What still having Connor Hellebuyck and Mark Scheifele around means for the Winnipeg Jets
“Our singular focus is winning,” Kevin Cheveldayoff said, then repeated, when speaking to The Athletic after the GM meetings on Friday.
“Every challenge that we approach, every opportunity, or every time we get a chance to look at a different situation, it’s about putting us in the best perspective, the best place to win,” Cheveldayoff said. “That hasn’t changed and it won’t change for our organization.”
He’d been asked about Winnipeg’s plans for Connor Hellebuyck and Mark Scheifele, the Jets’ franchise goaltender and No. 1 centre, for perhaps the 100th time this summer. Neither player has a contract for next season and Cheveldayoff expects both players to be in the lineup for Winnipeg’s Oct. 11 season opener in Calgary. Scheifele is already in Winnipeg and Hellebuyck is expected back soon; they’re key pieces of a Jets team that should compete for a playoff spot if Cheveldayoff plays his cards right.
But what are his cards?
Cheveldayoff’s Pierre-Luc Dubois blockbuster was the first: Gabriel Vilardi, Alex Iafallo and Rasmus Kupari are pieces a team acquires to stay competitive. The Canadiens’ second-round pick is a bonus asset, not the centrepiece: Cheveldayoff made Winnipeg’s intentions clear with that vital Dubois trade. Blake Wheeler’s buyout created cap space, making room for Iafallo’s contract, Vilardi’s extension and Vladislav Namestnikov’s UFA deal. Wheeler’s departure also opened Winnipeg’s door more broadly to a new era of leadership, although not before he said something that caught Hellebuyck’s ear.
“My main goal is to win a Stanley Cup and I’m starting to run out of time and I can feel it,” Hellebuyck said in April. “Wheels talks about this all the time. It just flashes by. And I’m starting to understand. You do need to be in the hunt every single year. You’ve got to make the most of your years. I’m going to make the most of whatever my situation is, and give my all and give everything I can in the spot or the team that I have.”
Hellebuyck is Winnipeg’s franchise goaltender, a Vezina winner and a two time runner-up. He’s on a short list for “best goaltender in the world.” He’s also 30 years old now, a father, a planner and has the courage to name the Cup as his ultimate goal.
The fact that Cheveldayoff’s summerlong body of work kept a playoff spot within reach might be what gives the Jets a chance to extend Hellebuyck at all. Try as I might and I can’t find any evidence that the door on a short-term Hellebuyck extension is closed. Cheveldayoff told The Athletic’s Michael Russo on Friday that there has been ongoing dialogue and that he looks forward to meeting face to face when everyone is back in Winnipeg. The degree to which Cheveldayoff can sell Hellebuyck on a path to winning — even for a very short, 1-2 year term — may dictate Winnipeg’s chance at signing its star goalie. I’m not saying a short-term extension is a sure thing but I doubt it would be on the table at all had the Jets’ offseason been committed to a rebuild.
The Scheifele situation is less clear. He’s back in town, skating with his teammates at the Hockey For All Centre — as he always does — and should be driven to have the best season of his life whether his next contract is with Winnipeg or signed as a UFA next summer. I’m not sure to what degree Scheifele’s years of service at a team-friendly $6.25 million AAV motivate him now, nor can we say whether Scheifele will maintain his production better or worse than the average steep decline for players between 30 and 35. It seems as though the next contract he signs could be fraught with long-term risk.
If Winnipeg keeps both players all season, a playoff spot should be within reach. The forward group is deeper than it was last season, although Dubois’ good days will be missed, while Hellebuyck alone should be able to keep the Jets in the hunt.
Without them, it could get ugly, pending Cheveldayoff’s ability to unearth a quality trade return. The Jets have no coverage whatsoever in goal, with 2024 UFA Laurent Brossoit still trying to prove he’s a bona fide starter even after his contributions to Vegas’ Cup win. Thomas Milic and Dom DiVincentiis are good prospects but years away from competing for the No. 1 job. Scheifele’s departure would leave its current question marks at No. 2C — Vilardi, Cole Perfetti and Namestnikov — fighting for the No. 1 centre job.
My opinion is that Cheveldayoff stuck the landing on his first two tricks of summer — Dubois and Wheeler — but, in hindsight, those were the easier plays to make. Getting value for a 25-year-old centre — even one whose actions limited the pool of teams for Cheveldayoff to shop from — seems more straightforward than handling Hellebuyck and Scheifele. It seems absurd to say, given that I expect both of those players to play at a very high level for at least the next two to three seasons, but betting big on 30 year olds in the NHL is a dangerous game. Combine that with the Jets’ lack of immediate replacements and I think Cheveldayoff’s job is harder now than it was this summer.
Back to the cards Cheveldayoff has to play.
Hellebuyck and Scheifele’s quality are chief among them. If either player’s destiny is to become a trade deadline rental, Hellebuyck’s elite goaltending and Scheifele’s first-line caliber offence will drive a return. Winnipeg’s awkward spot in the “win now, win later” life cycle of an NHL team has no bearing on either player’s ability to help put a contender over the top. A lot bounced right for the Jets to get Morgan Barron, Brad Lambert, Elias Salomonsson and Milic for Andrew Copp in 2022 but Cheveldayoff’s recent track record is good here.
Winnipeg’s other asset? The $2.5 million in cap space the Jets will start the season with, assuming they start with 13 forwards, eight defencemen and two goalies. By deadline day, Winnipeg is projected to be able to add over $10 million in cap hit. If Cheveldayoff’s bets pay off and the Jets are in the hunt, he could approach the deadline as a buyer.
There are too many “ifs” involved to speak confidently here, but if I’m Cheveldayoff and if I have Hellebuyck at the table, my pitch is as transparent as possible. Here is the roster I’ve built. Here is how much I believe in you as a goaltender. Here is our cap space and our projected cap space and, no, nothing is promised in this sport but here is everything I hope to be able to do to make a short term stay in Winnipeg well worth your while.
That’s easy to write. In truth, the constant gardening (or whack-a-mole?) that comes with being an NHL GM must be way more complicated than that. I just think Winnipeg needs its franchise goaltender, has few options beyond Scheifele at centre and is otherwise looking at a trade deadline that promises to be as stressful as any in recent memory.
