Sports is mostly about the money in every facet, not just on-ice decisions.
If a season ticket holder for 20 years suddenly loses his job, and temporarily cannot afford to renew his seats, even just for one year...does the team show any loyalty? No, he goes to the back of the line like anybody else, and they happily take the next guy's cash.
If a team significantly underperforms relative to the previous season, are there any decreases in pricing for tickets and merchandise, let alone any noteworthy incentives to the investors? Not a chance.
And I'm not necessarily saying there SHOULD be. Just that sports are business, and teams care primarily about profits, so fans are simply wallets. And while the entertainment industry might finally have the diversity and convenience to change things in the near future, historically most markets have had enough fans on a waiting list in reserve, that it would take a gigantic blunder to put any real dent in the golden goose.
Sure, the PR staff and the broadcasting team sells the story lines and the emotional angle. And I'm sure that on some level, each owner and front office does want to win. But The Detroit Red Wings organization doesn't look at Bob from Wyandotte as a husband with 2 kids and a mortgage, who learned to love hockey by being cousins with Ted Lindsay's neighbor. They see revenue sharing and sales figures and marketing trends, and they make decisions based on financial risk vs return on investment.
And this rebuild is no different, which is my point. The Wings are trying to make safe moves with relatively quick turnaround, to buffer the transition and with primary focus on getting back to selling out LCA, not to chase another Cup at all costs.