America’s Biggest Lottery Winner Jack Whittaker was 57 when he decided to buy a lottery ticket at a small store in West Virginia. A successful businessman who really didn't need to strike it rich, Whittaker played the lottery that day in December of 2002 because the prize was truly a fortune- $314 million. The next morning he learned he had won it all-the largest lottery win in the history of the United States. Whittaker soon surprised everyone with his generosity. He bought property and a car for a worker at the store where he bought the winning ticket. He shared 10 percent of his windfall with his church. He promised to set up a charitable organization to care for the poor of West Virginia. He seemed sensible, saying he’d continue to work at his company and "answer his own phone.” Unfortunately, Whittaker was soon to experience the unforeseen difficulties that come to lottery winners. People would wait for him to drop by his favorite store, and then they would beg him for money-with sad stories of sickness and hard luck. Whittaker had to hire three people just to open letters asking him for money. Reportedly, he grew extravagant with his money. At a local club, he was seen taking out $50,000-just to impress people. Trips to casinos for gambling grew common. He even shut down his charitable organization. Witnesses said he became a troublemaker at clubs, causing problems and growing irate when refused a request. Whittaker loved his granddaughter, Brandy, immensely-she was "his world, " as he said. After winning, Whittaker fulfilled his granddaughter’s dreams: a new car and to meet the hip-hop star Nelly. According to Brandy's friend, she had a constant supply of money; it wasn't unusual for her to receive $5, 000 in one day from her grandfather. With such money, her lifestyle gradually changed for the worse as she started to use illegal drugs with her friends. Her car was full of trash and money-and bills would occasionally fly out the window, according to another friend. On December 4, 2003, Brandy disappeared. When they didn't hear from her over the next five days, the Whittakers called the police. Soon after, Brandy's body was found. She had died from taking a large amount of illegal drugs. Whittaker is struggling with health problems. Reports say none of his fortune remains. And the money may have cost him his beloved granddaughter.