Jerry bought the team for $150 million. Jerry is winning, every year. Jerry continues to win. What's the incentive to make a team better when your investment continues to grow despite consistently mediocre results?
This is the key to what is wrong with them.
I think early in his Cowboys ownership he really cared about winning but that's changed. I've got a lot of friends who are tight with the Jones family inner circle and they've been telling me for a few years now he cares more about cruising around the mediterranean in his yacht then chasing Super Bowls.
I would rank Jerry's priorities this way:
1. Money
2. Fame/attention, celebrity owner, etc,etc.
3. Winning
This sucks hard for fans of pro teams when their ownership gets this mindset. And with so much money in TV, taking the "he won't get another dollar from me" stance is not scaring any of them.