  

    Holik never scored more than 34 points in a season for that $4 million, and now Atlanta is in Winnipeg.  Probably not his fault, but moves like this contributed to Atlanta’s poor performance and lack of attendance.

    For Holik, he has the honor of receiving two of the worst contracts in NHL history.

Boston Bruins: Martin Lapointe

3 of 30

    Lapointe potted a career high 27 goals for Detroit in 2000-2001.  That was enough for the Bruins to fork over $5 million a year to wear a B on his chest.

    Unfortunately, Lapointe never lived up to that contract or that career year by never scoring more than 17 goals or topping 40 points. 

    Those numbers are pretty good for a third liner but terrible for a guy you just locked in to a $5 million cap hit.  After the lockout season, Bruins fans did not shed any tears as Lapointe landed in Chicago.

Buffalo Sabres: Christian Erhoff

4 of 30

    Is it unfair to list a guy who hasn’t skated a minute with the Sabres as their worst signing ever?

    Probably, but signing an aging Erhoff to a 10-year $40 million contract takes the cake for Buffalo. 

    Erhoff is not a terrible player, he will help the Sabres power play and probably put up any where from 30 to 50 points from the blue line for them.  But 10 years? $40 million?

    That seems like a lot for a guy who, as a defenseman, isn’t very good at defense. 

    For proof, see his recent minus-13 Stanley Cup Playoff performance for Vancouver.

Calgary Flames: Jay Bouwmeester

5 of 30

    After four productive years in Florida, the Panthers and Bouwmeester could not come to terms and the rights to the restricted free agent were traded to Calgary.  

    The Flames were able to ink the big defenseman to a five-year, $33 million deal.  Calgary assumed that they had found another anchor on defense, who could also score. 

    Bouwmeester has yet to find the scoring touch he had down south as he has regressed from a 40-point defenseman to a guy in the 20s.  For that kind of money, it appears that the Flames got duped.

Carolina Hurricanes: Alexei Ponikarovsky

6 of 30

    The Carolina Hurricanes have been a successful franchise since relocating down South.  Trying to find free agent busts for them is like trying to find a highlight of a Sedin not falling over. 

    For that reason, newly signed Alexei Ponikarovsky is the winner here.

    Again, it may be harsh to rip a guy who hasn’t played yet, but Ponikarovsky is going to make over a million dollars for Carolina next year.  A million dollars for a guy who is over 30 and scored 15 big points last year. 

    Fifteen points gets you over a million in today’s NHL?  I need to start skating more.

Chicago Blackhawks: Cristobal Huet

7 of 30

    In 2008, the Blackhawks signed goalie Huet from the Capitals for a stunning four-year, $22.4 million contract. 

    In his two seasons with Chicago, he was beaten out by Nikolai Khabibulin and Anti Niemi. 

    The Blackhawks won the Stanley Cup behind Niemi and Huet’s contract contributed to the salary cap mess Chicago was in.  In 2010-2011, Huet played for HC Fribourg in Europe, two years into his huge contract. 

    What is even more amazing, is that Huet gets his name on the Stanley Cup.

Colorado Avalanche: Ryan Smyth

8 of 30

    Smyth was the heart and soul for over a decade in Edmonton. 

    After spending the last part of the 2006-2007 season with the Islanders the Avalanche swooped in and signed the free agent to a five-year, $32 million contract.  They were hoping to get that same gritty stand-in-front-of-the-net guy that had won the fans over in Edmonton. 

    While he wasn’t terrible in Colorado, he wasn’t $32 million good.  He only lasted two seasons in Denver and scored 40 goals before being shipped to Los Angeles.

Columbus Blue Jackets: Scott LaChance

9 of 30

    The Blue Jackets picked up the veteran defenseman for a smooth two-year, $4 million contract in 2002. 

    For that money they got five assists and a combined minus-43 from the veteran.  That is money well spent.  They could have found a pee-wee player to luck into five assists in two seasons for a lot less.

    The Blue Jackets have flown under the radar for most of their existence and will have to do better to make noise in the NHL.

