Originally Posted by
CrackPipes and Kakfights
I talked to my tax attorney about this and, although I realize it may be a grey are, if you are a pro and have earned cash in your "account," it is highly likely going to be taxable income to you in that year regardless of when you pull it off. If in a later year you can't collect you can probably take a bad debt deduction.
I do know that all those people who had fictitious income with Madoff had a real problem because they paid taxes for years on phantom income and had trouble taking the losses.
However detection risk is low (but that is what a lot of people who had Swiss bank accounts also thought).
Poker sites aren't bank accounts, so it's not the same as Swiss bank accounts.
Poker sites holding your money could be said to be an IOU.
Or it could also be looked at that your cashout is "paying" you for "work" you previously did, so the taxable income is considered for the year you get paid.
For example, if I did work on December 28, 2015, but received payment on January 4, 2016, then I would have to declare that income for my 2016 taxes, NOT my 2015 taxes.
Payment matters, date of work does not matter.
http://biztaxlaw.about.com/b/2013/12...ears-taxes.htm
I'm sure that, in light of the COUNTLESS online gambling scandals where people "win" money but never get paid, it could be argued successfully to the IRS that you have not actually earned money on these unlicensed, illegal sites until you actually get paid.
It's a different story on a legal site such as WSOP.com, as that is licensed and regulated by a US entity, and you could not make the case that you weren't sure if you would ever get paid.
I compared this to making drug deals when discussing it on radio. If you make a drug sale in late 2015 but don't get paid until 2016, it's still 2016 income. And if the guy you sell the drugs to never ends up paying you, then you don't have to declare it as income.
I realize that online poker is a bit different, because you can request cashouts at will, but as long as you can show that you kept a reasonable sum of money there for the games you needed to play (for example, I couldn't claim that $200k on Bovada for 30-60 limit is appropriate), then I think you are justified to hold money on there indefinitely, provided you are actively playing.
This is all a grey area and there is no case law on illegal online poker in relation to cashouts and taxes. So I could be wrong, but I think this line is pretty safe.