I think it’s simple- Jerry doesn’t want to win bad enough to do what it takes to win a championship. It’s not a big secret. The winning owners of the last 26 SBs all hired a qualified GM and delegated authority to them, then held them accountable for results. Jerry wants play big shot more than he wants to win.
"...People high in the personality trait of narcissism, who psychologists refer to as everyday narcissists, are people who have a grandiose sense of self-importance or superiority. Everyday narcissists are status-oriented and motivated to pursue goals like fame and financial wealth that either enhance their social status or demonstrate their superiority to others...
...However, I think the larger take away is that personality traits influence the pursuit of meaning in life... For everyday narcissists, financial and material rewards are a meaningful part of life, whereas for people low in the personality trait of narcissism they are not..." - Dr. Andrew Abeyta, Social Psychology, North Dakota State University (PsyPost interview (link)
I agree. The answer is simple. People have been stating the answer for years.
Jerry Jones does want to win. He wants to win his way. You are right. Jones wants to win by amassing enormous wealth while flaunting to the entire world he can be richer than anyone else
and be a football genius at the same time. Most observers should agree that is not a focused personal strategy for winning at all costs in my opinion.
Jones does want to play big shot but the underlying question is why? Why is his motivation isolated on a remote island, while most professional team sports owners are huddled together on the mainland? Jones has been literally spitting this explanation into peoples' faces for decades but it remains largely unaccepted.
HIs inflexible behavior is not simple greed and/or ego. All the other owners share those personality traits but at a far lesser degree than Jones. What makes Jones different from his peers?
Answer: Jerry Jones is a narcissist.