To be a successful team in the NHL, a general manager needs to make the correct free agent signings and build within their system of prospects. Although this may not sound too challenging to NHL fans, that cannot be any more incorrect. Even the best of the NHL’s general managers have made monumental mistakes when it comes to trying to build their teams into contenders and with that, criticism should not always be given so harshly. Yet, some mistakes are simply unforgivable to many fans because it set back their teams immensely.
With all of that said, in this article, we will be looking at fifteen players who did just that. Now, it is important to note that the majority of players on this list were the victim of bad contracts and tried their best to achieve success. However, there are also others who simply did not care for the team that they played on and were focused primarily on the money. Nonetheless, at the end of the day, each player on this list did negatively impact the team they played for because they left a significant dent on their salary cap. We all know the lingering effects of a bad free agent signing.
Now, let’s look at fifteen players who ruined their franchises for years.
15 Scott Gomez
When Scott Gomez joined the NHL during the 2000 NHL season, he won the Calder Memorial Trophy and Stanley Cup with the New Jersey Devils. With this, Gomez built on his career and during his prime, was a top player. When he hit the free agent market in the 2007 NHL offseason, he decided to sign with the Devils’ number one rival, the New York Rangers, to a seven year, $51.5 million deal.
Soon after this contract was signed, it became clear that the Rangers made a mistake because Gomez quickly showed signs of declining. However, the Rangers moved him at the perfect time and ended up getting their current captain Ryan McDonagh in the deal. The Canadiens felt the worst of the deal at the end of the day because they bought him out and also lost an elite player in the process.
14 Rick DiPietro
Rick DiPietro was expected to be the franchise goalie of the New York Islanders for years when he was drafted by them first overall in 2000 NHL Entry Draft. Once DiPietro grew accustomed to the skill level of the NHL, he put up some solid numbers and even could have been classified as of the league’s best. With this, the Islanders then signed DiPietro to a 15 year, $67.5 million extension during the 2006 offseason.
After signing this extension, DiPietro made his first All Star game appearance in 2007, but that would quickly come to an end. DiPietro would spend the next few seasons injured for the majority of the year. The injuries and lack of consistent playing time made him drop in skill as well. At the beginning of the 2013 offseason, after years of struggling, DiPietro was bought out and finally off the cap.
13 Vincent Lecavalier
After shockingly being bought out by the Tampa Bay Lightning during the 2013 offseason, Vincent Lecavalier did not have any trouble finding a new team. Lecavalier quickly signed with the Philadelphia Flyers on a 5 year, $22.5 million dollar deal. At the time, the contract was met with great praise because although the term was long, the cap hit was fairly small for a star centre.
However as soon as Lecavalier joined the Flyers, it became apparent that he had dropped in skill. As a result of this, the Flyers had a very difficult time spotting him in the lineup and he became a winger. This made him drop in points immensely and even begin to dislike the team. After three miserable seasons, Lecavalier was traded to the Los Angeles Kings and actually turned it around before retiring.
12 Ilya Bryzgalov
The Philadelphia Flyers signed another top free agent during the 2011 offseason when they got their franchise goalie in Ilya Bryzgalov. Bryzgalov’s contract was mammoth, as he signed a nine year, $51 million deal. This contract was supposed to be the one that made the Flyers finally fix their horrendous goaltending problem and obtain their Stanley Cup.
Yet the pressure of playing on a big market club made Bryzgalov’s play drop dramatically. Bryzgalov could not match the success he had in Arizona and quickly became resented by the Flyers’ fanbase. Besides playing poorly, his huge cap hit made him impossible to move and the Flyers fell off. In 2013, they luckily bought him out, but this contract still impacts them, since they traded superstar Jeff Carter to make it happen.
11 Dion Phaneuf
When the Toronto Maple Leafs traded for Dion Phaneuf during the 2009-2010 NHL season, it was seen as a franchise changing move. Phaneuf was one of the league’s top young defensemen and had already been on the cover of the NHL 09 video game. Phaneuf played well during his first few years with the team, became captain, and signed a 7 year, $49 million extension.
This contract would end up being a big mistake by the Leafs because at the end of the day, they needed to start another rebuild. The failures of the Leafs were often blamed on Phaneuf, even though it was not necessarily warranted. Nonetheless, the Maple Leafs knew they needed to rid of his contract to make a new push in their rebuild and they luckily made it happen during the 2015-16 season.
10 Jimmy Hayes
Jimmy Hayes made a huge step in his career during his last year with the Florida Panthers during the 2014-15 season. Soon after this, the Boston Bruins decided to bring in the hometown kid and gave him a 3 year, $6.9 million dollar deal. This deal was seen as a smart move by the Bruins because Hayes was young and seemed to be progressing into a top-6 forward.
Yet, it became apparent that Hayes’ career year was a bit of a fluke and that he could not handle the pressure of an Original Six market. Hayes’ stats dropped off dramatically in his two seasons in Boston and as a result, he was bought out this past offseason. Although the duration of the contract was short, it did restrict the Bruins from bringing in someone with more talent.
9 Nathan Horton
Nathan Horton was one of the primary reasons why the Boston Bruins won the Stanley Cup in 2011. Horton was a spectacular power forward during his prime because he not only played fantastically in the physical side of the game but also put up very solid numbers. When Horton became a free agent in 2013, he left Boston and signed a seven year, $37.1 million deal with the Columbus Blue Jackets.
This seemed like arguably the best signing of that offseason because Horton was still only 26 and easily in his prime. Yet, Horton developed a degenerative back condition that sidelined him long term very shortly into his first season. Since then, Horton has not been able to return to the NHL. In this situation, the Blue Jackets were unlucky due to uncontrollable circumstances, but they luckily were able to get rid of the contract in a trade for David Clarkson.
