I don’t gamble online, but enjoy watching people play Crash on Roobet (for some reason). If you’re from the US, using a VPN on Stake or Roobet (online gambling sites), you win big, or even win a decent amount, how do you claim with no issue? Since it’s not legal in the US, how to you claim that on your taxes? Obviously if you play the lotto or scratch tickets, you have to pay taxes and can easily do it through the state you live in, but if you win online, on a website that’s not technically legal in US, how do you claim that money and not get in trouble?
The IRS doesn’t care how you get your money, just that you pay taxes on it. They don’t volunteer information to other agencies.
There are lines on the tax form to claim “miscellaneous income”. You tell them how much money you made, and you pay the appropriate income tax for that.
The IRS doesn’t care how illegal your money is, as long as they get their cut. You can also deduct expenses for your illegal enterprise.
The IRS would rather you pay taxes on your illegal income than not at all.
Generally you just have it transfered to your bank account and when tax season rolls around you claim it as casino winnings.
Some of those sites pay out in BTC making it even easier to hide/claim.
You claim it like any other casino winning. It’s not illegal for a US citizen to go abroad and gamble. The IRS is not going to check wether you actually went abroad or not.
Thanks for the answers y’all 
So let’s say that I bought 20$ of BTC and deposited it on an online gambling site for 22.48$ should I report that as a Capitol Gain even though I lost all of it and on top of that I wasn’t actually exchanging it for USD? Don’t online casinos just allow you to view the Balance on your account in the form of USD. I didn’t actually sell it for USD it is just displaying as that on the website right?