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Top 15 Worst NHL Free Agent Signings Of The Past 20 Years

Here is a look at the 15 worst free agent signings of the past 20 years.

The 2016-17 NHL season is over. So is the 2017 NHL Draft. All that's left now is to see where all the top free agents of 2017 land.

This year's crop is far more exciting than that of the last two. You can expect that general managers will once again throw out money desperately to land players they expect to make an impact. As usual, some GMs will not learn from mistakes from the past.

Throughout history (especially the last 20 years), many NHL teams have given a TON of money to a player they thought could take them to the next level. And hey, you didn't have to trade any players or draft picks away to land this player! Just pay him what he wants and you got a superstar!

Not exactly. Some of the most lucrative free agent signings in NHL history actually provided a team with a desire to attach a receipt to those contracts. Here is a look at the 15 worst free agent signings of the past 20 years.

15 Blues Pony Up for Paul Kariya

via hockeysfuture.com

Back in the 2007 offseason, the St. Louis Blues looked like geniuses for signing flashy scorer Paul Kariya to a three-year contract worth $18 million. Kariya was a sure thing to score 30 goals and 70 points in a season, and the Blues desperately needed to find some scoring help on their frustrating team.

Kariya's first season in St. Louis wasn't so bad. He scored 16 goals and 65 points. But the next season, he was limited to 11 games due to a severe hip injury. The Blues obviously had to pay their star a lot of money while he recovered.

The next season, Kariya had just 18 goals and 43 points -- one of the worst seasons of his Hall of Fame career. The Blues never got what they paid for, as Kariya struggled to find his place in St. Louis.

14 Maple Leafs Swing and Miss on Mike Komisarek

via pensionplanpuppets.com

Mike Komisarek was a solid No. 2 or 3 defenceman on the Montreal Canadiens, but he was never worth that much money. He had never scored more than 19 points in a season, but the Toronto Maple Leafs felt inclined to steal him from their arch-rivals but giving Komisarek a five-year contract worth $22.5 million.

Komisarek didn't do any scoring in Toronto (he scored no more than 10 points in a season), and wasn't even responsible in his own end. Komisarek played just 34 games in 2009-10, 45 in 2011-12 and just four in 2012-13 before being bought out by the Leafs.

Toronto has always had a knack for paying players top-dollar. But this team expected to Komisarek to earn every penny of the $22.5 million. Instead, he essentially took money and ran away from them.

13 Teemu Selanne Fails in Colorado

via thescore.com

Teemu Selanne and Paul Kariya were best friends with the Mighty Ducks of Anaheim, but weren't able to win a Stanley Cup together. The two players decided to chase a ring together and joined the Colorado Avalanche for the 2003-04 season. Kariya chose to take a modest one-year deal worth $1.2 million. He had a terrible season, but at least didn't cost Colorado much.

Selanne, on the other hand, took a one-year deal worth $5.8 million and was coming off a 28-goal and 64-point season with the San Jose Sharks. Joining the likes of Peter Forsberg and Joe Sakic meant there was no excuse for Selanne to fail.

Well, he did. He scored just 16 goals and 32 points -- the worst season of his career up to that point. The Avalanche were supposed to win a Stanley Cup, but their free agent catches failed and the Sharks took out Selanne's new team in the second round of the playoffs.

12 Red Wings Overpay Stephen Weiss

via thehockeywriters.com

On paper, Detroit Red Wings general manager Ken Holland looked like a genius for getting Stephen Weiss on a five-year contract worth $24.5 million. This was a player who had scored 20-plus goals four times and was capable of posting 50-point seasons when healthy.

But Weiss struggled big time in Detroit, to say the very least. The speedy centre played in just 26 games in 2013-14 and scored just two goals and a pair of assists. The following season, he had just 25 points in 52 games.

In the 2015 offseason, Holland just played it safe and bought out the final three years of Weiss' contract. The former Florida Panthers standout hasn't played in the NHL since, as other teams have been weary of giving him a chance after flopping big time in the Motor City.

11 Nikolai Khabibulin Disappoints in Edmonton

via oilersnation.com

The Edmonton Oilers were in desperate need of a new number one goalie, and 2004 Stanley Cup champion Nikolai Khabibulin appeared to be an ideal fit. After winning 25 games with the Chicago Blackhawks in 2008-09 and leading them to the Western Conference Final, Khabibulin got paid by the Oilers.

