A friend of mine and I were having a recent discussion on whether it's risky if one would cash out winnings above a certain dollar amount via ATM machine (although we can't agree on the dollar amount?) with a prepaid debit card and not claim the winnings; again, not saying it is okay to scam any government and not pay your taxes. The dollar amount would surely be a major factor.
For example, the Bookmaker card which is directly connected to an Australian bank (not the states) but still branded by ****. If you read the fine print from this bank, they maintain anonymity but would be forced to give records upon certain legal situations.
I maintain it would be risky, he does not, thoughts?
Also, are there any cappers here that don't keep records of their bets due to the blurred line of the laws with regard to online gambling and just deposit winnings over 10K in their banks and pay the taxes under "other income" instead of from “gambling winnings”?
If so, how does this work? How do you explain 10K, 20K, 50K, 100K, (for example) when you get audited? Neither one of us are even remotely close to being high rollers like the above would indicate, but for the casual player, there has to be some kind of guideline for people to follow, right?
Do you just explain that you have earned income offshore from consulting work? Not sure how one could go about doing this without a lack of documentation. But also, am not familiar with how the IRS would probe a situation like this? Seems like they would be happy as long as you reported any and all income albeit offshore derived or not.
Where is a tax attorney when you need one? Ha-ha.
Any help / input would greatly be appreciated - thanks!