Losing All Your Money
Winning money is the easiest part, Keeping it is a B*#ch for some. 
I’m sure you heard of those classic ‘lottery winner not prepared to handle his winnings’ case, but this one has a moral to it’s story. It’s a typical case of why you shouldn’t trust financial advisors when you’ve just won millions. Andrew Cicero thought he had it made the day he won $5.5 million in a lottery and rode home in a limousine. But 12 years later, the former Muskego resident is living on a pension and Social Security in a Milwaukee apartment. Cicero, 72, has sued a Milwaukee accounting firm over tax advice he says cost him $170,000. He’s also in arbitration with Salomon Smith Barney after losing $600,000 or more in bad investments.
Here’s where he screwed it up. Cicero was due to get 25 annual payments from Wisconsin Megabucks that would start at $98,000 and increase annually. But by 2000, he decided to sell his future payments for a lump sum of about $2 million. He planned to invest the money and live off the earnings and interest. He claims his financial advisers from Salomon Smith Barney had most of his money invested in technology stocks, a move his lawyer said was “breathtakingly irresponsible.”