First of all, unless someone won the entire $330 Million themselves, which they didn't, if they took the lump sum, it would only be ~$160 Million BEFORE taxes. The Usurper, 0bama would want 40% of that, so that leaves ~$ 96 Million. If they took the payments, which I believe is over 25 years, that would wind up about $7.2 Million per year after taxes. (that cumbersome 40%)
If I won it, I would be able to spend about $5-15 Million right off the bat. (new house with some land, pay for the kid's college, new vehicles, a nice yacht and an airplane) After that, I don't what the hell I'd spend it on. I'd probably donate to a few different charities every year. I MIGHT even be able to change how a few of them are run, e.g., the Navy Relief Society, The American Red Cross, etc.