You'd have thought this one wouldn't have ended so badly. When Jack Whittaker won $315 million playing Powerball in 2002 -- the largest single jackpot at the time -- he was already a millionaire, so he knew how to handle money. He'd spent decades building a successful water and sewer pipeline company in West Virginia (worth a reported $17 million) and already lavished clothes and gifts on his wife and granddaughter Brandi Bragg, who lived with them part-time.
But winning the lottery gave him something entrepreneurial wealth never did: fame. And that, Whittaker later said, was more than he and his family could handle. He volleyed continual requests for money and endured the public airing of his strip club, gambling and drinking habits. His wife of nearly 42 years divorced him. And then there were the thieves. They stole Whittaker's briefcase containing $545,000 from the strip club, and in another incident, stole $100,000 that Whittaker had left in plain sight on the passenger seat of his car. Some of his employees also embezzled funds.
Although Whittaker set up a foundation that constructed churches, funded college scholarships and donated to those in need, trouble plagued his own family. His beloved Brandi had been only 15 when Whittaker won the lottery. By 17, she was dead, her body found wrapped in tarp behind a junked van. An autopsy revealed recent cocaine use. Not long after, Whittaker's daughter and Brandi's mother, who suffered from recurring lymphoma, was also found dead [source: Samuels].