When William "Bud" Post won $16.2 million in a 1988 lottery, one of the first things he did was try to please his family, according to this Bankrate article.
Unfortunately, his kin was of the unfriendly sort. Post's brother hired a hit man to kill him, hoping to inherit some money. Other family members persuaded him to invest in two businesses that ultimately failed. Post's ex-girlfriend sued him for some of the winnings. Post himself was thrown in jail for firing a gun at a bill collector.
Over time, Post accumulated so much debt that he had to declare bankruptcy. He now relies on Social Security for income. "Lotteries don't mean (anything) to me," he is quoted as saying—after he lost all his money.