I'm not buying that. The McCaskeys had one of the greatest teams of all time and they wouldn't spend the money to keep it. Instead they dismantled the team to save money. Remember, there was no salary cap back then and Bears had nationwide popularity to keep the cash flowing. If they really cared about winning, they would have bolstered that team instead of dismantling it to save money.
If they cared about winning, they wouldn't have let Wanny destroy the franchise over 6 horrible years. If they cared about winning, they wouldn't have kept Sweaty Teddy employed since 1983. Instead they kept on promoting his ass until he became president so the team can wallow in mediocrity for 2 fucking decades.
They are stupid, but not that stupid. The McCaskeys have been around football their whole lives and have more inside info on the game than we'll ever have. If you've been raised in a restaurant and lived there your whole life, and you still think serving rotten meat to your customers is OK, you're either an absolute moron or indifferent to harming your customers. If the problems are obvious to message board meatheads, I'm sure silver spoons with expensive educations are aware too.
I don't think the cheapness label really applies anymore (it absolutely did in the 80s and 90s) but I completely agree with you it's hard to claim they badly want to win when they refuse to make changes such as putting a "football guy" into the President position (that is just one example). I have no doubt they wish they could win but they clearly think they know better than others far more qualified or they wouldn't be so damn stubborn about real organizational changes.