Dallas Stars: Sean Avery

10 of 30

    Everyone’s favorite pest signed with Dallas in 2008 for $15.5 million over four years at Avery. 

    Avery and Stars GM Brett Hull were former team mates and you have to wonder if Hull let his heart get in the way of good judgement.  Avery didn’t last the season, made some controversial comments, got suspended and racked up 10 points in only 23 games.

    He was back in New York by the end of the season. For Avery, he got paid and ended up back in New York which makes him the only winner here.

Detroit Red Wings: Uwe Krupp

11 of 30

    The Red Wings and the Colorado Avalanche had a heated rivalry in the '90s.  Uwe Krupp was a key player for the Avalanche and raised some eye brows when he jumped to Detroit in 1998.

    Detroit signed the defenseman to a four-year, $16 million contract which was pretty good money in 1998. 

    Krupp only managed 30 games for Detroit, suffering a back injury that limited his playing time to only eight games in the second year.  He was shipped to Atlanta following that season.

Edmonton Oilers: Sheldon Souray

12 of 30

    Sheldon Souray signed a five-year, $27 million contract to man the Oilers' blue line. 

    He was supposed to jump start their power play.  His demise wasn’t all his fault as he suffered several injuries and ended up with he and his salary buried in Hershey last year. 

    He had one good year with Edmonton, but unfortunately, the other two were terrible disappointments and in the end, the Oilers overpaid.

    Edmonton finally bought out his contract which means he is on the market again. Any takers?

Florida Panthers: Ed Jovanovski

13 of 30

    The Panthers made a big splash in this year's free agency.  In a lot of circles, they have greatly improved. 

    But are the contracts they signed good ones?

    Case in point, Ed Jovanovski.

    The Panthers brought back their one time star for a surprising four-year, $16.5 million contract this offseason.

    That's four years for a player who is entering his 17th season in the NHL and contributed 14 points last season.

    Fourteen points.  That's only 14 more than you did. 

    Florida will regret this contract in about two years.

Los Angeles Kings: Rob Blake

14 of 30

    The Kings signed their old friend for a second stint in Hollywood in 2006 for two years, $12 million. 

    Hoping to rekindle the magic he had before leaving for Colorado the Kings saw Blake’s production dip to some of his career lows.

    Going from a 50-point defenseman to a 30-point defenseman is not what Los Angeles was hoping their $6 million a year was buying them.

    Blake ended up leaving Los Angeles to play for the rival Sharks.

Minnesota Wild: Martin Havlat

15 of 30

    After an impressive 29-goal, 77-point season in 2008-2009 with Chicago Havlat hit the free-agency market.  The Wild, looking for scoring snatched him up with a six-year, $30 million deal.

    Havlat never lived up to that deal, only scoring 18 goals in his first year with the Wild.  Not what you expect for a $5 million a year player. 

    It makes you wonder what Chicago knew when they didn’t sign him.  The Wild moved Havlat this offseason to San Jose for another over priced player in Danny Heatley. 

    The problem is that Heatley will cost the Wild more.  Had Havlat lived up to his contract this move would not have been necessary

Montreal Canadiens: Sergei Samsonov

16 of 30

    The Canadiens took the plunge on Samsonov in 2006 for a cool two-year, $7.05 million. 

    That’s a lot of loonies for a guy who was always cited as someone with great potential but never quite lived up to it.  He had some decent years in Boston, but with Montreal, he was an utter disappointment.

    He only scored nine goals in his one-year stint with the Canadiens before being waived in February. 

    At $7 million for a partial season and nine goals, that's not good no matter what exchange rate the loonie is getting!

Nashville Predators: Radek Bonk

17 of 30

    The Predators don’t sign many free agents, so finding a bad one is hard to do. 

    You could argue that their two biggest free-agency signings,  Jason Arnott and Paul Kariya, were bust merely because neither could lead the Predators past the second round of the playoffs.  But it wouldn’t be fair to those guys as they had good years in Nashville. 

    So Bonk gets the prize. 

    Bonk was supposed to be the next big thing in the NHL, he had a scoring touch and a cool name. 

