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Top 25 Worst Free Agent Signings in NHL History

July 1st has become one of the biggest days on the hockey calendar. On the first day of every July, NHL contracts expire and players officially become free agents with the ability to sign wherever they want.

Despite the constant repetition of the old adage that "championships are not won in July," teams and fans are always more than happy to boast their massive hauls in free agency. Though teams can assemble the pieces of an amazing team through free agency, it can also be the downfall of many teams. Massive contracts given out to the wrong player can create holes that organizations can not climb out for years.

What exactly makes a free agent signing terrible? There is a combination of factors that cause a signing to be terrible for a team with production, contract length, price and age being major issues that cause teams to shoot themselves in the foot.

Sometimes you can easily evaluate how poor a signing is simply by their production. A dropoff in points can signify a team not properly using the available talent or putting their players in the wrong scheme to produce the best results.

Possibly the biggest factor to a bad free agent signing is the contract. Rarely will a one-year contract be considered terrible based on the fact that it should not set a team back in the long term. A short-term experiment can be excused if it falters. The second part of examining a contract is just how much money a player is receiving. Sports history is littered with players that received massive amounts of money because teams do not know how to properly manage money or simply overpay.

The truth is, age slows everyone down. But age especially impacts professional athletes. Once a player passes that 30-year mark is when longer-term contracts start to become a poor idea. Signing older players to a younger squad to provide veteran leadership is a good signing, but signing an aging player with the hopes he will be a main contributor is flawed.

So without further ado, here are the worst free agent signings in NHL history.

25 25. Todd Bertuzzi – Anaheim Ducks 

via canada.com

At one point in his career, Todd Bertuzzi was arguably the best power forward in the NHL. However by the time the Anaheim Ducks signed him to a two-year, $8 million contract, he had become a shell of his former self.

24 24. Stephen Weiss – Detroit Red Wings 

Kim Klement-USA TODAY Sports

When Stephen Weiss’ contract ran up with the Panthers, many dubbed him one of the more underrated players in the league thanks to his playing in Florida. The Detroit Red Wings agreed and paid the center $24.5 million over five years.

23 23. Valeri Kamensky – New York Rangers 

via russkiyhockey.wordpress.com

Despite being 33 years old and coming off his worst season since his sophomore season, the New York Rangers signed Russian winger Valeri Kamensky to a four-year, $17 million contract in 1999. The signing went about as well as you would expect.

Kamesnky would score 17 goals and 66 points in two seasons with the Rangers. Though Kamensky spent those years dealing with nagging injuries, the former goal-scorer was never a specifically great fit in New York.

22 22. Teemu Selanne – Colorado Avalance 

via gamewornauctions.net

The Colorado Avalanche signed Teemu Selanne to a one-year, $5.8 millon contract in 2003 with the hopes that a pairing with newly signed Paul Kariya would flourish like it did in Anaheim.

Selanne was a complete bust and wound up on the fourth line for the Avs during his one season with the team and you would imagine he might have ended up in the AHL if it was not for his contract.

21 21. Mark Messier – Vancouver Canucks 

via canucksarmy.com

Mark Messier is rightfully in the NHL Hall of Fame, but most people like to forget about his time spent with the Vancouver Canucks. Messier signed a three-year contract, with options for two more years, worth nearly $20 million to go back to Canada for the Canucks.

During his tenure with the team, Messier was given the captaincy over long-time (and soon to be traded) captain Trevor Linden and also demanded that he be given the number 11 despite the number being unofficially retired following the death of Wayne Maki.

20 20. Chris Drury – New York Rangers 

via newyork.cbslocal.com

Once again the New York Rangers horribly overpaid for a slightly above average, aging forward. Chris Drury was given a five-year, $32.25 million contract in the summer of 2007 after posting 60 or more points in the previous two seasons.

During his tenure with the Rangers, Drury’s production started to decline with father time looming large over the center. Each season saw Drury play fewer games and score fewer points as the Rangers watched their investment deteriorate.

19 19. Sergei Samsonov – Montreal Canadiens 

via hfboards.hockeysfuture.com

The Montreal Canadiens continued to show their affinity for diminutive, goal scorers when they went out and gave Sergei Samsonov a two-year, $7.05 million dollar contract in July of 2006. The Russian winger had produced five seasons of 20 or more goals, largely for the Boston Bruins.

The aging process started to hit Samsonov and his small stature became a huge hindrance. Samsonov spent more than a few games as a healthy scratch during the 2006-07 season and only tallied nine goals in 63 games.

