Win? Win with what? Would you sooner had Chevy sign Chariot & Myers to bad contracts and trade Laine due to cap reasons? Chevy choose to sign our young new core instead of signing older D to bad deals.
Whether you agree or not with the strategy Jets went all in the last two years to win while they had as much of a complete team (due to ELC deals) & aging core as they could. Buff, Little, Wheeler all play significant roles and Jets went for it and fell short like all NHL teams except two of them over those two years. Now they need to rebuild the cupboards with picks & prospects & rebuild the D core. The last two years was their urgency to win and went all in to win, you can't do that every year no team can.
I would sooner they take on a couple bad contracts for picks, but as a private business it's their right to save the money if they like. That is a possibility in a small market team like us, if that drives people crazy I would suggest those people cheer for the Leafs or Rangers who have unlimited money to spend......were not them so people can accept that or cry about it which does nothing or cheer for another team.