This is probably the most popular pick that Cowboys fans would dream for. Gruden is a type of guy that can get along with Jerry, get along with the media, get along with players, and still get the results you want. He will cuss you out, be your best friend and cuss out your mother if it means getting the best out of you. His energy is high, he loves football and he hates to lose. He has a history of being a champion and has always coached at a high level. Gruden also seems to love the Cowboys as well, especially Tony Romo. If you don’t believe me, go watch any Monday Night Football broadcast with the Cowboys. The only problem with this pick is that he is getting paid a lot of money to just be a broadcaster, working two days a week during the season. So Jerry might have to open the wallet up a bit if Gruden is going to start wearing Silver and Blue.