NHL Free Agents: The 25 Worst Free-Agent Signings Ever

Brad KurtzbergContributor IJuly 6, 2012

NHL Free Agents: The 25 Worst Free-Agent Signings Ever

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    Earlier this week, we took a look at the best free agent signings of all-time. Now we look at the flip side: the worst free-agent signings ever in NHL history.

    The basic formula involved is high cost plus low production equals a bad signing.

    Sometimes, it's nobody's fault. A player signs a big contract, gets injured and cannot play again. The team is on the hook for a lot of money and gets little in return.

    Other times, the player doesn't pan out in his new city or was just overrated or overpaid to begin with.

    So here it is, a look at the worst free-agent signings in NHL history.

25. Scott Lachance, Columbus Blue Jackets

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    Defensman Scott Lachance seemed like a bargain when he signed a two-year, $4 million contract with Columbus in the summer of 2002. He had been a steady if unspectacular NHL player with the Islanders, Canadiens and Canucks for 11 seasons.

    While Lachance wasn't a high-profile signing for the Blue Jackets, he delivered very little to the team. In two years in Ohio's capital, Lachance failed to score any goals and managed just five assists in 138 games. He was also a combined minus-43 with the Jackets.

    After leaving Columbus, Lachance spent a year in Switzerland and a year in the AHL before hanging up his skates for good.

24. Jay McKee St. Louis Blues

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    In the summer of 2006, the St. Louis Blues signed McKee, known as one of the better shot blockers in the league, to a four-year, $16 million contract.

    The deal never worked out for either side. In his first season in St. Louis, McKee was limited to just 23 games due to a broken finger, two lower body injuries and a bad knee. He failed to register a point and was a minus-nine.

    McKee was never known for his offense, but in three seasons with the Blues, he never played more than 69 games in any season and scored a total of just three goals and 17 points.

    The Blues bought McKee out of the final year of his contract, and he played only one more year in the NHL with the Penguins before retiring.

23. Sergei Samsonov, Montreal Canadiens

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    The Canadiens thought they were getting a dangerous offensive weapon when they signed Sergei Samsonov to a two-year, $7.05 million deal in the summer of of 2006.

    The Russian winger already had five seasons of 20 goals or more, including a pair of 29-goal seasons for Boston. But Samsonov didn't produce for the Habs, scoring just nine goals and 26 points in 63 games and putting up a minus-four rating.

    The Habs were so disappointed in Samsonov that they placed him on waivers during his first year with the club and traded him to Chicago the following summer.

    Since then, Samsonov has become a journeyman, playing for Chicago, Carolina and Florida, which brings his career total to six NHL teams.

22. Uwe Krupp, Detroit Red Wings

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    Uwe Krupp was a very good NHL defenseman for the Sabres, Islanders, Nordiques and Avalanche between 1986 and 1998. He even scored the Stanley Cup-winning goal for the Avs in 1996.

    In the summer of 1998, the Red Wings inked the big native of Germany to a four-year, $16 million contract.

    Unfortunately, Krupp's back gave out, and he played only 22 games for Detroit in 1998-99. He and the Red Wings were later involved in a lawsuit about his injury and treatment.

    After missing two-and-a-half seasons, Krupp tried a comeback with the Wings, but managed to play in only eight games in 2001-02. The following year, he was sent to Atlanta but played in only four games for the Thrashers before his back forced him to retire.

    If Krupp would have stayed healthy, he may have been a great addition to the Red Wings, but injuries effectively ended his career and made his signing an expensive and unproductive one for Detroit.

21. Mike Keane, New York Rangers

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    The New York Rangers and GM Glen Sather went on a free-agent spree in the 1990s and early 2000s, bringing in big-ticket free agents each year in a desperate attempt to upgrade their talent level and sell tickets.

    In the summer of 1997, the Rangers signed gritty forward Mike Keane, who had already won two Stanley Cups, to a four-year contract worth an average of about $2 million per season.

    They expected Keane to add grit and leadership and the occasional goal, but the former Canadiens and Avalanche winger never really fit in on Broadway.

