NHL’s 10 Worst Contracts From the Salary Cap Era

It’s hard to build a winning team in the NHL. Even if you draft well, it can all be undone by one bad contract. When one of those contracts happens to be of the epically bad variety, the stink can affect the team for years.

There are some unique contracts from the pre-cap era – like Sergei Fedorov capitalizing on a 6-year, $38 million offer sheet from the Carolina Hurricanes – but that’s a story for another time. Since the salary cap was implemented in 2005, more than a handful of contracts have left heads shaking. Here are the ten worst.

10.) Alexander Semin, Carolina Hurricanes – 5 Years, $35 Million (2013)

Semin signed a “show me” deal with the Hurricanes ahead of the 2012-13 season after years of solid production for the Washington Capitals. He delivered with 13 goals and 44 points in 44 games during the lockout-shortened season.

His reward? A 5-year, $35 million extension. Semin was okay in the first season of his deal – 22 goals, 42 points in 65 games – but fell off quickly after that. It was so bad that the Hurricanes bought out the final three seasons of his contract. He gave it one final shot in 2015-16 with the Montreal Canadiens, registering one goal in 15 games before calling it a career.

9.) Darnell Nurse, Edmonton Oilers – 8 Years, $74 Million (2021)

You know a contract is bad when the best part of it involves offloading it. After signing this huge deal, the Edmonton Oilers regretted it almost immediately. Nurse’s offense stagnated, which was bad enough.

On top of that, his defensive game was widely panned, routinely landing him on “worst contracts” lists year after year. The Oilers finally moved his deal to a young San Jose Sharks team that needed major help on the blue line. He still has four seasons remaining, though a rapidly rising cap slightly massages this abysmal deal.

8.) Zach Parise/Ryan Suter, Minnesota Wild – 13 Years, $98 Million (2012)

Even when they were signed, the dual 13-year, $98 million contracts given to free agents Zach Parise and Ryan Suter were head-scratchers. Yes, this was the era of handing out contracts with double-digit term, but these were still extravagant numbers.

Both were solid but never great, failing to help the Minnesota Wild do much of anything during their tenure. Both were bought out ahead of the 2021-22 season after failing to rise to an elite level at any point. While the signings showed noble intentions, both fell flat. Even still, both were productive enough to keep these from being the worst deals ever.

7.) Jonathan Huberdeau, Calgary Flames – 8 Years, $84 Million (2022)

Giving Jonathan Huberdeau a huge deal felt like a no-brainer following an 85-assist, 115-point season with the Florida Panthers in 2021-22. The blockbuster trade that sent Matthew Tkachuk to Florida in return for Huberdeau looked bad on its own, but the massive contract the Flames gave Huberdeau has made it much worse.

Huberdeau has experienced a massive falloff since arriving in Calgary and has become a major problem. His 28-goal, 62-point 2024-25 season has been his best, nearly half of what he posted in his final season with the Panthers. The Flames still have four seasons remaining on one of the league’s most immovable contracts.

6.) Scott Gomez, New York Rangers – 7 Years, $51.5 Million (2007)

Coming out of the 2004-05 lockout, the Rangers were all about making splash moves. They signed a few names to big deals, Gomez being the most notorious. The deal made sense at the time – the Rangers were signing a reliable playmaking top-line center to play with Jaromir Jagr.

Instead, they got a major letdown. Gomez had 70 points that first season but quickly fell off, and the Rangers tried to get out. He was traded to the Canadiens just two seasons into the contract, and it only got worse from there. He steadily declined and became a barely serviceable NHLer by the fifth year of the contract. At $7.35 million per season, that was a massive miss for the salary structure of the time.

5.) Vincent Lecavalier, Tampa Bay Lightning – 11 Years, $85 Million (2009)

Lecavalier was the face of the Tampa Bay Lightning and one of the game’s premier scorers when it came time for a contract extension. His production had dipped slightly to 40 goals and 92 points in 2007-08 but was still a near point-per-game player when he signed this massive extension that July ahead of his age-29 season.

It didn’t take long for the Lightning to regret this deal. Lecavalier remained a solid player, but injuries and age started to catch up with him. Tampa Bay cut bait, buying out the remaining seven years of his contract after 2012-13. Lecavalier signed with the Philadelphia Flyers but couldn’t find that same magic, retiring after the 2015-16 season – just seven years after his extension was signed.

4.) Ilya Bryzgalov, Philadelphia Flyers – 9 Years, $51 Million (2011)

The Philadelphia Flyers have been on an endless journey to find a definitive No. 1 goalie. Their search seemed to be over in 2011 when they gave Ilya Bryzgalov a massive free-agent deal after three very good seasons with the then-Phoenix Coyotes.

Bryzgalov was solid that first season – 33-16-7, 2.48 goals-against average and a .908 save percentage – but fell off quickly and lost the starting job. The Flyers bought out their massive mistake after just two seasons, and it looks like they were right to act. Bryzgalov barely registered a blip on the NHL radar over the next two seasons before calling it a career.

3.) Ville Leino, Buffalo Sabres – 6 Years, $27 Million (2011)

Some historically bad deals were signed in 2011, and the Buffalo Sabres had two of them. They signed Christian Ehrhoff to a 10-year, $40 million deal before having to buy him out just a handful of seasons later. That isn’t as bad as the contract they gave to Ville Leino that summer.

Leino’s fall off was instantaneous. He went from 19 goals and 53 points in his final season with the Flyers to just eight goals and 25 points that first season in Buffalo. He lasted all of three seasons – 10 goals in 137 games – before the Sabres bought out his contract and effectively ended his NHL career.

2.) David Clarkson, Toronto Maple Leafs – 7 Years, $36.75 Million (2013)

When signing a free agent, you never want to buy high. Not only did the Toronto Maple Leafs do that with David Clarkson, but they handed out a $36 million contract after only one good season. Clarkson’s inexplicable 30-goal campaign in 2011-12 with the New Jersey Devils somehow set him up for life.

The Maple Leafs gave Clarkson – who never had more than 17 goals in a season previously – a massive deal to add grit and an edge to their lineup. He immediately reverted to being a bottom-six player, scoring just five goals and 11 points in 60 games that first season. He was moved to the Columbus Blue Jackets after just 118 games and 15 goals. But hey, sometimes you pay a premium for water bottle police.

1.) Rick DiPietro, New York Islanders – 15 Years, $67.5 Million (2006)

You know a deal is insane when the acting general manager refuses to sign it, is fired by the owner and replaced with someone willing to okay it. Just 24 years old at the time, Rick DiPietro seemed to be coming into his own as one of the better young goalies in the league, and New York Islanders ownership wanted to lock him up long-term.

Still, this deal was bananas. In DiPietro’s defense, he received Vezina Trophy votes and even made the All-Star Game within the first two seasons of his contract. Unfortunately, injuries decimated the remainder of his career. Over the next five seasons, DiPietro suited up for just 50 games before hanging up the pads. The buyout on this massive mistake will see the Islanders pay DiPietro $1.5 million per year through the 2028-29 season – 23 years after it was signed.

A Lot of Money for Little Return

For the most part, the common factor in these deals is a combination of poor judgment, a lot of money, and very little in return. For some, like DiPietro, injuries played a role. Most of the others were simply shooting for the moon and saw the rocket explode on takeoff.

With today’s landscape, including a rising salary cap and dwindling free agent market, we are undoubtedly going to see more regretful deals in the way of signing young talent. Potential is at a premium these days, and we are sure to see a few deals from this list pushed off for newer pacts.