The Winnipeg Jets are coming off a relatively unspectacular season, all things considered. They started off hot but cooled off by the second half and nearly fell out of the playoffs. Their season then ended with a thud in a five-game loss to the Vegas Golden Knights in the first round.

Heading into the offseason, the Jets were one of the teams many had an eye on. However, it wasn't because they looked to be big spenders but because they looked to be tearing it down. So far, they've made moves in this direction, like trading Pierre-Luc Dubois and buying out Blake Wheeler.

Winnipeg's roster now looks substantially different, and the team has a different set of expectations as well. With that said, here is the Jets' biggest roster concern heading into the 2023-24 NHL season.

Jets' biggest roster concern deep into 2023 NHL free agency

Team in transition

Yes, the Jets have made a couple of moves to apparently hit the reset button and look to the future. However, one could easily argue that they didn't go far enough.

Two players, in particular, stand out as potential trade targets who have yet to be moved: Mark Scheifele and Connor Hellebuyck.  These two are arguably the Jets' biggest remaining stars, yet both of them reportedly have no interest in signing an extension in Winnipeg.  Despite that, both of them are still on the roster more than a month into free agency.

If the Jets want to keep competing, as they have said throughout the offseason, then this could make sense. After all, having one of your top scorers and Vezina-winning goalie still in the fold is pretty important if the goal is to win. Where this falls apart, though, is the fact that the Jets were just a first-round exit a few months ago, and the second half of the regular season was rough as well. Are the Jets expecting to go further next season after parting ways with two other key players?

What makes more sense is that Winnipeg could be waiting to deal Scheifele and Hellebuyck until the trade deadline. Both players are in the final year of their deals (both make around $6.1 million) and would be very attractive trade targets around the deadline. With how much teams are willing to trade at the deadline, the Jets could get a massive haul for both players.

However, there are a couple of issues with this line of thinking as well. First, the Jets could still get huge hauls for both players right now, possibly even greater than at the deadline, because the acquiring team would be getting them for a full season. Just look at the package they got for Dubois; three NHL forwards and a second-round pick is quite the fetch.

Second, this approach of trading them at the deadline could lead to the Jets overachieving in the first half of the season, then falling back to Earth after dealing these players. If that happens, then it could hurt the Jets' draft position in 2024. For a rebuilding team, which Winnipeg would be after these moves, a lower draft position is obviously not a good thing.

Winnipeg is not having a bad offseason by any means, the return for Dubois alone makes it a good one. However, it's easy to feel like the Jets should've gone all the way with this retool instead of being half in and half out.