He probably had friends in the IRS or paid someone off in the IRS.
Very difficult, if not impossible (to paraphrase Rocco Lampone).
IRS agents are under the very watchful eye of the Justice Department. If an IRS Agent takes a bribe, the forensic accountants will catch them, and they know it.
I'd say that Tony washed his money the way most wiseguys do: Through assorted small businesses. Not one big one.
Plus, I'm sure that as a "Waste Managemant Consultant," he would be smart enough to be on the books for a very substantial salary.
