I think his idea of winning is different then yours. You want the team to win on the field, he wants the business he owns to be successful financially.
Compare The Cowboys to McDonald's, the CEO of McDonald's could care less if the hamburger they offer is the nastiest one in the fast food market because customers are still going to buy it because of the marketing name. Same for the Cowboys, we fans are still going to buy the product even though the team has not won anything for decades just because of the name. Why should Stephen change anything when he is winning. He has a very successful business.
We just happen to follow a business owner that likes to have a hands on approach with his product he is selling. Other business owners (team owners) have very little input with the day to day operations of their business as they have trusted employees to do that. No matter which way it's done the bottom line is it's a product name and as the owner it's your job to put the product in the market place to create income.