    Keane produced just eight goals and 18 points in 70 games for the Rangers and was a minus-12 before being dealt to Dallas at the trade deadline along with Brian Skrudland for Todd Harvey. Keane won another Stanley Cup with the Stars in 1999.

20. Kelly Hrudey, San Jose Sharks

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    The Sharks needed help in goal in the summer of 1996 and looked to Kings goalie Kelly Hrudey to help solve the problem. They signed the 35-year-old to a two-year deal worth nearly $5 million.

    Hrudey never was successful in San Jose. His record in two years was an unimpressive 20-40-7, and his save percentage stayed below .900 both seasons.

    Hrudey realized his playing days were over and went on to a successful second career as a broadcaster, which has included working for "Hockey Night in Canada" and Sirius/XM radio.

19. Ziggy Palffy, Pittsburgh Penguins

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    When the NHL lockout ended, Penguins owner Mario Lemieux came to an agreement with high-scoring winger Zigmund "Ziggy" Palffy on a three-year, $13.5 million contract.

    Palffy already had six seasons of 30 or more goals with the Islanders and Kings and was expected to add some offensive punch to the Penguins lineup. Instead, Palffy announced his retirement after just 42 games with the Penguins, allegedly due to a shoulder injury.

    In his half season in Pittsburgh, Palffy had 42 points in 42 games, but that was all he ever did in Pittsburgh. His retirement was short-lived, however. He returned to play in his native Slovakia a year later and scored 82 goals in 99 games over two seasons.

18. Paul Kariya, St. Louis Blues

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    The St. Louis Blues had missed the playoffs for two straight years when they signed Paul Kariya to a three-year, $18 million contract in 2007. Kariya had been one of the league's best setup men and was expected to help lead St. Louis back to he playoff promised land.

    In his first season with the Blues, Kariya scored 65 points, 11 fewer than he produced in Nashville the previous season.

    Unfortunately for both the Blues and Kariya, that would be his best season in St. Louis. A hip injury limited him to 11 games the following year (he already had 15 points), and when he returned to action in 2009-10, he finished with a pedestrian 43 points in 75 games.

    That would be the end of Kariya's NHL career. He finished with exactly 989 points in 989 games, but only 123 of them came in his three seasons in a Blues uniform.

17. Valeri Kamensky, New York Rangers

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    Valeri Kamensky was another one of Glen Sather's high-priced free agent failures.

    In 1999, the Rangers signed Kamensky to a four-year, $17 million contract.

    After three straight very productive seasons for the Avalanche, Kamensky had an off year in 1998-99, but that didn't deter the Rangers from adding the talented Russian winger.

    Unfortunately, it was the beginning of his slide at age 33, and Kamensky was never a big-time offensive player in the NHL again.

    In two seasons with the Rangers, Kamensky scored a total of just 27 goals and 66 points and was a minus-31. Injuries slowed him down, and he was never a good fit with the Broadway Blueshirts.

    The Rangers bought Kamensky out of the two final years of his contract in July 2001.

16. Alexei Kovalev, Ottawa Senators

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    The Ottawa Senators hoped that 36-year-old Alexei Kovalev still had something left when they signed him to a two-year, $10 million in the summer of 2009. Unfortunately for the Sens, Kovalev's productive days were behind him.

    In two seasons with Ottawa, Kovalev scored just 32 goals and 76 points in 131 games, a far cry from his output with the Rangers, Penguins or even his most recent stint in Montreal.

    Kovalev did have a few highlights in Ottawa. He had a four-goal game on January 3, 2010, and picked up the 1,000th point of his NHL career. But Kovalev gave an inconsistent effort and got inconsistent results.

    The Senators traded him back to Pittsburgh in February of 2011, and he finished out his final NHL season with the Pens before heading back to the KHL in 2011-12.

15. Martin Lapointe, Boston Bruins

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    Martin Lapointe was coming off a career-high 27-goal season with the Red Wings when the Boston Bruins signed him to a four-year deal worth $20 million.

