Winnipeg Jets GM Kevin Cheveldayoff beams, emphasizes family as pivotal trade deadline approaches

Kevin Cheveldayoff’s midseason media availability struck me as more passionate, more personal and more Manitoban than I can remember.

“I’m a Prairie boy,” he said when asked about his pride in the Jets’ small market run to the top of the NHL. “I grew up north of Saskatoon in a little town called Blaine Lake, 550 people. I played my junior hockey in Brandon. I’ve spent the most time of my life here in Winnipeg. There’s a sense of pride. When you come from the prairies, there’s always that feeling that you need to punch above your weight.”

It may be the most relatable thing Cheveldayoff has said from his place at the podium; I imagined Manitobans from places like Lac du Bonnet, Steinbach, Winkler, Flin Flon, Virden, The Pas and Deloraine hearing themselves in his words. In Winnipeg, where we are used to being outshone by places like Toronto, Vancouver and New York, we understand the notion that we must outperform our big-market rivals to be seen as their equals. There is a reason that no one in Winnipeg is shocked that it took this long for “the national media” — a phrase whose meaning changes depending on what we need it to mean — to catch on to the Jets’ excellence in 2023-24.

To be clear, Cheveldayoff was also adamant that Winnipeg hasn’t actually accomplished anything yet. The Jets have won a franchise-record eight straight games, bringing their record to an NHL-best 28-9-4 for 60 points in 41 games. They have given up the fewest goals in the league (95) while going the second-longest stretch of games in the expansion era (31) allowing three goals or less. They’ve even done all of this without knowing their full power; Gabriel Vilardi’s recovery from injury was followed by Kyle Connor’s injury and now a potential lower-body injury for Mark Scheifele, who left Thursday night’s game.

But January standings mean squat.

Maybe that’s why parts of Cheveldayoff’s Thursday news conference felt like a call to arms. He referred to the Jets as a family, shared that he absolutely sprinted down the stairs on Tuesday when Scheifele was struck in the head by a puck, and said that, when Rick Bowness left the team to be with his wife Judy after her seizure, Cheveldayoff challenged the team: “We talk about being a ‘family’ but now we’ve got the chance to walk it.”

Winnipeg’s response to its challenges helped Cheveldayoff put his best forward on Thursday. The Jets have skyrocketed from first-round fodder that lacked “pushback” to the top of the NHL. On Thursday night, when Gabriel Vilardi and Nikolaj Ehlers scored to steal a game from Chicago’s grasp in its dying minutes, they capped off an exhausted, improbable comeback put together exactly the right way.

The Jets didn’t cheat the game. They didn’t rush up the ice for offence, make hope plays into the middle of the ice or try to take on their opponents all by themselves. With Scheifele out, pulling up hurt during a second-period backcheck, the Jets buckled and then found a way to win. It was the first time in a long time it didn’t feel like the Jets “deserved” to win — and yet, there they were, stealing two points, with everyone in the lineup earning a piece.

Laurent Brossoit’s 20 saves included plenty of quality; Josh Morrissey’s late third-period pinch drew a penalty; Cole Perfetti’s power-play wizardry gained momentum; Adam Lowry’s determined puck protection and pristine centring pass set the table; Vilardi’s finish tied the game; Ehlers’ rocket boots won it with 1:05 left in the third. Despite a horrible second period, the Jets had won a game they “should” not have won and they made it feel inevitable.

So check your expectations at the door. Forget last season’s angst. Forget the snow. This Jets team is in the middle of something special even when down, tired and out.

The last time Cheveldayoff spoke to a group of reporters at the Matt Frost Media Centre at Canada Life Centre, it was to address a first-round playoff exit. He was contemplative to the point of frustration: With major decisions looming on Blake Wheeler, Pierre-Luc Dubois, Scheifele and Connor Hellebuyck, the clearest plan he would commit to was the need to evaluate. The need to “assess” was an underwhelming mission statement the day he made it and every day until Dubois landed Vilardi, Alex Iafallo, Rasmus Kupari and a second-round pick.

“It’s the nature of this job that you are looked at with a very critical lens,” Cheveldayoff said on Thursday. “You should not get into this industry if you don’t think that that’s part of the equation.”

So what comes next?

Winnipeg has earned the right to be seen as a team that needs minor tweaking as opposed to roster surgery to take the next step. It’s also earned the right to be rewarded by a GM who started the season with cap space. Cheveldayoff will meet with his professional and amateur scouts next week to iron out the team’s needs, wants, and assessment of the market. Cap space will also be a factor; the team is projected to be able to add approximately $5 million worth of contracts on deadline day but that number will change depending on injuries, call-ups and performance bonuses.

The Jets will get an update on Scheifele’s status on Friday, while the now-healthy Kupari has been assigned to Manitoba on a conditioning loan and Ville Heinola has been assigned there as a regular roster player. Every little bit counts, including the $850,000 in performance bonuses that Perfetti is eligible for based on his entry-level contract. The idea of being able to add $5 million in contracts could change at any moment.

