What is the worst NHL contract ever signed? There are a lot of NHL free agency mistakes or poor extension signings that happen by teams each season. Although, the worst signings are the ones that still haunt teams and fan bases today.
Worst NHL contract ever
When analyzing some of the worst NHL contracts of all-time, there are a few things to look at. One of the first is the contract length, as long-term deals can really hurt a franchise in the long run. 10, 12, or even 15-year deals usually never work out for the team.
Another thing to look at is the average annual salary. If a player is being paid more than he should be, then the money would have been better spent elsewhere.
The last thing to look at is production during the length of the contract. A contract may look good when first signing, but it all depends on a player’s production after. If he significantly underperforms after signing, it could become the worst NHL contract ever.
Ilya Kovalchuk: 15 years, $100,000,000 with Devils
Initially, the NHL rejected a 17-year, $102 million contract in place for Ilya Kovalchuk and the Devils. They then agreed on a 15-year deal for $100 million during free agency in 2010.
Kovalchuk would go on to play only three and a half years for the Devils under the 15-year contract, before announcing his retirement from the NHL to go play in the KHL instead.
Although the retirement did free up over $6 million of cap space per year for the Devils, it left them with cap-benefit recapture fees of about $250,000 a season for 12 years. In addition, the rejected 17-year contract due to circumvention of the salary cap led to the Devils losing a third-round draft pick.
David Clarkson: 7 years, $36,750,000 with Maple Leafs
The Toronto Maple Leafs paid a steep price for David Clarkson in the summer of 2013, giving him a seven-year deal for over $36 million.
What makes this one of the worst NHL free agency signings ever is that the Maple Leafs paid more than 75% of Clarkson’s contract upfront in signing bonuses.
The next two seasons after signing the contract, Clarkson would score just 15 goals in 118 games. He didn’t even last two seasons before the Maple Leafs deemed him a bust and traded Clarkson away to the Columbus Blue Jackets.
Ville Leino: 6 years, $27,000,000 with Sabres
The Buffalo Sabres made a big mistake in signing Ville Leino in 2011 to a six-year $27 million dollar contract. Leino came off of a great year the season prior with the Flyers but had not yet proved if he could do it again.
The Sabres decided to take a shot on the Finnish forward, and it did not pay off. Leino would go on to have 25 points in his first season with the Sabres, far below his previous season where he had 53 points.
He then went on to score two goals in the next 66 games for the Sabres until he was eventually waived in 2014.
Rick DiPietro: 15 years, $67,500,000 with Islanders
Rick DiPietro’s 15-year, $67.5 million contract with the New York Islanders in 2006 may be the worst NHL contract ever. It also was the beginning of the end for career-length contracts, which almost never work out.
DiPietro would end up playing for the Islanders for seven seasons after signing the contract but was the starter for only the first two years. After playing 129 games the first two seasons of the contract, DiPietro played only 50 games the rest of his Islanders career.
The Islanders eventually used a compliance buyout (where the team pays two-thirds of the remaining salary over double the remaining length of the contract) on DiPietro’s contract in 2013 and will still be paying $1.5 million each season until 2029 for him not to play for them.
Alexei Yashin: 10 years, $63,997,944 (after 24% new CBA reduction) with Islanders
DiPietro’s contract was not the first long-term contract the Islanders messed up. In 2001, the Islanders signed Alexei Yashin to a 10-year contract worth almost $64 million (after new CBA reductions).
The problem with this contract was all about the length of the deal, as it would end up costing New York in the long run.
Yashin had five great seasons with the Islanders but would end up leaving to go play in Russia after the 2006-07 season. The Islanders bought out his contract after that season and had to pay roughly $2.2 million each year after that through 2015.
Vincent Lecavalier: 11 years, $85,000,000 with Lightning
By the time the contract kicked in for the 2009-10 season, Vincent Lecavalier was already past his prime. The post-contract production along with the contract length makes this one of the worst NHL contracts of all-time.
After a 72-point season to kick off the new contract, Lecavalier significantly regressed. He would go on to play three more seasons with the Lightning.
In 2013, just four seasons after his contract began, Lecavalier was bought out. With the length of the buyout being 14 years for over $32 million, the Lightning will still be paying him until 2027.
Ilya Bryzgalov: 9 years, $51,000,000 with Flyers
This contract was a tough one for the Philadelphia Flyers to swallow. Ilya Bryzgalov didn’t even last two years after signing a monster nine-year, $51 million contract in 2011.
After leading the Flyers to the playoffs in his first year on the contract, he played just 40 more games for the team. He was then bought out in the 2013 offseason.
The buyout cost the Flyers $23 million, as they will continue to pay it out through the 2026-27 season.
Roberto Luongo: 12 years, $64,000,000 with Canucks
When Roberto Luongo signed a 12-year contract extension with the Vancouver Canucks in 2009, it looked as though he would be staying there for the rest of his career. Unfortunately, things turned ugly quickly, as Luongo only lasted three and half more seasons with the team.
In the 2011-12 season, Luongo was beginning to be replaced by Cory Schneider. In the 2012 offseason, the Canucks resigned Schneider and tried to trade Luongo. They were unable to, however, because of the large contract. He was finally traded to Florida in 2014.
Luongo retired from the NHL in 2019, but the Canucks are still paying over $3 million against the salary cap until the end of the 2021-22 season.
Scott Gomez: 7 years, $51,500,000 with Rangers (followed by Canadiens)
The New York Rangers signed Scott Gomez to a $51.5 million contract in 2007. Gomez’s contract did not look terrible until traded to the Montreal Canadiens in 2009.
After registering 59 points in his first season with the Canadiens, Gomez’s production decreased significantly to 38 points the following year. He would end up playing 32 more games with the team before being waived in 2013.
In his final two seasons with the Canadiens, Gomez was making $8 million and $7.5 million per year. It was an insane price for a combined 49 points in 118 games. That alone makes it one of the worst NHL contracts of all-time.
Christian Ehrhoff: 10 years, $40,000,000 with Sabres
The Buffalo Sabres made one of the worst NHL free agency signings when they gave Christian Ehrhoff $40 million for 10 years in 2011. Let’s just say that he did not last long in Buffalo.
Ehrhoff played well prior to coming to Buffalo, having three straight 40-point seasons. That changed when with the Sabres, as his highest point total with the team was 33 points.
He lasted three seasons before being released via compliance buyout, where he is still owed over $850,000 each season through 2028. His $13 million signing bonus also adds to the pain and makes it a strong contender for the worst NHL contract ever.