    Lapointe was a gritty forward who could provide some steady offensive production and had already won a pair of Stanley Cups in Detroit.

    The Bruins were counting on him to produce when he joined them in 2001, but in three years in Boston, Lapointe never totaled more than 40 points in a season and was considered the league's most overpaid player by many members of the media.

    After the lockout, Lapointe signed another free agent deal with the Blackhawks. His brief, unproductive career in Boston was over.

14. Teemu Selanne, Colorado Avalanche

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    It was supposed to be a match made in heaven: Teemu Selanne and Paul Kariya both signed with the Colorado Avalanche in the summer of 2003 and were supposed to recreate the magic they had together when they starred for the Mighty Ducks of Anaheim.

    Selanne signed a one-year contract with the Avs worth $5.8 million. The dynamic duo of Selanne and Kariya were supposed to bring the Stanley Cup back to Denver.

    Unfortunately for the Avalanche, Selanne was mediocre in 2003-04. He scored just 16 goals, matching his career low until that time and totaled just 32 points.

    The Avalanche were eliminated in the second round of the playoffs, and after the lockout, Selanne rejoined the Ducks and once again started scoring goals at a consistent clip.

    For all the sizzle the signing of Selanne and Kariya produced, their play in Colorado was a bust.

13. Mark Messier, Vancouver Canucks

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    Absolutely nothing went right when Mark Messier signed a huge free-agent contract with the Vancouver Canucks in the summer of 1997.

    Popular Canucks captain Trevor Linden "voluntarily" allowed Messier to wear the "C," but was soon traded to the New York Islanders in a deal that was never popular with Vancouver fans who loved and respected Linden for all of his years in a Canucks uniform.

    Messier also wanted his No. 11 back, but the Canucks had unofficially retired it for the late Wayne Maki, who died unexpectedly in 1974. Messier got his wish, but neither of these things helped endear him to the fans of Vancouver.

    Messier was reunited with his Stanley Cup-winning Coach in New York, Mike Keenan, but the marriage didn't work as well in the Pacific Northwest. "Moose" only scored more than 20 goals in one of his three seasons in Vancouver and never totaled more than 60 points. He was a double-digit minus player in all three seasons, and he never led the Canucks to the playoffs despite his reputation as one of the greatest captains in NHL history.

    The fans of Vancouver never fully accepted Messier, and at this point in his career, age and injuries started to slow him down on the ice.

    Messier re-signed with the Rangers, where he finished his career, playing four more seasons.

    Overall, Messier's time in Vancouver started with a lot of fanfare, but didn't work out for either the player or the team.

12. Michael Nylander, Washington Capitals

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    Michael Nylander had two productive seasons with the New York Rangers, mostly playing on a line with Jaromir Jagr. In the summer of 2007, the Washington Capitals signed the talented Swede to a four-year contract worth $19 million.

    Unfortunately for the Caps, injuries and age slowed Nylander down, and he never even came close to producing at the level he was being paid.

    In his first season with the Caps, Nylander tore his rotator cuff and missed half the season. He was off to a good start, scoring 37 points in 40 games.

    After the injury, Nylander was never the same. The following year, he scored just nine goals and 33 points in 72 games. The Capitals unloaded Nylander before the 2009-10 season, and he has not played in the NHL since.

11. Todd Bertuzzi, Anaheim Ducks

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    The Ducks added Todd Bertuzzi to their lineup before the 2007-08 season, signing him to a two-year-contract at $4 million per season.

    While Bertuzzi's statistics were not horrible (14 goals, 40 points in 68 games), they weren't close to what Anaheim thought it was receiving when they signed the power forward.

    Unfortunately, Bertuzzi was considered a cancer in the clubhouse, and GM Brian Burke was only too happy to waive him after one year with the Ducks.

    Bertuzzi later signed with Calgary and then Detroit, and while he was steady and productive, he never matched the numbers he put up before the lockout (and the infamous Steve Moore incident).

    For the Ducks, he was more trouble than he was worth.