18 18. Nathan Horton – Columbus Blue Jackets 

Jerome Miron-USA TODAY Sports

Despite the fact that Nathan Horton was dealing with various injuries, including concussions, in the two seasons leading up to the 2013 offseason, the Columbus Blue Jackets signed him to a seven-year, $37.1 million contract.

An offseason shoulder surgery kept the forward out until Januray and Horton would only play 36 games in the full season. Horton was then diagnosed with a degenerative back condition later in 2014, which just compiled to his ever growing injury list.

17 17. Ryane Clowe – New Jersey Devils 

Kim Klement-USA TODAY Sports

After making a name for himself as a part of the ever choking San Jose Sharks, Ryane Clowe would end up signing as a free agent with the New Jersey Devils in the summer of 2013. Clowe was given a five-year, $24.25 million contract despite being two seasons removed from being productive.

Clowe would go on to play just 43 games with 26 points in his first season with the Devils and a mere 13 games with four points in 2014-15.

16 16. Alexei Kovalev – Ottawa Senators 

via lapresse.ca

Alex Kovalev did not have the best of reputations around the NHL, with many thinking that he's a little bit lazy, but it is hard to argue with the numbers he has produced. The Ottawa Senators decided they were done watching the Russian goal-scorer hurt them and signed the then-36-year old to a two-year, $10 million contract.

In Kovalev’s four full years with the Montreal Canadiens before he signed with the Sens, he averaged 65 points per season, but would go on you tally just 16 points per season in Ottawa.

15 15. Ilya Bryzgalov – Philadelphia Flyers 

via fromrussiawithglove.com

The Philadelphia Flyers were just a good goaltender away from being a real threat to represent the East in the Stanley Cup Finals leading into the summer of 2012. The Flyers decided it was time to spend the money and signed Ilya Bryzgalov to a ridiculous nine-year, $51 million contract.

Bryz was coming off two amazing seasons with the Phoenix Coyotes, which saw him post a combined .920 save percentage with 15 shutouts and a trip to the All-Star game.

Throughout a down season with the Flyers, Bryzgalov’s confidence was noticeable shaken and he had openly stated that during several interviews that the first season in Philly.

14 14. Mike Komisarek – Toronto Maple Leafs 

via cbc.ca

The Toronto Maple Leafs were struggling mightily in their own end with a combination of mediocre defense and terrible goaltending when they signed Mike Komisarek to a five-year, $22.5 million contract in 2009.

Komisarek built a reputation for being one of the toughest, stay-at-home defensemen in the NHL with the Montreal Canadiens, which including leading the NHL in blocked shots and finishing second in hits the year before signing with the Leafs.

13 13. Martin Lapointe – Boston Bruins 

via bleacherreport.com

Though there can be a lot of useless rhetoric spewed by the media, when a player is widely considered one of the worst contracts in sports for several seasons, there is a reason. The Bruins signed Martin Lapointe to a four-year, $20 million contract after a career season with the Red Wings.

Lapointe, who was a grinder during his career, only notched 83 points in three seasons with the Bruins before they moved on from the overpaid winger.

12 12. Uwe Krupp – Detroit Red Wings 

via sikids.com

Uwe Krupp was an above average NHL defenseman for 12 years, including three All-Star appearances, before the Detroit Red Wings gave him a four-year, $16 million contract in the summer of 1998.

Age finally caught up to the German-born defenseman though, as his back deteriorated quickly and Krupp would play only 22 games in the 1998-99 season. After being absent for a year, Krupp would return in the 2001-02 season and play just 12 more games over two seasons before retiring.

11 11. Cristobal Huet – Chicago Blackhawks 

via bleacherreport.com

Cristobal Huet had a legitimate case for one of the top netminders in the East during his time with the Montreal Canadiens, but the Chicago Blackhawks were not getting that goalie. Huet signed a four-year, $22.5 million contract with the ‘Hawks in the summer of 2008.

During his tenure in Chicago, Huet was unable to win the starting job from either Nikolai Khabibulin or Antti Neimi before he was loaned to Fribourg-Gotteron of the Swiss League to help with the Blackhawks awful salary cap situation.

10 10. Theo Fleury – Chicago Blackhawks 

via blackhawkup.com

By the time Theo Fleury made his last NHL signing with the Chicago Blackhawks, his off-the-ice issues were taking over his life. The ‘Hawks signed the troubled forward to a two-year, $8.5 million contract in 2002. Before he ever suited up for the team he was suspended 25 games by the league for substance abuse.

