re: Taxes and Crypto

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So what if I deposited money into a offshore sports book, withdrew money using Bitcoin, but do not technically have any gambling winnings because total amount deposited by CC >> than the amount withdrew via bitcoin?

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If you withdrew in BTC, there is no tax event. However, if you trade that BTC for USD or another coin, your cost basis would be whatever the USD value was when you withdrew the BTC from the sportsbook (if you can prove that). If you can't prove that, your cost basis is $0 and you get taxed on the entire value when you make a taxable transaction