Well...The Ilitch family does own a casino.....'
I would call what happened with Kyle Beach significantly more than an "oopsie." It was a massive organizational failure that had dire consequences.
When talking about books and movies and whatnot I see what you're saying because it can be different as it often involves the distant past. But if the Ilitch family had done something like the Wirtz's, I'd definitely have a hard time rooting for the Wings. Probably not forever, but a while (assuming they were still in charge).