    After floundering around the league he was able to get a two-year deal for $2.95 million out of the Predators in 2007.  That’s big money in Nashville, and Bonk was a disappointment only scoring 23 goals in those two seasons. 

New Jersey Devils: Ilya Kovalchuk

18 of 30

    The Devils had traded for Kovalchuk at the end of the 2009 season hoping that he would provide them with the 50 goal scoring ability he had shown in Atlanta. 

    After the season Kovalchuk became a free agent and part of one of the most bizarre and dramatic free agency frenzies ever seen. 

    Bidding between New Jersey and Los Angeles took off with the Devils finally landing him for a whopping 17 years and $102 million.  That contract was voided by the league and the Devils amended it down to 15 years and $100 million for Kovalchuk’s skills. 

    It turns out that his skills are purely one dimensional, and after he and the team got off to a terrible start, the contract became an albatross. 

    Kovalchuk ended the season with a respectable 31 goals, but that contract could hamstring the Devils for years to come. 

New York Islanders: Alexi Yashin

19 of 30

    OK, this one is a bit of a cheat since technically Yashin was traded to the Islanders on draft day (for Zdeno Chara, which makes this all the worse) from Ottawa to New York. 

    The reason he is on the list is because the first thing New York General Manager Mike Milbury did was re-sign him ( he had a year left on his contract) to what may be the most ridiculous contract of all time. 

    Ten years and $87.5 million for a player who never scored over 100 points and was a bit of a headache for the Senators. 

    Yashin came out of the gates strong, scoring 40 goals his first year on Long Island, but Islander fans saw his production decline each year after, and his contract made him un-tradeable. 

    Tired of paying a guy that much dough for 16 goals a season, the Islanders bought out his contract in 2007 and Yashin is now in the KHL stealing money from Russian teams.

    The biggest question to come out of this signing is, how does anyone take Milbury seriously anymore?

New York Rangers: Wade Redden

20 of 30

    Selecting the worst free-agent signing for the New York Rangers is tough work. 

    There are so many to choose from.  Drury?  Holik? Gomez? So many choices.  But the winner is Wade Redden. 

    Redden played eleven seasons with Ottawa before Glen Sather backed up a truck full of gold and signed him to a six-year, $39 million contract. 

    Let that sink in for a minute. 

    That's $39 million for a guy, who was decent in his prime and who had already played 11 years. 

    After only 14 points in 2009-2010 the Rangers waived him and re-assigned him to Hartford of the AHL.  The bright side? He is now the highest paid player in AHL history…so he has that going for him.

Ottawa Senators: Alex Kovalev

21 of 30

    The Senators picked up the veteran winger for $5 million per year in 2008 hoping they would get the 2007, 35-goal scoring player. 

    Instead they got a guy past his prime, prone to taking shifts off and only 32 goals in two seasons. 

    They finally unloaded him to the Penguins during this past season.  They fell for the trap of over paying for past glory, the problem being that past glory was while he wore other teams' sweaters.

    It is a mistake many teams have made and will continue to make in the future.

Philadelphia Flyers: Darien Hatcher

22 of 30

    Hatcher seemed like a perfect fit for the style of play preferred in Philadelphia. 

    The Flyers inked the physical defenseman to a four-year, $14 million contract in 2004. 

    Hatcher was never the same player in Philadelphia.  His physicality declined as well as his production and he retired after three seasons in black and orange.

    Sometimes, what seems like a sure thing bites you in the hind quarters, and it did here for the Flyers.

Phoenix Coyotes: Brett Hull

23 of 30

    The Coyotes signed the Hall of Fame goal scorer to a two-year, $4.5 million contract in 2004 which doesn’t seem like a huge deal. 

    When you consider that Hull only played five games and recorded one assist for Phoenix that contract becomes a complete joke. 

    One assist for $4.5 million. 

    Not only that but Phoenix "un-retired" his father’s jersey (which was retired for his time in Winnipeg and not the desert) for him to wear. 

    What more do we need to see to realize that team needs to be taken away from Phoenix!?

