Jets' trade deadline plans, interest in Jonathan Toews: 5 takeaways from GM Kevin Cheveldayoff

DENVER — Winnipeg Jets GM Kevin Cheveldayoff gave a midseason address on Tuesday.

For 65 minutes, Cheveldayoff spoke about his trade deadline plans; interest in signing Jonathan Toews; Logan Stanley’s role; plans for Nikolaj Ehlers, Neal Pionk and the rest of its free agents and more.

Here are the five most important takeaways from a deep, wide-ranging and often passionate conversation.

Winnipeg is interested in UFA centre Toews

Cheveldayoff said Winnipeg would love to sign Jonathan Toews if Toews deems himself ready to return to NHL hockey.

“It would be a real welcome conversation to see if there’s a fit both ways,” Cheveldayoff said. “I think it would be a great story for his career, too. Not that he needs another story to his career. But I think he’s proud of his roots and would be an interesting fit.”

Cheveldayoff and Toews know each other well, having won the 2010 Stanley Cup together in Chicago. It was the first of three Cup wins for Toews — the one in which Toews was at his most productive and won the Conn Smythe Trophy as playoffs MVP.

“From my understanding, what went on with his body is very difficult,” Cheveldayoff said. “I think he’s going to have to push himself to get his body to respond and see how it responds.”

Toews turns 37 in April. He missed the 2020-21 season with Chronic Immune Response Syndrome, plus six weeks in February and March of 2023 to deal with the effects of long COVID-19. He has not played in the NHL in either of the two seasons since then. Toews spent the healthy portions of his career winning things: an incomplete list includes three Cups, a Conn Smythe, a Selke, a Mark Messier Leadership Award, two Olympics gold medals, and a championship at the 2016 World Cup of Hockey.

Cheveldayoff says Toews’ journey to full health is a unique one. He’s in touch with Toews’ representatives and says he’d likely be just as interested in Toews if his NHL return can’t be managed until next season.

“Knowing Jonathan and knowing what standard he holds himself to as an athlete, and what impact he wants to have in games when he plays, I think it will be an interesting journey to watch how things unfold with him. … He’s going to want to play to win.”

Cheveldayoff may hate the term, but he’s ‘all in’ this season

Winnipeg is projected to have approximately $11 million to work with on deadline day. Cheveldayoff will use as much of it as the market allows.

This season’s Jets are uniquely power-play dependent but also one of the best teams we’ve ever seen in Winnipeg. They’re playing with Connor Hellebuyck at his peak. It makes sense, then, that there’s urgency to compete for the Cup here and now. Cup contention was part of the pitch that helped Cheveldayoff retain Hellebuyck and Mark Scheifele.

Cheveldayoff spoke to that urgency, although he bristled at how the media talks about it.

“The headline, ‘The Jets are all in,’ those are wacky headlines. We’ve been all in since Day 1,” Cheveldayoff said. “Whether you have to make a tough decision to trade somebody … that’s all in. You don’t just pick and choose when you have to make tough decisions.”

His point is that adding players at the deadline is not the only time he’s doing everything in his power to help his team win. He spoke to the pain of trading Andrew Copp, despite the way it yielded Morgan Barron, Brad Lambert, Elias Salomonsson and Thomas Milic because it took an integral piece of the 2022 team out of the dressing room. He also shared that the year Winnipeg acquired the trade deadline fit that’s set the standard for all of the moves since, Paul Stastny in 2018, the Washington Capitals won the Cup after adding depth players.

“That being said, we have been as aggressive as we’ve needed to be or wanted to be and we’ll see how things unfold,” he said.

To that effect, I asked Cheveldayoff if he sees the same second-line and top-four defence holes that I do. He said the bigger question is whether the market can provide the players that fit those holes.

“Right now there’s still a lot of dancing going around, a lot of conversations that are (still) at 30,000 feet,” he said. “Everyone might have these guys out there in trade rumours or trade talks and stuff like that, but that doesn’t necessarily mean that’s what’s happening behind the scenes on the phone calls. Some teams might extend some players, some teams might decide to keep their own rentals because that’s where they’re at.”

Timing will be big for the Jets as they look to maximize their additions. The Jets are building cap space by the day so the sooner they strike, the less cap space they’ll have to work with when they shop.

