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The Worst Free Agent Signing In Each NHL Team's History

For whatever reason, general managers are willing to throw around more money than ever before in free agency.

Every NHL team has a different history. But there are still some things every single one of them have in common. One of those things is the fact that each team has wasted a ton of money on at least one player in free agency.

For whatever reason, general managers are willing to throw around more money than ever before in free agency -- even though there's a salary cap that didn't exist until the 2005-06 season. So why didn't they pay more for free agents back then? And why aren't they more conservative with their spending now?

These GMs haven't ignored the fact that most lucrative free agent signings turn out to be complete busts down the road. It's kind of funny. Ask 100 fans for each of the the 30 NHL teams (sorry Vegas, this list doesn't apply to you), and you'll have no problem coming to a consensus on who they think is the worst free agent signing in their club's history.

But in case you do, here is a reminder of the worst free agent signing in the history of every NHL franchise.

30 Anaheim Ducks: Mathieu Schneider

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The defending Stanley Cup champions didn't know if captain Scott Niedermayer was returning or not. So they tried to play it safe by signing Mathieu Schneider to a two-year contract worth $11.25 million. Niedermayer would indeed return, and the Ducks maintained Chris Pronger the blue line.

Schneider was just a year removed from a 21-goal season, so the Ducks had hoped he could provide ample offence from the blue line. That didn't happen, however. He scored just 12 goals and 39 points in 65 games. Again, he wasn't all that needed with Niedermayer returning.

The Ducks traded him to the Atlanta Thrashers, getting rid of his albatross contract once and for all. Give Anaheim credit for attempting to replace Niedermayer if he did retire, but the commitment to Schneider was too much.

29 Arizona Coyotes: Mike Ribeiro

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Mike Ribeiro had a big season for the Washington Capitals in 2012-13, scoring 13 goals and 49 points in 48 games. The Caps weren't able to meet his contract demands, but the Coyotes swooped in and gave him a four-year contract worth a total of $22 million.

The traditionally budget-conscious Coyotes chose the wrong player and time to dish out money on. Ribeiro had attitude and off-the-ice problems and became a problem in Arizona. He did score a respectable 16 goals and 47 points, but the Coyotes were less than pleased with his personality.

Ribeiro was bought out by the Coyotes after just one season in The Desert, and would eventually join the Nashville Predators. Ribeiro had a couple of strong seasons in The Music City, so the Coyotes didn't have much of a reason to give up on him. Nonetheless, it was an easy $22 million bucks for Ribeiro.

28 Boston Bruins: Martin Lapointe

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Martin Lapointe was a mainstay on the '90s Detroit Red Wings, helping them win back-to-back Stanley Cups in 1997 and 1998. He had a career year in 2000-01, scoring 27 goals and 57 points in a contract year. The Boston Bruins were impressed enough and gave Lapointe a four-year contract worth $20 million.

Lapointe didn't disappoint in his first season, scoring 17 goals and 40 points while helping the Bruins finish first in the Eastern Conference standings. The next two seasons were letdowns for Lapointe, however. He scored a total of 23 goals and 43 points over that frame.

The 2004-05 lockout wiped out the final year of Lapointe's bad contract, so there was one bright spot for the Bruins. Lapointe just wasn't able to find any success in Beantown the way he did in Hockeytown.

27 Buffalo Sabres: Ville Leino

via thehockeyhouse.net

Coming off consecutive playoff appearances, the Sabres were in good position to add more talent in the 2011 free agent market. New owner Terry Pegula also encouraged the Sabres to spend more money in the offseason, so they signed Ville Leino to a six-year contract worth $27 million.

Leino was coming off a 19-goal, 53-point season for the Philadelphia Flyers. The move made a ton of sense at the time. Looking back, the move made absolutely no sense whatsoever.

Leino did next-to-nothing in Buffalo. Over his three seasons with the Sabres (worth noting he only played eight games in 2012-13), Leino only scored a total of 10 goals and 46 points. The Sabres used a compliance buyout to rid themselves of the contract, and Leino would take his talents overseas.

