"We Have to Push Forward" - Jets' GM Kevin Cheveldayoff Spearheading Organizational Review

The 2025-26 Winnipeg Jets did not live up to the lofty expectations set over the past number of dominant NHL seasons. 

Reaching their peak last spring, the Jets concluded the 2024-25 season as the Presidents' Trophy winners as the team with the No. 1 record in the league following regular season play.

Their performance sizzled out in the postseason, as they narrowly dodged a first round knockout, before falling to Dallas in the second round. 

This time around, they hardly made it to Christmas before their big blows came.

Injuries to star players Connor Hellebuyck, Cole Perfetti and Dylan Samberg got the team off on the wrong foot from the get to, before an uncontrollable snowball tumble to the bottom of the league's 32 clubs - by way of an 11-game losing streak - set the wheels in motion for an extremely disappointing finish. 

And the message from general manager Kevin Cheveldayoff was clear: nothing about the Winnipeg's season met expectations.

Moving forward, everything is under review.

Speaking at the team’s year-end availability, Cheveldayoff struck a familiar tone that balanced accountability with patience, making it clear that the organization is once again not rushing into decisions following a season that fell short of its internal standard.

Think Vegas Golden Knights, and then imagine the exact opposite. That is how Cheveldayoff and Mark Chipman's Jets tend to operate. 

“We all feel the emotions, the disappointment, of not living up to those expectations,” Cheveldayoff said. “When you go through something like this as an organization, it’s incumbent on everyone, starting with myself, to ask critical questions.” 

And what might those questions be? Well, for starters, maybe something about the inconsistency displayed by the club that came into the season as a heavy playoff favourite.

According to the league's soon-to-be longest-tenured GM, the Jets' team defence was not up to task this year. And despite building its identity around structure and limiting chances, that foundation slipped.

“This past season we didn’t have enough consistency,” he said. “Clearly this was an area that wasn’t strong enough… that’s going to be the crux of the matter and we have to understand why.” 

The numbers backed that up. Winnipeg played 40 one-goal games, but saw a drop in its overall point percentage. And that was a sign, in Cheveldayoff’s view, of how thin the margins were and how often the team came up short in key moments.

Cheveldayoff was unable to deflect all responsibility. Instead, he openly questioned his own decision-making, including whether the organization may have relied too heavily on past success in hopes of a strong 2025-26 campaign.

“Did we think we were just going to get to the playoffs because of past performance?” he asked. “Did we skip a step? That’s where I have to grade myself.” 

He acknowledged offseason decisions - particularly roster bets that didn’t fully materialize - as part of that evaluation.

“Some of my offseason bets… that’s something that’s on me. There’s no question,” he shrugged. 

Still, he emphasized that inaction is a greater mistake than risk-taking. "The biggest mistake in this game is not trying,” he added.

As has been the case since the Jets returned to the Great White North, 'patience' has been a theme dropped by Cheveldayoff at his annual meetings with the media.

And the 2026 edition was no different.

He repeatedly stressed that the organization is in the early stages of a thorough evaluation process that will include players, coaches and analytics staff.

But of course, no major decisions are imminent.

“We’re not ready to turn the page on this one here for a bit,” he said. 

That extends to the coaching staff, including the team's current head coach Scott Arniel, who also spoke Monday.

“I’m not going to sit here and make any bold proclamations. We’ll keep on evaluating.”

Just how long those evaluations will last is anyone's guess.

Sure, Chevy's disappointment remains at the forefront of his mind as he watches 16 other clubs battle on a nightly basis for a chance at Lord Stanley's mug, but although he'll be watching the games from his couch at the cottage, his belief in Winnipeg's core group remains. 

“I firmly believe in this core,” he said. “It’s a group of guys that have the ability to keep pushing this team.” 

But at the same time, he also acknowledged that nothing is guaranteed, especially in the National League.

“Nothing will be given to you,” he said. “You still have to earn it.”

That mindset should shape how the team approaches the offseason, particularly with several veteran players nearing their mid-30s and Winnipeg's competitive window beginning to shutter.

As Chevy mentioned in his opening statements on Monday, the Team's defensive structure will need a reboot for 2026-27. After being such a strength the past two seasons, last year will either be an anomaly or the new standard. The GM hopes for the former.

“Defence to me is a mindset,” he said. “When we play the way that we need to play, we’re a very, very tough team to beat.” 

The challenge now is rediscovering that identity over a full 82-game season.

Cheveldayoff also offered insight into the many challenges of team-building in 2026.

With the salary cap continuing its steep ascent, free agency has become less fruitful; teams are increasingly able to retain their own players, leaving fewer external options available to clubs like Winnipeg.

“You either trade, draft and develop, or try to find them in free agency,” he said of player acquisitions. 

The departure of Nikolaj Ehlers to Carolina last summer was cited as a key example of how difficult it can be to replace elite, unique talent - particularly when trying to replicate speed and offensive impact.

While the Jets have integrated younger players in recent seasons, Cheveldayoff acknowledged that internal development will be on the forefront of the minds of Jets fans next season.

“Changes have begun,” he said. “It may not seem like we’re not changing… we’ve been changing as it’s gone on here.” 

“The pressure’s on those guys, too, to come in and help be part of the solution.”

Although stating that moving a core piece was not out of the equation, the possibility of doing so is definitely slim to none, at least judging by his long-term track record.

“Certainly open to talk about anybody,” he said. “But anything we do is about making this group one step closer to winning a championship.” 

Although it won't happen this year, Chevy is adamant the Jets will return to the playoffs and host whiteout street parties again in the near future. 

“I’m sorry that we’re not planning the Whiteout,” he said. “That’s our job… to make (the fans) proud.” 

But for now, the task at hand is continue re-evaluation his team, his decisions and the personnel moving forward. 

The answers may take some time to discover, but his goals and expectations remain: 

To build a team capable of competing for the Stanley Cup - and ensure this season’s outcome is not repeated.