He just wants to be recognized as one of the guys.
I forget which book it was outlining the early 1990's Cowboys, but there was a story in there about how shortly after the Cowboys won the Super Bowl one year, Wandstadtt, Jimmy, Bob Ackles, and a few others were all sitting at a table talking. Jerry strolled up, drink in hand, and wanted to make a toast. He had recently fired Ackles, and this was when Jimmy was getting tired of him and all that. So he didn't have get a warm reception and he basically told them to fuck off and stormed off in a rage.
That might've been the day he made the any of 500 coaches comment.
But it shows how more than anything, he wants to fit in and be one of the guys. All those guys at that table had busted their ass griding in the industry for years. And this jackwagon thinks he can just buy his way into the club.
You know, with how dumb Cowboys fans are, and how good of an owner Jerry Jones is otherwise... he could be reverred as an owner. Absolutely loved and adored, if he would just get out of the way, and hire the right people.
His team would have more success. He'd still be rich. The fans would love him as an owner.
But he cares more about having control and making the decisions.
Its baffling.