26 Calgary Flames: Dennis Wideman

Sergei Belski-USA TODAY Sports

Dennis Wideman has been a solid offensive defenceman throughout his career, but not one worthy of a $26.25 million contract over five years. But the Calgary Flames chose to pay him that much in the 2012 offseason, even though they were an ageing team that should have been preparing for a rebuild.

Wideman's contract expired after the 2016-17 season, and the Flames are looking back and regretting it. He had one good season (in 2014-15), with Calgary, scoring 15 goals and 56 points. That was it, though. He didn't score more than 22 points in the other four seasons.

It's not just that the term was too long, but the Flames had no reason to pay a solid but not spectacular defenceman so much money. Again, it didn't make sense for a rebuilding team to hand out such a big contract. Easily the worst in their history.

25 Carolina Hurricanes: Alexander Semin

via hockeyworldblog.com

The Hurricanes haven't actually had a disastrous contract signing during free agency itself. As such, I had to include Alexander Semin and that $35 million contract over five years he was given in 2013. Semin was a pending UFA, so he does qualify as a "free agent signing" here.

Semin performed well for Carolina in the lockout-shortened 2012-12 season, scoring 13 goals and 44 points in as many games. Semin would score 22 goals and 42 points in 2013-14, but then the wheels came falling off.

The former Russian star scored just six goals and 19 points the following season. Semin was bought out just two years after signing that mega extension. Definitely not one of the smartest moves for the well-respected GM Jim Rutherford, who just led the Penguins to consecutive championships as

24 Chicago Blackhawks: Cristobal Huet

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After just narrowly missing the playoffs in 2008, the Blackhawks decided it was important to add Cristobal Huet in goal -- even though they already had a solidified No. 1 goalie in Nikolai Khabibulin.

Cristobal Huet was given a four-year contract worth $22.4 million. He did go a respectable 20-15-4 in his first season with the Blackhawks, but Huet didn't earn the starter's role from Khabibulin. The next year, he lost his starting job to Antti Niemi -- who guided Chicago to a Stanley Cup championship.

The Blackhawks couldn't find any takers for Huet and loaned him to a team in Switzerland. So they only got two seasons out of Huet. And he was one extremely expensive backup goalie. His salary was simply too much for the Blackhawks, and it led to Stan Bowman gutting significant pieces of their 2010 championship squad just to get under the cap.

23 Colorado Avalanche: Teemu Selanne

via thescore.com

Joe Sakic, Peter Forsberg, Milan Hejduk, Rob Blake and Adam Boote weren't enough for the Colorado Avalanche heading into the 2003-04 season. They made a superteam even more super by signing former Mighty Duck stars Paul Kariya and Teemu Selanne. The former took a significant pay cut and accepted a one-year deal worth $1.2 million.

But Selanne took a one-year pact for $5.8 million, which ate up significant payroll. Neither player lived up to expectations in their one season for the Avalanche. Selanne, a perennial 30-goal man, scored just 16 goals and 32 points for Colorado that season. He added a mere three assists in 10 playoff games, as the San Jose Sharks dashed Selanne and Kariya's Colorado Cup dreams in the second round.

So much for a superteam, Mr. Selanne.

22 Columbus Blue Jackets: Nathan Horton

via mapleleafshotstove.com

The Blue Jackets were coming off a surprise playoff berth in 2014, so they decided to build upon it. Power forward Nathan Horton was signed to a lucrative seven-year contract worth $37.1 million. Boom, the Jackets now had a replacement for Rick Nash (who departed two years earlier), who was a consistent 20-goal scorer.

But Horton's tenure in Columbus was a disappointment from the beginning. He needed offseason shoulder surgery and didn't make his debut until January. Horton had just five goals and 19 points in 36 games.

Horton hasn't played in three years, as a severe back injury has kept him out of hockey. The Jackets sent him to the Toronto Maple Leafs for David Clarkson; just a plain swapping of two terrible contracts.

21 Dallas Stars: Antti Niemi

Sergei Belski-USA TODAY Sports

The Stars have had a solid goalie in Kari Lehtonen since the 2009-10 season. Prior to the 2014-15 season, he had posted a trio of 30-win seasons with Dallas. Nonetheless, the Starts made an extremely questionable move by signing Antti Niemi to a three-year contract worth $13.5 million. For what? Why did they need to carry another No. 1 goalie when they already had a true, established No. 1 in Lehtonen?

