Top 15 NHL Free Agent Signings Teams Quickly Regretted

The worst mistakes in the NHL are usually made on July 1. Despite history telling them otherwise, GMs seem to think that they'll be able to get a big missing piece in their pursuit of a Stanley Cup. D

The worst mistakes in the NHL are usually made on July 1. Despite history telling them otherwise, GMs seem to think that they'll be able to get a big missing piece in their pursuit of a Stanley Cup. Depth defensemen are often paid like top pairing blueliners, third liners are paid like top-six forwards and teams make an insanely long commitment to players who are hitting the market after one good year in the NHL.

There are also times where guys may be coming off a bad stint with a team, but had success earlier on in their careers, so teams feel they can help revitalize a player. While we can usually see within a few years of a long-term deal if a signing was worth it, there are times when a player starts so poorly with his new team, the GM will quickly pull the plug on their mistake. There are times when it's as little as a few dozen games in.

Whether it was through a trade, placing a player on waivers or simply terminating the contract, there have been plenty of times where teams quickly moved on from a mistake. Some GMs refuse to acknowledge their mistakes and keep a player around even when it's clear they're ineffective. The best GMs are able to avoid mistakes and when they do make one, they quickly move on. Struggling franchises keep bad FA signings around to save face and that usually results in prolonged droughts.

Here, we'll be looking at times when teams overpaid for a player in July and quickly found themselves regretting the move. They quickly realized the mistake they made and soon exhausted all avenues in getting rid of that player. It could be through a trade, a buyout, burying them in the minors or mutually terminating their deal.

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15 P.A. Parenteau

Rick Osentoski-USA TODAY Sports

P.A. Parenteau has proven to be an effective second line winger if he is healthy. That's usually a pretty big if. Parenteau enjoyed a breakout season with the Islanders as he was entering his contract year, finishing with 67 points with the Islanders. The Avalanche signed him on July 1, 2012 and the signing looked like a good one after Parenteau put up 43 points, playing in all 48 games of the lockout shortened 2012-13 season.

Parenteau would have trouble staying healthy the next year, as his numbers dipped to 33 points and he fell out of favor with coach Patrick Roy. He was traded to the Canadiens in 2014 for Daniel Briere. Parenteau would only last one year in Montreal before his contract was bought out. He's now enjoying a bounce back season in Toronto.

14 Mike Ribeiro

Jerome Miron-USA TODAY Sports

Mike Ribeiro is a guy that you can always count on to produce as a second-line center, but he's a player who always wear out his welcome. It's best to sign him to short-term deals, but the Coyotes learned the hard way in the 2013-14 season that Ribeiro is not a long-term solution. The Coyotes signed him to a four year, $22 million deal, only to buy out the remaining three years after just one season. Craig Morgan of reported Ribeiro was late for practices, missed meetings, buses and even engaged in a shouting match with coach Dave Tippett. He then signed a one-year deal with Nashville.

13 Scott Gomez


Scott Gomez was coming off a one-year arbitration deal in New Jersey when he signed a seven-year, $51.5 million deal with the Rangers. Gomez would pay dividends for the Rangers in his first season, scoring 70 points and adding 11 points in 10 playoff games. His numbers dipped to 58 points the following year and Glen Sather immediately saw a declining asset with a bad contract on his hands. In a genius move, Sather traded Gomez to Montreal in a deal that landed him Ryan McDonagh, who is now his team's captain.

12 Nathan Horton

Greg Bartram-USA TODAY Sports

Nathan Horton left the Boston Bruins after their run to the Stanley Cup Final in 2013, with reports of him wanting to go to a less stressful hockey market. He found one in Columbus, who signed Horton to a seven-year deal worth $37 million. Horton would have to have shoulder surgery before suiting up for the Blue Jackets, missing the team's first 40 games. The next season, he was diagnosed with a degenerative back injury that may end his career. Seeing the situation as having a player on a bad contract that couldn't help them, the Jackets traded for an even worse contract.

11 Ryan Smyth 


Ryan Smyth was visibly devastated when the Edmonton Oilers trade him to the Islanders at the 2007 trade deadline. Rather than return to Edmonton though, Smyth would sign a five year, $31.2 million deal with the Colorado Avalanche. Smyth had trouble staying healthy his first season, missing 27 games and even though he was healthier the next season and produced, the Avs figured out they were in rebuilding mode and had to get younger. Smyth would be traded to the Kings after the 2008-09 season. It wasn't that Smyth wasn't a useful player, but the Avalanche realized they weren't a free agent away from contending for a Stanley Cup.

10 Daniel Briere

Jean-Yves Ahern-USA TODAY Sports

Daniel Briere was ultimately bought out by the Flyers after health issues and declining numbers plagued his last couple of seasons in Philadelphia. He still gave them several great seasons and an amazing 2010 playoff, so it wasn't a bad signing. After the buyout, Briere signed a two-year, $8 million contract with his childhood team, the Montreal Canadiens. Briere would only register 25 points in 69 games and often found his ice time reduced by coach Michel Therrien. Clearly not the same player he once was, the Habs shipped him to Colorado for Parenteau after just one season.

