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When the beginning of July comes each summer, hockey season takes off again. The Stanley Cup Finals ended a few weeks ago and there has been a lull in the sport. But after watching the Finals each team wants to get there and has their sights set on the top free agents of the summer. July is free agent month and every team in the NHL wants to add the best players that are available for their run to the Cup.

But every signing comes with a risk. The player is getting signed to a new contract based on what he has already accomplished. There is no guarantee that the production will continue. Sometimes it improves or stays on par for what has been done in the past. But all too often the big signings don’t work out and there is less production on the ice than the general manager was expecting. Those are considered busts. They don’t work out well for the team obviously as it’s just a huge waste of money. On the other hand it usually works out well for the players that receive huge amounts of money, and give nothing in return.

Based on the money that was paid to the player, and the following production that they offered, here are the 15 worst free agent signings in NHL history.

15. Alexei Kovalev – Ottawa Senators 

Via silversevensens.com

In 2009 the Ottawa Senators signed Alexei Kovalev to a two-year contract that was worth $10 million. He had been a top goal scorer in the NHL for many years and Ottawa thought he still had plenty left on his stick. It turned out that they were wrong.

He played two years with the Senators and in 131 games he totaled just 32 goals and just 76 points. While that’s not bad for the average player, Kovalev was supposed to be far better than average. After all he had been previously in his career.

Ottawa ended up trading him to the Pittsburgh Penguins, who they had signed him away from. After that season he went over to play in the KHL. For his time with the Senators he was paid $312,500 per goal scored.

14. Ryane Clowe – New Jersey Devils 

Kim Klement-USA TODAY Sports

For many years Lou Lamoriello was the general manager of the New Jersey Devils and the fans had a saying “In Lou We Trust.” Every move he made over the years seemed to work out in favor of the team, no matter how questionable some of them were at the time of the transaction. In his last couple of years with the team however, that changed. Ryane Clowe is a perfect example of why everyone lost their faith in Lou.

In 2013 Clowe signed a 5-year contract with the Devils that was worth $24.25 million. Previously he had played with the San Jose Sharks and the last two years he hadn’t done anything special so the deal was a little surprising.

He hardly played in New Jersey and when he did he was average at best. He got into 56 games over two years before being forced to retire due to a major concussion. He scored a total of 30 points in those games. While the circumstances that led to his retirement are sad, the fact of the matter is that before he got hurt he didn’t produce in a Devils uniform.

He was paid about $9.7 million for those 30 points, which averages out to be about $323,000 per point.

13. Wade Redden – New York Rangers 

During eleven years of play with the Ottawa Senators Wade Redden was one of the top defensemen in the NHL. When he became a free agent in 2008 the New York Rangers wanted him badly. So they gave him a six-year contract that was worth $39 million.

He repaid New York that season by scoring the fewest points since his rookie year and in his second year playing at Madison Square Garden he put up even worse numbers. He spent two seasons with the Rangers and scored a total of 40 points. He spent the next two years with the Rangers' AHL team. A huge fall for a former All Star.

For his time in the NHL with the Rangers he earned about $325,000 per point that he scored.

12. Ilya Bryzgalov – Philadelphia Flyers 

Via fromrussiawithglove.com

In 2012 the Philadelphia Flyers had a solid squad. The only position that they were lacking was in goal. So they decided to go out on the free agent market and get a goalie that they thought would get them to the Stanley Cup Finals. The lucky winner was Ilya Bryzgalov, who signed a nine-year contract that was worth $51 million.

Bryzgalov had put up two fantastic seasons with the Phoenix Coyotes that saw him earn 15 shutouts and he was voted to an All Star team. But he didn’t take that talent to Philadelphia.

Two plus seasons wearing the black and orange saw Bryzgalov win a total of 52 games while he earned about $17 million. The win total was that of an average goalie and certainly not what a highly paid goalie should be putting up. It worked out to about $327,000 per victory.

11. Stephen Weiss – Detroit Red Wings 

Rick Osentoski-USA TODAY Sports

Stephen Weiss had spent some time with the Florida Panthers. Many people around the NHL thought that he was an underrated player because he played for such a bad team. But it turned out that he was just the best of a collection of stiffs down in south Florida.

