I honestly, honestly, don't know what I would buy with a $500M lottery.... $300M in cash.
There was a time I could really dream big on that stuff and yes I'd have an airplane and so forth but none of that really interests me anymore. I'd probably buy a Cessna 206, new, and continue a charade that it didn't happen. I'd fly 1 trip a month for Delta so my kids think I have a job and then tell the rest of the family that I was good at investing and pay off their debts.
However, I know I'd buy Sandra Bullock for Timbo. And I'd buy Lance Armstrong for Curly.