“The script isn’t even written yet. All I can say is we’ll be prepared as we always are to make the proper decisions,” Cheveldayoff said.

It was pointed out that Winnipeg is a playoff-calibre team; isn’t part of Cheveldayoff’s job, then, to size up a playoff run and try to shore up any weaknesses with a long postseason in mind?

“I really haven’t had a chance to address a lineup with Vilardi and Kyle Connor in it,” he said. “Things evolve every single day so anybody who makes bold proclamations at 40 games hasn’t really felt the ups and downs and the rollercoaster of an NHL season.”

Scheifele’s Thursday night injury certainly proved that point, yet the Jets still won their eighth game in a row. They carry The Athletic’s best odds of winning the Stanley Cup. Something special is happening here and the fastidious Cheveldayoff, who is on something of a hot streak from the Andrew Copp trade through this fall’s extensions for Scheifele, Connor Hellebuyck and Nino Niederreiter, says he’ll be ready.

Centres rumoured to be available include Elias Lindholm, Sean Monahan and Adam Henrique. Chicago’s Jason Dickinson holds appeal, as does Philadelphia’s Travis Konecny. Nick Seeler or Chris Tanev could have appeal on defence.

But that all depends on the market and Winnipeg’s homework, which cranks into high gear at its staff meetings next week.

“I think the swing, if you’re taking one, you want to do something that fits,” Cheveldayoff said. “There’s a lot to say about chemistry and this group has really good chemistry. So if you’re going to add you want to add people to add to that chemistry.”

“Fit” is a vague concept and difficult to plan for; Namestnikov worked because Bowness was so familiar with him. Niederreiter was a player Cheveldayoff had done his homework on for quite some time. Bowness connections include Dickinson, who he coached in Dallas, and Tyler Johnson, who he coached in Tampa Bay. Cheveldayoff’s homework isn’t public business, which is part of what makes the deadline fun to cover in a market like Winnipeg.

Cheveldayoff did say that the Jets have been in touch with representatives for pending UFAs Brenden Dillon and Dylan DeMelo.

“Either myself or Larry Simmons have had conversations with each of their respective agents and those are conversations that are going to continue. I’m not telling you there’s negotiations ongoing or anything like that. When you’re in our situation here, you try to be as transparent as possible, given the different parameters but sometimes you can only be transparent so far. They’re big parts of our team. There’s no question about that. We’re not having the success we’re having here without those guys.”

DeMelo and Dillon are two of many Jets who have bought into the city, the organization, and the idea of punching above their weight. It would be convenient for storytelling’s sake if they were also from the prairies, as opposed to Ontario and B.C., but each defenceman is emblematic of the idea that Winnipeg can get big results from modest places. The Jets paid two second-round picks and one third-round pick for two top-four defencemen and, for this season at least, have the two of them signed for $6.9 million between them. That’s a lot of surplus value. (Talks with RFA’s like Perfetti, Logan Stanley, Declan Chisholm, and David Gustafsson are likely taking a backseat to deadline and UFA preparations for now.)

It’s true that much of what Cheveldayoff says is difficult to code. That’s by design. We know that he’s taken big swings when the team’s performance has warranted it. We’ve seen recent success with smaller swings, too. Ultimately, his trade deadline work will depend on what his current players are able to deliver for the next two months.

To that end, consider what Chicago was saying in its dressing room after Winnipeg came back to win.

“They’re consistent. They don’t cheat the game,” defenceman Connor Murphy told reporters. “I think a lot of their play comes from their defensive game and they just stick with it and try to get pucks and bodies around the net, as simple as that sounds, and win battles and they know if they stick to their game things are going to come. We ended up breaking exactly how they wanted.”

Can you imagine that quote being said about the Jets in recent years?

It’s a point of pride for the Jets’ GM, who cited coaching, depth, star power, and even a bit of luck as reasons for Winnipeg’s ascent to the top of the NHL.

“It’s just important that the players understand that winning just doesn’t happen,” Cheveldayoff said. “There has to be a process. There has to be that buy-in to that certain thing. Adam has done a great job but Josh Morrissey’s done a great job. Mark Scheifele has done a great job. Brenden Dillon’s done a great job. Dylan DeMelo. Those players are all leaders as well. Everyone feels like this is their team, their contributions matter.”

The last word is also Cheveldayoff’s, on family.

“Our organization, it’s a small one as far as our infrastructure, our staffs. We’re a tight-knit group. But as much as the players are a family, our hockey operations is a family as well, our business operations is a family, so there’s lots of those things. You never want to disappoint a family member and I think that we all have that kind of feeling for each other.”

(Photo: Jonathan Kozub / NHLI via Getty Images)

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