Tony was a yuppie gangster. He even admitted it in the first season when he was talking to his mother about going to the retirement community. And because he was a yuppie that was only concerned about himself and the disrespect he showed to some of the older gangsters in his family and New York I don't think he would have fared well in prison. In the end if he was facing a major RICO indictment I think he would have flipped.