Connor Hellebuyck sat out the Winnipeg Jets’ season opener Friday night, not because he was injured, but because he requested a trade and is currently suspended for not reporting to training camp. The Jets lost to Boston in overtime, marking the first time in more than a decade that Hellebuyck wasn’t between the pipes to start the season. That absence, combined with a stumbling start, now raises a crucial question: Will early struggles force GM Kevin Cheveldayoff to lower his asking price, or will he maintain his demanding posture in trade talks?
The setup for this analysis is clear from the reporting. Hellebuyck, 33, revealed in August he wanted out. According to Sportsnet’s Elliotte Friedman and Winnipeg Sun reporter Paul Friesen, Cheveldayoff’s stated goal is simple: find a trade that helps the Jets now.
That framing suggests urgency, but it’s also a negotiating position. Teams shopping star players typically demand premium returns. A GM seeking “immediate help” is really saying he won’t take less for a cornerstone goaltender just to move him quickly.
One loss doesn’t change that leverage, yet. The early results matter only if they develop into a pattern.s strategy is clear: the GM said the door remains open for Hellebuyck to return, but he’s actively shopping the goaltender and seeking a return that provides immediate help.
The contract, $8.7 million average annual value through 2030-31 with a full no-movement clause, makes any deal complex. San Jose has “kicked tires,” but no serious framework has emerged.
The Jets’ loss in overtime on Friday adds a new wrinkle to that calculus.
Connor Hellebuyck: Rookie goaltending and the opening-night question
Stuart Skinner made his Jets debut in goal and stopped 26 shots in overtime, but couldn’t preserve a win despite the team leading late in the second period. But the broader reality is unavoidable: Winnipeg now has a proven alternative to Connor Hellebuyck on the roster.
Skinner has been a capable NHL starter elsewhere. His presence removes the immediate crisis that might have forced Cheveldayoff’s hand.
That said, one loss and one debut tell nothing definitive. The real test is whether the Jets can compete this season without Hellebuyck, or whether this opening night hints at deeper problems that demand solutions faster than the GM’s reputation for patience would suggest.
The bargaining-power paradox
Cheveldayoff’s stated goal is simple: find a trade that helps the Jets now.
The Winnipeg Jets have 81 games left. The early results matter only if they develop into a pattern.
If the Jets win their next five games, Cheveldayoff’s position strengthens: he can tell potential suitors, “We don’t need to panic. We’re competitive without him.” If they lose three of four, he enters a harder negotiating position, one where a buyer might say, “You need help more than we do; lower your price.”
The ambiguity works both ways. A slow start could either prove Winnipeg’s urgency is real, justifying a lower ask, or prove they’re not in crisis, allowing Cheveldayoff to hold firm.
What the reporting actually tells us (and doesn’t)
Here’s what we know from the sources: Hellebuyck requested a trade. He’s suspended. Cheveldayoff wants a return that helps immediately. See how the Jets face a tough early test and what awaits them against other rivals.
The goaltender’s contract has a full no-movement clause, limiting the market. San Jose kicked tires. No deal has materialized as of late September.
What we don’t know: whether Cheveldayoff would accept a conditional future pick if a contender offered it, whether the Jets have a “floor” price they won’t breach, or how long Cheveldayoff is willing to hold Connor Hellebuyck out if no ideal deal emerges. The absence of recent reporting on serious conversations suggests either that the asking price is too high for interested teams or that the market simply isn’t there for an aging, expensive goaltender with a full no-movement clause.
One opening loss doesn’t change the fundamental problem: Hellebuyck has limited who can acquire him. Even a team with cap space and a need at goaltender has to convince Hellebuyck to waive his clause. San Jose’s interest didn’t progress to a framework. That’s a major constraint no one-game sample can override.
The longer game
The most likely scenario is that Cheveldayoff continues to wait for the right offer while monitoring how the season develops. If the Jets stay competitive, say, in a playoff position by December, his refusal to take a mediocre offer looks vindicated. If they struggle, he may face pressure to settle, but even then, Hellebuyck’s no-movement clause means the goaltender controls the final decision.
Friday’s loss is a data point, not a turning point. The Winnipeg Jets will play 81 more games, and so will every other team in the league. Early-season form is notoriously volatile.
What to watch: Winnipeg’s record in October, the tenor of reporting on Cheveldayoff’s trade talks, and whether any team steps forward with a serious proposal. Only then will we know whether this slow opening forced his hand or reinforced his patience.
Reporting from Bleacher Report and NHL.com contributed to this story.
