1. The health of up and coming star players: Nikolaj Ehlers and Cole Perfetti need to stay healthy for the 2023-24 Winnipeg Jets to stand a chance. Projected to finish right near the playoff bubble line, Winnipeg will need a full 82 games from its speedy forwards. Unable to deliver over the past few seasons, Ehlers and Perfetti have put in the work this offseason, but will that pay off as the rigours of day-to-day NHL play and travel once again do a number on their bodies.

2. Connor Hellebuyck needs to retain his form as a Vezina Trophy candidate: Better yet, Hellebuyck - who just agreed to remain in Winnipeg for another seven years - needs to not only finish as a candidate or finalist, but rather win the trophy as a member of the Winnipeg Jets. Sure, he has voiced his displeasure in a rebuild in the ‘Peg, but a Vezina-winning season should go a long way to helping the Jets get Hellebuyck's ultimate goal of winning a Stanley Cup.

3. Gabe Vilardi finds his touch with Mark Scheifele and Kyle Connor: The Winnipeg Jets’ biggest move of the offseason was unloading Pierre-Luc Dubois to Los Angeles for Gabe Vilardi, Alex Iafallo, Rasmus Kupari and a draft pick. The three players now on the Jets need to prove to management that they made a wise decision. Of those three, it is up to the team’s new top-line winger Vilardi to show his abilities in an expanded role that he never had the chance to see in L.A. Alongside Kyle Connor and Mark Scheifele, Vilardi will need to display his scoring touch to remain that go-to option at the top of the lineup and on the power play.

Most-likely Scenario: The Jets sneak their way into the postseason based off of less media attention towards the now signed Scheifele and Hellebuyck. The two struggle to find the success they have seen in past years, casting some doubts into the eyes of Jets faithful.

Worst-case Scenario: The Pierre-Luc Dubois trade backfires and Gabe Vilardi finds himself as a day-to-day third-line player, unable to hit the 20-goal mark, while Alex Iafallo's season ends with an early injury. Rasmus Kupari demands a trade out of Winnipeg as the cold winter months roll in.