9 Vincent Lecavalier

Eric Hartline-USA TODAY Sports

While the Tampa Bay Lightning eventually grew to regret the 11-year deal they had given Vincent Lecavalier back in 2009, he wasn't a complete liability for them. The Flyers swooped in after the Lightning used a compliance buyout on Lecavalier and gave him another ridiculous contract, this time a five-year, $22.5 million deal. Lecavalier had a decent first season in Philly, scoring 20 goals and 37 points. He was a trainwreck the following year though, dipping to 20 points in 57 games. They tried shopping him in his second season, but it wasn't until midway through the 2015-16 season they found a taker in the Los Angeles Kings. The Kings took Lecavalier with the understanding that he will retire this summer and not be on their books going forward.

8 Ryane Clowe

Kim Klement-USA TODAY Sports

Ryane Clowe was a couple of years removed from his career best season, having peaked at 24 goals and 62 points in the 2010-11 season. After a stint as a rental player with the Rangers, Clowe signed a five-year, $24.5 million deal with the Devils. Clowe often found himself battling injury problems in New Jersey, while his numbers dipped tremendously on an offensively challenged New Jersey team. He retired last fall after doctors refused to clear him from a concussion suffered in 2014. It's likely that Clowe would have been shopped around before his concussion problems surfaced.

7 Wade Redden


Even though Wade Redden made a lot of money as a New York Ranger, he probably still regrets signing a six-year, $39 million deal just because of where his career went from there. Redden couldn't deal with the enormous expectations and his numbers plummeted. Redden was eventually buried in the minors before the new CBA in 2013 allowed the Rangers to buy him out. Redden lasted just two years in New York and they would have been perfectly happy letting Redden play out his entire contract in the AHL.

6 Sergei Samsonov


Sergei Samsonov was seen as a possible answer to scoring woes for the Canadiens back in 2006. Samsonov was coming off a good run in Edmonton and was given a two-year deal, worth $7.05 million. After nine goals and 26 points in 63 games, the Habs placed him on waivers. He went unclaimed, but was then traded to Chicago in the summer of 2007. It was quite remarkable how quickly the Canadiens came to realize that he was not the answer.

5 Sean Avery


Sean Avery was coming off a very effective season in New York, scoring 15 goals for the Rangers and then four in eight playoff games. The Stars thought it was enough to sign him to a four-year, $15.5 million contract. This was perhaps the quickest fall from grace ever experienced with a team. Just 23 games into the season, Avery was suspended by the NHL due to his "sloppy seconds" comment regarding his ex-girlfriends dating other NHLers. The Stars placed him on waivers and Avery would eventually wind back with the Rangers.

4 Jeff Finger


The Toronto Maple Leafs thought they were signing one of the most effective defencemen in the NHL when they handed the blueliner a four-year deal, worth $3.5 million a season. It turns out though, that the player the Leafs thought they were getting was Kurt Sauer, who was the one who put up the glowing numbers the Leafs were talking about. After a season and a half, Finger was sent to the minors and remained there until the end of his contract.

3 David Clarkson

Tom Szczerbowski-USA TODAY Sports

David Clarkson wasn't known as a player in Toronto. He was simply known as a contract, as in the seven-year, $36.75 million contract he signed with the team in 2013. Many Leafs fans must have seen this as a bad signing immediately, but it took the team slightly longer to figure it out. For starters, Clarkson found himself suspended for the first 10 games of the Leafs' season after he left the bench to fight in a preseason game. It soon became apparent that his 30-goal season in 2011-12 was an anomaly and he was traded to Columbus for Nathan Horton's contract midway through his second season.

2 Tomas Kaberle


Tomas Kaberle didn't help the Boston Bruins at all as a rental player in their quest to the 2011 Stanley Cup. He was brought on by the Bruins to help their power play, but they were awful with the man advantage that spring. They managed to win the Stanley Cup despite that and happily let Kaberle walk to free agency. The Carolina Hurricanes thought they could revitalize him and signed him to a three-year, $12.75 million deal with Carolina. After just 29 games, the Hurricanes dealt him to the Canadiens for Jaroslav Spacek, who was on an expiring contract.

1 Alex Semin

Jean-Yves Ahern-USA TODAY Sports

Alex Semin could have been on this list twice, as the Hurricanes quickly regretted signing him to a five-year extension after his one-year deal for the short 2012-13 season worked so well. That year, Semin scored a point a game, 44 in 44 games. Semin's numbers would dip in the next two seasons, plummeting down to 19 points in the 2014-15 season.

Desperate for talent at right wing, Monreal signed him this past summer to a one-year, $1.1 million deal. While it was a low-risk deal, he played just 15 games, scoring just one goal. If that's not immediate regret, I don't know what is.

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Top 15 NHL Free Agent Signings Teams Quickly Regretted