Cheveldayoff Faces Diverging Roads for the Jets’ 2025 Trade Deadline 

Does the Winnipeg Jets’ runaway success this season make it more important for general manager Kevin Cheveldayoff to go all-in at the upcoming trade deadline, or less?

The longtime GM is about to arrive at two diverging roads and needs to figure out which one to trek down to give his team the best shot at glory.

Conventional Wisdom Says Cheveldayoff Should Add

On one hand, it’s conventional wisdom that teams with Stanley Cup dreams should add a rental or two to bolster their group for a hopefully-lengthy playoff run, even if they have to part with draft picks or prospects. A well-timed rental for a win-now team can make a big difference difference.

It’s tough to imagine Cheveldayoff not adding to his group on or before the March 7. deadline His club owns a 42-15-3 record to sit first in the entire NHL and just had a franchise-record 11-game winning streak.

The Stanley Cup window appears as open as it’ll ever be and Cheveldayoff has the cap space available to make a big splash by bringing in another impact forward and/or defenceman. He has explained before that one of the ways he tries to respect the players who have signed long-term in Winnipeg to win — Kyle Connor, Connor Hellebuyck, Josh Morrissey, Mark Scheifele, and others — is by putting them in the best possible position to do that, and that sometimes means giving them a new teammate.

Kevin Cheveldayoff Winnipeg Jets
Kevin Cheveldayoff, general manager of the Winnipeg Jets (Photo by Jonathan Kozub/NHLI via Getty Images)

Cheveldayoff is a proponent of the draft-and-develop model and does not part with future assets lightly, but has shown the willingness to deal them at the deadline when he believes his team is a legitimate threat to win. Over the years, he’s acquired proven producers such as Paul Stastny, Kevin Hayes, Sean Monahan, and Tyler Toffoli in attempts to push his team over the hump, with varying degrees of success.

There are certainly a plethora of targets on selling teams, and potentially some available players no one is even talking about as available. Cheveldayoff’s acquisitions of Stastny in 2018 and Monahan last season were fairly “off the board.”

Related: Jets Should Target These 4 Centres at the Trade Deadline

Acquiring a pure rental is one strategy, but another is to snag someone with term on their contract (which Cheveldayoff likes to do because Winnipeg is not a prime destination for unrestricted free agents) or someone who might be open to re-signing. He acquired Dylan DeMelo, Nino Niederreiter, and Vladislav Namestnikov at past deadlines, and while those signings were not considered “flashy” at the time, all three re-upped in Winnipeg (Niederreiter once and DeMelo and Namestnikov twice) and are reliable contributors.

Jets Don’t Have Glaring Weaknesses to Address

On the other hand, it’s tough to identify an area where the Jets truly need help. Sure, they’d like another top-six calibre centre or top-four defenseman, but they don’t have any massive weaknesses that make a trade an absolute necessity. They have been the class of the league all season, which they started 15-1-0. In addition to the 11-game winning streak, they have had two separate eight-game winning streaks. They have high-octane stars capable of turning a game on its head. They have established lines and defensive pairings that work well together. They have a good number of consistent depth offensive contributors. They have the best goaltender in the league. They have solid defence for the most part.

The biggest need likely is another d-man who can push the gaffe-prone Logan Stanley out of the lineup for the playoffs (head coach Scott Arniel and his staff curiously do not view any of Ville Heinola, Haydn Fleury, or Colin Miller as that guy, but that’s a conversation for another day.)

Cheveldayoff Must Consider Jets’ Chemistry

Cheveldayoff must be mindful that whoever he brings in does not disrupt team chemistry. The Jets now have a strong team culture that former head coach Rick Bowness implemented and Arniel, captain Adam Lowry, and the rest of the leadership core have built on. The team is tight-knit, every player is well aware of how they need to play to be successful, and no one puts themselves above the collective like some did in the Blake Wheeler era when the locker room was fractured and the team was mentally fragile. Adding someone with a big ego or who won’t buy in to the team ethos could do more harm than good.

Kyle Connor Mark Scheifele Gabriel Vilardi Winnipeg Jets
The Jets are a tight-knit team with a strong culture, so Cheveldayoff must be sure to not disrupt chemistry with any move. (Photo by Jonathan Kozub/NHLI via Getty Images)

“Kevin Cheveldayoff certainly has had a history of being aggressive, but the moves last season did not pan out,” TSN’s John Lu said on That’s Hockey earlier this week. “You look at how the Jets have been this season, being at or near the top of the league all year long, Kevin Cheveldayoff said at the halfway point of this year that he is not going to be making moves that would potentially mess with the chemistry of this team. The Jets have been one of the elite squads in the NHL this season and so any move, whether it’s impact or whether it’s depth, he has to make sure — and he wants to make sure — that anybody that he brings in is going to be a good fit with the group that he has in hand right now.”

The chemistry and the culture the Jets have has arguably never been better,” Lu continued. “So he could be aggressive, but the deal… has to be a good fit in the dressing room as well as one that will help the team on the ice.”

Cheveldayoff’s Decision Won’t Be Easy

If Cheveldayoff stands pat or only tinkers and the Jets make a third-straight early playoff exit, he’ll be accused of not doing enough. If Cheveldayoff pulls the trigger on a blockbuster for someone who doesn’t work out, he’ll be accused of doing too much by trying to fix what wasn’t broken. Really, unless the Jets win the Cup or at the very least go deep into the playoffs, his moves will be questioned. Such is life as GM in a hockey-crazed city like Winnipeg.

We’ll soon find which road Cheveldayoff chooses to travel and we’ll hear from him why he decided to go he did. In the offseason, we’ll debate whether he made the right choice for the best team he’s ever had when the window was as open ever. Talk about pressure.