I don't think you are giving JT enough credit. Yes, he's been involved in some close decisions but by no means were they robberies. If you asked people about the two Hopkins fight, my guess is that about half the people would say JT actually won the fight. And it's easy to see why. It's also easy to see why some would claim that Hopkins won one or both. Point here is that he didn't steal anything. He put himself in position to stay close in those fights. I thought a draw was the right call in the Winky fight. JT hasn't lived up to his expectations but he's not no bum either. The guy is someone you must account for at SMW now.
It would hurt Roy's career. Beating JT would just go to show that Roy Jones isn't shot like people pretend, and that his losses were not due to being over the hill... which I already believe.