The five best and worst long-term NHL contracts

RIck DiPietro was the poster boy of bad NHL contracts before the latest CBA.

Signing players to long-term contracts can be risky business for NHL general managers.

Even when reliable building blocks such as Patrick Kane and Jonathan Toews are locked up to eight-year extensions, it’s worth asking whether the team has made a smart investment. There have been plenty of deals that have worked out in recent years, but there’s also been a few mistakes – see David Clarkson or Dion Phaneuf.

With that in mind, here’s a look at five of the best and worst long-term contracts in NHL history (all numbers courtesy of


Rick DiPietro, New York Islanders (Total contract: 15 years, $67.5 million): When you think of cautionary tales for bad NHL contracts, DiPietro immediately jumps to mind. The Islanders believed they were being innovative when they handed the goaltender a 15-year contract, but injuries derailed his career and it turned out to be a horrific investment. DiPietro was bought out by the Islanders following 2012-13, the first season in which teams were allowed to use compliance buyouts.

Alexei Yashin, New York Islanders (Total contract: 10 years, $87.5 million): To be fair to Mike Milbury, there wasn’t a salary cap in place when the Islanders handed out this mega- deal. Yashin never quite lived up to the expectations on Long Island. He scored just 119 goals in 346 games after Milbury gave up Zdeno Chara and a draft pick that became Jason Spezza to acquire the Russian. The final four years of Yashin’s deal were bought out after the 2006-07 season.

Ilya Bryzgalov, Philadelphia Flyers (Total contract: 9 years, $51 million): The Philadelphia Flyers thought they had solved their decade-long hole in net with the acquisition of Bryzgalov. Boy were they wrong. Bryzgalov lasted just two seasons with the club (during which he posted a .905 save percentage) before the team used one of its compliance buyouts on the veteran netminder.

Scott Gomez, New York Rangers (Total contract: 7 years, $51.5 million): Gomez only played two seasons with the Rangers after signing his free-agent deal. He had 32 goals in 158 games before the Rangers were able to convince the Canadiens into taking Gomez’s contract in a trade for defenceman Ryan McDonagh. So sometimes even the worst deals work out.

Vincent Lecavalier, Tampa Bay Lightning (Total contract: 11 years, $85 million): Like DiPietro, Lecavalier became a poster boy for overpriced NHL contracts. The Lightning handed this deal out later in Lecavalier’s career just after he had reached his peak years. The general rule is to never pay for past production. He still was an effective player early into the 11-year deal, but wasn’t the superstar they were hoping for. The Lightning weren’t satisfied as the years went on and bought out their former captain following the lockout-shortened 2013 season.

Dishonourable mentions: Roberto Luongo, Ilya Kovalchuk, Jordan Staal


Sidney Crosby, Pittsburgh Penguins (Total contract: 12 years, $104.4 million): Considering his history with concussions, there was some risk when the Penguins handed Crosby his 12-year deal. However, it’s tough to criticize investing in the best player in hockey — especially at a fair price of $8.7 million per year. Assuming he stays healthy, there’s nothing not to like about this deal.

Drew Doughty, Los Angeles Kings (Total contract: 8 years, $56 million): When you consider Phaneuf’s eight-year extension and what Matt Niskanen got as a free agent, this looks like a huge steal for the Kings. Doughty is the most complete defenceman in hockey and has already won two Stanley Cups at age 24. He still has five more seasons on his contract and he will just be right around the peak years of his career by the time his deal ends.

Duncan Keith, Chicago Blackhawks (Total contract: 13 years, $72 million): Keith’s deal doesn’t expire until he’s 39-years-old, but he has proved to be a wise investment. Even when he’s in his later years, he’ll be able to be an effective Top 4 defenceman. He is one of the most consistent players at his position in terms of offensive production and has been a key cog on two Stanley Cup winning teams with Chicago. His cap hit of $5.4 million has proven to be ridiculous value when you consider that Brooks Orpik signed for similar money as a free agent.

Patrice Bergeron, Boston Bruins (Total contract: 8 years, $52 million): Bergeron’s deal doesn’t kick in until next season, but it still looks like one of the best in hockey. The Bruins centre is one of the best two-way players in the game and getting him at $6.5 million is great value. When you contrast his deal with Dave Bolland, who got only a million less as a free agent, it looks even better. There’s a sizeable gap between those two.

Erik Karlsson, Ottawa Senators (Total contract: 7 years, $45.5 million): The Swede is under contract until the 2018-19 season, but the Senators have to be thrilled with this signing. Karlsson is ascending and has proven to be among the best at his position when healthy. If he ever hit the free agent market, Karlsson would get a lot more than the $6.5 million per season he’s getting now.

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