Suspicious circumstances: The future looked bright for India-born Illinois lottery winner Urooj Khan — an owner of several dry-cleaning operations in the Chicago area — when he scratched off $1 million on a lottery ticket he bought at a 7-Eleven. But on July 20, mere days before he was to collect his $425,000 lump sum of after-tax winnings, Khan suddenly died. Finding no initial signs of foul play, medical examiners at first ruled the death to be of natural causes. But after his family insisted his death be investigated further, a toxicology report found lethal levels of cyanide in his blood. While no one knows yet who may have poisoned Khan, an in-law who has had run-ins with the IRS has reportedly lawyered up.

Blowing money on blow: Want to know how to fritter away a multi-million lottery fortune? Ask Michael Carroll: The unemployed Brit has blown a £9.7 million jackpot he won in 2002 (approximately $15 million at the time) and as of 2010, was hoping to get his old job back as a garbageman. At first, Carroll lavished gifts on friends and family, but soon started spending on less admirable causes: Cocaine, parties, cars, and, at one point, up to four prostitutes a day. "The party has ended," he told the UK's Daily Mail, "and it's back to reality. That's the way I like it. I find it easier to live off £42 dole than a million." 

Philanthropic pauper: Janite Lee, a wigmaker who immigrated from North Korea to St. Louis, won an $18 million lotto jackpot in 1993. She used the winnings to better her community, sinking millions into the construction of a nondenominational church and a reading room at Washington University. She also donated so much to the Democrat National Committee that she was ranked 31st on a list of "soft money" donors — right beneath Boeing. Several of Lee's investments turned sour; she spent hundreds of thousands on gambling. Lee filed for bankruptcy in 1997.

Money can buy haplessness: After winning $16.2 million in the Pennsylvania lottery in 1988, William 'Bud' Post should have had it made, but that was hardly the case for the shotgun-toting rough rider of Erie, Pa. "His problems," reported The Washington Post, "included a brother who tried to hire a contract murderer to kill him and his sixth wife; a landlady who forced him to give her one-third of the jackpot; and a conviction on an assault charge, after Mr. Post fired a shotgun at a man trying to collect a debt at his deteriorating dream house in northwestern Pennsylvania." In 1996, the cash-strapped former millionaire auctioned off the rights to his remaining lotto payments. After repaying his lenders, he was again in the clear — that is, until he bought two homes, a truck, a luxury camper, computers, and a $260,000 sailboat. "I was much happier when I was broke," he said. He died in 2006, on a $450-per-month disability check.

The guy who couldn't catch a break: Vietnam veteran Wayne Schenk thought the $1 million New York lotto he won would pay for his costly lung cancer treatments, but he was wrong. New York lottery officials rejected his request to receive the amount in a lump sum. He only received one $50,000 payment — well short of the $125,000 initial outlay required for the specialized care — before he passed away in 2007.

Fool me once, shame on you: In a bizarre twist of luck, New Jersey resident Evelyn Adams won the state's lottery twice — and managed to squander her $5.4 million total winnings. Adams, a compulsive gambler, spent the bulk of her payout at Atlantic City casinos. She wound up in a trailer. "Winning the lottery isn't always what it's cracked up to be," she later told reporters.

Curse of the Powerball: It was called the gift of a lifetime: West Virginian Jack Whittaker won a $315 million Powerball jackpot on Christmas Day 2002. But when strangers descended on him demanding a piece of the fortune, he turned to alcohol and strip clubs. He also lavished cars, diamonds and cash on his granddaughter, 17-year-old Brandi Bragg. Bragg's life as a normal teenager spiraled out of control; she spent tens of thousands on shopping sprees, diamond stud earrings for boyfriends, chartered planes to Vegas — and lots of crack cocaine. Meanwhile, Whittaker's marriage disintegrated as he became notorious for his philandering ways, once offering a local woman $10,000 to strip and dance around in her panties (she declined). In 2004, two years after Whittaker won his fortune, his granddaughter was found dead of an apparent overdose. With the bulk of Whittaker's jackpot merely a memory, Whittaker told reporters his dream Powerball win had turned into a life's nightmare. "I wish we had torn the [lottery] ticket up," he said.

This article — originally published on June 8, 2010 — was last updated on January 10, 2013.