One thing I like about Jerry Jones is he wants to win.
Two, he's honest about wanting to win.
Although I frowned upon the TO signing, Jerry Jones basically was open about it, saying it's not everyday you get a chance to sign a TO. This involves risk but the upside may be huge. Then he paid TO his money (which is what TO really wanted - to be paid what he was worth) and allowed the offense to flow around TO's talents. Conclusion: a happy TO.
He doesn't play it safe, which causes him to have huge busts but also huge success.