Lengthy summer to-do list for Cheveldayoff Stanley Cup continues to elude Jets general manager after 14 seasons at the helm By: Mike McIntyre Posted: 6:21 PM CDT Wednesday, May. 21, 2025

Kevin Cheveldayoff once again finds himself staring down a lengthy summer to-do list. However, the Winnipeg Jets general manager believes he’s getting closer than ever to checking off the elusive item that is constantly at the very top: Build a Stanley Cup champion.

“I truly believe we’ve got a bunch of winners in that room,” Cheveldayoff said Wednesday as he met the media to wrap up his 14th year at the helm.

The Jets won more than anyone during the regular season, with a 56-22-4 record that had them on top of the NHL standings. But they came up 10 wins short of the ultimate goal in the playoffs.

“It was a historic year in many ways for the franchise. Getting the Presidents’ Trophy is certainly something we’re proud of,” said Cheveldayoff. “But, obviously, there’s still some work to be done.”

It wasn’t lost on Cheveldayoff that he was sitting inside Canada Life Centre putting a bow on the 2024-25 campaign on the same day the Jets would have been hosting Game 1 of the Western Conference Final against the Edmonton Oilers had things worked out a little differently. Instead, the Dallas Stars have that opportunity while the Florida Panthers and Carolina Hurricanes battle it out for Eastern Conference supremacy.

“There’s several teams that are participating right now that have been there before, and that’s what we want to get to. We want to get to that point where you have the battle scars, you have the knowledge that you know what to expect and what it’s going to take to go beyond that next level,” said Cheveldayoff.

To that extent, he and head coach Scott Arniel spent this week meeting individually with every player for 15-20 minute sessions in which they discussed the recent past, the present and the future. The theme of “unfinished business” was a constant theme.

“We may not have all the answers for you here yet, because there’s still lots of dissection that will go on with us here. But to a man, everybody certainly was looking for more and it’s incumbent upon us to try to take those next steps,” said Cheveldayoff.

“Hopefully the experience we went through will help those players in future times.”

The Jets raised plenty of eyebrows when they only added depth forward Brandon Tanev and depth defenceman Luke Schenn at the trade deadline, leaving approximately US$6 million in available salary cap space on the table. Does Cheveldayoff regret not being more aggressive, especially since injuries began to pile up during the playoffs and Winnipeg’s depth was severely tested and offence dried up?

“This group earned the right to be together. If there were opportunities where we felt that we could add players that were going to help us win, we were obviously fully prepared to do that,” he said.

“It was a historic year in many ways for the franchise. Getting the Presidents’ Trophy is certainly something we’re proud of.”–Kevin Cheveldayoff

Cheveldayoff tried to take some bigger swings but ultimately struck out due to a variety of factors including being outbid on a player, the target not wishing to waive a no-trade clause to come to Winnipeg or the other team ultimately pulling him off the market.

“We kind of had a mutli-layered plan going into the deadline as to how we wanted to attack it and wanted to give ourselves the greatest flexibility that we could. But if the players aren’t there to be a fit in your lineup, you don’t just go grab a player to shoehorn something in,” he said. “You don’t just spend (cap space) for the sake of spending it.”

Cheveldayoff could be busy writing cheques over the next few months as he tries to keep as much of this roster intact while also adding some new elements he hopes can get them over the top. Forward Nikolaj Ehlers leads a list of pending unrestricted free agents which also includes Tanev, Mason Appleton and defenceman Haydn Fleury.

“Nikolaj has been a player who’s grown up in our organization. Drafted, developed him. Someone we think the world of,” said Cheveldayoff.

“We will be putting our best foot forward with him to try to make our case to be one of those guys who can be a unique Jet-for-life type player. We’ll see where it all goes.”

Cheveldayoff recently had a two-hour meeting with Ehlers’ agent and plans further talks once Ehlers is finished playing for Denmark at the World Championships.

“The relationship is great. He did contribute to the success of this organization on many fronts and we hope that’s something that can continue. If he does go in a different direction than obviously as an organization we’ll have to evolve as we have in the past with other things,” he said.

Cheveldayoff also has a trio of important restricted free agents in need of new details including defenceman Dylan Samberg and forwards Gabe Vilardi and Morgan Barron.

“Hopefully the experience we went through will help those players in future times.”–Kevin Cheveldayoff

“I think the exciting thing for us is that we have some of those kind of players that are on this side of the 30-plus years. Those are some of the guys that have capacity to grow, so those are some of the guys that we challenge the most,” said Cheveldayoff.

“The contracts and that, that’s going to take care of itself. We’ll work on that. We’ll find a way to find common ground.”

There’s also the upcoming NHL draft — the Jets own the 28th-overall pick — to be followed by July 1 free agency, summer development camp and perhaps working on contract extensions for captain Adam Lowry and top sniper Kyle Connor, who will both be heading into the final year of their deals next fall.

“I’m very open to both of those guys in their conversations that I believe they’re a big part of our success, and want to keep it that way,” said Cheveldayoff.

He spoke repeatedly about the character of the Jets and how they rallied last weekend around Mark Scheifele following the death of his father. The majority of the team were taking a charter to Thursday’s funeral service in Ontario before they disperse for the off-season.

“I think when times are at their lowest, that’s when people really show themselves,” said Cheveldayoff, who lost his own father when he was 17.

“As a group this year that’s what it’s been about. They’ve held each other accountable behind the scenes more so than people even know. They’ve been hard on each other, they’ve pushed each other, they’ve argued with each other. I don’t know that we’re going to win the Presidents’ Trophy again next year. But I feel very comfortable sitting here saying that group of players wants it. They want to push. They want to be pushed.”

For many of those reasons, he hopes the narrative is starting to shift when it comes to Winnipeg’s perception around the NHL, specifically with players who might balk at coming here in trades or free agency.

“We will be putting our best foot forward with him (Nikolaj Ehlers) to try to make our case to be one of those guys who can be a unique Jet-for-life type player. We’ll see where it all goes.”–Kevin Cheveldayoff

“The players want to win. We have a goaltender that’s the best in the world. Players want to play in a fan base that cares. We’ve got some of the most passionate fans in the league,” said Cheveldayoff.

“You can never force a player to want to play somewhere. But I know if I were one of them I’d want to play in a place where I matter. I matter to the fans, I matter to my teammates and I matter to the thought of trying to win a Stanley Cup. And in the future there may be guys that don’t want to. We’ll move on. We’ll find the guys that do. And we’ll do our best to make this city proud.”

mike.mcintyre@freepress.mb.ca

X and Bluesky: @mikemcintyrewpg