Winnipeg doesnt care about the Cup.
Their only goal is just to be good enough to be in playoff hunt, they’ve shown that with all their moves.
They’ve been a complete mess the last couple of years and nothing has changed.
I think there's a business aspect to this. Rebuilds in small markets take a long time. Buffalo, Ottawa. Edmonton was languishing before they got 2 Hall of Famers in the draft. Even other Canadian markets like Vancouver struggle to get back to the playoffs once they're out.
There's a good chance that, even if they had sold Dubois for futures, and sold Scheifele and Hellebuyck for futures, it would still take 7+ years before the team even sniffed the playoffs again. When you can't speed up the process by a couple of years by signing some good pieces in free agency to augment what you're building, it takes a lot of luck or a lot of time.
Even this current group, including the time in Atlanta - the team went from 2007 to 2015 with one playoff appearance, getting swept by the Ducks in 2015. By the time the team was competitive, it had been 10 years since the team last looked decent, when they won the SE and lost in 4 straight.