The Detroit Red Wings gave him a contract for five years that was worth $24.5 million. Weiss had to know that he had hit the jackpot. He should have felt guilty because he had to know he didn’t have it in him to perform up to that level.

After two years in Detroit and 78 games the Red Wings bought him out. In those 78 games he put up just 29 points. So his time on the ice in Detroit earned Weiss about $338,000 per point scored. Not too shabby.

10. Teemu Selanne – Colorado Avalanche 

Via thescore.com

Teemu Selanne is a perfect example of getting paid for what he had done previously. The Finnish Flash had put together some outstanding seasons in the NHL prior to joining the Colorado Avalanche. In 2003 the Av’s gave him a one year deal that was worth $5.8 million.

Selanne apparently didn’t like playing in Colorado as he ended up playing on the fourth line and his production was so bad that he would have ended up being demoted to the AHL if he didn’t have such a huge contract. He scored the lowest number of points in any full season that he had played to that point. His 16 goals and 16 assists for a total of 32 points on the season earned him a cool $362,500 per goal, or per assist. Either way it was a complete bust for Colorado.

Selanne would get back to his normal production as soon as he left Colorado and moved on.

9. Sean Avery – Dallas Stars 

Via sportsday.dallasnews.com

Let’s get something clear right off the bat. Sean Avery had no hockey skills and should never have been signed to an NHL contract at any point. So in that regard, any contract that he was given was a bust. How he stayed in the NHL as long as he did is a complete mystery. If there was a Hall of Shame Avery would be a first ballot inductee. He was obnoxious, annoying, and never possessed any real hockey talent. So when Brett Hull, who was the general manager of the Dallas Stars in 2008, gave Avery a four-year contract for $15.5 million it was a joke, and a bust in the making.

To show the level of class that Avery had, one time, with reporters around, he referred to his ex-girlfriend and then current girlfriend of Dion Phaneuf, as “sloppy seconds.” Maybe that’s something a scorned guy might say in private but certainly not in the locker room in front of reporters.

Avery lasted just 23 games in Dallas and scored a total of 10 points. So during his time in Dallas he earned about $387,500 per point that he scored. He may not have been a good hockey player but he obviously knows something about negotiating contracts.

8. Sergei Samsonov – Montreal Canadiens 

The Montreal Canadiens like goal scorers. But too often they seem to get them after they have scored all of the goals that they are going to score. A good example of this is Sergei Samsonov. He had spent a good portion of his career with the Boston Bruins and he had put up 20 goals or more in a season five different times. So Montreal signed him to a two-year contract that was worth a little more than $7 million. And then he stopped scoring goals. Imagine that.

During the 2007 season Samsonov scored just nine goals in the 63 games that he played. The Canadiens traded him away after the season. But not before paying him about $389,000 per goal scored.

7. David Clarkson – Toronto Maple Leafs 

Recently the Toronto Maple Leafs made huge changes across the board in their front office. Anyone that wonders why this was done needs to look no further than David Clarkson. Clarkson had spent many years with the New Jersey Devils and he was a huge fan favorite. But that in no means says that he was a great player. He was more along the lines of an average player. And the Maple Leafs made him a very rich average player.

You can’t fault Clarkson for signing a seven year contract that was worth a little under $37 million. He would have been stupid not to take the offer. But those that made the offer thought he was going to be a great player for some reason. That’s all on them.

Clarkson spent only 118 games with Toronto and he scored just 26 points. He combined that with a -25 rating on the ice.

There wasn’t one single person (except maybe for Clarkson) that was happy with these results. Toronto traded him to the Columbus Blue Jackets for Nathan Horton. Horton had been another major free agent bust in Columbus, but he never played a single game with the Maple Leafs. So after paying Clarkson around $404,000 per point scored, they traded him away for nothing.

6. Valeri Kamensky – New York Rangers 

Via flickr.com

The New York Rangers like to spend money. But they don’t always spend it wisely. Countless times over the years they have over paid for a free agent and received minimal to zero return for their money. Valeri Kamensky was coming off one of his worst seasons in the NHL when the Rangers signed him to a 4-year contract that was worth $17 million in 1999. You probably know the results of this one already.

