The NHL is more than just the best hockey league in the world -- it's also a business, and one that can be very fickle. It's hard to predict the future based off of player performance, and signing smart, valuable contracts is one of the toughest jobs that general managers face.
A bad contract can haunt an NHL team for years. From risky bets that never panned out to vastly overpaid skaters that didn't earn their paychecks, these deals are among the worst in NHL history.
David Clarkson: 7 years, $36.75 million
The contract that Clarkson signed with the Toronto Maple Leafs is incredibly forgettable but ranks among some of the worst. He was a big part of the New Jersey Devils' run to the 2012 Stanley Cup Final, scoring 30 goals during the regular season, and that earned him favor on the open market when he became a free agent in 2013. But Clarkson had not proven himself on a serious level yet, and was an immediate disappointment for the Leafs.
Clarkson's career in Toronto got off to a tumultuous start when he picked up a 10-game suspension for leaving the bench to join a fight during the preseason. He wound up being suspended 12 games in total during the 2013-14 season -- that was more than his points total of five goals and six assists in 60 games.
The following year, Clarkson was traded to the Columbus Blue Jackets in exchange for Nathan Horton, a player who had medically retired at that point. Toronto would rather pay a player who would never take the ice for them than give Clarkson a spot on the roster. He played 25 games for the Jackets over two seasons before hanging up the skates due to injury.
Jonathan Huberdeau: 8 years, $84 million
Huberdeau is one of the best players on this list, but that doesn't take away from the fact that his contract is absolutely unmoveable. He fell victim to recency bias after putting up an impressive 115-point season with the Florida Panthers in 2021-22, which led the Calgary Flames to lock him up that summer all the way through the 2030-31 season.
Huberdeau earns $10.5 million annually, putting him above guys like Sergei Bobrovsky, Aleksander Barkov, and Jack Eichel. But Huberdeau hasn't earned his paycheck the way those other skaters have. Since signing the contract, his best season was the 2024-25 campaign when he scored 62 points in 81 games. Eichel, meanwhile, put up 94 points in 77 matchups the same season.
If the Flames wanted to buy out Huberdeau's contract, they would be paying him through the 2036-37 season. He has a full no-movement clause, so it would appear that Calgary is going to have to ride this one out. Huberdeau is still a valuable addition to the Flames roster, but at $10.5 million per year, he would need to chip in a lot more offensively for the contract to be worth it in the long run.
Scott Gomez: 7 years, $51.5 million
The career of Scott Gomez got off to a blazing hot start with a 70-point season, a Stanley Cup, and a Calder Trophy under his belt after his first year in the NHL. He continued to be an integral part of the Devils lineup, with 33 goals and 84 points in the 2005-06 season. But when the summer of 2007 rolled around, Gomez decided to chase his payday on the open market and signed with the New York Rangers.
This deal wasn't immediately terrible. Gomez managed to tally 70 points in 81 games during his first season on Broadway, and followed that up with 58 points in 77 games the following year. But considering the fact that he was earning upwards of $7.3 million per year, Gomez was not providing the return the Rangers had hoped for and he was dealt to the Montreal Canadiens.
That's where things truly went downhill for Gomez. His production dropped off exponentially in his second year with the Habs, recording 38 points in 70 games, and then in 2011-12 he scored just two goals and 11 points in 38 matchups. He even went more than a calendar year without scoring a single goal. That led the Habs to buyout the remainder of his contract.
But a bad contract doesn't mean he was a bad player. Gomez was a solid skater with great instincts and leadership who simply got overpaid, failing to live up to the hype established during his days with the Devils.
Rick DiPietro: 15 years, $67.5 million
The New York Islanders took a huge gamble in 2006 by signing 25-year-old goalie Rick DiPietro to a groundbreaking 15-year contract, and the risk didn't pay off.
DiPietro at that point had shown a lot of promise as a young goaltender with a 53-42-10 record, 2.72 GAA and .905 SV% in his two seasons as the Isles starter. But the record-setting contract length was questionable at best in a position where goalies typically have shorter periods of time in their prime.
The first two years of DiPietro's contract went fairly well with a 2.70 GAA, .911 SV% and eight shutouts across 125 games. Unfortunately, injuries derailed DiPietro's career and limited him to just 50 games from 2008 to 2013. That's when the Islanders bought out the remainder of his massive contract. To this day, New York is still paying him $1.5 million per season and will continue to do so through the 2028-29 campaign.
The head-scratching decision to give DiPietro 15 years is still one of the most confounding choices of all time, and he regularly lands on lists summarizing the worst contracts because of that.