It’s been a tumultuous 12 months for the Winnipeg Jets, going from Presidents’ Trophy winners in 2024-25 to a non-playoff team last season.
And with their focus on vaulting back up in the standings and making the postseason again, the franchise was hit with a major hurdle over the summer with star goaltender Connor Hellebuyck asking to be traded - a move that has yet to happen.
General manager Kevin Cheveldayoff spoke to TSN Hockey Insider Darren Dreger on Wednesday, looking ahead at how the Jets are trying to move forward ahead of the upcoming season.
This transcript has been edited for length and clarity.
Darren Dreger: So, it’s just another run-of-the-mill off-season for Kevin Cheveldayoff?
Kevin Cheveldayoff: Yeah, the off-seasons always take on their own life. I think, as a manager, from the end of the hockey season to the drop of the puck to begin the next season, it’s always a busy time. There’s lots of things on the go. The business of hockey actually ‘wakes up’ as opposed to ‘goes to sleep’ in the summertime. So, you know, there’s always different nuances that you’re dealing with.
DD: I think you’ve said this publicly. Connor Hellebuyck isn’t the first player to ask for a trade in the National Hockey League, obviously. But if you go back to even post-draft in June - now we’re in October - did you think that it would drag on to this point?
KC: Well, in situations like this, you never know. You don’t have a crystal ball. When I was first made aware of the situation - the conversations that Connor’s representation and myself had - were very clear and explicit that this could take a while. What ‘a while’ means I guess, is still undefined.
DD: You’re not going to get into the nitty gritty of this, but we’re talking about a franchise player - we’re talking about a Hall of Famer, a decorated star goaltender in the National Hockey League. So from a fan perspective, help us make sense of why a return like that has to be of significant value to help your current team, but also in recognition of the asset that Hellebuyck is. It can’t be futures driven entirely.
KC: What it’ll ultimately be, that’ll be a decision that’ll be made when something presents itself. I think right now the focus, quite honestly, is in two separate silos.
I think as we sit here today, there’s a level of excitement that the puck is going to drop on a new season here right now. There’s 23 individuals in that room that fought their way through training camp to earn the right to be on the roster here right now. The thing that I must commend them and the coaches on, is that training camp has been all about the Winnipeg Jets and that’s what it’s going to be moving forward here.
The second silo obviously is the job that I have to do, and I think the players and the coaches have done a great job of focusing on what they can control and what’s in front of them and letting me do the work behind the scenes.
DD: And including your goalies. You know you’ve got an experienced guy in Stu Skinner who’s playing for his third NHL team now - two of them Canadian, by the way - and you just picked Clay Stevenson off waivers. I know both those men are excited about this opportunity, so what do you see in that?
KC: Well, nervousness a couple days ago not knowing if we get Clay, so we’re certainly excited that the waiver claim was successful there.
I think Stu is someone that we’ve talked about before, that there’s been a level of interest and excitement on both sides, on the side of (assistant coach) Wade Flaherty who kind of runs the goaltending department for us and the desire to want to work with Stu, but the mutual desire that Stu has always felt that there’s maybe some good synergy there.
And then things start to unfold - as you get into the conversations, you find out that Stu and Clay Stevenson have a good relationship already. They know each other well. And when we started to have those conversations internally that this could be a waiver claim for us, there was that level of excitement.
So the thing about the National Hockey League is that it’s very unpredictable. And as we head into this season, the canvas is blank right now and it’s up to us to paint the picture.
DD: Many in the media look at that picture and say, “Okay, well this is a team that’s taking a step back.” I ran the label of ‘underdog’ by Stu Skinner and by Cole Perfetti. Perfetti especially didn’t appreciate it. But you’re okay with it, aren’t you?
KC: I think obviously going into last season, there was a level of expectation that was put on us - by ourselves - and we didn’t reach it. So there’s a level of humility, there’s a level of humbleness. And this isn’t about predictions, this isn’t about anything. This is about 23 guys in that room - some of which were here for several years, some of which are new - and there’s something to prove in there.
I think last year going into the season, we were something like the third oldest team in the league. And I think I saw a stat the other day where we’re middle of the pack - 14 or something like that. Everyone talks about transitioning and different things like that. There’s a lot of new players in that room. There’s going to be some ups and downs. But one thing that hasn’t changed is for us to be successful, we’re going to have to play a certain way. You can talk about individuals.
You can talk about different things like that. But the collective team game that the Winnipeg Jets have to play has to be our identity. And that’s taking care of our own end and letting the rest take care of itself. The structure, the way you need to play, the standards that we set for ourselves and hold ourselves to, that’s going to be the key to our success.
DD: So talk about some of these younger players. Gabe Vilardi, I think, took a step last year. Now you look at Cole Perfetti. It’s not about the contract, it’s about the opportunity. And man, he’s got a big one playing with Mark Scheifele and Kyle Connor.
KC: That’s what it’s all about, isn’t it? You know, like taking that next step. The National Hockey League is a very, very difficult league. You have to work hard to get in there and then you have to work hard to kind of make some noise in it.
We’re so excited for Cole - excited that he’s part of the long-term solution of this organization. There’s people in the game you want to cheer for, and he’s one of them. You want them to take that next step.
Gabe Vilardi is a perfect example of another one. Gabe is someone that has persevered in this game, has been open about talking about people working on their mental health and helping them improve. And when you see him wanting to take on a different role…he came into our exit meetings last year and said, “Next year, I want to be a driver. I want to do something on a line and carry a line and do some different things.”
Those are wonderful words to hear when you see a player like that wanting to take charge and make an impact. And he has a great chance to do that starting with the line with Viggo Bjorck and Isak Rosen. And nothing’s ever etched in stone. Coaches will try to plan and see how it goes, and hopefully there’s some chemistry there.
DD: Explain a little bit of what you’ve seen from Viggo Bjorck and Isak Rosen - two young players, very much unproven, but the talent and the skill set is definitely there.
KC: Isak has been someone that has checked all the boxes that he can at the American Hockey League level and kind of gone through the apprenticeship of pro hockey that you need to do. It’s time for the next step and it’s time for a young player like that to prove that he belongs and can play a big role.
With Viggo, from the moment we had the opportunity to draft them, there’s been an excitement level within the organization that we haven’t seen for a while. And I don’t want to put too much pressure, obviously, on a young player like that because, again, this is a tough league and it’s going to get tougher from Game 1 through Game 30, through Game 84. The thing about him is that he’s very smart and he’s very responsible defensively. So that immediately gives a coach a level of trust. Whenever you talk about opportunity or ice time - whether it’s a veteran player or a young player - does the coach trust you? We’ll see how it goes, but we’re excited for him.
We’re at a time in the organization right now where we need some of these younger players to step up and spread their wings.
DD: You talked about defence - team defence - earlier. I mean, what do you want Winnipeg Jets fans to see and take away when they leave this building or they watch you on the road? What has to be the identity of this team for you to be successful?
KC: I think we lost a little bit of that element of speed last year that helped us to become that smothering defensive team. That team that spent less time in their own end and more time transitioning the puck up the ice. So I would hope on any given night that the fans are going to come away from the game saying they worked their butts off. they were structured, and they were detailed. Two years ago, we were on the right side of all the one-goal games. Last year, we weren’t. We have to find a way to have that confidence and that comfort to be able to play in those one-goal games and come out on the positive side of it - because that’s what this league is. It’s a series of one or two-goal type of games. And if you can’t be comfortable in those games, you have some trouble. So that’s where our identity needs to be established early.
