In a league where players so often get paid for what they've done rather than what they're going to do, you're going to see some bad deals. But these ones are superstar-level bad and are made worse with a flat salary cap.
One of the first things you realize when you do a list such as this one is that a couple of the guys on it are almost certainly going to be inducted into the Hockey Hall of Fame someday. But for now, the only place they’re enshrined is the Hall of Fame of Bad Contracts.
Erik Karlsson, Drew Doughty, Carey Price, all deservingly on this list. I mean, these are superstar-level bad deals. And the worst part of them is they’re all going to last a long, long time. There were only two criteria for a contract to appear on this list. No. 1, it has to be bad. No. 2, it has to have at least five years remaining on it after this season. So that means the likes of Phil Kessel, Loui Eriksson, Andrew Ladd, Brent Seabrook, P.K. Subban (let us catch our breath for a second here), Kyle Okposo, Milan Lucic, Jamie Benn, Jakub Voracek, Nikita Zaitsev, Frans Nielsen and Mikko Koskinen are exempt.
Probably a couple of things to keep in mind while you read this. First, things can change. We doubt they will, but they can. Second, don’t blame the player. There is not a person among us who would not leverage our talents and gladly accept this kind of money and term if someone were willing to give it to us.
So, without further ado, here’s our list. We put them in alphabetical order because, well, they’re all pretty millstoney:
DREW DOUGHTY
It’s this simple. If Doughty does end up being selected for the Canadian Olympic team in 2022, it will be on reputation and reputation alone. Because there’s very little in his game the past couple of seasons that suggests he is among the elite defensemen in the NHL. But he’s certainly being paid like it, both now and for the long-term future. At $11 million a season, he has the second-highest cap hit in the NHL among defensemen.
MATT DUCHENE
The only thing keeping this from being a dead heat with teammate Ryan Johansen is that Johansen’s deal runs for only another four years and is therefore exempt from this list. But both players were signed basically to the same contract for the same reason. And neither has delivered. In his endless quest for a No. 1 center, Nashville Predators GM David Poile is paying both Duchene and Johansen No. 1 center money without the production. With five more years at $8 million per season, Duchene has to be more to the Nashville Predators than a good guy who really likes country music.
OLIVER EKMAN-LARSSON
One of the weird things about this deal is it came after the 2017-18 season, when Ekman-Larsson was defensively a bit of a disaster. But that did not stop the Coyotes from signing him to a contract that carries an $8.25 million cap hit for each of the next six seasons after this one, which will take Ekman-Larsson past his 35th birthday. There still may be time to salvage this one, but after what was a down year last season, the Coyotes have to worry that their franchise centerpiece is becoming a declining asset.
ERIK KARLSSON
Part of what makes this deal so bad, and what is difficult to separate, is what the San Jose Sharks gave up to get Karlsson. Among other things, the Ottawa Senators got Josh Norris and the draft pick that netted them Tim Stutzle. That and the fact that his $11.5 million cap hit for this season and six more after that is currently the highest in the league among defensemen. It’s clear injuries and mileage have taken their toll on Karlsson, who isn’t close to offensively productive as he used to be and worse defensively. The uncanny breakout passes are still there and the zone entries are strong, but it’s pretty clear Karlsson has lost a good amount of the speed that made him effective at both ends of the ice.
CAREY PRICE/SERGEI BOBROVSKY (TIE)
Like other guys, Price and Bobrovsky are on this list through no fault of their own. In a cap world, especially in a flat-cap world, you simply cannot give that kind of money and term to a goaltender. Full stop. Or in this case, not full stop enough. The difference in their salaries is just $500,000 a year, with Price at $10.5 million and Bobrovsky at $10 million, with both under contract for another five seasons after this one. Another reason why these guys are on the list is that, almost without exception, a team can never really tell what it’s going to get from its goaltender from one season to the next.
JEFF SKINNER
The Skinner contract is one of a number of reasons why we’re referring to Jason Botterill as ‘former Sabres GM’ these days. And perhaps that’s not fair because he would have been roasted for letting Skinner go after a 40-goal season in 2018-19. But 14 goals last season and zero in 10 games this season? As the kids say, woof. But the good news is the Sabres are on the hook for only $9 million in cap space (which represents 11 percent of their allotment), this season and for the next six after that. And he has a complete no-move clause, which means the Sabres have to use up one of their roster spots on him for the expansion draft. Sometimes it’s just better to let a guy walk.
JACOB TROUBA
When Trouba forced his way out of Winnipeg, the Jets received a little-known commodity by the name of Neal Pionk in return. Almost three years later, the Jets would make that trade every day of the week and twice on Sunday. At $8 million for five seasons after 2020-21 Trouba earns almost double what the next highest-paid defenseman on the Rangers makes, which should not be a surprise considering the Rangers also employ the likes of Brendan Smith, Jack Johnson, Tony DeAngelo (for now) and Adam Fox on an entry-level deal.
MARC-EDOUARD VLASIC
A couple of years ago, a defense tandem of Erik Karlsson and Marc-Edouard Vlasic would have struck the fear of God into almost every one of the San Jose Sharks’ opponents. But now it’s the Sharks, and whoever it is who signs their players’ paychecks, who are waking up in cold sweats. Part of the problem for Vlasic, who is on the books for $7 million in cap space for five seasons after this one, is that there was a time when he was insanely underpaid. And now he’s insanely overpaid. It often works that way in hockey because there are still people out there who are prepared to pay big dollars and term for what a player has done rather than what he’s going to do.