im pretty sure that whatever winnings you have would be taxed in the tax bracket that they fell into. somewhat vague, but im pretty sure that is how it works.
i am pretty sure that in a casino you have to fill out tax forms for any winnings over 10k, but it is pretty easy to get around that.
hopefully someone else can elaborate on this, as i dont really have any concrete details. my general thought process on this though is that it is better to play it safe. as much as i would hate to give up a significant portion of my winnings to the irs, it is significantly bettert than getting audited/nailed for tax evasion.
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