[BigF]

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Cardcoutner, BAD IDEA. I hate to be the person who tells you this, but your broker (If they are in the US) has a record of your stock sales and that can screw you depending on what "huge" is. Sorry you have to pay taxes, if you have held the stock for over a year it is only 15% in most cases. Oh and as for that "I would have paid tax on money I don't have anymore" logic that is just crazy talk and you have a limited grasp of the basic principals of taxation and accounting.

Ginko again I hate to be the one to tell you this, but you owe taxes on any money won so yes the money in your poker account is infact taxable. The cardroom is not regulated by the US government and has no reporting requirements so for now the IRS can not 'see' into the poker room so if you decide not to pay taxes they would almost have no way to 'see' that money. The IRS of course can estimate your winnings based on your cashouts or some unknown formula.

Overall the IRS can and will put someone in jail for tax evasion (of course they'd prefer a payment with interest and penalty) but if you make a mistake and made a good faith effort you will generally be ok and just have to pay the correct amount.

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Even the OP gets it.