The Winnipeg Jets have some huge decisions to make after losing some key players and risking losing Hellebuyck and Scheifele next season, writes Adam Proteau.

You’re reading THN.com’s “off-season outlook” series, in which we’re examining each NHL team’s recent season, in addition to its strengths and weaknesses, as the 2023-24 season draws closer. We’ve broken down every team in alphabetical order, and today, we’re focusing on the Winnipeg Jets.

2022-23 Grade: C+

Biggest Positive Heading Into the Off-Season

The Jets got into the 2023 Stanley Cup playoffs in no small part due to their 18-7-1 start to the regular season. But anyone who paid close attention to them knew they essentially backed into the post-season, going 12-12-2 in their final 26 regular-season games and landing the final Western Conference wild-card berth. 

Similarly, their first-round playoff series against the Vegas Golden Knights began on a winning note with a Game 1 victory, but Vegas quickly overwhelmed the Jets with four straight wins to take the series in only five games. In the Golden Knights’ four wins, they outscored Winnipeg 18-9, meaning not even star goalie Connor Hellebuyck could make up for the lack of defense in front of him.

Their total collapse left a strong, lingering, terrible taste in the mouths of savvy Jets fans, who could see this was not an elite team they were rooting for. Per the rumor train, Hellebuyck sees the truth of Winnipeg’s status as well, making it apparent he doesn't plan to re-sign with a team that has to give it their all just to be first-round fodder. 

The writing was on the wall for franchise cornerstone forward Blake Wheeler as well, with Wheeler taking a buyout in the final season of his contract and signing as a UFA with the New York Rangers this summer. Jets GM Kevin Cheveldayoff also turned a page for his team by trading top-six forward Pierre-Luc Dubois to Los Angeles.

The Dubois trade – moving another player who indicated he wasn’t interested in a long-term contract extension in Winnipeg – actually turned out to be the best news Jets fans had this off-season. Cheveldayoff acquired two very useful forwards in youngster Gabe Vilardi and veteran Alex Iafallo. That gives them two decent-enough top forward lines, as well as a defense corps that is totally intact from last season.

That said, is that nearly enough for them to keep pace in the competitive Central Division and ward off competitors such as Nashville, St. Louis and Calgary for another wild-card spot this season? We don’t think so. 

The Jets look destined to finish in the mushy middle of the West, not quite good enough to make the playoffs, and not nearly bad enough to land at the top of the draft and set themselves up for a shot at a foundational talent. Management is doubling down on their remaining veterans, and they may very much regret it.

Biggest Need Heading Into the Off-Season

This category may change for the Jets depending on what they get back in any trade for Hellebuyck. And the dealing of top center Mark Scheifele also isn’t out of the realm of possibility, even if Scheifele’s modified no-trade clause (per PuckPedia) makes a trade more difficult to complete. 

As things stand, Winnipeg’s biggest need is more offensive production from its forwards. In 2022-23, they averaged 3.00 goals-for per game, ranked 21st in the NHL.

Adding Vilardi and Iafallo will help them put more pucks into the opposition’s net, but they need more scoring support from their bottom two forward lines to help take pressure off the top two lines. Cheveldayoff has approximately $4.54 million in salary cap space, but he also has two RFAs – blueliner Logan Stanley and forward Rasmus Kupari, who was the final piece that came over from the Kings in the Dubois trade – in need of new contracts. The Jets will likely wind up with something along the lines of $2 million to $2.5 million in cap space.

That won't land them a difference-maker among remaining free agents or in any trade, so barring any dealing of Hellebuyck and/or Scheifele, what you see right now is likely what you’re going to see from them on opening night of the 2023-24 campaign. Not very encouraging.

Bottom Line for Winnipeg This Off-Season

The Jets have made the playoffs in five of the past six seasons, but in their past four post-season appearances, they’ve won just a single series. They’ve also won just eight playoff games in that span. It very much feels like they’re an exercise in diminishing returns, and the departures of Wheeler and Dubois make them a longer shot simply to get to the playoffs. 

Team ownership has no desire to remove Cheveldayoff, frustrating fans who are looking for a new approach and a new era for the franchise. And the desire for many of their players to pull the chute on the team and seek greener pastures elsewhere is extremely alarming for their fortunes in the next few years.

Another administration might have taken the full-rebuild route with the Jets. That is our long-stated preference for any team trying to escape the mushy middle. But this management team believes their core should largely remain in place, and that’s a recipe for more disappointment next season.

Institutional denial of what many others can readily see is an absolute killer for any NHL team’s bottom line, but that’s exactly what we believe is happening in Winnipeg. Last season wasn’t enough of a reality check for Jets brass, and they may be in line for an even starker slap in the face in 2023-24.