15 Lottery winners who got unlucky after their win
Winning the lottery seems like the ultimate stroke of luck. Millions of people buy tickets every week, dreaming of that life-changing moment when their numbers come up.
But for some winners, striking it rich turned into their worst nightmare. The phrase ‘lottery curse’ exists for a reason, and these stories prove that sometimes getting everything you want can cost you everything you have.
From murder plots to family betrayals, financial ruin to deadly addictions, these lottery winners discovered that their jackpot came with a price tag they never imagined. Here are 15 lottery winners whose ‘lucky’ tickets led them down paths of misfortune, tragedy, and regret.
Abraham Shakespeare
Abraham Shakespeare won $30 million in the Florida lottery in 2006, taking home $17 million after taxes. The 43-year-old illiterate day laborer couldn’t read or write, but he thought his money troubles were finally over.
Instead, Shakespeare found himself constantly pestered by people asking for money, leading him to tell his brother, ‘I’d have been better off broke.’ In 2008, he met Dorice ‘Dee Dee’ Moore, who claimed she wanted to write a book about his rags-to-riches story but actually began stealing from him.
Shakespeare disappeared in April 2009, and his body was found buried under a concrete slab in Moore’s backyard with two bullet wounds to the chest. Moore was convicted of first-degree murder and sentenced to life in prison without parole.
Jack Whittaker
Jack Whittaker won $314.9 million in Powerball on Christmas Day 2002, the largest single-ticket jackpot at the time. The West Virginia construction contractor was already worth $17 million before his win, but the lottery turned his life upside down.
Within a year, thieves broke into his car while it was parked at a strip club and stole $545,000 in cash he kept in a suitcase. His granddaughter Brandi, who received a $2,000 weekly allowance, was found dead in 2004 with drugs in her system.
Whittaker later admitted, ‘I wish I’d torn that ticket up,’ as the money brought him nothing but lawsuits, addiction problems, and family tragedy.
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Urooj Khan
Urooj Khan won $1 million on an Illinois scratch-off ticket in June 2012. The 46-year-old Indian immigrant and dry cleaner owner was excited about using the money to pay off his mortgage and donate to St. Jude Children’s Research Hospital.
His check was issued on July 19, 2012, but Khan died the next day at home after eating dinner. Initially ruled a natural death, further testing revealed Khan had been killed by cyanide poisoning after a family member insisted on more investigation.
Despite an extensive police investigation, Khan’s murder remains unsolved more than a decade later.
David Edwards
David Edwards was a 46-year-old unemployed ex-convict living with his parents when he won part of a $280 million Powerball jackpot in 2001. He took a lump sum of $27 million after taxes and immediately went on a spending spree, buying cars, 200 collectible swords, and homes in Florida and California.
Edwards estimated he spent $12 million in the first year alone. He and his wife became heavy drug users, and within five years the money was gone and Edwards was living in a storage unit contaminated with human waste.
He died penniless in hospice care in 2013 at age 58.
William ‘Bud’ Post III
William ‘Bud’ Post III won $16.2 million from the Pennsylvania lottery in 1988 while struggling with money and odd jobs. He quickly found himself in debt after trying to help his siblings start a restaurant and used-car business.
Post’s brother was arrested for hiring a hitman to kill him and his sixth wife. He was also tricked by his landlady into giving up a third of his winnings.
Post filed for bankruptcy, served time in jail for firing a gun at a bill collector, and was living off disability payments when he died broke in 2006 at age 66, leaving behind his seventh wife and nine children.
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Jeffrey Dampier
Jeffrey Dampier won $20 million in the Illinois lottery in 1996 and invested in a popcorn business while giving millions to friends and family. His generosity couldn’t save him from his own family when his sister-in-law Victoria Jackson, who was having an affair with him, murdered him in 2005 at age 39.
Jackson and her boyfriend orchestrated the murder because she stood to gain from his death.
Evelyn Basehore
Evelyn Basehore, a New Jersey convenience store clerk, won $3.9 million from her state’s Pick-6 lottery game in 1985. Lightning struck twice when she won another $1.4 million shortly after.