8 Roberto Luongo
During his prime, Roberto Luongo was easily the best goalie in the NHL and is the main reason why the Vancouver Canucks had immense success during the early 2010s. The Canucks basically stole him from the Florida Panthers back in the 2006 offseason and from there Luongo became their best player. Because of this, the Canucks gave him a 12 year, $64 million extension in the 2010 offseason.
Luongo continued to be one of the league’s best during his time with the Canucks, but management grew very impatient with him. Luongo did not deliver the city a Stanley Cup and with the team moving toward a rebuild, his contract became a huge burden. Luongo’s play also started to drop because of the pressure, but luckily for both parties, he got traded back to the Panthers in 2014.
7 Mike Komisarek
During his prime, Mike Komisarek was one of the most lethal and tough NHL defenders in the entire league for the Montreal Canadiens. When Komisarek hit the open market during the 2009 NHL offseason, he was rewarded for his great play and signed a five year, $22.5 million deal with the Toronto Maple Leafs. This quickly would become a bust.
Komisarek never seemed to adjust to the Maple Leafs and there are a handful of reasons for this. First, Komisarek joined a Maple Leafs team that was having management issues and were on the cusp on an inevitable rebuild. Komisarek also dealt with an abundance of injuries and it made him drop in skill dramatically. Luckily for the Leafs, they bought his contract out in 2013, but it still left a huge dent on their cap for years.
6 Shea Weber
Now, this is definitely not a knock on Shea Weber because he is still among the league’s top defensemen and was a sensational leader for the Nashville Predators. Without Weber, the Predators would not have tasted any success in the league for years, but he helped them immensely. Yet, Weber an atrocious contract because he signed a 14 year, $110 million offer sheet with the Philadelphia Flyers, which was matched.
This contract’s term would have left a huge impact on the Predators’ small market, but they were extremely fortunate to move it for another top defensemen, P.K. Subban. This trade was definitely a huge mistake by the Canadiens because Subban will be in his prime for many more years for cheaper, while Weber will be on the decline. Overall, the Predators lucked out big time.
5 Wade Redden
During his time with the Ottawa Senators, Wade Redden emerged into a franchise defenceman for the club. Redden helped the Senators make the Stanley Cup Finals during the 2007 playoffs and was one of the main reasons why they made it that far. After the 2007-2008 NHL season, Redden became a free agent and opted to sign with the New York Rangers on a six year, $39 million deal.
The contract seemed like a smart move by the Rangers because they had a lot of cap space and were pushing to become contenders yet again. However, it became apparent fairly quickly that Redden had dropped in skill and by the 2010-11 season, he found himself as an AHLer. Redden eventually was bought out during the 2013 offseason and the Rangers were finally able to rid of his cap hit.
4 Alexei Yashin
If you are looking for a player who seemed to stop himself from reaching his maximum success, the best example is Alexei Yashin. Yashin had all the skill in the world during his time in the NHL, yet his behaviour is what ultimately made him hated. He was a money seeking player who did not put in his best effort, which is why he got traded from Ottawa to the Islanders. He did not change at all from there and got worse.
Upon arriving with the Islanders, Yashin was given a 10 year, $87.5 million deal and from there, he basically checked out. Yashin never displayed the same skill as he had in Ottawa with the Islanders and he quickly became one of their least favourite players. After years of mediocrity, the Islanders finally bought him out during the 2007 offseason and reshaped their entire franchise.
3 Brad Richards
Like many players on this list, it is important to note that Brad Richards had a very storied career. He is a two-time Stanley Cup winner and even won the Conn Smythe Award back in 2004. So it is easy to understand why Richards was given a nine year, $60 million dollar deal with the New York Rangers during the 2011 NHL offseason.
When Richards was in New York, he was still a very talented player and helped the Rangers out immensely with his playmaking ability. In fact, Richards did not necessarily even have a bad year as a Ranger, but his contract’s cap hit and term was far too much for him to show signs of declining. With that, the Rangers bought out his deal in 2014 and still are dealing with a portion of his cap today.
2 Ilya Kovalchuk
Ilya Kovalchuk was one of the best snipers during his tenure in the NHL and because of this, was rewarded immensely when he hit the open market during the 2010 offseason. After being traded to the Devils a few months before, Kovalchuk signed a 15 year, $100 million deal with the club. This would end up being one of the worst contracts in the history of the NHL.
Kovalchuk was still a franchise player during his time in New Jersey, but bailed on them and decided to join the KHL. This hurt the Devils immensely because they invested so much money on their top player and he did not want anything to do with them in the blink of an eye. The Devils lost so much acquiring him, including a first round pick due to his contract. Now, they are stuck in a prolonged rebuild.
1 David Clarkson
At one point in time, David Clarkson emerged himself as a top power forward in the NHL and as a result of this, managed to sign a seven year, $36.75 million deal with the Maple Leafs back in 2013. Clarkson had just come off a 30 goal season with the Devils and seemed to be the answer the Leafs needed to help with their rebuild. This would not be the case.
Clarkson displayed his true skill when he joined the Leafs and that was nothing more than a fourth liner. Now, that is not a knock on Clarkson, but he was expected to do far more for the Leafs with that massive contract. The Leafs because even worse of a team because they could not work around his deal. However, a saving grace came their way when they were able to flip him to the Blue Jackets for the injured Nathan Horton. They got rid of arguably the worst contract ever and now they are in a far better place today.