[llleisure]

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raptor,

He is completely 100% incorrect. You absolutely owe taxes on winnings, not withdrawals.

He gave this example: "If you fly to Spain, enter a tournament and win, take the winnings in chips of the casino there if that's an option and place those chips in a casino box in Spain, how is that different than what I'm saying?"

In that example, you absolutely owe taxes on the value of the win.

How likely you are to be caught committing tax fraud of this nature is a whole different question. Just hope nobody turns you in to the IRS after you suck out on them.

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Like I said: Get a CPA and pay him, DO NOT take tax advice off the Internet.

And now, for some tax advice. [img]/images/graemlins/grin.gif[/img]

If you buy a stock and it goes up but you don't sell it, you don't pay tax on the unrealized gain. That "gain" in a stock you never sold when it was up can turn into a loss just like a "win" of chips not cashed in can turn into a loss. 100% certain on the stock angle - first hand experience. How/when/why is an UNREALIZED gambling gain taxed? Is the treatment different if you file as "Professional Gambler" versus not? (Pretty sure answer here is yes but again, ask a professional, not me.)

The point about flying over seas and keeping the winnings in chips was that until the chips are cashed, that isn't a realized gain. I'm NOT saying you shouldn't pay taxes on winnings - if you get access to the money, via a debit card or however else, you owe taxes. But if the money remains in play and can wind up being a net loss, I *really* don't think you have to pay taxes. And that advice is worth exactly what it costs - nothing.

Ask a CPA you are referred to by someone you trust - pay the CPA a fair price for his advice (hundreds not thousands of dollars probably - the advice doesn't come as a % of the money you're asking about) and trust THAT advice.

The IRS web site has all this info if you care to go try and parse it yourself but for the money you're playing with, you really should get a good CPA that does this stuff all the time. Go search on the IRS web site for "gambling income" and "taxable income" and stuff like that if you want...

PS - I'm not just talking out my ass here. I've probably paid more in taxes than many HSNL pros. I've never cheated and always paid what I had to - if anything I probably didn't take as much advantage as many people do. My CPA (a family member) was way too damn honest - try and avoid that quality in your CPA if you can lol.