Despite his team’s historic start to the 2024-25 season, the milestones achieved, and the fact the Winnipeg Jets are a top team in the Western Conference, general manager Kevin Cheveldayoff knows one of the most stressful parts of the regular season is coming up.
‘It is some of the most sleepless nights, the couple days before the trade deadline,” said Cheveldayoff on Tuesday. “It’s training camp and trade deadline time that you’re sitting there sweating bullets.”
The 2025 trade deadline arrives on March 7. No two deadlines are ever the same and the strategies going into them differ depending on cap space and where each team is at.
In 2018, Winnipeg acquired Paul Stastny in an under-the-radar move (until it was announced) that helped push the Jets into the Western Conference Final. Last season, Sean Monahan became a Jet over a month before the actual deadline, with the Jets also adding Tyler Toffoli on deadline day.
What will this year’s edition look like? Cheveldayoff said it’s tough to predict, especially with the 4 Nations Face-Off on the calendar. The other challenge is the fact that teams are bound by the 23-player roster rule until deadline day.
“Last year, we felt that Monahan fit exactly what we were looking for and Montreal was willing to do it on any time frame, they were just ready to go and we were able to make it happen then. Not every team is in that mentality when it comes to having players available,” said Cheveldayoff. “The bigger question is the assessment of the market. Are there the right plugs to fill those holes? I think every team is going to have some holes and I think every team is going to have some desires and hopes.
“There is still a lot of dancing going around. There are a lot of conversations that are at 30,000 feet right now.”
In a sense, every NHL general manager is having to deal with what’s best for their team at the current moment – with current information – while also having an eye on what’s coming up.
While he’s assessing his team’s current needs, Cheveldayoff also knows that he has a number of key free agents – both unrestricted and restricted – at the end of the season.
Players like Nikolaj Ehlers and Gabriel Vilardi are on career-year paces, Alex Iafallo continues to show his versatility, and Dylan Samberg’s handling of top-four minutes on the blue line are all things that Cheveldayoff has to factor in.
“I’ve had conversations with them but I wouldn’t categorize them as negotiations,” said Cheveldayoff. “That’s the tough side of the business side too. Say you have multiple guys in the same position, it’s like your kids, do I have to pick which one is my favourite?”
Of course, how the UFAs are handled also impacts the RFAs. Cheveldayoff knows the importance of making sure the Jets don’t open themselves up to offer sheets, so there is a tight rope to walk – with the final salary cap number not formally announced at this time.
“We kind of know where the number might go, but we don’t really know where that number might go yet,” said Cheveldayoff. “The good part is it looks to be going up as opposed to stagnant for those four years.
“The biggest thing, and every conversation I have with any one of the agents, is we’re trying to win. You don’t want to upset the apple cart, it’s all about trying to win right now.”
His commitment to that goal hasn’t changed. He likes the group that’s in the room and how they play for each other on a nightly basis.
“It’s a group you want to win so badly for,” said Cheveldayoff. “When I walk through the room, I feel indebted to them for what they’ve given the community, the organization. I feel it’s my obligation to try and help them achieve their goals of winning the Stanley Cup, and the fans as well.”
There is a long way to go, and a lot of decisions to be made. But while a lot of the focus is on the final destination, it’s important to enjoy the process along the way.
“We’re at chapter 48 right now. Every one is a book,” said Cheveldayoff on his team through 48 games. “You’re trying to set a standard and set the expectations of the group, of the players, the belief, and the values of what it’s going to take to win.”