Fleury would only play 54 games in the 2002-03 season, scoring 33 points, but the season will be more remembered for his actions off the ice. Fleury and several Blackhawks teammates went out to a strip club and the diminutive forward got into a brawl with the bouncers, but never had any recollection due to substance abuse.

9 9. Bobby Holik – New York Rangers 

via sikids.com

Glen Sather decided that it was best for the New York Rangers to sign a relatively average 12-year NHL pro to a five-year contract worth $45 million dollars in the summer of 2002.

Holik was still rather average during his tenure with the Rangers posting a respectable 91 points over two seasons. The Czech center was being paid $9 million per season, which means that it cost the Rangers about $200,000 per point.

8 8. Sheldon Souray – Edmonton Oilers 

via news.nationalpost.com

Teams are always going to pay big bucks for offensive defenseman who can quarterback the powerplay. The Oilers gave Sheldon Souray a five-year, $27 million contract in the 2007 season.

7 7. Brad Richards – New York Rangers 

via bleacherreport.com

Brad Richards seemed like a sure thing, a true top line center who had proven time and again to be a consistent performer, then the New York Rangers signed him. The pride of Murray Harbour, PEI, Richards inked a nine-year, $58.5 million contract in 2011.

Richards would score 66 points in his first season in New York, his lowest since his sophomore season in the NHL. Though his numbers were far from terrible, the center was being paid over $10 million during that first season.

6 6. Wade Redden – New York Rangers 

via nydailynews.com

Wade Redden was one of the most consistent performers in the NHL for his 11 year career with the Ottawa Senators, so the New York Rangers threw a lot of big numbers at him during the 2008 offseason. Redden would sign a six-year, $39 million contract to play in the Big Apple.

5 5. Scott Gomez – New York Rangers 

via hockeyforum.com

Scott Gomez was a great player during his tenure with the New Jersey Devils and a more than capable top line center for the team, but the New York Rangers overpaid for the Alaskan-native. Gomez was signed to a seven-year, $51.5 million contract on July 1st, 2007.

Gomez did not put up terrible numbers during his tenure with the Rangers, producing 0.81 points per game. The real killer was that Gomez’ annual salary had him more money than players like Sidney Crosby and Alexander Ovechkin.

4 4. David Clarkson – Toronto Maple Leafs 

Ed Mulholland-USA TODAY Sports

David Clarkson was never more than an average NHL player with the occasional flash of goal scoring ability, but that did not stop the Toronto Maple Leafs from inking him to a massive seven-year, $36.75 million deal.

Clarkson came into the hotbed of the hockey world with a monstrous amount of pressure, which he folded under. The Etoboicoke, Ontario-native would amass 26 points and a -25 rating through 118 games with the Leafs.

3 3. Sean Avery – Dallas Stars 

via cbc.ca

Sean Avery will likely go down in history as the most obnoxious player to ever play in the NHL. Despite producing more 250-plus-penalty minute seasons than 16 goal seasons, co-general manager Brett Hull gave the pest a four-year, $15.5 million contract in 2008.

Avery ended up playing just 23 games in Dallas, as his attitude and playstyle were never suited for the team. Infamously, Avery would call Elisha Cuthbert, his ex and then girlfriend of Dion Phaneuf, “sloppy seconds.”

2 2. Jeff Finger – Toronto Maple Leafs 

via ehteamsports.wordpress.com

The Toronto Maple Leafs were on the lookout for a player to shore up their blueline in the summer of 2008 and the team decided to give a four-year, $14 million contract Jeff Finger, who had only played one full season in the NHL.

Finger did produce his best offensive season of his career in 2008-09 for the Leafs, but his inability to play in the defensive zone saw the free agent acquisition sitting in the press box a few too many times during the following season.

1 1. Ville Leino – Buffalo Sabres 

Timothy T. Ludwig-USA TODAY Sports

The Buffalo Sabres were desperate to make a splash in free agency as their team was fading more and more into the bottom tier of the league, so they threw a six-year, $27 million contract to Ville Leino. The Finnish forward was coming off his best season in his NHL career with 53 points in 2010-11.

What would follow was one of the most embarrassing runs from a player in NHL history. During his 137-game tenure with the Sabres, Leino scored 10 goals which including a staggering zero in 2013-14.

Leino was last seen signing one-year contracts in the KHL.

Do you think there were worst free agent contracts? Can you possibly think of a GM worse than Glen Sather are overpaying for players? Let us know in the comments below.

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Top 25 Worst Free Agent Signings in NHL History