Say you win, and you clear $50 million. I would want to give my immediate family (parents, brother, sisters) each a few million, but I don't know how it would be possible to do so without being taxed a second time on the money (taxed first when collecting the winnings, then a second time because it is income to them).___________________________It's not income to them, it's a gift. Gifts are not income, but they are subject to gift tax, which is actually assessed against the donor (giver). Gifts in excess of the annual exclusion, currently, $11,000, are taxable. Taxable gifts are applied against the lifetime exemption amount of $1 million (smaller than the estate tax exemption amount, currently), before you actually PAY a gift tax.As for the charitable angle, remember, you have a contribution limit of 50% of AGI, subject to a 5 year carryover.And you're right about the withholding, but so what? If you have enough charitable contributions, or whatever type of deductions, it just lowers your taxable income, and you get a refund, just like withholding from wages. (Though you ought to consider applying some or all to the next year's estimated taxes, too.)Bill
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