Niemi's first season with Dallas was solid. He went 25-13-7 but posted a woeful 2.67 goals against average and .905 save percentage. Dallas did win the Central Division, so many well spent?

Not exactly. Niemi then went 12-12-4 with a horrid 3.30 goals against average and .892 save percentage. The Stars put him on waivers and eventually bought out the final year of his contract. This move didn't make sense in 2015, and it doesn't make any sense in 2017.

20 Detroit Red Wings: Stephen Weiss

via thehockeywriters.com

Because the Red Wings were so darn good at drafting and finding hidden gems in the '90s and early 2000s, GM Ken Holland didn't have to hand out such contracts to star players. But as the Red Wings became a playoff bubble team in the mid-2010s, Holland got desperate. A little too desperate, in fact.

In the summer of 2013, Holland signed talented centre Stephen Weiss to a five-year contract worth $24.5 million. Weiss was good for 20 goals and 50 points when healthy. But the problem was he couldn't stay healthy.

Hernia surgery cut his 2013-14 season down to 26 games, where Weiss registered just two goals and a pair of assists. The following season, he scored just 25 points in 52 games. Detroit desperately wanted to void his contract, so Holland gave up and bought out the final three years of the albatross deal.

19 Edmonton Oilers: Sheldon Souray

via blueshirtbanter.com

The Edmonton Oilers really missed Chris Pronger. The future Hall of Famer nearly guided Edmonton to the 2006 Stanley Cup championship, but demanded a trade and was sent to the Anaheim Ducks. A year after the trade, the Oilers signed big and offensively-gifted blueliner Sheldon Souray to a five-year contract worth $27 million.

Sheldon Souray was coming off a 26-goal season with the Montreal Canadiens, so this looked like a major win for a team looking to replace the loss of Pronger. Souray was limited to 26 games in 2007-08 and posted a mere 10 points. The following season, he earned his salary by scoring 23 goals and 53 points.

Then the injuries piled up again, and the Oilers grew frustrated with Souray. He spent time in the minors and had the fifth year of his contract bought out. And so ended the most overpaid tenure in the franchise's history.

18 Florida Panthers: Dave Bolland

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Dave Bolland was an extremely underrated piece of the 2010 and 2013 Chicago Blackhawks championship teams. The gritty two-way centre was able to shut down the opposition's top players and always had a knack for delivering clutch goals. This was a guy who scored the 2013 Cup-clinching goal in the final minute in Game 6, after all.

The cap-strapped Blackhawks dealt Bolland to the Toronto Maple Leafs. He had a respectable eight goals and 12 points in 23 games, but an injury ruined his promising season. The Florida Panthers saw enough and handed Bolland a five-year contract worth $27.5 million.

Bolland would only play in 78 games through the 2014-15 and 2015-16 seasons with Florida, scoring a total of seven goals and 28 points. He was traded to the Arizona Coyotes, but hasn't played for them as injuries have kept him out of hockey. Bolland's agent said he'll probably never play again.

17 Los Angeles Kings: Rob Blake

via calisportsnews.com

The Hall of Famer is easily one of the most decorated defenceman in NHL history. Rob Blake captured a Stanley Cup with the Colorado Avalanche in 2001, won Olympic gold with Canada in 2002 and posted 240 goals and 777 points in 1,270 games. He's also the Los Angeles Kings' highest-scoring defenceman ever, according to QuantHockey.com.

After five seasons with the Avalanche, Blake returned to Los Angeles in 2007 on a two-year deal worth $12 million. His first year was solid, as Blake posted 14 goals and 34 points. But the next year was disappointing, as Blake finished with nine tallies and 31 points.

Blake's return to Los Angeles was far from spectacular, as the Kings were among the NHL's worst teams in 2007 and 2008. He then joined the rival San Jose Sharks, retiring after the 2009-10 season.