Kamensky spent two years with the Rangers and totaled 17 goals scored and just 66 points. Kamensky was once one of the best snipers in the league but those days were now long gone. But he cashed in on his previous seasons as the Rangers paid him based on them. Then they bought him out after the second season. While playing in New York he earned $500,000 per goal that he scored. Wow.

5. Jay McKee – St. Louis Blues 

At one point in his career Jay McKee was one of the best shot blockers in the NHL. In 2006 the St. Louis Blues rewarded him with a $16 million contract for four years. But the toll of blocking all of those shots would be felt shortly after signing the new deal.

He missed most of his first year in St. Louis with several injuries. He had a bad knee, two other lower body injuries, and a broken finger. He only played in 23 games and didn’t score a point.

He ended up playing three years with the Blues but they weren’t very good ones. They ended up buying out the final year of his contract. He had never been known as a major point scorer but St. Louis had hoped for more from him. During his three years there he scored only 17 total points. So it breaks down to about $706,000 per point scored. That’s amazing.

4. Scott LaChance – Columbus Blue Jackets 

Scott LaChance was a solid defenseman for many years in the NHL. He carved out a career that spanned over 10 years. He was a stay at home type of player that didn’t score a lot of goals or points but was valuable to any team. So when the Columbus Blue Jackets signed him to a 2-year deal in 2002 that was worth $4 million, it looked like a solid addition for a decent price.

It’s a good thing that Columbus wasn’t expecting a lot of goals from him. He didn’t score a single one during his two years there. And while he wasn’t a major point scorer either, the five that he put up over 138 games with the Blue Jackets can be considered more than disappointing. He also had a rating on the ice of -43 during that time. But Columbus proved to be a very generous team as they paid him $800,000 per point that he scored. Not a bad payday at all.

3. Mike Komisarek – Toronto Maple Leafs 

Mike Komisarek was another great shot blocker during his days in the NHL with the Montreal Canadiens. The Toronto Maple Leafs needed one so in 2009 they gave him a five-year contract for $22.5 million. It turned out to be just another free agent signing that the Maple Leafs regretted.

He didn’t play very much in Toronto due to injuries and just an overall horrible performance when he was on the ice. In 2013 they finally demoted him to the AHL. But during his time with the Maple Leafs he earned about $18 million and scored a total of 19 points. The financial breakdown on that is about $947,000 per point scored. The Canadiens are still laughing about that deal.

2. Chris Drury – New York Rangers 

We have already spoken about how the New York Rangers like to spend money. In 2007 they spent a ton on Chris Drury. He wasn’t an average player but he wasn’t great either. Over his career he was the beneficiary of having some very good line mates that made him look better than he really was. But New York didn’t realize that as they signed him to a five-year contract that was worth a little more than $32 million.

The deal worked out ok overall for New York as Drury’s first two seasons in the Big Apple were pretty good. The third season of the contract saw a dramatic downturn in Drury’s point production but the fourth year was the worst yet. New York smartened up before the fifth year started and bought him out.

In the 2011 season Drury played in only 24 games and scored one goal and added four assists for a total of five points. So in his final season with the Rangers he earned $6.45 million per goal scored, or just under $1.3 million per point scored. Either way you want to look at it, the Rangers didn’t even come close to getting a good return on that contract. But it was better than what the Detroit Red Wings ended up paying Uwe Krupp.

1. Uwe Krupp – Detroit Red Wings 

Uwe Krupp hit the contract lottery with the Detroit Red Wings in 1998. For 12 seasons he had been one of the top defensemen in the NHL and was a three-time All-Star. So Detroit signed him on for four years at $16 million.

Unfortunately for the Red Wings, they didn’t realize that Krupp’s career was pretty much over. In the 1999 season he played in just 22 games. Then in the 2000 season and again in the 2001 season, he didn’t play at all. He came back to the ice for the 2002 season but only played in 12 games over the rest of his time with Detroit. His grand total of points scored for all of his time with the Red Wings was just six points. So the financial breakdown for Krupp’s time in Detroit is a staggering $2.6 million earned per point that he scored. If Sidney Crosby could get paid that kind of money the Penguins would be out of business.

SOURCES: thesportster.com, bleacherreport.com, thehockeywriters.com, torontosun.com, wikipedia.org

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