I have said this at numerous other forums, and may have put it in a thread here as well, but all I would say is pay the taxes on your winnings and don't worry about the rest. I have been called very colorful names for this advice, but in the doubtful event you do get prosecuted for off shore gambling (in my case the winnings are from sportsbooks and horses) they will look into your financial dealings and if you can't prove you lost money then the IRS will get involved in a hurry. My favorite example of this is Pete Rose, he didn't violate some grey area of the law, he flat out broke federal statutes, and quite a few of them, but what did he serve time for? TAX EVASION and nothing else. If you think sticking your local bookie will get you in trouble, brother you haven't seen anything yet.
I can argue that this is a good idea simply because if you ever get a pyout via check from an offshore outfit the majority of them do have accounts in the US and the check you get wil from a US bank, I have got several and know this is the case, there is a paper trail. Pay the taxes on any winning you would normally claim and don't even think about the rest.
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