The Connor Hellebuyck trade rumors have reached a fascinating stage, and one destination that suddenly deserves much more attention is the San Jose Sharks.
Hellebuyck has publicly confirmed that he asked the Winnipeg Jets for a trade several months ago and reiterated that his position has not changed as training camp approaches. Winnipeg, meanwhile, says it continues to work through the situation but has no trade update. That already makes Hellebuyck one of the biggest names potentially available in the NHL.
Now comes the surprising part: San Jose is increasingly being discussed as a legitimate landing spot.
Sportsnet included the Sharks among five potential destinations for Hellebuyck. Sharks beat writer Curtis Pashelka subsequently examined whether acquiring him would be one of Mike Grier’s smartest moves or one of his riskiest, and San Jose Hockey Now spent part of its August 30 podcast debating what a realistic Sharks offer might look like.
To be clear, there is no confirmed report that San Jose and Winnipeg are currently negotiating a Hellebuyck trade. This is a trade-fit analysis based on the developing public discussion.
But the more I examine the Sharks roster, their timeline and their goaltending situation, the less crazy this idea becomes.
Why Connor Hellebuyck Suddenly Makes Sense for the San Jose Sharks
San Jose isn’t behaving like a rebuilding team that wants to wait another three or four years.
The Sharks finished 39-35-8 last season and have surrounded their talented young core with considerably more veteran experience. Mason Marchment went so far as to tell NHL.com that reaching the postseason is the “bare minimum” for San Jose this season.
That changes the conversation.
Macklin Celebrini, Will Smith and the Sharks’ collection of young talent give Mike Grier something every rebuilding general manager eventually needs to recognize: there comes a point when accumulating prospects has to turn into trying to win.
Hellebuyck could accelerate that transition immediately.
Yes, the 33-year-old had a down 2025-26 NHL season by his remarkable standards, finishing 23-23-11 with a 2.86 goals-against average and .895 save percentage in 57 games. But we’re still talking about a three-time Vezina Trophy winner who won both the Hart and Vezina in 2024-25 and who NHL Network recently ranked as the league’s No. 2 goaltender entering the new season.
I wouldn’t look at one .895 season and conclude Hellebuyck has suddenly forgotten how to stop pucks.
I’d look at his body of work.
And I’d ask whether putting an elite veteran goalie behind an improving San Jose roster could transform the Sharks from an interesting playoff hopeful into a legitimate problem in the Pacific Division.
The Yaroslav Askarov Question Could Decide Everything
This is where a potential trade becomes uncomfortable for San Jose.
Yaroslav Askarov has been viewed as a major part of the Sharks’ future since San Jose acquired him from Nashville in 2024. He completed his first full NHL season with a 21-20-4 record, 3.63 goals-against average and a .884 save percentage across 47 appearances. He was also named the Sharks’ Rookie of the Year.
Those aren’t dominant numbers, but judging a 24-year-old goalie strictly by his first full NHL season would be shortsighted.
That’s why I don’t believe San Jose should view Hellebuyck as simply an “upgrade over Askarov.”
The real question is much bigger:
Would the Sharks rather have five seasons of an established elite goalie beginning at age 33, or gamble on Askarov becoming their franchise goalie for most of the next decade?
That is the decision Mike Grier would really be making.
The Connor Hellebuyck Trade Has a Salary-Cap Problem
This is one area where the Sharks-Hellebuyck speculation needs more scrutiny.
PuckPedia currently projects San Jose at approximately $3.34 million in cap space. Hellebuyck carries an $8.5 million cap hit through 2030-31, while Askarov carries a $2 million cap hit for 2026-27.
That means a straight Hellebuyck-for-Askarov exchange adds approximately $6.5 million to San Jose’s cap commitment.
My calculation:
So no, San Jose cannot simply send Askarov to Winnipeg and call the trade complete under its current projected roster.
Grier would need another corresponding move, salary retention, a different roster configuration or some combination of those mechanisms.
Interestingly, Winnipeg’s cap situation would become considerably more flexible. Replacing Hellebuyck’s $8.5 million hit with Askarov’s $2 million would increase Winnipeg’s projected space from roughly $4.48 million to approximately $10.98 million, before accounting for any other assets in the trade.
What Should the Sharks Actually Offer the Winnipeg Jets?
A hypothetical proposal circulating online has included Askarov plus premium draft capital, but I think San Jose has to be extremely careful here.
Hellebuyck is unquestionably the more accomplished goalie. But Winnipeg has lost some leverage because the trade request is now public, and Hellebuyck has a full no-movement clause this season. He can effectively decide whether San Jose is even an option. His clause changes beginning next season to a modified structure involving a 10-team approved list.
Here’s how I value the situation.
My ceiling would be Askarov and a top-10-protected 2027 first-round pick.
I would hesitate to add San Jose’s 2028 second-rounder unless Winnipeg retained salary or returned another meaningful asset.
Why?
Because giving Winnipeg Askarov, an unprotected first and another significant pick would mean San Jose is paying simultaneously for Hellebuyck’s past accomplishments and assuming the risk of what his game looks like at ages 35, 36 and 37.
That’s too aggressive for me.
Would I Trade for Connor Hellebuyck if I Were the Sharks?
Yes, but only at the right price.
San Jose is approaching the stage of its rebuild where being aggressive makes sense. Celebrini is already a franchise player. The supporting cast is developing. The organization has added veterans. Expectations have risen.
Hellebuyck could be the kind of acquisition that immediately changes what opponents think when they see San Jose on the schedule.
But Askarov isn’t a throw-in.
If Winnipeg wants Askarov plus San Jose’s best prospects plus premium unprotected draft capital, I’d walk away.
If the framework becomes Askarov plus a protected first-round pick, and Hellebuyck tells the Sharks he genuinely wants to spend the next five years in San Jose?
Then Mike Grier has a very difficult decision.
And that’s what makes this one of the more fascinating Connor Hellebuyck trade rumors of the summer.
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