He cares about winning, it's just way below a couple of other things on the totem pole of importance to him.
The revenue, the Cowboys being "relevant" and always talked about, him being recognized as a football guy, him meddling and staying "comfortable" and never admitting he's wrong all take a front seat to actually winning....but he does want to win. He just doesn't care enough about it to supersede those other things.
I'm not even sure it will get better when he passes away. Stephen doesn't look better but is still an unknown as to what he'll do. Always two there are, a master and an apprentice.
All the things you mention--the desire to win, wealth, fame, recognition, micromanaging, self-gratification, arrogance--Jerry Jones holds in equal measure. He does not simply see these as separate attainments and aspirations as others do.
Jones is exactly the same individual now as the person who put up $90 million of his own money, borrowed $50 million and bought the franchise. He eliminated the old guard (Landry, etc.), installed his own (e.g. Johnson) and super-aggressively marketed both the franchise and the league. It all "worked." Two Super Bowls. AND a huge return on investment. Ultimate success was attained (and only attained) his way.
He has not changed how he does things. He does not equate what his franchise
has not done after Johnson as
his shortcomings. He would have conceded he was part of the problem by removing himself as GM
like he publicly said he should have. Not winning is the failures of others. He "knows" what it takes to win at everything, both on and off the field, because he has already done just that.
Jones does not think like most people. That is why network cameras caught him totally pissed Sunday. He believes he is a football genius but was taken completely by surprised. Everything he did should have clicked on the field. It didn't. It hasn't for decades.
Most people, especially business people, understands what he purposefully ignores. His business plan for ultimate success became flawed when what actually worked on the field--championship level coaching and equally superior roster building--were removed from it. It is why he keeps stumbling every year and does not fully understand why he trips over his own feet.
In short, he is not the Uncle Jerry people have in their family--someone they know might fail at something and then try to do something differently. Who is he? He is Jerry Jones minus Jimmy Johnson. That's it in a nutshell.