10 Big Lottery Winners Who Lost Everything

Meet 10 lottery winners whose wealth cost them dearly.

While winning the lottery is a pipe dream for most of us, about 70 percent of the people who have won millions end up back where they started, with nothing to their name.

When someone gets a big windfall of cash, distant relatives, fair-weather friends and even complete strangers come out of the woodwork looking for a piece of the pie — they may even kidnap or murder the unlucky lottery winner to get it.

However, what you’ll often find is that the worst enemies of big lottery winners are themselves. Here are 10 of the biggest lottery winners who lost everything.

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 they divorced soon after and split the winnings 50/50.

Dampier still had a sizable bank account when he met Crystal Jackson, who he later married and moved with to Tampa Bay, Florida, to be closer to her family. He took care of their finances and splurged on gifts for the family, particularly her sister Victoria (with whom he was having an affair).

In 2005, Dampier was murdered by his sister-in-law and her boyfriend Nathaniel Jackson (unrelated). Terri, Crystal’s other sister, was also at the scene of the crime. Both Jacksons were found guilty of Dampier’s murder and received 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 the town of Frostproof and chose to take his earnings in one lump sum. He then moved out of his middle-class Lakeland neighborhood and into a gated community, living a generally quiet life. Unlike other lottery winners, he didn’t blow the money — aside from his home purchase, he spent a little cash on a new car and a Rolex watch.

After a few months, he was dismayed with just how many people, from friends to strangers, wanted a cut. One was his business partner, Dorice Donegan “Dee-Dee” Moore, who gave herself control of the company’s funds and bought herself millions in cars and vacations, which she would later claim were gifts from Shakespeare.

In 2009, Shakespeare was reported missing — by that time, his family had not seen or heard from him in several months. Investigators were tipped off to Moore’s murderous plot and found Shakespeare’s body buried under 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: We think that $27 million is a lot for anyone, but if you don’t know how to manage your money properly (or hire someone who does), you may spend it all before you know it. It only took David Lee Edwards five years to spend his one-time payout. while he did have a money manager who attempted to help him keep the cash (or invest it wisely), he chose not to listen to that advice.

Edwards splurged on big-ticket items. He and his wife, Shawna, purchased two homes in one of Florida’s gated communities as well as a $200,000 Lamborghini Diablo and a $90,000 Dodge Viper. He even bought a private plane, so he could get back and forth from Florida to his Kentucky hometown easily.

Soon, he and Shawna became addicted to drugs. He would also supply his friends with drugs, and when they died from overdoses, he paid for their funerals. The couple soon lost everything. They went from the gated community to living in a storage unit and contracted hepatitis due to their drug use.

Shawna eventually left Edwards to get remarried but has been in and out of jail ever since. Edwards died penniless and alone in hospice in 2013 at age 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, took the winnings in installments, which amounted to about $666,666 a year. Together, they lived the high life, traveling the world and even meeting celebrities.

But it wasn’t long before Alex’s gambling addiction took hold to the point where he gambled every day in Las Vegas for three months, living in a $1,000-a-night hotel room. On top of everything else, the couple was charged with with tax fraud and owed the Sunshine State $2.5 million in overdue charges.

In 2008, Alex Toth died at age 60. He was still facing tax fraud charges at the time of his death.

William ‘Bud’ Post III

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Lottery winnings: $16.2 million

Year: 1988

Bottom line: William “Bud” Post always had money issues, but when he won the Pennsylvania lottery, he thought his problems were finally behind him. He took the money in installments but would spend it as soon as he got it, buying everything from a restaurant and used-car business for his siblings to a mansion and private plane for himself.

Once, his brother tried to kill him for the money. Post also allegedly promised to share his winnings with Ann Karpik, his landlady and occasional girlfriend. She later sued him for one-third of his winnings and won. When he refused to give her the money, the court froze his remaining assets. Due to the court’s decision, Post had to sell what little he had left.

As a repo man attempted to take his car, Post shot at him and ended up serving time. He was living off Social Security when he died at 66 years old in 2006.

Michael Carroll

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Lottery winnings: £9,736,131

Year: 2002

Bottom line: Michael Carroll was likely just too young to handle his winnings — he was only 19 when he won Scotland’s Lotto.

He was working as a trash collector when he won and quickly blew the money on drugs, fast cars and women. He also became a target for people seeking his riches. In 2006, his five dogs were killed, and blackmailers threatened his family. His wife, Sandra, also left him for sleeping with prostitutes.

Carroll was so broke by 2010 that he reapplied for his trash collector job. He’s since gotten back together with his wife and seems have settled into normalcy. He states that he has no regrets and is 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. He promised he would be responsible with the money, but that’s not how things went.

Hays lived the high life and went through the money within a decade, declaring bankruptcy in 2007. He then became addicted to opiates after back surgery, lost his home (in a 2017 fire) and his job. By this time, he had turned to cheaper street drugs.

In 2017, he robbed or attempted to rob 11 banks, from which he took $39,424. When he was caught, he was sentenced to 33 months in prison and forced to pay back the money. He was released in 2020 and is currently 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, but instead of spending the money on herself, she had more charitable efforts on her mind. She focused instead on philanthropic donations and became a major donor for the Democratic Party. She dined with Bill Clinton, Al Gore and even South Korean President Kim Daw-Jung.

Lee spent the money before it came in, which put her behind in the many payments she had to make, and on top of what she owed, there were plenty of penalties. By 2001, she had to file Chapter 7 bankruptcy. At that time, she had less than $700 to her name and had accumulated approximately $2.5 million in debt.

Billy Bob Harrell Jr.

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Lottery winnings: $31 million

Year: 1997

Bottom line: Billie Bob Harrell Jr. won the Texas Lotto jackpot in June 1997. At that time, he was broke, and receiving a $1.24 million annual payout seemed like a godsend.

He quit his Home Depot job, took his family on vacation, donated to his church and bought luxury items for friends and family. But his millions also attracted unwanted attention, and he was conned into several bad business deals and investments. His money ran out, and he and his wife separated.

In 1999, he died by suicide. Shortly before he died, he 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: Whittaker was already wealthy when he won the lottery in December 2002 — he worked as West Virginia construction company president. Because he already had money when he won, he knew how to manage it, but that didn’t stop his demons from taking over.

After his win, he spent his time drinking and hanging out at strip clubs. He was robbed a number of times, and his bank account had been drained. In 2004, his granddaughter’s boyfriend overdosed in his home. Three months later, his granddaughter died the same way, and her mother (his daughter) died in 2009. In 2016, his house burned to the ground with everything inside.

He died in 2020 and was said to be broke at the time of his death.