Winning the lottery not as much fun as advertised

And you think you've got problems? 60 year-old Andrew Cicero wins “$5.5 million” in 1995. It's actually 25 annual payments, starting at $98,000/year and then increasing. In 2000 he trades in the remainder of the payments for a lump sum of about $2 million.

Then he lets Smith, Barney invest it. They put about 98% in individual stocks, mostly high-tech. Oops. His accountants tell him that the lump-sum lottery buyout can be treated as capital gains income. Double oops. (He paid almost a quarter million in penalties and interest.) He gets divorced. Triple oops.

He's living on his pension and Social Security now.