The Bad Luck of Winning - NYTimes.com: "There is, to take one of the most prominent examples, the story of Jack Whittaker, a West Virginia businessman who won a $315 million Powerball jackpot in 2002. A decade later, his daughter and granddaughter had died of drug overdoses, his wife had divorced him, and he had been sued numerous times. Once, when he was at a strip club, someone drugged his drink and took $545,000 in cash that had been sitting in his car. He later sobbed to reporters, “I wish I’d torn that ticket up.” I read about Whittaker, and a host of other sad stories about lottery winners, in a recent e-book written by Don McNay entitled, “Life Lessons From the Lottery.” McNay is a financial adviser and newspaper columnist, based in Kentucky, whom I’ve gotten to know over the years. He specializes in helping people who have come into sudden money. He is convinced that the vast majority of people who win big-money lotteries, like the recent Powerball prize, wind up broke within five years. “The money just overwhelms them,” he told me the other day. “It just causes them to lose their sense of values.” Every once in a while, a lottery jackpot, like the recent Powerball, becomes so large that it attracts national attention. People who normally understand that lotteries are a sucker’s game, can’t resist buying a ticket or two. It all seems like good fun. It is worth remembering the damage lotteries do — sucking money from the disadvantaged, while burdening the winners with sums they can’t handle — and remembering as well this is the doing not of some nasty corporation but of government. Whatever else lotteries are, they aren’t harmless. It is impossible to know whether the Hills will be able to remain “normal” once they cash their nine-figure check. McNay says that those who do the best are the people who are able to remain anonymous, take the money in annual increments, find a good financial adviser who can insulate them from all the new friends they are going to have, and spend their money with some real purpose in mind."