Lottery Winners Who Lost Everything After Hitting the Jackpot
Winning the lottery is a fantasy for millions of people, but sudden wealth does not always lead to lasting happiness. For many jackpot winners, a life-changing prize brings pressure, unwanted attention, poor financial decisions, and personal tragedy. Some reports suggest that a large share of people who win millions eventually lose their fortunes and return to financial hardship.
When someone receives a major cash windfall, distant relatives, old acquaintances, opportunists, and even strangers may appear looking for money. In the worst cases, lottery winners have been manipulated, threatened, robbed, kidnapped, or murdered by people hoping to benefit from their good fortune.
Still, the greatest danger for many big lottery winners is not always other people. Sudden wealth can magnify existing problems, including addiction, reckless spending, gambling, bad investments, and poor money management. These stories show how quickly a dream prize can turn into a cautionary tale.
Jeffrey Dampier
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Lottery winnings: $20 million
Year: 1996
Bottom line: Jeffrey Dampier and his then-wife won the Illinois Lottery jackpot, but their marriage ended soon afterward. The couple divorced and split the winnings equally, leaving Dampier with a large fortune of his own.
He later met Crystal Jackson, married her, and moved to Tampa Bay, Florida, to be closer to her family. Dampier handled the finances and was generous with gifts, especially for Crystal’s sister, Victoria, with whom he was also having an affair.
In 2005, Dampier was murdered by his sister-in-law Victoria and her boyfriend, Nathaniel Jackson, who was not related to the family. Crystal’s other sister, Terri, was also present at the crime scene. Victoria and Nathaniel Jackson were convicted of Dampier’s murder and sentenced to life in prison.
Abraham Shakespeare
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Lottery winnings: $30 million
Year: 2006
Bottom line: Abraham Shakespeare bought the winning Florida Lotto ticket in Frostproof and chose to receive his prize as a lump-sum payment. After the win, he left his middle-class neighborhood in Lakeland and moved into a gated community, where he lived a fairly quiet life.
Unlike many lottery winners, Shakespeare did not immediately waste his money. Aside from buying a home, he spent some of it on a new car and a Rolex watch. However, he soon became overwhelmed by people asking for financial help, from friends to complete strangers.
One of the people who entered his life was Dorice Donegan “Dee-Dee” Moore, who became his business partner. Moore gained control of company funds and spent millions on cars and vacations, later claiming the purchases were gifts from Shakespeare.
In 2009, Shakespeare was reported missing after his family had not seen or heard from him for months. Investigators were eventually led to Moore’s plot and found Shakespeare’s body buried beneath a concrete slab in her boyfriend’s backyard. Moore was sentenced to life in prison without the possibility of parole.
David Lee Edwards
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Lottery winnings: $27 million
Year: 2001
Bottom line: David Lee Edwards won a $27 million prize, but his fortune disappeared in only a few years. Although he had a money manager who tried to help him preserve and invest the winnings, Edwards ignored much of the advice.
He and his wife, Shawna, spent heavily on luxury purchases. They bought two homes in a gated Florida community, a $200,000 Lamborghini Diablo, a $90,000 Dodge Viper, and even a private plane so Edwards could travel easily between Florida and his Kentucky hometown.
Eventually, the couple developed serious drug addictions. Edwards also supplied drugs to friends, and when some of them died from overdoses, he paid for their funerals. Before long, he and Shawna lost everything. They went from living in a gated community to living in a storage unit, and both contracted hepatitis linked to their drug use.
Shawna later left Edwards and remarried, but she continued to face legal trouble. Edwards died penniless and alone in hospice in 2013 at the age of 58.
Alex and Rhoda Toth
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Lottery winnings: $13 million
Year: 1990
Bottom line: Alex Toth won the Florida Lottery in 1990. He and his wife, Rhoda, chose to receive their prize in installments, giving them about $666,666 per year.
At first, the couple enjoyed their new wealth. They traveled around the world, lived extravagantly, and even met celebrities. However, the money did not last.
Alex’s gambling addiction became a major problem. At one point, he gambled every day in Las Vegas for three months while staying in a hotel room that cost $1,000 per night. The couple also faced tax fraud charges and owed the state of Florida about $2.5 million in overdue payments.
