I know the perception of Jerry is he's a free spender, old and wants nothing more then to win a SB before his time is up which is why some might find this thread interesting:
https://twitter.com/JoeyIckes/status/1771297616850026678
The part of me that hates the Cowboys loves this but the part of me that loves sports died a little. What a depressing thing. Imagine having billions of dollars, owning a professional sports team that’s been in your family your whole life, and all you care about is getting another billion.
Yea and honestly I hate it to hear but don't find it surprising. I've met Jerry a few times since then, and once before, and got in his suite for end of a game a long time ago due to mutual friends of his youngest son. They lost and I expected him to be angry and maybe even at some point look over at me and ask who the hell I was sitting up in his suite. I was even trying to lay low(and stuck out like a sore thumb because I was under dressed, every single person was wearing a suit jacket and pants and I was in a pullover and jeans).
Anyway dude was all smiles. Stuffed his face with a hotdog, sat next to me at his bar in his suite and asked what I thought of the place, flashed us a huge grin when we left and thanked us for coming. A real gracious host, always is, I want to give him credit for that but he did not seem the least bit bothered and it was an important loss, 20-17 and dropped them to 8-5. I remember telling my friends afterwards that I get angrier when I lose a fantasy football game, this dude did not seem to give AF. They were all reminding me that he won today no matter what, new stadium, packed house, big day financially. Kind of like what you are saying I found it a bit depressing, I had hoped he'd care more about actually losing. Just remember that being the first time I started to think pro owners might not care about winning as much I assumed, that it might be more the secondary goal.