Jerry Jones' biggest failure has been not adhering to the meaning of the old saying, "Do not re-invent the wheel." Jones bought the team and what he conceived for achieving ultimate on-the-field success was a wheel made up of Jimmy Johnson and him.
His wheel paid off. Then part of the wheel fell off. Jones mended the wheel with Barry Switzer. The wheel was still new, under warranty and paid off again. Then the warranty ran out.
First, Jones tried being the entire wheel. It did not work. Along the way, Jones has tried mending the wheel with others like Jason Garrett and Will McClay. It still has not worked.
Regardless of what his critics may say, Jones is a brilliant money making machine. The OP proves that point yet again. The league, who initially balked at his revenue initiatives, eventually embraced him--eventually acknowledging his overall impact on the league's profitability and fame by honoring him with a Gold Jacket.
Jones' continual ultimate on-the-field shortcomings has been his refusal to accept that the old wheel stop cutting it decades ago. The best business owners recognize who are underachievers and replace them. It is a very common business practice, even within the National Football League. Commonly, general managers are short-term managers.
Jerry Jones. His wheel is nicked. Dented. Banged up. He keeps jacking up the car, takes the wheel off, pries off the tire, hammers out what he sees, puts everything back together and set off again down another road--leaving fans wondering if the wheel has been mended well-enough to keep the tire pressured. Or watch it fall flat. Again.