Alex Toth died in 2008 at the age of 60 while still facing tax fraud charges.
William “Bud” Post III
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Lottery winnings: $16.2 million
Year: 1988
Bottom line: William “Bud” Post had struggled with money before winning the Pennsylvania Lottery. He believed the jackpot would solve his problems, but it created even more.
Post received the winnings in installments, but he spent the money almost as soon as it arrived. He bought a restaurant and a used-car business for his siblings, along with a mansion and a private plane for himself.
His fortune attracted conflict and danger. His brother once tried to kill him for the money. Post also allegedly promised to share his winnings with Ann Karpik, his landlady and occasional girlfriend. She sued him for one-third of the prize and won. When Post refused to pay, the court froze his remaining assets, forcing him to sell much of what he had left.
During one incident, Post fired at a repossession worker who was trying to take his car, which led to time in prison. By the time he died in 2006 at age 66, he was living on Social Security.
Michael Carroll
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Lottery winnings: £9,736,131
Year: 2002
Bottom line: Michael Carroll was only 19 when he won the lottery, and his sudden fortune quickly became difficult to manage. Before the win, he worked as a trash collector.
Carroll spent much of the money on drugs, fast cars, and women. His wealth also made him a target. In 2006, his five dogs were killed, and blackmailers threatened his family. His wife, Sandra, left him after he slept with prostitutes.
By 2010, Carroll was so broke that he applied to return to his old trash collector job. He later got back together with his wife and appears to have settled into a more ordinary life. Carroll has said he has no regrets and considers himself lucky to be alive.
James Hayes
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Lottery winnings: $19 million
Year: 1998
Bottom line: Security guard James Hayes was 35 when he bought a winning Quick Pick lottery ticket at a USA Gas Station. After winning, he promised to handle the money responsibly, but that promise did not last.
Hayes lived extravagantly and went through his fortune within about a decade. He declared bankruptcy in 2007. After back surgery, he became addicted to opiates, then lost his home in a 2017 fire and also lost his job. By then, he had turned to cheaper street drugs.
In 2017, Hayes robbed or attempted to rob 11 banks, taking a total of $39,424. After he was caught, he was sentenced to 33 months in prison and ordered to repay the money. He was released in 2020 and began writing a book about his experiences.
Janite Lee
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Lottery winnings: $18 million
Year: 1993
Bottom line: After winning the lottery, Janite Lee moved her family into a gated community in St. Louis, Missouri. Unlike some winners who focused on luxury spending, Lee became known for her charitable giving and political donations.
She donated generously and became a major donor to the Democratic Party. Her new status allowed her to dine with Bill Clinton, Al Gore, and South Korean President Kim Dae-jung.
However, Lee spent money before it arrived, which caused her to fall behind on payments. Penalties and debts piled up. By 2001, she filed for Chapter 7 bankruptcy. At the time, she had less than $700 to her name and about $2.5 million in debt.
Billy Bob Harrell Jr.
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Lottery winnings: $31 million
Year: 1997
Bottom line: Billy Bob Harrell Jr. won the Texas Lotto jackpot in June 1997. At the time, he was struggling financially, so an annual payout of $1.24 million seemed like a blessing.
Harrell quit his job at Home Depot, took his family on vacation, donated to his church, and bought expensive gifts for friends and relatives. But the money also attracted people who wanted to take advantage of him.
He was drawn into several bad business deals and investments, and his fortune began to disappear. His marriage also suffered, and he and his wife separated.
In 1999, Harrell died by suicide. Shortly before his death, he reportedly said, “Winning the lottery is the worst thing that ever happened to me.”
Jack Whittaker
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Lottery winnings: $315 million
Year: 2002
Bottom line: Jack Whittaker was already wealthy when he won the lottery in December 2002. He was the president of a construction company in West Virginia and understood how to manage money. Even so, his massive jackpot was followed by years of personal loss and trouble.
After the win, Whittaker spent much of his time drinking and visiting strip clubs. He was robbed several times, and money was taken from his accounts. In 2004, his granddaughter’s boyfriend died of an overdose in his home. Three months later, his granddaughter died in the same way. In 2009, his daughter also died.
In 2016, Whittaker’s house burned to the ground with everything inside. He died in 2020 and was said to be broke at the time of his death.