Depends on the amounts. If its a legal win they have to pay it. Problem becomes if your gambling 3x your wages and you cant prove savings it goes to Anti money laundering, then you have a more grey area for payment. Rightly so to, you see some crazy stuff attempted. I once had a guy ask if he can give me 50k a week in cash and in return we send to his bank from the casino 35k a week. SO TEMPTING. But you have 2 issues. One – what the hell do you do with 50k in cash a week. You cant just walk it into the bank. Two – Thats 25 years in jail per count, and there are 3 counts (ML, fraud, tax evasion)