Wednesday’s Powerball jackpot is now expected to be an unimaginable $500 million, the second-biggest jackpot in history behind March’s $656 Mega Millions pot. But winning the lottery can have its pitfalls. Distant relatives and fair-weather friends can come clamoring for their share; spouse can turn on spouse; kidnapping and murder can suddenly become very real threats. And sometimes, the greatest danger to the newly well-off can be the winners themselves. Here are ten cautionary tales of some of the biggest-winning losers in lottery history.

Urooj Khan

Illinois Lottery / AP
Illinois Lottery / AP

This undated photo provided by the Illinois Lottery shows Urooj Khan, 46, of Chicago’s West Rogers Park neighborhood, posing with a winning lottery ticket.

Winnings: $1 million
Time until bust: 1 month

Chicagoan Urooj Khan found out the hard way that the lottery isn’t always a winning game. The 46-year-old had sworn off lottery tickets, save for just one more in June 2012, buying a scratch-off at his local 7-Eleven convenience store. And he wouldn’t need a single ticket more after he revealed a $1 million jackpot on the ticket. Khan chose to cash out the reward in one lump sum instead of installments, waiting for his $425,000 check from the state. The check was issued on July 19, but Khan wouldn’t have the chance to cash it — he was pronounced dead the very next day.

Authorities determined his death was of natural causes due to hardened arteries and didn’t conduct an in-depth autopsy since foul play wasn’t suspected. (At 46, Khan was just a year over the cut-off age of 45, which has since been raised to 50). Examiners did gave Khan a simple toxicology test, the AP reports, which didn’t show any traces of opiates, cocaine or carbon monoxide.

But when a relative pressed for a more thorough autopsy in August, the Medical Examiner’s office conducted an extensive chemical test. The subsequent result came as a shock: Khan had actually ingested cyanide, a lethal poison. Though the bitter white powder, which can kill a person in minutes, is widely known as a poisonous substance, Cook County Medical Examiner Stephen Cina says it’s extremely rare. Cina told the AP he’s only seen two cases of cyanide poisoning in the 4,500 autopsies he’s conducted. Chicago police are now treating the investigation as a homicide though they have not yet revealed if there are any leads in the case. Someone did profit off of Khan’s $425,000, though — his winnings were cashed on August 15, likely by his estate.

Andrew “Jack” Whittaker

John Sommers II / Reuters
John Sommers II / Reuters

Winnings: $315 million
Time until bust: 4 years

Whittaker may have been the wealthiest man ever to win a major lottery jackpot. When the 55-year-old West Virginia construction company president won a $315 million Powerball jackpot in December 2002 — at the time, the largest jackpot ever won by a single ticket — he was already worth some $17 million. And Whittaker knew to distribute his new mega-wealth, pledging to give 10 percent of his fortune to Christian charities, donating $14 million to his Jack Whittaker Foundation, and even giving a $123,000 house, a new Dodge Ram Truck, and $50,000 in cash to the woman who worked at the convenience store where he had purchased his winning ticket.

But even Whittaker couldn’t escape his own demons. Beset by legal difficulties and personal problems, he began drinking heavily and frequenting strip clubs. On Aug. 5, 2003, thieves stole $545,000 from his car in a West Virginia strip club parking lot while he was inside. In January 2007, Whittaker reported to the police that thieves had completely emptied his bank accounts. On Jan. 25, 2004, robbers once again broke into his car, stealing an estimated $200,000 in cash that was later recovered. And a string of personal tragedies followed. On Sept. 17, 2004, his granddaughter’s boyfriend was found dead from a drug overdose in Whittaker’s home. Three months later, the granddaughter also died of a drug overdose. Her mother, Ginger Whittaker Bragg, died five years later on July 5, 2009. Whittaker himself is alleged to be broke — a claim he made as early as January 2007 for failing to pay a women who successfully sued him. He’s also being sued by Caesars Atlantic City casino for bouncing $1.5 million worth of checks to cover gambling losses. “I wish I’d torn that ticket up,” he sobbed to reporters at the time of his daughter’s death.

Billie Bob Harrell, Jr.

