Almost everyone assumed Connor Hellebuyck wanted out of Canada entirely. According to one Jets insider, that might not be true — and the team he’d consider joining could be a massive one.
Hellebuyck’s trade request became public last week after months of private discussions with the Winnipeg Jets front office. The assumption around the league has been that he’s targeting an American market, following a pattern set by several other U.S.-born stars who have left Canadian teams in recent years. But on the Bleed Oil Blue Podcast, Jets reporter Sean Reynolds was asked point-blank whether Hellebuyck would consider a trade to the Edmonton Oilers, a Canadian team most assumed would be off his list entirely.
“I think he would. I think it gives him a shot at doing what he feels he needs to do to complete his legacy, and that’s have some playoff success and that’s win a Stanley Cup,” Reynolds said.
Connor Hellebuyck’s future
Reynolds also pointed to Winnipeg’s aging core as part of what’s driving the situation from the front office’s side.
“The Jets core: Connor Hellebuyck, Adam Lowry, Mark Scheifele — they’re all 33 years old… they strongly feel the best days are still ahead with this group and that they’re going to head over and win a Stanley Cup. It’s a dangerous idea, because if it doesn’t work out in the next couple of years, it’s gonna collapse,” Reynolds said.
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The fit with Edmonton makes plenty of sense on paper. The Oilers have reached the Stanley Cup Final with Connor McDavid and Leon Draisaitl running the show, but inconsistent goaltending has been a recurring issue standing between them and a championship. Stuart Skinner has had his share of shaky playoff runs, and a proven, battle-tested goaltender like Hellebuyck, fresh off backstopping Team USA to Olympic gold, would address arguably their biggest remaining weakness.
Hellebuyck carries a $8.5 million cap hit for five more years, and his workload at 33 is worth watching after a down year by his standards in 2025-26. But if a genuine shot at the Stanley Cup is what he’s after, Edmonton might be one of the few Canadian teams that could actually get a yes.
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