Connor Hellebuyck has made it clear he wants out of Winnipeg, and if the Oilers are serious about chasing him, Stan Bowman is going to have to get creative fast.
Hellebuyck, the NHL’s 2025 Hart Trophy winner, has become the kind of name that changes a team’s entire outlook. After Quinn Hughes and Brady Tkachuk moved on from Canadian teams to the United States, plenty of people are assuming Hellebuyck will do the same.
But there’s another possibility here: maybe winning is the real pull. He raised some eyebrows when he re-upped with the Jets in 2023, despite being a year away from free agency, so this wouldn’t be the first time he’s gone against the obvious path.
For Edmonton, the appeal is obvious. Hellebuyck could give the Oilers one of their best chances yet at winning the Stanley Cup. The problem is just as obvious: the cap space isn’t there, and the assets are thin.
According to PuckPedia, the Oilers have only $1.93 million in cap space, so the first order of business would be clearing money. Tristan Jarry is the clearest place to start.
He has two years left on a deal that pays $5.375 million per season, and the Jarry move has been a total disaster. Bowman would probably have to eat some embarrassment here, because getting out from under that contract may require paying to move him.
Even so, the payoff is hard to ignore. Dumping Jarry would open up $5.375 million, and if Edmonton had to attach a second-round pick, there may be ways to soften the cost.
One route would be sending out a prospect goalie too, such as Connor Ungar or Samuel Jonsson. Teams like the Ottawa Senators and Columbus Blue Jackets have current needs for a backup goalie, which could help the Oilers work the market.
If Jarry is moved, Edmonton would sit at $7.3 million in cap space, still $1.2 million short of Hellebuyck’s salary. That means more trimming would be needed.
Trent Frederic looks like a long shot to move, given that he has seven years left at $3.85 million per season. Kasperi Kapanen is another possibility, though it would sting after his productive 2025 postseason. Still, his $2.6 million cap hit could bring back a pick, and he doesn’t have trade protection.
There are also five depth players making between $1.2 million and $1.75 million: Shakir Mukhamadullin, Spencer Stastney, Mattias Janmark, Ty Emberson and Colton Dach. Moving one or two of them for late-round picks would be the cleanest way to squeeze out a little more space.
The cap picture is ugly, but not impossible.
Then comes the bigger question: what would Edmonton actually have to send Winnipeg?
The prospect pool is already one of the worst in the league, and the Oilers don’t have a first-round pick in 2027 because it went out in the Jason Dickinson trade. Still, they do have draft capital to work with. Under the NHL CBA, teams can trade picks as far out as seven years ahead, which means Edmonton can deal selections all the way through 2033.
If the Oilers decide to go all in, a realistic framework could be two first-round picks, Matt Savoie and Davon Levi.
That’s a painful price, but Hellebuyck is one of the best goaltenders in the NHL and the kind of player teams spend years trying to find. For Edmonton, he would be the missing piece in the Cup equation.
The odds of making it happen are slim. But if Bowman wants to change the story in Edmonton and help push the Oilers toward the promised land, Hellebuyck has to be the name at the top of the list.
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