Getty Images
Getty Images

Winnings: $31 million
Time until bust: 20 months

Billie Bob Harrell, Jr. thought his problems were over when he won the $31 million Texas Lotto jackpot in June 1997. Nearly broke and constantly moving between low-paying jobs, with a wife and three children to support, the first of his $1.24 million annual payouts seemed like the light at the end of the tunnel. Instead, it was the beginning of anannus horribilis for the 47-year-old Texan. It started out joyful: he quit his job at Home Depot, took his family to Hawaii, donated tens of thousands of dollars to his church, bought cars and houses for friends and family, and even donated 480 turkeys to the poor. But his lavish spending attracted unwanted attention, and he had to change his phone number several times after strangers called to demand donations. He also made a bad deal with a company that gives lottery winners lump-sum payments in exchange for their annual checks that left him with far less than what he had won. When Harrell and his wife Barbara Jean separated less than a year later, it was the straw that broke the camel’s back. His son found him dead inside his home from a self-inflicted gunshot wound on May 22, 1999, shortly before he was set to have dinner with his ex-wife. While family members disputed the idea that Harrell could have committed suicide, he clearly wasn’t happy with his life; he’d told a financial adviser shortly before his death that “Winning the lottery is the worst thing that ever happened to me.”

William Post III

Getty Images
Getty Images

Winnings: $16.2 million
Time until bust: 3 months

William Post III proved Notorious B.I.G.’s adage true: more money, more problems. After Post won $16.2 million in the Pennsylvania lottery in 1988, he fell victim to crime, bankruptcy, tragedy and simply poor spending habits. In the two weeks after he received his first annual payment of nearly $500,000, he had already blown two-thirds of it, purchasing a restaurant, a used-car lot, and an airplane. His reckless spending continued; within three months, he was $500,000 in debt. But numbers were the least of his problems. According to Yahoo News, Post’s brother was arrested for hiring a hit man to try to kill him and his sixth (yes, sixth) wife; his relatives convinced him to invest in worthless business ventures; and his landlady duped him into handing over a third of his cash. He ultimately filed for bankruptcy, and faced a stint in jail for firing a gun at a bill collector.

“Everybody dreams of winning money, but nobody realizes the nightmares that come out of the woodwork, or the problems,” Post said in 1993, according to the Washington Post.

It seemed unlikely that the windfall could do anything but good for Post, who had already endured a hard-knock childhood in an orphanage and a nomadic young adulthood. According to the Post, he told reporters that he was surviving on disability payments and had a mere $2.46 in his bank account on the day he won millions. Still, the win did little improve his lot in life, and Post allegedly claimed, “I was much happier when I was broke.” Post died of respiratory failure in 2006 at age 66, leaving behind his seventh wife and nine children from his second marriage.

Keith Gough

David Jones / PA Wire
David Jones / PA Wire

Winnings: £9 million (about $14 million)
Time until bust: 5 years

Keith Gough didn’t squander the majority of his windfall fortune — a group of con men did. After Gough’s wife Louise hit the jackpot in 2005, the family spent their wealth normally: they bought a luxurious new home and Gough rented a $560,000 luxury box to watch his favorite soccer team, Aston Villa.  But he began drinking “out of boredom” after quitting his job at a bakery, he told newspapers, and his wife left him in 2007. While being treated in rehab, he met James Prince, a dastardly-named con man who convinced Gough to join him in a series of shady business deals, allowing Prince to tap Gough’s bank account to the tune of $1.1 million. Gough was also renting a $1.6 million house and paying annual salaries to a gardener and a chauffeur. But his riches wouldn’t be enjoyed for long: he died in March 2010 of a heart attack, believed to have been brought on by drinking and stress. At the time of his death he still had nearly $1.3 million in the bank.

Michael Carroll

Colin McPherson / Corbis
Colin McPherson / Corbis

Winnings: £9.7 million (about $15.5 million)
Time until bust: 8 years

Dubbed the “Lotto Lout” in his native England, Michael Carroll did exactly what those who come into sudden cash are advised not to do: he blew it all on drugs and hookers. According to the Daily Mail, the 19-year-old collected his £9.7 million (more than $15.5 million) in 2002 while wearing an “electronic offender’s tag,” distributed some to family and friends, and then unapologetically frittered away the rest on drugs, gambling and thousands of prostitutes. The British tabloid reported that by 2003, Carroll was allegedly smoking more than $3,000 worth of crack cocaine daily and regularly throwing indulgent parties at his $500,000 home.

