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The Winnipeg Jets come in at No. 17 on TheHockeyNews.com's NHL off-season rankings. Has GM Kevin Cheveldayoff done enough to get back into the Stanley Cup playoffs next season?

The past few seasons for the Winnipeg Jets have been a roller coaster.

After winning the NHL’s President’s Trophy as the top regular-season team in 2024-25, they fell completely out of the playoff picture this past season.

With the Colorado Avalanche, Minnesota Wild, and Dallas Stars all set to take another run at the Stanley Cup, the Jets will be in tough just to get into the post-season with how competitive the Central Division is.

GM Kevin Cheveldayoff is facing all sorts of pressure to turn things around, and he could have to make some pivotal decisions throughout the season that may change the fortunes of the franchise for a long time.

Let’s analyze Cheveldayoff's moves from this summer and discuss why the Jets are ranked 17th on TheHockeyNews.com’s off-season rankings.

Arrivals:

Mario Ferraro (D), Stuart Skinner (G), Noah Gregor (LW)

The Jets had a good defensive core before Mario Ferraro was brought in as a free agent. Despite trading away veteran D-man Logan Stanley to the Buffalo Sabres this past season, Ferraro’s addition gives Winnipeg some crucial depth for their back end.

While there have been significant trade rumors surrounding superstar goalie Connor Hellebuyck, the signing of Stuart Skinner – who split last season with the Edmonton Oilers and Pittsburgh Penguins – gives Winnipeg valuable depth regardless of how Hellebuyck's situation plays out.

Otherwise, Cheveldayoff stuck with his veterans this summer. While the Jets have $4.4-million in salary cap space at the moment, they might decide that having cap flexibility is the way to go as Winnipeg’s players try for what could be their final opportunity for a deep playoff run in 2026-27. 

That plan of action means Cheveldayoff has to be patient as he identifies the Jets’ flaws, and appropriately address them by the trade deadline.

Departures:

Jonathan Toews (C), Eric Comrie (G), Gustav Nyqvist (LW)

The Jets tried turning back time with last summer’s signing of future Hall-of-Famer Jonathan Toews.

While it was heartening to see the Manitoba icon playing for his hometown team, it wasn't an overwhelming success, with Toews producing only 11 goals and 29 points in 82 games. 

It’s telling the Jets’ first-round draft pick this summer was plucky center Viggo Bjorck, with their depth up the middle being a big concern.

There's no question he has the talent to make an immediate impact, but asking him to be a top-six forward could prove to be too much of an ask for an 18-year-old rookie playing North American hockey for the first time.

The Jets' departures like won't end up hurting their playoff chances a ton, but they look pretty similar to the group that struggled both offensively and defensively in 2025-26. Cheveldayoff is clearly betting on his core once again, and time will tell if that was the right move.

The Bottom Line: 

Cheveldayoff has clearly been loyal to the group of players who have reciprocated their commitment to the franchise, which is admirable. But if you haven’t gotten out of the second round of the playoffs since 2017-18, is that loyalty justified?

Sticking with a core is something you have to do in the NHL’s salary cap era, but there’s only a finite amount of patience any team’s fan base possesses. It feels like fans wouldn’t be upset if the Jets embarked on a drastically different direction.

If Hellebuyck sticks around, the Jets have a chance for a big rebound season and a long playoff run in 2026-27. Even if he is traded, there’s still enough of a foundation in place for Cheveldayoff to re-tool and try staying competitive for the foreseeable future. Whether or not that is the best course of action is up for debate.

If Cheveldayoff’s tweaks lead to a rejuvenated Jets squad, they will double down on their current design, spend to the cap ceiling, and make additions at next year’s trade deadline.

As long as the Jets remain in contention, Winnipeg fans will gladly live with whatever 2026-27 and beyond has in store.

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