Top 15 Worst NHL Free Agent Signings in Recent Memory

In most sports, there are certain teams that have a strong tendency to make bad moves. That doesn't apply to any league more so than the NHL. There are a small amount of NHL franchises that make up a

In most sports, there are certain teams that have a strong tendency to make bad moves. That doesn't apply to any league more so than the NHL. There are a small amount of NHL franchises that make up a very large amount of the terrible roster moves.

At one point during drafting for this article, about half the signings were made by the Flyers, Rangers, or Maple Leafs. Of course in their defense, I'm sure there's many franchises out there that would love to make terrible free agent mistakes, but are simply unable to attract the players in the first place.

Most free agent signings gone bad can be sorted into two different categories. The first are contracts given to players who had a single standout out season. Players who over-performed in their contract year after showing mediocrity in every previous season. When signing free agents, it's often helpful to consider the past few years rather than getting hyper focused on a single year.

The second category is players who get paid for their past. NHLers are often able to perform much better late in their careers than athletes of other sports. But even still, players in their mid 30s don't produce like they did in their prime years. Even still, it appears that many GMs are willing to pay for a player under the assumption that he's going to be the outlier.

It seems that many NHL GMs are prone to making poor roster decisions. Like a car wreck, it's always hard to look away. So without further ado, here are the 15 of the most terrible NHL free agent signings in recent memory.

15 Michael Nylander - Washington Capitals


Michael Nylander spent 2005-2007 playing in New York alongside Jaromir Jagr. There, he had two very impressive seasons where he tallied 79 and 83 points respectively. This netted him a star-level contract with the Washington Capitals in 2007 that paid out just under $5 million a year for four years.

To put it simply, it was not a good investment. Nylander failed to exceed 40 points in his two years in Washington. The 2008-09 season was the last he would play in the NHL.

14 Alexei Kovalev - Ottawa Senators

Eric Bolte-USA TODAY Sports

Alexei Kovalev signed a two year contract worth $10 million with the Ottawa Senators in 2009. Paying a 36 year old that much is quite the risky move. He had managed to maintain consistent production throughout his early 30s at about 65 points a season and he was paid as though he was going to continue it through his late 30s.

It didn't pan out like that, unsurprisingly. Shortly after joinging, he began a harsh decline. In his first season he recorded a mediocre 49 points and the following season a highly disappointing 27 before being traded to the Penguins.

13 Dave Bolland - Florida Panthers

James Guillory-USA TODAY Sports

Dave Bolland came over to Florida in the 2014 offseason on a five year deal worth just over $27 million. Over the previous two seasons, Bolland had played a combined 58 games. He had shown signs of some serious talent, but also struggled to stay healthy. This isn't the type of player you would typically give a five year deal to.

His inability to stay in the lineup has continued. In his first season with the Panthers, he played 53 games. This past season, he managed only 25. In sports, durability is a valuable trait and Dave Bolland doesn't have it. Fans should expect more from one of their highest paid forwards.

12 Vincent Lecavalier - Philadelphia Flyers

Sergei Belski-USA TODAY Sports

Vincent Lecavalier was drafted first overall in the 1998 NHL draft by the Tampa Bay Lightning. He was a long time superstar with the team and even won the Stanley Cup with them in 2004. However, he was bought out following the 2012 season. He was on the decline and the team couldn't justify keeping him on board with his cap hit of $7.73 million.

The Flyers signed him in free agency to a five year deal that paid out $4.5 million a year. The next season, he continued his decline, but at the reduced price it was still worth what he was being paid.

In the 2014-15 season, he fell off quite a bit further. He played in 57 games and managed a mere 20 points. This is not the type of production that's worth $4.5 million. Last season, he only played in seven games with the Flyers; often time finding himself as a healthy scratch.

His time with the team came to an end midway through the season when he was dealt to the Los Angeles Kings. The Flyers had to retain 50% of Lecavalier's salary as part of the deal.

