Andrew "Jack" Whittaker was already a millionaire when he won the $315 million Powerball jackpot.
The 55-year-old owned a construction company and had a net worth of about $17 million when he bought the winning ticket in 2002. Years later, he wished he never won the huge sum, Time reported.
"I wish I'd torn that ticket up," he said between sobs when his daughter died in 2009.
Being a savvy businessman, Whittaker distributed his money wisely, giving a hefty chunk to charities: $14 million to the Jack Whittaker Foundation and 10 percent of his fortune to Christian charities.
He even bought a $123,000 house and a new Dodge Ram truck to the woman who sold him the ticket. He also gave her $50,000 in cash.
Yet all the good deeds didn't turn away the tide of bad luck that set upon him after the big win.
Months after winning the jackpot Whitaker was overwhelmed with legal and personal issues. To deal with the stress he gave in to drinking and visiting strip clubs.
Thieves broke into his car outside a West Virginia strip club on Aug. 5, 2003, stealing $545,000 in cash. A few months later on Jan. 25, 2004, robbers again broke into his car and stole $200,000, which was later recovered.
In 2007, Whitaker said that thieves had emptied all of his bank accounts. But the thefts were light matters compared to what happened to his family.
His granddaughter's boyfriend was found dead from a drug overdose on Sept. 17, 2004. Three months later, the granddaughter died of a drug overdose as well.
Whitaker's daughter, Ginger Whittaker Bragg, died on July 5, 2009.
Whitaker isn't the only Powerball winner to face the dark side of fortune after buying the lucky ticket.
Urooj Khan won $1 million from a scratch-off ticket he bought at his local 7-Eleven. The 46-year-old swore that he would never buy another ticket before he bought the lucky one.
Unfortunately, that promise was ominous. He was issued a check on July 19 for the winnings, a lump sum of $425,000, but Khan died the very next day.
Authorities first said that there was no foul play, but when the family demanded a thorough examination of the body, the coroner found that Khan was poisoned with cyanide.
CORRECTION: A previous version of this article incorrectly stated the year Whitaker won the lottery. Whitaker won the jackpot in 2002. The Epoch Times regrets the error.