7
The winner who lost it all anyway
Jack Whittaker won the largest single jackpot in US history at the time and was broke within years.
$314.9mPowerball, Christmas 2002. He took about $114 million in cash.
Whittaker was already a successful businessman when he won, which was supposed to be the thing that made him different. He gave a great deal away, to churches, to a foundation, to strangers, and was robbed repeatedly, once of over half a million dollars left in a car.
Within a few years the money was gone, his granddaughter had died, and he said publicly that he wished he had torn the ticket up.
His story is the most cited in the genre for a reason: he was neither naive nor reckless with money by the standards of his life before, and it did not help.