Winnipeg’s early acquisition of Sean Monahan last season was a unique situation. Not only was Monahan available early — the Montreal Canadiens weren’t waiting until the deadline to move him — but the move came with a cost. The Jets benefited from striking early, then suffered because Declan Chisholm was waived and claimed by Minnesota. The 23-player roster limit binds teams until deadline day, so a follow-up move was necessary; Cheveldayoff doesn’t sound like he’s going to strike early this time around.

Ehlers? Pionk? Not all UFAs will be back

When Cheveldayoff referenced teams keeping their own rentals, Ehlers, Pionk, Mason Appleton, Alex Iafallo and Vladislav Namestnikov came to mind. Cheveldayoff has been in contact with all of their agents, although he was clear that communication isn’t the same as negotiation.

“The newsflash is we probably won’t get all of these guys signed, from a UFA standpoint,” he said. “We’ve got, obviously, some RFAs that are performing very well and are in various different stages of their years before unrestricted free agency. We’ll tend to that.”

Ehlers is the biggest star of the UFA crop. The Jets drafted him No. 9 in 2014 and watched the speedster develop into a top five-on-five scorer; now he’s on the top power play, it’s cooking and he’s on pace for the most productive season of his career — just in time to hit free agency.

“Nik’s someone that, obviously when you watch them grow up, they do kind of become like your kids, so to speak. It’s great to see the career that he’s had and having. At the end of the day, there’s nothing more that I’d love to do than raise a Cup with him,” Cheveldayoff said. “The business side will be the business side. Where that goes … that story’s still unfolding.”

I asked Cheveldayoff about the idea of a self-rental, wondering if he felt it would be dangerous for team chemistry to trade Ehlers — or any UFA — before the trade deadline, even if it was clear they were on their way out.

“You know, I guess it depends on the situation that you’re in. I think that, as a manager, you’re always trying to be prepared for everything. That preparedness doesn’t necessarily mean at the trade deadline.”

I can’t say I know exactly what he meant by that but it sounded as though Cheveldayoff might — might — have some other contingencies in place. He went on to talk about the number of moving parts and factors that his management team is currently discussing in meetings.

What kinds of factors?

“(Factors that) pertain to the individual. And that pertain to the team. And that pertain to the locker room. And that pertain to, you know, style, pertain to … some other things that I’m not even going to tell you.”

The Jets are passionate about Stanley

Logan Stanley is the subject of tremendous fan debate. His ice time and opportunity is the single most requested topic covered in this week’s mailbag — and rest assured, that’s coming soon. He was even booed — briefly, and by a minority of fans — after a giveaway led to Vancouver’s only goal in a 6-1 Jets romp last week.

Fans clearly want to know why Stanley is Winnipeg’s go-to depth defenceman.

“I’ve never told a coach who to put in the lineup,” Cheveldayoff said on Tuesday. “Obviously we sign players and there’s different development curves for players. Some get in early, some don’t. The coach’s job is, you have a roster of 23 and you try to make those decisions. We talk about all those things. Coaches make decisions. I’ve never seen a coach make a decision not with the best interest of trying to win.”

The Jets continue to prioritize Logan Stanley, the subject of much fan debate. (Bob Kupbens / Imagn Images)

Cheveldayoff was then asked about Stanley’s size and toughness — and whether or not Winnipeg would look to add more of it at the trade deadline.

“You look at what’s available out there on the marketplace,” he said. “If that’s something that you’re looking for, that’s something that you’ll certainly try to acquire. Sitting here today I can’t tell you who or what is really going to be on the market at this point yet.”

Cheveldayoff’s own assessment is that Stanley is a part of the 31-14-3 Jets, their highs and their lows.

“I’m not going to sit here and say the players are perfect, because they’re not. That’s part of the way the National Hockey League works. Sometimes you’ll have opportunities to maybe look at something different, but this is the group we have here right now,” he said. “It is interesting, because how many games did he play in the 15-1 run? He played quite a few. He played, and he’s part of a group of players that have gotten to this point. Whether he’s a bigger part or smaller part moving forward, we’ll see.”

It’s true that Stanley has played a role on a winning team. In grading Stanley a “D” in our recent report cards piece, I noted the Jets have won Stanley’s minutes — that, despite legitimate criticism of his game at five-on-five and on the penalty kill, it was important to keep things in context.

Scott Arniel and Dean Chynoweth run their bench such that their third pair doesn’t see elite NHL opposition nearly as often as the top four. Consider that Stanley’s giveaway to Nick Bjugstad against Utah led to a very different outcome than Dylan Samberg’s giveaway on Logan Cooley’s highlight-reel goal. It can simultaneously be true that Stanley occupies the most obvious position to upgrade, that he struggles defensively, and that the issues are not so big that they’ve tanked the conference-leading Jets.

