7 Lottery Winner Horror Stories You Won't Believe



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Lottery Montage

Riches to Ruin

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.

Waffle House Iconic Southern Restaurant Chain. Waffle House was founded in 1955.

1. 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 proceeded to sue Dickerson, but they lost when the court found that there wasn't an official contract to split the pot. She was then sued by Seward, who claimed that he was promised a new truck; Seward also lost.

Dickerson finally had a moment of clarity regarding how she needed to properly secure her assets, 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

Thief broken glass in car window

2. 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, winning $114 million after taxes. Unfortunately, he was bound for nothing short of an eruption of bad luck thereafter. Thieves ended up stealing $545,000 that Whittaker had stowed away 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. 

Businessman in suit in his office showing an insurance policy and pointing with a pen where the policyholder must to sign. Insurance agent presentation and consulting insurance detail to customer.
Wasan Tita/istockphoto

3. 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 proceeded to use her subsequent payouts to acquire a $200,000 loan from a company that preyed upon lottery winners who lacked financial literacy. After Mullins burned through that loan, she failed to pay the loan company back. The company ended up winning a $154,000 settlement — not a huge win, considering Mullins didn’t have any assets left over to tap into.

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On The Road

4. "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. 

Related: Why You Should Never Play the Lottery


5. 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 as part of 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. 

Related: Whole Lotto Luck: These Are the Luckiest (and Unluckiest) States in America

Tax word on wooden blocks with calculator, pen, magnifying glass and data analysis background. Tax concept
Jerome Maurice/istockphoto

6. 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 over how they'd put $200 down on a car they both needed, so Alex decided that it was a good time to purchase 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. 

Money on top of lottery ticket

7. 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 that wasn’t long for this world. Three months after a series of poorly conceived investments in addition to making some 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.