Connor Hellebuyck’s trade request is out in the open now, and that changes everything. Once a franchise goalie goes public, the situation stops being hypothetical.
He’s going to be moved. The only real questions are where he lands and what Winnipeg gets back.
Edmonton is the name that jumps off the page. The Oilers have elite talent, real depth, and a blue line that looks solid on paper.
They also brought in Mike Babcock to shore up the defensive side of the game, and they’ve suddenly found themselves without their projected starter until late October. That combination makes the fit feel a lot less far-fetched than it did a day ago.
Hellebuyck probably wouldn’t pick Edmonton first if he had his way, especially with signs pointing toward an American market. But if the goal is winning, the list of realistic options shrinks fast.
The Oilers are one of the few contenders without a settled No. 1 in net, and they have the cap space to make it work. They need a goalie, and they need one badly.
There are fair concerns here, too. Hellebuyck is 33 and coming off a down season on a Jets team that fell short of expectations.
Age, workload, and the possibility of decline are all part of the conversation. But he just helped Team USA win Olympic gold, and the idea is simple: put him behind a stronger roster and he can still deliver.
Carrying Winnipeg for years may have worn him down, but the talent is still there.
Winnipeg, meanwhile, doesn’t really have the luxury of standing still. Hellebuyck’s agent made the request public, and the Jets have already responded by acquiring Stuart Skinner, a clear sign they’re preparing for life after Hellebuyck.
They need to trade him. There’s no sitting this out and hoping it blows over.
They need a return, they need a goalie situation they can manage, and they need to move on.
That’s where Edmonton’s package gets interesting. The public nature of the request should bring the price down from what it would have been last season, but the Oilers still have real pieces to offer.
Tristan Jarry would head back the other way to make the money fit. He had a rough year in Edmonton, but he was strong in Pittsburgh before that, and a fresh start could help.
For Winnipeg, a Skinner-Jarry setup would at least give them competition and some stability.
The young talent is there too. Isaac Howard, who lit up the AHL as a rookie and looks NHL-ready, gives Winnipeg a forward with upside who can slot into a third-line scoring role. Then there’s Ty Emberson, part of Edmonton’s surplus of young defensemen, and he could help the Jets right away on the third pair.
The full idea looks like this:
Oilers Receive:
Connor Hellebuyck
Jets Receive:
Tristan Jarry
Isaac Howard
Ty Emberson
2028 1st-round pick
2026 2nd-round pick
It’s a strong offer. Winnipeg gets two young roster players, two premium picks, and a goalie who might rebound in a new setting. They could still chase a different goalie if another team puts a higher-end name on the table - San Jose and Yaroslav Askarov is the kind of example that would force a hard look - but Edmonton’s package is absolutely in the mix.
For the Oilers, the upside is obvious. Hellebuyck is signed through 2030-31 at $8.5 million AAV, and adding him would give Edmonton the kind of certainty in goal it hasn’t had in a long time.
A Hellebuyck-Levi tandem to open the season would change the tone around the team immediately. It would also send a very clear message about how serious Edmonton is about chasing a Cup and keeping Connor McDavid in blue and orange.
Finding clean comparables is tough because elite goalies almost never ask out. Jacob Markstrom went to Florida for Evan Rodrigues, Jesper Boqvist, and Ben Steeves.
Sebastian Cossa brought back a first-round pick. Devon Levi fetched a third.
Those deals all live in different worlds, but they help frame the market. Markstrom is the closest name in the group, though Hellebuyck is the better goalie, which is why the price would have to be higher.
At the same time, teams always hesitate to pay too much for a position that can swing wildly from year to year.
In the end, this is the kind of move that could help both sides. Winnipeg gets assets, flexibility, and a cheaper goalie with a shorter contract.
Edmonton gets a true No. 1.
Whether Hellebuyck thrives there is impossible to know. But it’s exactly the sort of gamble a contender would make without blinking.
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With that uncertainty hanging over camp, the Oilers may have reason to look beyond their current group and into the free-agent market, especially for help on the penalty kill and in goal. It is the kind of early-season headache that can force a team to make quick decisions on roster construction, and in Edmontons case the timing makes the next few weeks feel a lot more important than a typical September buildup. [Read more 🡒]