16 Minnesota Wild: Martin Havlat

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The Wild had lost franchise superstar Marian Gaborik to the New York Rangers in free agency. Needing to offset his departure quickly, the Wild signed Czech star Martin Havlat to a six-year contract worth $30 million.

Now, Havlat was a good player and all. He was coming off a 29-goal and 77-point season with the Chicago Blackhawks and had a knack for showing up big time in the postseason. But he was rarely healthy (playing at least 70 games just once in the previous six seasons), so the contract was too long and too rich.

Havlat did score a respectable 18 goals and 54 points in his first season with Minnesota. He added 22 tallies and 62 points the following year. Good totals, but not worth the $30 million. Havlat was traded to the San Jose Sharks for Dany Heatley. This trade turned out to be a disastrous for both teams, and both players saw their careers gradually decline after the deal.

15 Montreal Canadiens: Mike Cammalleri

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After bidding ado to long time captain Saku Koivu and fellow fan favourite in Alexei Kovalev in 2009 the Canadiens had to find a replacement quickly. Besides the addition of Brian Gionta, the Habs added speedy sniper Mike Cammalleri to a five-year contract worth $30 million. The timing of the deal made sense, as Cammalleri had just scored a career-high 39 goals for the Calgary Flames.

Cammalleri's first season was a modest success, scoring 26 goals and 50 points -- though a significant drop off from what he posted the season prior. The next season, Cammalleri had just 19 goals and 47 points in 67 games. Cammalleri then called out his team early in the 2011-12 season, which was a disaster for the Habs. He was traded back to Calgary, ending the worst contract tenure in Montreal Canadiens history.

14 Nashville Predators: J.P. Dumont

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The Predators had their most successful regular season ever in 2005-06. So they chose to build upon it and signed J.P. Dumont to a two-year deal. After registering consecutive 20-goal seasons, Nashville extended Dumont for four years, worth a total of $16 million. The Predators would have been better off letting him walk, because Dumont wasn't able to live up to the nice extension by any means.

Over his next three seasons, Dumont totaled just 16, 17 and 10 goals.  The talented power forward regressed after signing that big extension. As such, the Predators chose to buy out the final year Dumont's contract, and he never played in the NHL again.

The Predators chose the right time to initially sign Dumont. But they chose the wrong time to extend him.

13 New Jersey Devils: Ryane Clowe

via nhl.com

Ryane Clowe had a few nice seasons with the San Jose Sharks. From 2008-09 to 2011-12, he scored at least 17 goals in each season and hit the 50-point mark three times. But he struggled during the 2012-13 season and finished with three goals and 19 points in games split with the Sharks and New York Rangers.

Despite an off season, the New Jersey Devils paid Clowe $24.25 million over five years. That turned out to be one of the worst contracts of the decade, and easily the worst in franchise history.

Clowe scored just seven goals and 26 points in his first season with New Jersey. The following year, he posted just one goal and four points in 13 games. Concussions forced Clowe to retire after just two years into the contract, and he was hired as an assistant coach for the team last offseason.

12 New York Islanders: Alexei Yashin

via lighthousehockey.com

The Islanders don't have much of a history when it comes to handing out long-term contracts in free agency. Andrew Ladd would have appeared on this list, but he's only completed one season of his seven-year pact. It's also hard to ignore his strong finish to the 2016-17 season.

So we'll go back to 2001, when former Islanders GM Mike Milbury traded Zdeno Chara, Bill Muckalt and the second-overall pick (eventually used to select Jason Spezza), to the Ottawa Senators for Alexei Yashin.

We'll make a special exception and call Alexei Yashin a "free agent signing here." Milbury gave Yashin a 10-year contract worth $87.5 million. Now, Yashin remained a quality scorer on Long Island. But his attitude was toxic in the team's locker room, and the Isles bought out the remainder of his deal in 2007. It cost them over $2 million per season over the next eight years. Not a good move.

11 New York Rangers: Wade Redden

via cbc.ca

The Ottawa Senators had a tough salary cap situation and weren't able to extend perennial star defenceman, Wade Redden. Their loss looked like a huge gain for the New York Rangers, who signed him to a six-year contract worth $39 million in the 2008 offseason. This came a year after they handed out big deals to Scott Gomez and Chris Drury -- who both disappointed in New York.

