Big Lottery Winners Who Went Bankrupt

For most people winning millions—if not dozens or even hundreds of millions—of dollars would seem like it would easily set them up for life so that they’d never have to work another minute ever again. Unfortunately, that’s not always what happens, as there have been many cases of big lottery winners who went bankrupt throughout history.

With incredible sums of cash being given away regularly by the largest lottery institutions around the world, some winners occasionally find themselves overwhelmed upon the realization that they are suddenly sitting on a pile of cash that most people could only dream of. Due to a lack of guidance and foresight, these winners sometimes end up at the complete opposite end of this scenario: bankruptcy.

While some have lost their money due to bad luck and bad people, the downfall of others is purely the result of making one terrible decision after another. Here are a few of the most tragic lottery winner stories we’ve come across so far.

Jack Whitaker, Jr. Wished He Had Torn Up his Winning Ticket

Andrew Jackson "Jack" Whitaker, Jr. of Putnam County, West Virginia, was the sole winner of the $314.9 million US Powerball jackpot—the biggest American jackpot prize ever won by a single winning ticket up until that point—on December 26, 2002. The 55-year-old businessman already had an estimated net worth of $17 million prior to that fortunate event, so he was no stranger to a wealthy life. Despite Whitaker's financial status, his peers described him as a humble person.

Powerball Winner Jack Whitaker Jr.After claiming his $170 million lump sum payment from the Powerball lottery, Whitaker donated more than 10% of that money to charities. He also gave a $123,000 house, Dodge Ram Truck, and $50,000 cash to the lady who sold him the winning lottery ticket. He pampered his granddaughter with gifts as well, including $5,000 in regular pocket money.

However, it didn't take long before Whitaker started frequenting nightclubs and casinos. He also developed a drinking problem along the way. These habits led him to be more reckless when it came to handling money.

In 2003, he lost $545,000 in cash from a robbery while he was parked outside a club. This was followed by a series of personal tragedies that culminated in the death of his only granddaughter in 2004. After missing for weeks, this spoiled grandchild reportedly succumbed to a drug overdose and was found dead in an abandoned van.

In 2007, Whitaker told the police that thieves emptied his bank accounts, and he declared bankruptcy that same year. He was also facing charges for bounced checks he issued to Caesar's Atlantic City casino to cover his $1.5 million gambling debt. To add insult to injury, it was reported in 2009 that Whitaker's house was totally destroyed in a fire.

"I wish I’d torn that ticket up," said Whitaker later in a 2007 interview.

Billie Bob Harrell, Jr.: "Winning the Lottery was the Worst Thing that Ever Happened to me"

Lottery Winner Billie Bob Harrell Jr.Billie Bob Harrell Jr. won the $31 million Texas Lottery jackpot on June 28, 1997. Being nearly broke and accustomed to moving from one low-paying job to another, he opted for the $1.24 million annual payouts of the lottery prize in 25 years to secure his family's future.

Harrell immediately quit his job and purchased a ranch, cars as well as a dozen houses for his family members. He also gave 10% of his winnings to the Cavalry Tabernacle Pentecostal Church as a tithe. He continued his good deeds by distributing 480 turkeys for the poor.

However, Harrell's life took a bad turn when people began abusing his generosity. Relatives, friends, church mates, and even strangers constantly solicited money from him. His family members had to change their contact numbers often because of people harassing them.

The situation was made worse when Harrell's wife, Barbara Jean, filed for divorce in 1998 because of his infidelity and his carelessness in managing his money. The marriage split meant Bob's annual payments from his lottery prize would be divided between him and his wife.

To support his extravagant lifestyle, Harrell sold his 10 years’ of annual payments from the lottery to a company that promised him $2.25 million upfront. Harrell turned a deaf ear to the oppositions of his wife and a family lawyer who told him that he would be losing around $6 million of his annual lottery payouts with the deal.

Harrell eventually committed suicide in 1999 when his financial and marital issues took a toll on him. He told a financial adviser shortly before his death, "Winning the lottery is the worst thing that ever happened to me."

William "Bud" Post III: In Debt Just 2 Months After Big Lottery Win

Lottery Winner William "Bud" Post IIILiving was a constant struggle for carnival worker William "Bud" Post III who had spent 28 days in jail for issuing invalid checks until he won the Pennsylvania Lottery in 1988. The jackpot prize was $32 million but the Erie, Pennsylvania, native shared the money with another winning ticket. Post's $16 million win—$34.5 million if adjusted based on the 2018 inflation rate—was converted into 26 annual payments valued $498,000. That kind of allowance should easily last someone for life, right?


Post immediately went on a buying spree with his first payment. He spent $300,000 on gifts and investments, including a liquor license, restaurant lease in Florida, used-car lot and a twin-engine airplane. His debts ballooned to $500,000 in just three months, and he followed it all up with a mansion purchase in Oil City, Pennsylvania.

Post was later sued by Ann Karpik for a third of his lottery winnings in 1989. Karpik claimed that she had actually bought the winning ticket that Post had cashed. Post promised that he would split the prize with Karpik if the ticket turned out to have the winning numbers. The judge ruled in favour of Karpik, but Post refused to give her share. As a result, the judge froze the rest of Post's annual lottery payments until he agreed to resolve the dispute.

The drama in Post's life was also highlighted by his brother's failed attempt to assassinate him in 1989. By early 1990, Post already declared bankruptcy.

In 1998, Post was arrested on a $260,000 sailboat for evading his 6 to 24-month prison sentence that stemmed from an assault conviction. The assault case was filed after he fired his shotgun at a debt collector in 1992.

By the final years of his life, Post had somehow not only blown all of his money but also got himself $1 million into debt; things were so bad he was living on food stamps and a small monthly stipend. In 2006, less than 20 years after scoring that incredible jackpot, the heavily indebted lottery winner died from respiratory failure at the age of 66.

What Can We Learn From the Big Lottery Winners Who Lost It All?

From what these stories have demonstrated, even the biggest lottery jackpot prizes in history could be gone at a moment's notice without the right financial mindset. Just look at the tragic stories of Whitaker, Harrell, and Post! Despite the many millions they gained through their incredible windfalls, they still managed to lose them all due to a series of bad financial decisions.

Winning the world’s biggest lotteries certainly requires an incredible stroke of fortune, but making your winnings last requires just as much responsibility. Therefore, whether or not you end up like these people or live a meaningful and fulfilling life after you win a massive jackpot lottery is up to you. But if you want to play it safe, here are the top five things you should do after winning the lottery. We wish you the best of luck!

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