11 Matt Carle - Tampa Bay Lightning

Kim Klement-USA TODAY Sports

Matt Carle was a member of the Philadelphia Flyers from when they traded for him in 2009 to when he left as a free agent in 2012. He was a very polarizing player among the fan base. On one hand, he was a talented puck moving defenseman who was very capable on offense. On the other, he could be a liability on defense and had serious turnover issues.

Following the 2011-12 season, he signed a six year deal with the Lightning worth $33 million. Since joining, his turnover and defensive woes have persisted but his offensive touch has regressed tremendously. In four years with Philadelphia, he recorded fewer than 30 points on a single occasion. In four years with Tampa Bay, he's only exceeded 30 points once. Two years ago he failed to hit 20 and this past year he failed to hit just 10.

10 Mike Komisarek - Toronto Maple Leafs


Leafs fans will surely remember Mike Komisarek quite well.

In 2009, the signing was very exciting. They stole the former seventh overall pick away from their division rival, the Montreal Canadiens, on a five-year, $22.5 million deal. However shortly after signing, Komisarek suffered a season ending injury. This sent everything down the wrong path.

In over four years with the team, the defenseman only managed to play 158 games (out of a possible 294). When he was on the ice, he was nothing but a liability, failing to show the talent he previously had, as well as costing his team with reckless penalties. He quickly earned the disdain of the Maple Leafs' fan base.

9 David Clarkson - Toronto Maple Leafs

Tom Szczerbowski-USA TODAY Sports

David Clarkson became a full time Devil for the 2006-07 season. He stayed there for a total of five years. In his first four, he never managed to do anything overly special. He was a mediocre player who could be counted on for about 25 points a season. Then, in his contract year, he kicked it up a notch and scored 30 goals for the first time.

Players who have one good season before they're set to be free agents will always be very risky. Everyone knew it. Throwing caution to the wind, the Leafs still decided to hand him a seven-year deal averaging $5.25 million. The move drew an incredible amount of criticism from not only Toronto fans, but from fans around the league.

The critics were right. In two seasons with Toronto, Clarkson played a total of 118 games. He only managed 15 goals and 11 assists - a paltry total for a top six forward.

8 Wade Redden - New York Rangers


Wade Redden was the second overall pick in the 1995 draft by the New York Islanders (though he started and played the bulk of his career in Ottawa).

He quickly established himself as a high-end defenseman in the NHL. After spending 11 years with the Senators, he decided to test the open market and cash in as much as possible. Eager to grab an impact player, the Rangers quickly signed Redden to a six year contract that paid out $6.5 million per year on average.

Unfortunately, Redden's play quickly declined after joining New York. In fact, after just two full seasons, the defenseman was demoted to the AHL. He only went on to play 29 more NHL games, none with the Rangers.

7 Ryan Clowe - New Jersey Devils

Andy Marlin-USA TODAY Sports

The Devils allowed David Clarkson to walk following the 2012 season. They weren't willing to pay him because they felt he only had one good season and wouldn't be able to replicate that moving forward (they were correct).

Instead, they turned to Ryan Clowe. He played a similar style to Clarkson and historically had been a more productive player. However, over the past few seasons, he had failed to stay healthy, playing only 40 games in the season before he signed in new Jersey. He should have been a relatively cheap, high risk/high reward signing.

Except he didn't get a team friendly deal. He signed a five year deal worth $4.85 million per year on average. Nothing about this contract made sense. Unsurprisingly, it hasn't worked out. Clowe has failed to stay healthy in New Jersey, playing a combined 56 games over his first two years.

This is yet another example of why you shouldn't give long term deals to players who struggle with injuries.

6 Jeff Finger - Toronto Maple Leafs


Jeff Finger got a four-year deal worth $14 million in 2008 and no one knows why.

He had played in the AHL for four years before getting a little bit of NHL time in the 2006-07 season. The following year, he earned a full time role on Colorado's roster. He wasn't particularly special. There wasn't anything about him that you could point to and say "this is an area he excels at."

Even still, Toronto gave him a large contract and it did not pay off. It seemed that every defenseman that the Leafs brought in managed to out play Jeff Finger. His time came to an end after two years when they sent him down to the AHL for the remainder of his contract. He never played professional hockey again when it expired.

