Ka-pi96 said:
Sucks for you then that your government is so intent on stealing all your money they're even coming after your gambling winnings.
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If he lives in the U.S. it will be taxed when he comes back home.
Doing taxes he will have to report he made money in a foreign country. That money he brought back home then will be taxed, minus any foreign tax paid. Obviously since Canada is tax free on winnings, that means the whole $5,000.00 will be taxable.
It's why Apple/Google/Ect leave their money overseas. Once they bring it back to the U.S. soil it gets taxed.
So might want to spend that $5,000 in Canada before you come back to the states, unless that is you are a Canadian resident and this does not apply.