I think that Gruden could do a lot with this offense. He has never - as far as I know - even had a decent QB on one of his teams and he has still won. He has a bit of swagger/attitude about him and I like that as well.
He has a really good offensive mind and I think he and Romo would be outstanding.
I would love him to come here as OC - I know it would never happen though.
A winner is someone who recognizes his God-given talents, works his tail off to develop them into skills, and uses these skills to accomplish his goals.