I believe he was already wealthy before he won the lotto. He already had a helicopter, wish he would have willed to @HojiYes.
I believe that's a bit of the reason that Jack Whittaker had such problems after he won over $300M. One of the first things he tried to do was give a bunch of money to various acquaintances and his church. He was incensed to discover that gifts could be taxable. At the time, he ranted during at least one news conference on the unfairness of anyone having to pay gift taxes since he had already paid taxes on the money once. I always felt (and this is just my theory) that his attitudes toward legal authorities went to hell after that.
Of course, I don't think he ever complained about the taxes that were presumably paid by all the strippers he showered with cash. Or the people who picked up the money he would throw out the window of his new Lamborghini.
Whittaker's story is nothing but heartache and serves as a great cautionary tale about what can happen when someone who is completely emotionally ill-equipped to win anything gets millions of dollars dropped into their lap.