He was given a four-year contract worth $15 million, but turned out to be one of the worst signings in the franchise's history. Khabibulin went just 7-9-2 in his first season with a woeful 3.03 goals against average. He missed most of the season after needing surgery on a herniated disk.

According to QuantHockey.com, Khabibulin went just 33-67-5 in his brief four seasons with Edmonton. He had a terrible 3.00 GAA and .903 save percentage, as injuries and age contributed to a disastrous tenure with the Oilers. Khabibulin is among the worst free agent goalie signings ever.

10 Sabres Whiff on Christian Ehrhoff

via sbnation.com

Christian Ehrhoff had two great seasons with the Vancouver Canucks in 2009-10 and 2010-11, scoring 14 goals in each while accumulating a total of 94 points. He added 12 points in 23 playoff games during Vancouver's run to the 2011 Stanley Cup Final.

However, the Canucks re-signed Sami Salo and Kevin Bieksa and couldn't afford to re-up Ehrhoff. That's where the Buffalo Sabres swooped in on the German standout, signing him to a 10-year deal worth $40 million.

Ehrhoff's first season in Buffalo was a disappointment. He scored just five goals and 32 points and struggled to find the offence he displayed in Vancouver. Over the next two seasons, he had just 11 goals and 55 points. The Sabres bought him out after the 2013-14 season.

9 David Clarkson's Failed Homecoming to Toronto

via sportsnet.ca

There was so much hype when the Toronto Maple Leafs signed power forward David Clarkson to a seven-year, $36.75 million contract in 2013. The Ontario native was thrilled about playing for his home province team, and many pundits were comparing him to former Leafs power forward Wendel Clark.

Clarkson's tenure in Toronto was a disaster from the get-go. He was suspended for the first 10 games after leaving the bench to engage in a fight during a preseason game. Clarkson was limited to 60 games and scored a porous five goals and 11 points.

The next season, Clarkson registered just 10 goals and 15 points in 58 games. Luckily, the Maple Leafs were able to unload Clarkson to the Columbus Blue Jackets for another terrible contract. That bring us to our next guy..

8 Blue Jackets Give Nathan Horton $37.1 Million

via mapleleafshotstove.com

The Blue Jackets barely missed the playoffs in 2013, so they added ultra power forward Nathan Horton in the offseason to bolster their roster. Horton was signed to a seven-year contract worth $37.1 million, and the deal made sense at the time. He was a well-respected leader who had a 2011 Stanley Cup ring with the Boston Bruins and had six 20-goal seasons under his belt.

But Horton didn't play his first game with the Jackets until January, needing  to recover from offseason shoulder surgery. He scored a mere five goals and 19 points in 36 games. Horton hasn't played since, as a back injury is expected to sideline him for his career.

The Jackets swapped Horton's toxic contract for Clarkson's awful contract. Toronto cleared Horton's cap space by putting him on the long-term IR. It was just one way for both teams to get out of really bad deals.

7 Ville Leino Overpaid, Underachieves in Buffalo

via thehockeyhouse.net

Ville Leino had ONE good year with the Philadelphia Flyers in 2010-11. He scored 19 goals and 53 points. It was enough to intrigue new Sabres owner Terry Pegula, who wanted to spend a ton of money to help Buffalo compete long-term.

The Sabres signed Leino to a six-year contract worth $27 million. Quite a lot of cash for a player who had one good season. Buffalo would learn that the hard way, as Leino completely flopped with his new team.

In 2011-12, Leino scored just eight goals and 25 points. The next season, he had just two goals and four assists in eight games. Leino played 58 games in 2013-14, and didn't score a single goal. The Sabres bought out Leino's contract after 2013-14 and he went to play overseas.

6 Sheldon Souray's Cannon Disappears in Edmonton

via blueshirtbanter.com

There aren't a lot of defencemen these days who can score 20 goals. But Sheldon Souray scored 26 of them for the Montreal Canadiens in 2006-07, and had the Edmonton Oilers at "hello".

Souray was signed to a five-year contract worth a fancy $27 million, as the Oilers hoped he could fill the void left by Chris Pronger two seasons earlier. Souray's first year in Edmonton was awful -- he had just three goals in and 10 points in 26 games. He rebounded the next year with 23 goals and 53 points -- seemingly living up to that contract.

