If this has been going on since 1988 and nothing happened to him over that period, then he was probably reporting any casino winnings to the IRS as required by law. This is probably something that a serious money-launderer would do. One of the best ways to “clean” the money is to do it according to the letter of the law as far as the IRS is concerned.
Paddock used to be an IRS Aagent.