Redden, one of the best offensive blueliners of his era, couldn't find his game with the Blueshirts. In 2008-09, he scored a mere three goals and 26 points -- his worst season since 1998-99.

He scores just 14 points the following season before spending the next two years in the minors. The Rangers used a compliance buyout to rid themselves of Redden's awful contract during the 2012-13 season. Probably a smart idea.

10 Ottawa Senators: Sergei Gonchar

via fansided.com

After losing standout defenceman Anton Volchenkov in free agency, the Senators were desperate for a replacement. They wound up signing offensive blueliner Sergei Gonchar to a three-year contract worth $16 million in 2010. Gonchar had posted 50-plus points in four of his last five seasons, so the deal made plenty of sense on paper.

But once Gonchar left the Pittsburgh Penguins for the nation's capital, his career went downhill. He registered just 27 points in 2010-11 and had his worst offensive season since 1997-98.

The next year, Gonchar had just five goals and 37 points. He did have an okay 2012-13 season, scoring 27 points in 45 games. Ottawa paid Gonchar like a No. 1 defenceman, but they got a washed-up player instead. Easily the worst signing in their history.

9 Philadelphia Flyers: Ilya Bryzgalov

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The Flyers narrowly missed out on a Stanley Cup championship in 2010 and then were embarrassed by the Boston Bruins in the second round. The main reason? Goaltending. GM Paul Holmgren was so desperate for an upgrade that he traded away his two best scorers -- Mike Richards and Jeff Carter -- just so he could secure enough room to sign Ilyza Bryzgalov.

Philadelphia gave Bryzgalov a nine-year deal worth $51 million, and boy would they regret it. His first season with the Flyers wasn't that bad, as Bryzgalov won 33 games and took them into the second round of the postseason.

But Bryzgalov's next season was a joke. He went 19-17-3 and had a woeful 2.79 goals against average and .909 save percentage. The Flyers used a compliance buyout to rid themselves of the final seven years. That was an easy $51 million made by Bryzgalov.

8 Pittsburgh Penguins: Rob Scuderi 

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In his first stint with the Penguins, Rob Scuderi was a big piece of the team's blue line. The gritty, shutdown defenceman was instrumental in helping Pittsburgh win the 2009 Stanley Cup over the Detroit Red Wings. After winning his first ring, Scuderi would spend the next four seasons with the Los Angeles Kings.

Then in 2013, the Penguins brought back Scuderi on a four-year contract worth $13.5 million. Scuderi was 34 years old and had carried a ton of mileage on his body, so the contract was a big risk. The Pens learned that the hard way.

Scuderi was past his playing prime at this point of his career. he missed 29 games for them in 2013-14 and wasn't the reliable stay-at-home blueliner over his next two years in Pittsburgh. Scuderi was traded to the Blackhawks during the 2015-16 season, ending a disappointing return to The Steel City.

7 San Jose Sharks: Mikkel Boedker

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The Sharks reached their first-ever Stanley Cup Final in 2016, but the blazing Pittsburgh Penguins speed was too much. The much slower Sharks were eliminated in six games, and head coach Pete DeBoer emphasized his team's need for speed after seeing the Pens skate circles around his team.

Doug Wilson tried to address this problem by giving Mikkel Boedker $16 million over four years. He was coming off a 17-goal and 51-point season, so the signing did make sense at the time.

But Boedker's first season in San Jose was a huge disappointment. He mustered just 10 goals and 26 points, and the Sharks were eliminated in the first round by the Edmonton Oilers. So much for speed, after all. The Sharks and Boedker don't look like the right match at this point.

6 St. Louis Blues: Paul Kariya

via thescore.com

The Blues had two miserable seasons following the 2004-05 lockout, and they were desperate to find another scorer to get out of the Western Conference basement. Their solution? Signing perennial 30-goal man, Paul Kariya to a three-year contract worth a total of $18 million.

Kariya did notch 65 points in 2007-08, but he registered 16 goals which were the second-lowest of his career. Kariya then played just 11 games in 2008-09 after suffering a severe hip injury. The next season, he had a mere 18 goals and 43 points in 75 games.