Still, it’s clear Winnipeg has prioritized Stanley several times since trading up to draft him — including at the cost of other players I view as superior to Stanley. So I asked Cheveldayoff about his own role in Stanley’s opportunity. No, he doesn’t run the Jets’ bench but he did waive Chisholm and Johnathan Kovacevic instead of Stanley. He protected Stanley at the Seattle expansion draft, exposing Dylan DeMelo (while Appleton was ultimately claimed). I don’t view Ville Heinola as having an NHL breakthrough season but Stanley is taking minutes that could go to the 23-year-old defenceman. Heinola has previously asked for a trade — in the same, non-emergent “play me or trade me” way that Stanley did in 2023 — and one can easily imagine the Jets losing him at some point, too.

“If you go back to the playoffs series against Edmonton, everyone seems to forget the role that (Stanley) played there in winning four straight against Edmonton. He was a regular shift player, he played all the games. We go into Montreal, he’s the one that scores the two goals in Montreal. So he’s on a pretty good trajectory as a developing player at that point in time,” Cheveldayoff said. “Now he ends up having a bunch of injuries there. Does his development get changed? Or stalled or whatever? Just like Ville. Ville obviously had a very good camp last year and the unfortunate injury derailed him. And then the recurrence of the infection this year set him back again. Those are things you don’t know, you can’t prognosticate.”

GO DEEPER

Logan Stanley’s ceiling? Blake Wheeler’s decline? Sami Niku’s stagnation? Jets mailbag, part 2

Cheveldayoff then spoke about development.

“Do some players peak? Sure. Do some people stagnate? Sure. Do some people never develop? Sure. That’s the thing. One thing I do know for sure is developing in the National Hockey League is a very unforgiving thing. It’s either unforgiving for the player or the coach or the management. At the end of the day, the mindset is to win. And that’s what it’s always been here. Sometimes there’s collateral damage along the way and we wish things wouldn’t have gone in certain directions or other directions.”

Hellebuyck, Morrissey and Scheifele got to see Cheveldayoff’s playbook. Connor is next

Do you remember the way Cheveldayoff opened up his playbook to Hellebuyck and Scheifele in the summer of 2023, selling them on his vision for Winnipeg’s future and thus retaining his top centre and franchise goaltender?

“It was pretty unique. Behind the scenes, the biggest thing was there was a lot of transparency between their representatives and ourselves,” Cheveldayoff said at the time. “It was unique in a sense that we probably shared some things with the other camp about what was going on more so than we have ever done with anything else.”

Multiple players have expressed frustration to me about Cheveldayoff’s tendency to keep his cards close to the vest — not just with media but in talks with their agents — so I’ve wondered if the GM’s play with Scheifele and Hellebuyck represented a new way of doing business for the Jets GM.

I’ve asked Cheveldayoff about that concept a few times — on the day of those signings, at last year’s trade deadline, and again this year. My takeaway from our conversations has been that Cheveldayoff’s transparency, as effective as it was, is a play reserved for the team’s franchise cornerstones.

On Tuesday, I asked him if Ehlers or Pionk were so integral to the Jets as to be on the Scheifele/Hellebuyck level of transparency. He responded with a story about Josh Morrissey.

“Josh Morrissey was on that level back when he signed his bridge deal (in 2018). If you remember, at that point in time there was a brief holdout from training camp. We were both very, very desirous of trying to get a long-term deal done but the math just didn’t work … I said, ‘This is the problem. Two years from now, we’re in good shape. Next year, the rules of the cap, I can sign you. It’s got nothing to do with we don’t believe in you or anything like that.’”

Morrissey took Cheveldayoff at his word, signed a two-year bridge deal, and then committed to the eight-year, $6.25 million contract he’s on now.

“Every situation and circumstance might be different,” Cheveldayoff said.

It was clear to me in the moment that Ehlers and Pionk are not in the “here are my long-term plans and how you fit into them” echelon of GM-player transparency that Morrissey, Scheifele, and Hellebuyck were. That seems realistic; if the Jets didn’t have those three players, they’d be rebuilding, while there are ways to stay competitive without Ehlers or Pionk.

In the end, I suspect the next player with whom Cheveldayoff shares longer-term planning will be Kyle Connor, UFA 2026.

(Top photo of Kevin Cheveldayoff at the 2024 NHL Draft: Bruce Bennett / Getty Images)