Connor Hellebuyck’s trade request has the potential to send Winnipeg’s roster into a much bigger shakeup, and that’s exactly what makes this kind of blockbuster feel plausible. If the Jets decide to move their franchise goaltender after missing the 2026 playoffs just one year after winning the Presidents’ Trophy, it could force the organization into a hard look at where it’s headed.
That’s the backdrop for a massive proposal involving the Edmonton Oilers and two of Winnipeg’s biggest names, Mark Scheifele and Josh Morrissey.
Under this deal, Edmonton would land Scheifele and Morrissey. Winnipeg would get Jake Walman, Ryan Nugent-Hopkins, Spencer Stastney, Isaac Howard, a 2028 first-round pick, a 2029 first-round pick and a 2029 conditional second-round pick.
For the Oilers, the appeal is obvious: they’d be adding two impact players who would immediately reshape their Stanley Cup chase. Scheifele is coming off a huge season with 36 goals and 103 points in 82 games, and he’d give Edmonton another legitimate top-line centre behind Connor McDavid and Leon Draisaitl.
He could also handle the second-line job when Draisaitl shifts to McDavid’s wing, or even move to the wing himself. His $8.5 million cap hit runs through 2030-31.
Morrissey would fill another clear need. He put up 14 goals and 55 points in 77 games last season and logged heavy minutes in every situation. With a $6.25 million cap hit through 2027-28, he’d bring top-pairing value at a price that looks pretty good for a defenseman of his caliber.
Put McDavid, Draisaitl, Scheifele, Morrissey and Evan Bouchard in the same core, and Edmonton suddenly looks overwhelming. The price would sting, especially with Howard going the other way, but the Oilers would be making a straight-up bet on winning right now.
Winnipeg’s side of the deal is built around the idea that Hellebuyck’s request could trigger a wider reset. The Jets have already acknowledged his desire for a change, and moving him could push the team toward a retool instead of trying to keep the current group together.
Howard would be the headliner in the return. The former Hobey Baker Award winner has real top-six upside and could become a key piece of Winnipeg’s next competitive group. Stastney adds a younger NHL defenseman, and the collection of first-round picks gives the Jets more future assets to work with.
Nugent-Hopkins would bring leadership, defensive reliability and value on special teams. Walman would be able to step right into a top-four role and help stabilize the blue line after losing Morrissey.
There are obvious hurdles here. Contract protection and Edmonton’s limited cap room would make this a tough one to pull off, and Winnipeg could reasonably push for even more since Scheifele and Morrissey are both coming off strong seasons.
Still, if the Oilers are serious about maximizing the McDavid-Draisaitl window, this is exactly the kind of aggressive move they’d have to weigh. Winnipeg would get NHL help, a premium prospect and draft capital. Edmonton would get two stars and a core that might be the most talented in the league.
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