Connor Hellebuyck’s trade request has already kicked open the door to speculation, and the Edmonton Oilers are the kind of contender that naturally gets dragged into the conversation.
The longtime Winnipeg Jets goaltender asked out through a statement from his agent on Thursday, Aug. 27, and he’s only entering the third season of a seven-year contract that carries an $8.5 million cap hit. He wants a new situation, and with Hellebuyck’s résumé, that immediately turns into a league-wide guessing game.
He’s one of the NHL’s elite goalies - maybe the elite goalie - and his stated aim has been winning a Stanley Cup. Edmonton remains in its contending window, which is why it’s at least worth laying out what a deal might look like if the Oilers ever decided to chase him.
One possible framework starts with Isaac Howard and a heavy pile of picks. The thinking here leans on the recent Mikko Rantanen deal to Dallas, where Logan Stankoven and multiple draft selections changed hands.
Hellebuyck’s status would put him in that same tier, if not above it, and Howard would be the young headliner Winnipeg could build around. The Jets would also get a 2027 second-round pick, 2028 first-round pick, 2029 first-round pick and 2029 third-round pick, with the firsts listed as conditional.
For Edmonton, it would be a classic all-in move for a true difference-maker.
WPG receives: Isaac Howard, 2027 second-round pick, 2028 first-round pick*, 2029 first-round pick*, 2029 third-round pick
*Conditional picks
EDM receives: Connor Hellebuyck
A second idea keeps the Oilers from emptying the cupboard quite as much, but it comes with its own complications. In that package, Devon Levi and Viljami Marjala head to Winnipeg along with a 2028 first-round pick and a 2028 third-round pick, while Edmonton gets Hellebuyck and a 2027 sixth-round pick back.
Levi is still extremely young and would be stepping from one crowded goalie room in Buffalo into another in Edmonton. If Winnipeg took him, he’d be paired with former Oiler Stuart Skinner and could wind up with the most playing time of his career.
Marjala is the other key piece here. He’s 23 and coming off 60 points in 72 AHL games last season, and there’s a chance he could see NHL ice time this season.
Moving him would sting, but that’s also what might make the deal more appealing to a Jets team that would want to keep replenishing its forward group. For the Oilers, the upside is keeping a few extra picks in reserve for future moves.
WPG receives: Devon Levi, Vijami Marjala, 2028 first-round pick, 2028 third-round pick
EDM receives: Connor Hellebuyck, 2027 sixth-round pick
The third proposal shifts the focus to two more young Edmonton pieces: Beau Akey and Connor Clattenburg. Akey brings a steady, well-rounded game, and at 21, his hockey sense already stands out.
Winnipeg’s blue line is gradually getting older, so Akey could fit as a long-term fallback in the minors. Clattenburg, meanwhile, brings a harder-edged style.
His offense has shown flashes, but the real calling card is his work along the boards and his aggression. How that translates long term is still a question, but the progress is there and the next level looks close.
WPG receives: Beau Akey, Connor Clattenburg, 2028 first-round pick, 2029 first-round pick
However this market develops, the Jets’ next move will shape everything. Hellebuyck is reportedly open about where he wants to land, and that keeps the door cracked for just about any scenario. Edmonton has the assets to make a serious pitch if it chooses; the real question is whether Winnipeg wants to take the gamble.
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