Nope. Injuries limited Souray to 37 games in 2009-10, where he scored just four goals and 13 points. The Oilers sent him to the minors then bought out the final year of his contract, erasing the end of the worst free agent signing in Edmonton's history.

5 Mark Messier Robs Canucks

via theprovince.com

Mark Messier was a shell of his former self when the Vancouver Canucks gave him about $20 million for three years (according to the New York Times). But Vancouver was in desperate need of a star who could help sell tickets, so they chose Messier -- who won six Stanley Cups and was a well-respected veteran.

Messier turned out to be a huge waste of money for Vancouver. He had a respectable 22 goals and 60 points in 1996-97, but the Canucks remained one of the worst teams in hockey. The next year, his totals fell to 13 goals and 54 points. Then it was 17 goals and 54 points.

In 2012, Messier then took home an extra $6 million in an arbitration case against Vancouver. As such, many Canucks fans only have memories of a selfish, greedy and giant waste of money in Messier.

4 Rangers Waste Money on Scott Gomez

via zimbio.com

Scott Gomez was a thorn in the side of the New York Rangers for many years. The New Jersey Devils star scored 33 goals and 84 points in 2005-06. A year later, he regressed with just 13 tallies for 60 points. But that didn't stop Glen Sather and the New York Rangers from making Gomez a very rich man.

In 2007, the Rangers signed Gomez to a seven-year deal worth $51.5 million. He scored just 16 goals and 70 points -- good, but not great numbers. The next year, he had 16 goals and 58 points.

Somehow, the Rangers got the Montreal Canadiens to take on Gomez's contract -- while future star Ryan McDonagh went to the Blueshirts in the deal. Montreal was stuck with the disastrous deal until they bought out Gomez during the 2012-13 season.

3 Rangers "Steal" Chris Drury From Sabres

via ibtimes.com

Chris Drury was one of the NHL's purest goal-scorers in the 2000s. He had 20-plus goals seven times from 1998-99 to to 2006-07. In that final year, he scored 37 goals and 69 points as the Buffalo Sabres won the Presidents' Trophy and fell just three games short of winning the Eastern Conference.

The Sabres weren't able to pay Drury what he wanted, so the Rangers chose to sign him on a five-year contract worth a $35.25 million. With Gomez and Drury the Rangers were supposed to be a championship contender.

Drury did score 25 and 22 goals over his first two seasons in New York, but his production was quite a drop off from what he posted in Buffalo. His numbers slipped to a woeful 14 goals and 32 points in 2009-10. A year later? One goal and five points in 24 games.

The Rangers bought out the fifth year of Drury's contract in the 2011 offseason, and he would officially announce his retirement.

2 Ilya Bryzgalov Takes $51 Million From Flyers

via pennlive.com

The Philadelphia Flyers had goaltending woes contribute to an untimely exit in the second round of the 2011 playoffs. Desperate for an elite starter, GM Paul Holmgren shipped out superstars Mike Richards and Jeff Carter to make room for Ilya Bryzgalov -- who was coming off a 36-win season for the Coyotes.

Bryzgalov signed a nine-year deal worth $51 million, seemingly giving Philadelphia the missing piece to win a championship. Though he won 33 games in 2011-12, Bryzgalov posted a mere .909 save percentage and 2.48 goals against average.

The next season, he went just 19-17-3 and posted a horrid 2.79 goals against average and .900 save percentage. Thanks to the compliance buyouts that came with the new CBA in 2013, Philly was able to buy out Bryzgalov in 2013 without any salary cap-related consequences.

Perhaps Holmgren should have just kept Carter and Richards? While looking for another goalie?

1 Rangers Make Wade Redden a $39 Million AHLer

via cbc.ca

Oh, the Rangers didn't learn from their disastrous Scott Gomez and Chris Drury signings. In the summer of 2008, they signed former Ottawa Senators star defenceman Wade Redden to a whopping six-year deal worth a total of $39 million. Boy, did Glen Sather regret that.

Redden scored just three goals and 26 points in his first season with the Rangers -- his worst offensive production in nine years. In 2009-10, Redden had just two goals and 14 points -- and became the biggest whipping boy by the Rangers media and fans.

He was demoted to the minors and eventually bought out during the 2012-13 season. New York got absolutely nothing out of the Redden season -- except maybe a lesson: Stop paying so much money to players in their 30s.

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Top 15 Worst NHL Free Agent Signings Of The Past 20 Years