Jackpot Nightmares: Lottery Winners Who Lost Everything

Jackpot Nightmares: Lottery Winners Who Lost Everything


September 2, 2025 | Jesse Singer

Jackpot Nightmares: Lottery Winners Who Lost Everything


They Won, Then They Lost

Everyone likes to think about what they'd do if they won the lottery, But sometimes when you win, you actually lose—which is exactly what happened to these people. From big houses and fancy vacations to bankruptcy and hitmen, it's true that winning millions of dollars changed their lives...but it was definitely for the worst.

You won't believe how bad things got for these big winners.

William "Bud" Post ($16.2 Million)

Post won $16.2 million in the Pennsylvania lottery in 1988. But by the end of 1989, he was $1 million in debt.

He lost money in a number of family businesses, a former girlfriend sued him for a third of the winnings (and won), and his brother hired a hitman to take him out in the hopes of inheriting the cash. "It was totally a nightmare," said Post—who lived the rest of his life on food stamps and $450/month.

Gettyimages - 503640774, Business graph with arrows tending downwards - stock photo Business graph with arrows tending downwardsPeshkov, Getty Images

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Marva Wilson ($2 Million)

What happened to Marva Wilson's winnings is one of the saddest stories on this list—because she didn't spend all her money or waste it on extravagances. Instead, it was basically stolen from her by a woman named Freya Pearson...

Mikhail NilovMikhail Nilov, Pexels

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Marva Wilson ($2 Million)

After winning the Missouri lottery in 2008, elderly Marva Wilson became the target of Freya Pearson—a scam artist with kind words and bad intentions. Pearson ended up talking her way into Wilson's life and bank accounts, and soon all the money was gone (and Pearson was heading to prison for five years).

Man in JailRon Lach, Pexels

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Denise Rossi ($1.3 Million)

In 1996, Denise Rossi won $1.3 million in the California lottery. That's great, right? Well, it actually turned out great for her husband Thomas Rossi, who she tried to quickly divorce just after winning all that money. The problem was that she didn't tell her husband about the money beforehand. So, he took her to court and...

Lillian Leitzel factsShutterstock

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Denise Rossi ($1.3 Million)

The judge in the case ruled that Denise had intentionally broken asset disclosure laws to hide the jackpot winnings. And, this is the best part (for Thomas, at least), the judge awarded every dollar of the winnings to Thomas.

Nightmare clientsShutterstock

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Ibi Roncaioli ($5 Million)

An Ontario woman, Ibi Roncaioli, won $5 million in a 1991 lottery draw—and the choices she made with the money ended her life.

You see, she didn't tell her husband that she gave $2 million of the winnings to a secret child she had had with another man. And when he found out, he poisoned her with painkillers.Pills in waterFactinate

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Lara And Roger Griffiths ($2.76 Million)

Supposedly, prior to winning the big lottery jackpot in England in 2005, Lara and Roger Griffiths never argued. But that all changed after they became millionaires.

Hard Cash on a BriefcasePixabay, Pexels

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Lara And Roger Griffiths ($2.76 Million)

Well, first came the million-dollar barn-converted house, the Porsche, and the extravagant vacations. Then came the 2010 fire that destroyed their underinsured home, Roger driving off in the Porsche after being confronted by Lara in regards to emails about another woman, and the end of their fortune and their 14-year marriage.

Not supposed to seePexels

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Evelyn Adams ($4.5 Million)

Evelyn Adams didn't just win the lottery, she won the lottery twice. That's right, in 1985 and 1986, Adams won jackpots that ended up totalling in the $4.5 million range. Unfortunately, her luck ran out after that and she ended up gambling it all away in Atlantic City.

John Huston FactsWikimedia Commons

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Jack Whittaker ($314 Million)

In 2002, West Virginian construction worker Jack Whittaker became the biggest lottery winner of all time when he won the $314 million Powerball jackpot. Whittaker loved handing out money to family, friends, churches, diner waitresses, strangers... But instead of feeling lucky, he ended up—as he told ABC News—feeling like he was cursed. His wife left him, his house burned down, and he got in trouble with the law.

Jack Whittaker ($314 Million)Scott Gries, Getty Images

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David Lee Edwards ($27 Million)

In 2006, David Lee Edwards was broke and living with his wife in a storage shed—the shocking part is that in 2001, he won a $27 million jackpot. That's right—in just five years it was all gone. In fact, within the first three months, he'd already spent $3 million and that trend continued when, by the end of the first year, $12 million was out the window.

When he passed away in 2013 at the age of 58, Edwards wasn't just broke, he owed thousands of dollars.

David Lee Edwards ($27 Million)The Full Story Of The Man Who Won $280M (David Lee Edwards), Millionaire Post

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Mickey Carroll ($11.8 Million)

Imagine winning $11.8 million when you were 19 years old. Well, that's what happened to British teen Mickey Carroll (AKA the "Lotto Lout", as he was dubbed in the press). Maybe you would've been smart with the money and made it last and grow—but that ain't what Carroll did.

Mickey Carroll ($11.8 Million)Mickey Carroll Lottery Winner | Winning £10 Million & Losing It All | Lockdown Documentaries, LockDown Documentaries

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Mickey Carroll ($11.8 Million)

He raced through the money on parties, jewelry, cars, and other such things—and by 2016, he was working in a slaughterhouse for a few hundred bucks a week.

