Winning the lottery isn’t all that it’s made out to be. In fact, when you fully digest the scope of these horror stories, it almost seems like a curse.
One of the most common downfalls after winning the lottery? Lack of preparation after a major win. Let these cautionary tales make you think twice the next time you buy a lotto ticket.
When You Overpromise and Underdeliver
In 1999, Tonda Lynn Dickerson was busy muddling through her shifts as a Waffle House waitress when life as she knew it was turned upside down. One Waffle House regular, Edward Seward, left Dickerson a lottery ticket as a tip; a week later, Dickerson won a whopping $10 million. Not only was Dickerson beside herself with excitement, but her fellow Waffle House waitresses were also ecstatic — over the years, they claimed they’d promised to split winnings if one of them ever won the lottery. This is where things went south.
Dickerson decided not to split her winnings. Naturally, her coworkers weren’t thrilled and sued Dickerson, but they lost when the court found there wasn’t an official contract to split the pot. She was then sued by Seward, who claimed he had been promised a new truck; Seward also lost.
Dickerson finally had a moment of clarity regarding how she needed to secure her assets properly, and created a corporation with her family. The only issue? She then failed to pay taxes on the corporation, and the IRS pursued her for back taxes. She ended up losing, and had to pay upwards of $1 million in taxes.
The More You Win, the Faster You Can Lose It All
In 2002, a building contractor named Andrew Jackson Whittaker Jr., based in West Virginia, purchased a golden Powerball ticket and won $114 million after taxes. Unfortunately, he was bound for nothing short of an eruption of bad luck thereafter. Thieves stole $545,000 that Whittaker had stashed in a suitcase in his car in 2003.
After losing another $200,000 a mere year later, Caesars in Atlantic City ended up suing Whittaker for another $1.5 million in checks he’d written that bounced. It’s reported that, in a span of four years, Whittaker’s entire fortune was gone.
Generosity Can Be the Lottery Winner’s Ultimate Undoing
Suzanne Mullins found herself the victorious winner of $4.2 million in the Virginia Lotto back in 1993. Mullins opted to split the yearly payments between her husband, her daughter, and herself, leaving Mullins taking in around $47,000 each year. However, that wasn’t nearly enough to keep her from falling into debt. Mullins’ lawyer reported that she’d ended up giving her uninsured son-in-law around $1 million for his medical bills.
She then used her subsequent payouts to secure a $200,000 loan from a company that preyed on lottery winners lacking financial literacy. After Mullins burned through that loan, she failed to repay the lender. The company ended up winning a $154,000 settlement — not a huge win, given that Mullins didn’t have any assets left to tap.
“Spend, Spend, Spend” They Did
Vivian Nicholson was able to live out her dreams, but did so with such gusto that it contributed to her ultimate fallout.
In 1961, her husband, Keith Nicholson, won £152,300 in Britain’s football pools. Obviously, this was no small win at that time. Beside herself with excitement, Vivian told the media that she was ready to “spend, spend, spend.” Oh boy, did she.
Vivian and Keith went all in on fast and shiny sports cars, a new home, and a completely inflated lifestyle. After Keith’s death in 1965, Vivian was blindsided by a massive tax bill, and quickly declared bankruptcy. It was during this time that Vivian’s battle with depression and alcohol abuse worsened, leading up to her death in 2011.
If You Win Big, Keep It Low-Key
You can lead the most humble and pleasantly uncomplicated life until winning a monstrously oversized lottery win. That was the case for Willie Seely and his wife. In 2013, Seeley was one of three winners in a $450 million lottery drawing. He then had to divide his winnings with 15 co-workers through a work pool, ending up with just shy of $4 million after taxes.
The $4 million was enough for Seely to leave his job, make some fun purchases, and generally proceed through life a bit less weighed down by financial concerns. However, Seely and his wife shared that they felt like the money was a curse, and had to endure constant begging from estranged relatives and attention from the press.
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Take a Step Back and Slow Down
When you go from being worried about how to keep a roof over your head to having an impossible amount of money, making rational decisions can be tough. Consider Alex and Ronda Toth, who won the lottery in 1990 while Alex was on disability and Ronda worked double-time as a nursing assistant.
The Toths were already at a loss about how to put $200 down on a car they both needed, so Alex decided it was a good time to buy a lottery ticket. Allegedly, that lotto ticket purchase left the Toths with $24 in their account. The good news: They ended up winning $13 million—the bad news: The Toths’ estranged children came running with pleading hands from out of nowhere.
Once they’d managed to cut them all off, one of their kids attempted to have them killed. After they’d survived that harrowing life plot, they ended up being indicted by a grand jury for tax fraud. It’s reported that they owed a combined $2 million in back taxes, and were facing up to 24 years in prison. Before Alex could be sentenced to prison, he died at the age of 60 due to his failing health.
After a Lottery Win, Debt Isn’t Even the Beginning of Your Worries
Sometimes, winning the lottery can end up setting you back far more than you could’ve ever imagined. Such was the case for William Post III, who, in 1988, won $16 million, which wasn’t long for this world. Three months after a series of poorly conceived investments and irrational purchases, William Post III found himself beyond broke and $500,000 in debt.
You wouldn’t think that things could get worse, but then the poor guy’s brother hired a hit man to kill Post. The lottery winner ultimately ended up landing himself in jail for firing a gun at a bill collector. In 2006, he died from respiratory failure at 66 years old.
The House In The Blaze
Lara Griffiths and Roger Griffiths had never argued—until the day money changed everything. After they won a £2.1 million jackpot in 2005, they bought a spectacular barn conversion home, a Porsche, and flew to Dubai, Monaco, and New York.
Then disaster struck: their dream home was gutted by a freak fire. Under-insured, they were forced to live in temporary quarters for seven months, while the glamor began to crumble. Amid the smoke and stress, cracks emerged: Roger drove off in the Porsche after Lara confronted him about emails hinting at another woman, and their 14-year marriage ended.
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The Brother-Turned-Hit-Man
William “Bud” Post hit the Pennsylvania lottery jackpot in 1988—$16.2 million. At first glance, the dream had come true.
But within a year, Bud was more than $1 million in debt. A former girlfriend successfully sued him for a third of his winnings. His own brother? Arrested and later convicted for hiring a hit man to kill Bud and his then-wife, hoping he’d inherit the money.
He spiraled: sued, jailed for firing a gun at a collector, divorced, broke—living on $450 a month in food stamps until he died in 2006. He said: “I wish it never happened. It was totally a nightmare.”
The Double-Win That Vanished
Evelyn Adams had what most would call the ultimate “lucky break”: in 1985 and again in 1986, she won a combined fortune of more than $5.4 million in the New Jersey Lottery — the first person in the state to hit major jackpots twice.
At first, the world was hers: she cleared bills, bought a car, opened possibilities. But the very money that was supposed to secure her future became the seed of her undoing. She ramped up her lottery ticket spending, gambled lavishly at Atlantic City, gave away substantial amounts, made risky moves—and in time, the wealth melted.
Today, the same woman who once held multi-million-dollar checks lives in a trailer park. She once said she realised that “having it all” didn’t make the headaches go away—they just got louder.
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