Kariya would retire from the NHL after his contract expired in St. Louis. There were rumors about him heading back to Anaheim for one more year in 2010-11, but it wasn't meant to be. Neither was his tenure with the Blues.

5 Tampa Bay Lightning: Matt Carle

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Matt Carle was once a reliable top-four defenceman for the San Jose Sharks, Tampa Bay Lightning and Philadelphia Flyers. When healthy, he was a solid puck-moving defenceman capable of scoring 40-plus points in a season.

The Lightning were keen on bringing back Carle back, so they signed him to a six-year contract worth a whopping $33 million in the 2012 offseason. Carle did post a respectable 22 points in the 48-game 2012-13 season, but that would turn out to be his only good season in Tampa.

Carle's point totals began to decline significantly over the next three years. Last offseason, the Lightning opted to buy out the final three years of his contract. Carle would play six games for the Nashville Predators in 2016-17 before retiring for good.

4 Toronto Maple Leafs: David Clarkson

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Coming off their first playoff trip in nine years (2013), the Toronto Maple Leafs signed power forward David Clarkson to a seven-year contract worth $36.75 million. Many pundits were already comparing him to Maple Leaf legend and long-time fan favourite, Wendel Clark.

Clarkson scored 30 goals in 2011-12, but wasn't a proven goal-scorer otherwise. Nonetheless, the Maple Leafs had expectations for him to take this team to the next level. That didn't happen.

Clarkson scored just five goals and 11 points in his first season with the Leafs, which was highlighted by a 10-game suspension for leaving the bench during a preseason game to engage in a fight. Clarkson spent one more frustrating year in Toronto before being traded to the Columbus Blue Jackets in exchange for Nathan Horton's bad contract.

3 Vancouver Canucks: Mark Messier

via theprovince.com

Mark Messier was a six-time Stanley Cup champion and widely respected as one of the best captains in NHL history. But as he started to enter his twilight years, the New York Rangers chose to let him find a new home in the 1996 offseason.

The Vancouver Canucks were desperate to fill up their empty arena, so they signed a can't-miss Messier to a three year deal (the New York Times reported it was a contract worth around $20 million).

Messier was well past his playing prime and wasn't close to being an effective scorer any more. He had a miserable tenure in Vancouver, admitting he regrets taking up the captaincy. He also took the Canucks to court to steal another $6 million from them in an arbitration case. So if you come to Vancouver, try not to bring up Messier's name. Unless you want to make people's blood boil. The whole thing was a disaster.

2 Washington Capitals: Brooks Orpik

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After missing the playoffs in 2014 (for the first time in seven years), the Washington Capitals got aggressive in the offseason. They signed away defencemen Matt Niskanen and Brooks Orpik from the rival Pittsburgh Penguins. Orpik was given a five-year contract worth $27.5 million. Quite a bit for a 34-year-old who didn't have much offensive upside and carried a ton of mileage on his body.

Orpik hasn't been a disaster in Washington by any means, but he was never worth that big of a contract. It seemed like the Capitals simply overpaid him just so he wouldn't go back to the Penguins.

Now, the Capitals have won two Presidents' Trophies during Orpik's tenure in D.C. But he hasn't been that big of a factor in them, and his play in the postseason has been far from spectacular. This money should have been spent elsewhere.

1 Winnipeg Jets: Bobby Holik (Atlanta)

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Since the Winnipeg Jets returned in 2011-12, GM Kevin Cheveldayoff has been incredibly budget-conscious and has stayed away from spending much in free agency. So we have to go back to the days when the Jets were in Atlanta, playing as the Thrashers.

During the 2004-05 lockout, Atlanta signed 6-foot-4 centre Bobby Holik to a three-year contract worth $12.75 million. Holik had a ton of 20-goal, 60-point seasons under his belt. Now he was playing with Marian Hossa and Ilya Kovalchuk? Sign me up, coach.

Okay, well not exactly. Holik never scored more than 15 goals and 34 points during his three years in Atlanta. He was simply past his playing prime at this point of his career. Credit to Winnipeg for technically not handing out the worst contract in their history, if you know what I mean.

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