Mickey Carroll ($11.8 Million)Mickey Carroll Lottery Winner | Winning £10 Million & Losing It All | Lockdown Documentaries, LockDown Documentaries

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Gerald Muswagon ($10 Million)

In 1998, Gerald Muswagon won the $10 million Super 7 jackpot in Canada—but he couldn't handle the newfound wealth or fame. Muswagon partied a lot, bought a new house, and was very generous with his friends (buying them cars and TVs, etc). He also dropped a bunch of money into a logging business that failed. Just seven years after winning $10 million, Muswagon took his own life.

People partying with a dicso lights in a barPatrick Black, Jr, Pexels

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c($18 Million)

Janite Lee was a South Korean immigrant working at a wig shop when she won $18 million in the Illinois lottery in 1993. Her intentions with the money were good—but maybe they were too good? Lee donated massive sums of money to educational, political, and social causes—and within eight years, she filed for bankruptcy with $700 in her bank account and $2.5 million in debt.

BankruptcyViarami, Pixabay

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Alex Toth ($13 Million)

When you win the lottery, you can usually decide to get all the money in one lump sum or have it split up into annual installments. And while the latter would seem to be the smartest way to do it in order to make it last—Alex Toth proved that isn't always the case.

Money on the couchTima Miroshnichenko, Pexels

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Alex Toth ($13 Million)

After winning $13 million in 1990, he was set to receive annual payouts of $666,666. Well, his over-the-top lifestyle meant that eventually those payments weren't enough. Toth and his wife split, he checked himself into a mental institution, and he was eventually charged with tax fraud by the IRS.

Life-Ruining Secret FactsShutterstock

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Curtis Sharp ($5 Million)

New York resident Curtis Sharp won $5 million in 1982. However, the money didn't last long—thanks to casino visits, reckless spending, and multiple marriages and divorces that took big chunks out of the bank account.

Curtis Sharp ($5 Million)NY lotto classic tv commercial 1985, commercial classics 1975 - 1985

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Lisa Arcand ($1 Million)

Lisa Arcand, of Massachusetts, won $1 million in 2006—and given some of the other stories we've seen, the fact that it lasted her four years seems almost impressive. But in the end it was all gone—due mostly to the failure of a restaurant she opened in her hometown of Lawrence.

Trendy RestaurantsPixabay, Pexels

Sharon Tirabassi ($10 Million)

Tirabassi was a single mother living on welfare when she won 10 million Canadian dollars in the Ontario Lottery, and for almost 10 years life was good: houses, vacations, parties, etc. But it was less than a decade before she was once again renting an apartment and riding the bus to her part-time job.

"All of that other stuff was fun in the beginning, now it's like, back to life," she told The Hamilton Spectator.

Sinitta LeunenSinitta Leunen, Pexels

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Billy Bob Harrell Jr ($31 Million)

In 1997, Billy Bob Harrell Jr was a Pentecostal preacher working as a stock boy at Home Depot when he won $31 million in the Texas lottery. But the answer to his prayers soon became this preacher's living hell. Near the end of his life, he was quoted as saying: "Winning the lottery is the worst thing that ever happened to me".

Luckiest People factsWikimedia Commons, Santeri Viinamäki

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Billy Bob Harrell Jr ($31 Million)

Along with the trips, multiple houses, and a bunch of cars,  Harrell Jr was generous to a fault and unable to say no when asked for money. Throw in a few other financial troubles and it was all too much for Harrell Jr, who ended up taking his own life.

Men Cry FactsShutterstock

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Urooj Khan ($1 Million)

Remember Ibi Roncaioli, who was poisoned by her husband? Well, she isn't the only lottery winner to suffer said fate. The same thing happened to Chicago businessman Urooj Khan, who passed away in 2012, just a few weeks after winning $1 million (he hadn't even received the money yet).

Co-Worker KarensShutterstock

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Urooj Khan ($1 Million)

At first, his passing was thought to be of natural causes—but further investigations revealed cyanide was involved. But unlike the Ibi Roncaioli case, where the perpetrator was known, the person (or persons) involved with Khan's passing have never been determined.

Investigation boardFer Gregory, Shutterstock

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Keith Gough ($11 Million)

When Keith Gough passed away in 2010, he was broke and alone and drinking his troubles away. This sad ending was made even sadder by the fact that just five years earlier, Gough had won almost $11 million in a British lottery. But extravagant spending, gambling on racehorses, and being conned out of $1 million was what led to the state of his life only half a decade after becoming a multi-millionaire.

Keith Gough ($11 Million)David Jones - PA Images, Getty Images

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Luke Pittard ($1.9 Million)

$1.9 million is a lot of money—but it doesn't go as far as some people think it does these days. Well, not just these days, back in 2006 as well—which is what McDonald's employee Luke Pittard found out when he won a British jackpot for just under 2 million bucks. Because...

Ray Kroc FactsFlickr

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Luke Pittard ($1.9 Million)

It was just 18 months later—after a trip to the Canary Islands, a wedding, and a house—that Pittard was working at McDonald's. But he didn't seem too stressed out about it either.

"They all think I'm a bit mad but I tell them there's more to life than money...I loved working at McDonald's before I became a millionaire and I'm really enjoying being back there again".

Workers serve customers at McDonald's restaurant.8th.creator , Shutterstock

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Jeffrey Dampier ($20 Million)

In 1996, Jeffrey Dampier won $20 million in the Illinois lottery. 11 years later, his life ended in his truck.

At first, things were good. He moved his family to Florida, gave millions to his friends and family, and invested in a popcorn business. But there was one person who didn't want some of his money—she wanted it all.

No power herePexels

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Jeffrey Dampier ($20 Million)

Victoria Jackson was Dampier's sister-in-law and his secret affair partner. And she wanted the money. So, she and her new boyfriend lured Dampier to a secluded meeting spot and ended his life.

Scorched earthShutterstock

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