Pittsburgh Penguins: Ziggy Palffy

24 of 30

    Ziggy Palffy was supposed to be a NHL superstar. Someone forgot to tell him as he never quite reached that level during his long career. 

    After some decent seasons with the Kings the Penguins grabbed him for a three-year, $13.5 million deal. 

    Palffy only played 42 games with the Penguins before retiring.  He cited a lingering shoulder injury as the reason for his retirement. 

    That makes the three years he played in Slovakia following his retirement all the more interesting. $13.5 million for 42 games makes Palffy the worst signing ever for the Penguins.

    While Ziggy could play guitar, he couldn't play the power play in Pittsburgh. 

St. Louis Blues: Paul Kariya

25 of 30

    Paul Kariya once scored 50 goals and 100 points in the NHL.  Without a doubt, he was a star during the horrific trap era. 

    In 2007, after some decent seasons with the Predators, Kariya signed with the Blues to a three-year, $18 million contract. 

    Kariya never lived up to the contract, due mostly to injuries that limited him to only 11 games in 2008 and led to his retirement after last season. 

    Kariya will mostly be remembered for his great days in Anaheim, but the Blues overpaid for those years without seeing a glimpse of it.

    Once again, a team reaches for past glory only to fall short.

San Jose Sharks: Kelly Hrudey

26 of 30

    The Sharks signed the veteran Kelly Hrudey in 1996 as a free agent looking for what they called "consistency in goal" to become a contender. 

    Hrudey was signed for two years at $2.4 million a year. 

    In 1996, that was a pretty good contract for an older player.  The Sharks didn’t quite get consistency from Hrudey and weren’t contenders.  He only won 20 games for San Jose and never had a save percentage above .900. 

    The writing was on the wall for Hrudey and his head band, and he hung ‘em up after the 1997-1998 season for the comfort of the CBC broadcast booth.

Tampa Bay Lightning: Ryan Malone

27 of 30

    Not all big free-agent contracts turn out to be complete busts.  While they may result in some production out of a guy, the contract itself was still too much.

    Ryan Malone is one of these guys.

    The Lighting gave Malone seven-year, $31.5 million contract in 2008 which was front loaded for $6 million in the first year. 

    Malone is a good player and has been good for the Lightning, but paying a guy that much money for 40 points a season is a big stretch. 

    With their recent drama signing Stamkos, you have to wonder if they were regretting that big deal from 2008.

Toronto Maple Leafs: Jeff Finger

28 of 30

    Jeff Finger had played two unimpressive seasons with Colorado.  Then, in 2008, Toronto general manager Cliff Fletcher forked over a four-year, $14 million contract. 

    Finger had a decent first year in Toronto in 2008-2009 by scoring 23 points (although maybe not $14 decent) only to see that total plummet to 10 points in 2009 and then a demotion to the AHL in 2010. 

    Hey, he did manage to rack up five big assists last year with the Toronto Marlies…so that’s something.

Vancouver Canucks: Mark Messier

29 of 30

    Vancouver looked to make a big splash by reuniting the Captain with Mike Keenan in 1997.  They gave the future Hall of Famer $6 million a year. 

    In return Messier wrestled the captaincy away from Mr. Canuck Trevor Linden (he was eventually traded by Kennan), demanded he be allowed to wear the number 11 which had been retired due to former Canucks  Wayne Maki’s death and led Vancouver to zero playoff appearances. 

    All in all the signing of Mark Messier set the Canucks back and was nothing but a complete disaster.

    Please, can every Canucks fan reading this stand up and join me in a nice hearty "Messier Sucks!" chant.  It will make you feel better.

Washington Capitals: Michael Nylander

30 of 30

    The Capitals gave Nylander a four-year, $19 million contract after a couple of good years with the New York Rangers. 

    Nylander was terrible in Washington as he suffered injuries and went from a 50-point player to a mid 20-point player.  They tried to unload his salary after three seasons with little luck. 

    He now plays in Europe. Not really what the Capitals had in mind when they inked him.

    This deal may seem frustrating to Washington fans but, let's be honest, they seem to like frustration.