10. Bobby Holik, New York Rangers

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    It's still hard to imagine what Glen Sather was thinking when he signed Bobby Holik to a five-year, $45 million contract in 2002.

    Holik was a good player, but he had never scored more than 29 goals or 65 points in a season, and Sather was paying him like he was a superstar.

    The contract was so out of whack with Holik's abilities that he almost had to fail to live up to it. The gritty native of the Czech Republic had one unproductive season (35 points in 64 games) and one season more in line with his past output (25 goals and 56 points) before Sather realized his error and bought out the remaining three years of his contract.

9. Chris Gratton, Philadelphia Flyers

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    The Flyers paid dearly for the services of Chris Gratton. They signed the restricted free agent to a five-year, $16.5 million contract, which was a lot of money back in 1997. It included a $9 million signing bonus.

    Since Gratton was restricted, Philadelphia also had to give the Lightning Mikael Renberg and Karl Dykhuis to acquire Gratton's rights.

    In the end, the 6'3", 220-pound Brantford, Ontario, native produced 22 goals and 62 points in his only full season in the City of Brotherly Love.

    The following year, he scored only one goal and eight points in 26 games before the Flyers dealt him back to Tampa Bay, ending his brief tenure as the savior of hockey in Philadelphia.

8. Ryan Smyth, Colorado Avalanche

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    The Colorado Avalanche thought they scored big time when they signed "Captain Canada" as a free agent in 2007, paying the former Oilers and Islanders winger $31.25 million for a five-year deal.

    But the feisty Smyth never lived up to the hype his contract created while playing in the Mile High City. In his first season with the Avalanche, nagging injuries limited Smyth to 55 games and he scored just 14 goals and 37 points.

    The following year, Smyth's numbers improved to 26 goals and 59 points, but was a minus-15 in a difficult season in Colorado that saw the Avs finish in last place and miss the playoffs.

    The Avalanche needed to rebuild, and they realized Smyth could still get them something in return if they traded him now at the age of 33. So, Colorado dealt Smyth to the Kings for defensemen Kyle Quincey and Tom Preissing and a fifth-round draft choice.

    Smyth wasn't terrible in Colorado, but he suffered injuries both seasons and was not a good fit on a Colorado team in transition. He was also not worth the high salary the Avs paid to obtain his services.

7. Sheldon Souray, Edmonton Oilers

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    It was a dream come true for Sheldon Souray when he signed with the Edmonton Oilers, the team he grew up rooting for as a kid. To add to the dream, Edmonton ponied up $27 million for five years when they obtained Souray in 2007.

    But the contract proved to be an albatross for both the team and the defenseman with one of the hardest shots in the league. In his first season in Edmonton, Souray was often hurt and only played in 26 games and scored just 10 points.

    In 2008-09, he had an All Star season with the Oilers, topping the 20-goal mark and totaling 53 points.

    The following season injuries completely derailed Souray's campaign. He suffered a concussion early on and then a hand injury that later got infected. He played in only 37 games and was an embarrassing minus-19.

    Souray wasn't happy with they way the Oilers handled his injury and demanded a trade before the 2010-11 season. There were no takers due to Souray's high salary and repeated absences from the lineup. Both sides made ugly accusations through the media. The Oilers eventually waived their highly-paid defenseman, but he went unclaimed and eventually was loaned to the Hershey Bears of the AHL, exiled from the NHL because of his high cap hit.

    Edmonton bought out the final year of Souray's contract in the summer of 2011 and he signed as a free agent with the Dallas Stars in 2011-12. His long and ultimately unsuccessful time in Edmonton was over.

6. Cristobal Huet, Chicago Blackhakws

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    The Chicago Blackhawks signed Cristobal Huet to a four-year, $22.5 million contract, hoping he would lead the team to their first Stanley Cup since 1961.

    Huet did get his name on the Stanley Cup with the Blackhawks, but he never became the goalie Chicago paid more than $5 million per season to obtain.

    First, Huet failed to beat out Nikolai Khabibulin for the starting job, and the two shared time. Then, during the Hawks Stanley Cup run in 2010, Antti Niemi took over as starter shortly before the playoffs began. In the Stanley Cup playoffs that year, Huet played only 20 minutes in net.

