I honestly don't think there has been much of an arc. Jerry is what he's always been - a rich guy who bought one of the most expensive toys in the world, and by god, he's going to play with it.
His best decision as owner remains the very first one he made: to hire Jimmy. Every bit of success he's had over the years flows from that.
I never bought the whole "wildcatter" thing - wow, what a risk, signing Deion Sanders! Only a maverick would do that! And he's routinely credited for being some great salesman, I mean, look at what he's done for the Cowboys! They've gone from the most popular team in the NFL in 1989 to...the most popular team in 2025! Yes, I know they were not doing well financially in '89, but let's be real - it was the most valuable brand in the NFL. All it needed was for someone to come along and pump some new life into it - which Jerry did, thanks to hiring Jimmy.
But his fundamental disrespect for the role of coaches (and professional football people in general) doomed his relationship with Jimmy and prevented him from fielding anything close to the best team he could in the last three decades.
The man is a failure. A rich kid who bought a jewel, dusted it off, and presented it as something that would not exist without him. He's always been that guy. He's still that guy. And his nepo baby son is even worse.