The 5 Worst Contracts in NHL History

The 5 Worst Contracts in NHL History
New York Islanders’ Nassau Coliseum | Bruce Bennett/Getty Images

As the 2015-16 NHL nears its end, you can bet that each of the 30 NHL general managers will continue to discuss every player on their rosters and how their contracts affect the teams. The contracts that tend to get the most attention are the expiring deals, especially the ones that may send a player to unrestricted free agency. The GMs have to decide if they want to offer new deals to these players, how much to pay, and how long they’ll pay for.

The majority of these potential free agents — at least the ones the GMs want to keep — will be in line for a raise. How the GM determines the raise amount is a tricky proposition, based just as much on what the player can do for the team in the future as it is on how much the player benefited the team in the past. Sometimes a GM nails it and gets the amount and length of the contract just right, paying the player what they are worth while keeping the team’s salary cap in line for both the short- and long-term future.

Oh, and the GM must go through the same analysis for every player who may become a free agent on the other NHL teams as well, in order to decide if they should sign any free agents who will hit the market.  Sometimes the GM misses the mark entirely in their analysis of a potential free agent or trade. Here are the five worst contracts in NHL history.

5. Scott Gomez

In 2000, Scott Gomez, then with the New Jersey Devils, won the Calder Trophy as the NHL’s best rookie. Gomez scored 19 goals and 70 points that season. He stayed with the Devils through the 2007 season before cashing in on his offensive prowess and signing as a free agent with the New York Rangers.

The Rangers ponied up in a big way to land Gomez, signing him to a seven-year contract worth $51.5 million. He played two years for the Rangers, scoring 70 points in his first season and 58 in the next. The Rangers then traded Gomez to the Montreal Canadiens for Ryan McDonough, the current captain of the Rangers. Gomez did not have much success during the three seasons he spent with the club.

He never topped the 50-point plateau with the team and was bought out at the end of the 2012 season. The buyout cost the Canadiens $6.66 million, which was spread over four years. Since being bought out by Montreal, Gomez has played for San Jose, Florida, New Jersey, St Louis, and Ottawa. His current contract with Ottawa, worth $575,000 for this season, is a one-year deal.

4. Alexei Yashin

Alexi Yashin was coming off seasons involving 94 and 88 points when New York Islanders general manager Mike Milbury basically pulled up to Yashin’s house with a truck loaded with cash. How much, you ask? How about $87.5 million over 10 years. Oh, and to land Yashin, Millbury traded Zdeno Chara and a draft pick. That draft pick turned in Jason Spezza.

The best year Yashin had in New York was his first season with the club, when he scored 88 points. By 2007, the final year he played for the Islanders, Yashin’s production fell to 50 points. New York bought out the final four years of his deal, and he never played in the NHL again, finishing his career in 2012 skating in the KHL. So, not only was the contract a disaster, but the players the Islanders gave up transformed into top-level NHL players.

3. Ilya Bryzgalov

The 5 Worst Contracts in NHL History
Goalie Ilya Bryzgalov | Doug Pensinger/Getty Images

The Philadelphia Flyers haven’t had much long-term luck in the goaltending department, so when they see a netminder who looks like he could be a savior they get excited. Such was the case with Ilya Bryzgalov. In 2011, the Flyers signed Bryzgalov from the Phoenix Coyotes to be their starting goalie. The contract was a nine-year deal worth $51 million, and the team had to trade high-profile players, Mike Richards and Jeff Carter, to get Bryzgalov into the fold .

While the goaltender was an amusing interview, Bryzgalov only lasted two seasons in Philly before they bought him out. In the end, the Flyers were forced to fork out $23 million over 14 years to get rid of the player who they thought would lead them to Stanley Cup glory. Bryzgalov ended up playing just 42 more NHL games between 2014 and 2015.

2. Ilya Kovalchuk

Some NHL contracts make you scratch your head in wonder. Some make you question the sanity of the general manager. And then there is the contract that was offered to Ilya Kovalchuk by the New Jersey Devils — a deal that defied just about every rule. Kovalchuk was coming off seasons of 87 and 91 points when he began the final year of his contract with the Atlanta Thrashers.

With the team unable to meet Kovalchuk’s demands for a new deal, they traded him to the Devils in exchange for Niclas Bergfors, Johnny Oduya, Patrice Cormier, and a first-round draft pick. When it came time to make a deal with Kovalchuk, the Devils offered him 17 years at $102 million. The NHL didn’t like the contract’s structure — which paid him significantly less in the final years than it did in what one would consider his prime scoring years — so the league nullified it.

When the Devils came back with a 15-year-deal worth $100 million and restructured the per-year dollars to the league’s liking, the deal was signed. The contract, on paper, made Kovalchuk a Devil from 2011 through the 2025 season. But he didn’t come anywhere close to playing out his monster contract, announcing that he was retiring from the NHL in July 2013. Kovalchuk’s contract still had $77 million on it when he walked away from the Devils. He went back to the KHL after leaving the Devils.

1. Rick DiPietro

The 5 Worst Contracts in NHL History
Rick DiPietro | Jared Wickerham/Getty Images

Today, Rick DiPietro is a member of the Hahn & Humpty radio show on ESPN Radio 98.7, with “Humpty” serving as his nickname in that equation. DiPietro gained that nickname due to the numerous injuries he experienced during his NHL playing days with the New York Islanders. Get it? Broken body equals Humpty Dumpty. Regardless, it’s a job DiPeitro does not need.

After all, the Islanders are paying him $1.5 million a year through 2029. How did that shake out? DiPietro was drafted first overall in the 2000 Entry Draft by the Islanders and played well early in his career, backstopping the club for no less than 50 games a season between 2004 and 2008. His play during the early portion of his career earned him a contract worth $67.5 million over 15 years.

Between 2009 and 2013, DiPietro played a total of 50 games for the Islanders as the injuries piled up and he struggled to stay healthy. In 2013, the Islanders bought out the remaining eight years on DiPietro’s contract. The terms of the compliance buyout stated that DiPietro would receive two-thirds of the $36 million and that the $24 million he was due would be paid out over twice the length of the remaining years on the deal. The result: DiPietro would receive $1.5 million a year through 2029 for not playing hockey for the New York Islanders.

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