He's an intelligent guy and I have a feeling he's very much aware of what the feds have on him and what they don't. He's probably the closest thing to a "classic crime boss" LCN nowadays has. He's got the gangster history and the wealth, he's generally well liked by civilians and mob colleagues alike, he has the political connections, he's living in a million dollar house, etc... He's the type of "boss" you generally see in crime movies and shows and he's actually a real life version of it in this day and age. In itself that's pretty astounding if you ask me.