Perhaps unsurprisingly, Carroll’s behavior drove away his wife and young daughter. Just eight years later Carroll had already spent all his winnings. He went back to living off his £42 ($67) per week unemployment benefits but claimed the return to a more humble lifestyle suited him just fine.

“The party has ended and it’s back to reality,” Carroll told the Daily Mail in 2010. “I haven’t got two pennies to rub together and that’s the way I like it. I find it easier to live off £42 dole than a million.”

The next year, however, Carroll admitted to having attempted suicide twice after he’d frittered his millions away.

Janite Lee

Ted Morrison / Gallery Stock
Ted Morrison / Gallery Stock

Winnings: $18 million
Time until bust: 8 years

Janite Lee was the rare lottery winner who chose to spend her brand-new wealth on someone other than herself. Lee, an immigrant from South Korea, was working at a wig shop when she hit the Illinois Lottery in 1993. After moving her family into a million-dollar gated community in St. Louis, she spent much of her $620,000 a year on philanthropic efforts. Her political contributions found her dining with Bill Clinton and Al Gore, and her educational donations put her name on a reading room at the Washington University School of Law. But she sold the rights to her annual payment for a lump sum, and in less than a decade Lee was in bankruptcy court to put her debts to rest. When the 60-year-old Lee filed for Chapter 7 in 2001, she had less than $700 to her name and $2.5 million in debts.

Callie Rogers

Phil Noble / PA Wire
Phil Noble / PA Wire

Winnings: £1.9 million ($3 million)
Time until bust: 6 years

When British teenager Callie Rogers won £1.9 million ($3 million) in July 2003, she showered her friends and family with gifts. The then-16-year-old from Cumbria, England treated her loved ones to presents such as cars, homes and lavish vacations. She also spent hundreds of thousands of pounds on partying, breast implants and designer clothing. But in 2009, the Daily Mail reported that Rogers was facing bankruptcy. “I’ve just wanted to make people happy by spending money on them,” she told the tabloid. “But it hasn’t made me happy. It just made me anxious that people are only after me for my money.” She reportedly attempted suicide twice after winning it big and told the Daily Mail she was now ready to embrace her poverty. To make ends meet, she started working three cleaning jobs and moved in with her mother. “My life is a shambles and hopefully now [the money] has all gone I can find some happiness,” she said. “It’s brought me nothing but unhappiness. It’s ruined my life.”

Jeffrey Dampier

Getty Images
Getty Images

Winnings: $20 million
Time until bust: 9 years

Jeffrey Dampier used the $20 million he won from the Illinois Lottery in 1996 to start a popcorn business and to purchase presents for family members — including his sister-in-law Victoria Jackson, with whom he was having an affair. But Jackson turned on him in 2005, when she and her boyfriend Nathaniel Jackson (no relation) plotted to rob Dampier. After the couple bound his hands and feet, Nathaniel forced Victoria to make a choice: “Shoot him or I’ll shoot you,” he reportedly said. Victoria chose to live, and the owner of Kassie’s Gourmet Popcorn in Tampa’s Channelside entertainment district perished from a bullet to the back of his head.

Evelyn Basehore

Jake Rowland / Gallery Stock
Jake Rowland / Gallery Stock

Winnings: $5.4 million (in two separate jackpots)
Time until bust: 15 years

You’d think someone lucky enough to win the lottery twice would respect its sanctity. Evelyn Basehore hit a $3.9 million Pick Six jackpot in 1985 and then won $1.4 million in the same game just five months later, beating odds set at 1 in 15 trillion. But she couldn’t rein in her spending habits. She gave away much of it to friends; much of the rest went to support her hefty gambling habit at the slot machines in Atlantic City. “Winning the lottery isn’t always what it’s cracked up to be. Everybody wanted my money. Everybody had their hand out,” she told Bankrate after she went bust around 2000 and moved into a trailer park in Brick, N.J. She recently admitted to the New York Post that she still plays the lottery from time to time. Can lightning strike thrice?

 

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