5 Ilya Bryzgalov - Philadelphia Flyers

James Guillory-USA TODAY Sports

If you look at Ilya Bryzgalov's numbers, they aren't as bad as you might expect given how much criticism he got. In his first year in Philly, he posted a 2.48 GAA and a .909 save percentage. Those were pretty on par with his career numbers.

To afford his nine-year, $51 million dollar contract, the Flyers traded away fan favorites Jeff Carter and Mike Richards. This started things off on the wrong foot. Then couple that with the fact that he made comments to the media that didn't sit right with the fans as well as having a knack for allowing incredibly soft goals (especially during the playoffs). It becomes more understandable why fans quickly soured on him.

Those who had been defending him quickly backed away following his second season with the team as he sharply regressed. He posed a 2.79 GAA and a .900 save percentage in 40 games which led to his buyout the following off season.

4 Scott Gomez - New York Rangers

Brad Rempel-USA TODAY Sports

Unlike many signings on this list, Scott Gomez actually played pretty well for the Rangers. He recorded 70 points in his first season and 58 in his second with the team. He even maintained his point-per-game production in the playoffs as well.

The issue was that Gomez was simply not worth what he was being paid. In 2007, he signed a seven-year contract worth $51.5 million, resulting in a $7.36 million cap hit.

To put that in perspective, for the 2007-08 season the NHL salary cap was $50.3 million. Gomez took up 14.63% of the Rangers cap space. Today, the salary cap is at $71.4 million. So Gomez' contract in 2007 would be comparable to a player today making $10.44 million a year. Currently, only Patrick Kane and Jonathan Toews earn that much.

3 Sean Avery - Dallas Stars


The Dallas Stars brought Sean Avery on board for the 2008-09 season. The intent was to add toughness and a bit of offensive depth to their bottom six. Avery was known as an agitator, someone who could get under the skin of his opponents. In addition, he could be counted on for about 30 points a season. Not eye popping numbers but certainly not terrible.

Evidentially, the Stars determined Avery's skill set was worth nearly $4 million a year. What they got was an embarrassment. He did next to nothing on the ice and only managed to cause strife within the locker room. He only managed to play 23 games with Dallas. His time there was seemingly spent attempting to make himself the NHL's most hated player, an achievement he would shortly accomplish.

2 Nathan Horton - Columbus Blue Jackets


Nathan Horton signed a seven-year contract with the Blue Jackets worth $37.1 million. This was for a player who had only played 89 games over the past two seasons and scored 54 points. He wasn't a bad player, but Columbus certainly overpaid.

Though, while everyone acknowledged that they overspent, most were okay with it. Columbus had plenty of money to spend and no one to spend it on. They had to overpay to attract top free agents and so they did.

Unfortunately, injuries got the best of Horton and, in the end, he only managed to play a handful of games with Columbus. While the story is sad, the signing still has to go down as one of the worst ever. The Blue Jackets gave a large contract to a guy who only played 35 games with the team.

1 Ville Leino - Buffalo Sabres

Timothy T. Ludwig-USA TODAY Sports

Ville Leino was never an impactful player at any point in his career until he joined the Flyers in 2009. They got him in a trade with Detroit midway through the season for next to nothing. He ended up being a key piece on the Flyers' Stanley cup run that year. In 19 playoff games, he recorded a very impressive 21 points.

He continued that production into the next season, where he scored 19 goals and put up 53 points in 81 games. However the following offseason, Philly decided to make big changes and Leino was not part of it.

He ended up signing a massive six-year deal with the Buffalo Sabres worth $27 million. It didn't take long for him to become a joke around the league.

In his first season with Buffalo, he recorded a highly disappointing 25 points in 71 games. In his second, he only managed to play in eiught games. In his third season, some were hopeful for a rebound year. What they got was 58 games of Ville Leino, but not a single goal.

Throughout his tenure, it constantly felt like it couldn't get any worse, but then Leino would push the limits even further. He was bought out the following off season and Buffalo has yet to live it down.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in NHL

Top 15 Worst NHL Free Agent Signings in Recent Memory