Her fortune quickly evaporated as she bought expensive gifts for family members, made terrible investment choices, and gambled her money away in Atlantic City casinos.
Janite Lee
Janite Lee was an immigrant from South Korea working in a wig shop when she won $18 million from the Illinois Lottery in 1993. She moved her family into a mansion in St. Louis and gave $1 million to Washington University School of Law, which built a library in her name.
Lee also donated heavily to politicians, including Bill Clinton and Al Gore. Despite her initial generosity and good intentions, Lee eventually gambled away most of her fortune and filed for bankruptcy.
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Lou Eisenberg
Lou Eisenberg’s $5 million lottery win in 1981 was the biggest ever seen at that time. The New Yorker retired early from his handyman job installing lightbulbs and started following through on nearly every suggestion from friends and family about how to spend his money.
He bought a beachfront condo, traveled the world with his wife, and gave away large amounts due to his kind heart. At last report, Eisenberg was living in a mobile home in Florida, getting by on Social Security of $1,800 per month.
Alex Toth
Alex Toth won $13 million from the Florida Lottery in 1990 and opted to take the money in installments, with annual payouts calculated at $666,666. He and his wife Rhoda lived large, traveling extensively and meeting celebrities including Oprah Winfrey and Donald Trump.
But Toth frittered away much of his money gambling and never hired an accountant to pay his taxes properly. The couple were charged with tax fraud, and just before the case was to go to trial, Alex Toth died of a heart attack in 2008 at age 60.
Tonda Dickerson
Tonda Dickerson won $10 million after a customer gave her a lottery ticket as a tip while she was working at a Waffle House. Her coworkers felt they deserved an equal part of her win and sued her.
She initially lost but won on appeal because she won in Florida but lived in Alabama where gambling was illegal. Dickerson was then sued by the man who gave her the ticket, claiming she promised to buy him a truck if she won.
Her ex-husband tried to kidnap her, but she managed to shoot him and take him to a hospital. The IRS also sued Dickerson in a case they lost, earning her a reputation as one of the unluckiest lottery winners.
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Denise Rossi
Denise Rossi won $1.3 million in the lottery in December 1996, but she didn’t tell her husband about the windfall. Eleven days after winning, she filed for divorce, hoping to start life fresh, single, and rich without sharing the money.
Her plan backfired when her ex-husband discovered the win and sued her for violating disclosure laws. The court ordered her to pay her ex-husband the entire $1.3 million in 20 annual installments, effectively giving up her entire winnings.
Arthur Neal Jr.
Arthur Neal Jr., an 86-year-old grandfather, was found murdered in the basement of a Detroit home in February 2015. Family told media outlets that he had won $20,000 in the lottery shortly before his disappearance, though officials couldn’t confirm the win since the ticket was never cashed.
Prosecutors say 20-year-old Quanzell Hood killed Neal in an attempt to steal the cash, and Hood was sentenced to 23-50 years in prison.
Ronnie Music Jr.
Ronnie Music Jr., a Georgia man, was sentenced to 21 years in prison in April 2017 after he invested part of his $3 million lottery winnings in a crystal meth ring. The 45-year-old purchased large quantities of methamphetamine with money he won from a scratch-off ticket.
Music’s decision to turn his lottery luck into a drug operation landed him behind bars for over two decades.
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Amanda Clayton
Amanda Clayton won a $735,000 jackpot in Michigan but was arrested in April 2012 for allegedly collecting food stamps and public health insurance despite her windfall. The 25-year-old was charged with fraud and sentenced to nine months probation.
In October 2012, Clayton was found dead from what appeared to be a drug overdose.
When Fortune Becomes Misfortune
These stories remind us that money, even when it arrives as a dream come true, can’t guarantee happiness or safety. Many of these winners discovered that their jackpots attracted the wrong kind of attention, from family members who felt entitled to a share, to criminals who saw them as easy targets.
The sudden wealth often revealed character flaws or created new pressures that ultimately destroyed the very lives the money was supposed to improve. While millions still chase that life-changing jackpot, these cautionary tales serve as sobering reminders that sometimes the biggest prize can exact the highest price.
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