When Jack Whittaker won the lottery, he didn't really need the money; he was already worth a little over $1 million thanks to his contracting firm, and had a pretty comfortable life in West Virginia. Still, that's not to say that when he won $315 million from a multi-state Powerball, the biggest prize ever given to a winner, the money wasn't welcome. He used it to build churches, donated 10% of his winnings to Christian charities, and even started his own foundation with $14 million called, rather uncreatively, the Jack Whittaker Foundation. 

But, he wouldn't be on this list if things turned out well for him. He was robbed at one point, thieves taking about $500,000 from his car parked outside of a strip club (Where did he even put it, on the passenger's seat?) and he was arrested for drunk driving on one occasion and threatening a bar manager on another. He became an alcoholic, and he divorced his wife. His granddaughter, who he'd been supplying with a weekly allowance of $2,100, died of a drug overdose more or less funded by his checks.

Whittaker later said that he wishes he'd torn the ticket up.