    The following year, he was loaned to a team in Switzerland to help alleviate Chicago's salary cap issues.

    In the end, the Blackhawks paid a lot of money for Huet, but got very little in return.

5. Scott Gomez, New York Rangers

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    Scott Gomez reveals both the strengths and weaknesses of Glen Sather's tenure as GM of the New York Rangers.

    First, Sather signed the former Devils center to an absurd seven-year, $51.5 million contract in 2007. Gomez had a respectable first season on Broadway, totaling 70 points, but the following two years, his play fell off and his point totals dipped to 58 and 59 points respectively, hardly worth more than $7 million per season.

    But as bad as Sather's decision to pay Gomez all that money was, he shrewdly was able to trade the Alaska native to the Montreal Canadiens, who were then stuck with his very high salary and rapidly decreasing production.

    Gomez was never a bad player in New York, but he was being paid as one of the top-five players in the game while he was not even the best player on his team.

4. Jeff Finger, Toronto Maple Leafs

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    For some reason known only to them, the Toronto Maple Leafs signed defenseman Jeff Finger to a four-year, $14 million contract in 2008.

    Finger was not a big point producer, and he was not an overpowering player in his own zone. He had never scored more than eight goals or 19 points in a season, nor had he racked up a lot of penalty minutes.

    Needless to say, Finger didn't become Superman when he signed a star's contract. He scored six goals and totaled 23 points in his first season in Toronto and was an unimpressive minus-seven. Finger remained what he always was, a serviceable second or third-pair defenseman.

    After two years in Toronto, the Leafs waived Finger, and he spent the last two seasons with the Toronto Marlies of the AHL, a victim of his high salary cap number and poor production.

3. Theo Fleury, Chicago Blackhawks

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    Chicago was the last stop on Theo Fleury's controversial and colorful NHL career.

    Fleury signed a two-year, $8.5 million deal in 2002 after his rocky three-year stint with the Rangers. The NHL suspended Fleury for 25 games for violating the league's substance abuse policy before his first season in Chicago even got underway.

    Unfortunately, at this time in his life, Fleury was not doing well off the ice and his many personal issues caught up with him. He played only 54 games for the Hawks and scored 12 goals and 33 points. During the season, he was involved in a brawl in a strip club which he later had no recollection of because of his substance abuse issues. This was a low point in Fleury's life.

    After the season ended, Fleury was again suspended by the league, and his NHL career came to a close. The Blackhawks never got a good return on the money they paid Fleury, but at least he was able to straighten out his life after leaving hockey.

2. Wade Redden, New York Rangers

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    Wade Redden signed a six-year, $39 million deal to join the Rangers on the first day of free agency in 2008.

    There were already rumors of possible substance abuse problems while Redden was playing in Ottawa, but Rangers GM Glen Sather was not deterred.

    Redden scored only five goals and 35 points in two seasons with the Rangers and quickly became a target for the fans at Madison Square Garden who didn't appreciate so little production from a player earning more than $6 million per year.

    Eventually, Redden was exiled to the AHL to help give the Rangers salary cap relief. He has played the last two years in Hartford and is still earning his high salary but providing the Rangers with no help on the ice.

1. Sean Avery, Dallas Stars

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    The Stars signed super pest Sean Avery to a four-year, $15.5 million contract

    Avery did more than stink on the ice, producing just three goals and 10 points in just 23 games, he was disruptive in the locker room and embarrassing off the ice.

    He deliberately made a rude and sexually suggestive comment to reporters in Calgary about an opposing player who was now dating one of his former girlfriends. The league suspended Avery shortly after that. Besides the bad press, Avery was about as popular in the Dallas locker room as foot fungus.

    After he served his suspension, the Stars placed Avery on waivers and he was later re-claimed by the New York Rangers.

    In the end, Dallas got nothing but problems from Avery both on and off the ice and was only too happy to cut ties with him just a few months after adding him to its roster.