The occasion has given me a chance to update my speculation on what I'd do if I won. I've learned a little more about how the tax laws work, and (assuming what I've been told is right, which is always open to question -- even when the IRS themselves tells you!) the charitable contribution deduction is limited to half of gross income in a given year. Also, I've been advised that it is no longer legally possible (if it ever was) for me to create a new charitable foundation, claiming the endowment money as a charitable deduction, and then letting the money out over time. I would have to donate the money I wanted to deduct directly to already-existing charities in the year that I got it. Since I want to donate the money to small organizations that would use the money directly for my idea of good, rather than to big established organizations that would use much of it for being large established organizations, disposing of millions of dollars in a single year would be rough. So my current plan would be to take the 26-year payout. Each year, my intention would be to max out the charitable deduction within the year. The rest (after the first year, when I'd put away all the money I'd ever need for myself) I would try to use for worthwhile things, but I wouldn't be limited to tax-deductible worthwhile things, such as funding lobbyists for issues I care about or investing in small businesses which I approve of to give them the freedom to look beyond short-term profits.