5 Of The Dumbest Lottery Winners Who Blew It All By Making Foolish Decisions (2024)

When someone wins millions of dollars, it’s not always a dream come true. These five people won millions, and now they’ve been dubbed as some of the “dumbest” lottery winners of all time.

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What would you do if you won millions of dollars? You may choose to pay off your mortgage or maybe go on a dream vacation. Would you consult a financial planner or start spending like there was no tomorrow? The last place you’d want to see yourselves is on a list of some of the dumbest lottery winners of all time. How about if you won the lottery not once, but twice?

#1 Evelyn Adams won two different multi-million jackpots in the span of just four months.

According to The Sun, Adams scored $3.9 million in October 1985 and another $1.4 million in February 1986, making her the first person in the history of the New Jersey Lottery to win multiple million-dollar jackpot prizes. Of the 22 states at the time with lotteries, none had had a two-time winner. The odds of winning the first jackpot were 1 in 3.2 million, the second, 1 in 5.2 million.

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Unfortunately, playing the lotto wasn’t Adams’s only addiction. She was also a compulsive gambler. Another issue the two-time winner reported was giving away money to friends and acquaintances, and even when it was a “loan,” nobody felt obligated to pay her back. Ultimately, by 2012, Adams had spent all her winnings, having lost her money to gambling in slot machines in Atlantic City casinos and a string of unsuccessful business deals. “Winning the lottery isn’t always what it’s cracked up to be,” she said while reported to be living in a trailer. “I won the American dream but I lost it, too. It was a very hard fall. It’s called rock bottom.”

#2 Micheal Carroll was dubbed the “lotto lout” by the British press after he won £9.7 Million.

Carroll was indeed a rags-to-riches story. At just 19 years old and while working as a trash man, he scooped up £9.7 million on the lottery in 2002. However, he quickly rubbed the public the wrong way. His wife left him after he blew his winnings on booze, drugs, sex, and friends. According to The Sun, Carroll hosted wild sex parties, which he called “Roman-style orgies,” and he once boasted that he had bedded 4,000 women. The “Lotto Lout” also spent his days partying with pals in luxury destinations such as Jamaica, Barbados, and Puerto Banus.

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His life spiraled out of control. The millionaire, who immediately gave £4 million of his winnings away, appeared in court more than 30 times. The good times came to an end in 2012 with all his winnings blown, leaving the former trash man on welfare for six months. He finally found work in Scotland as a coalman. The one silver lining is his ex-wife took him back and they married again in 2021.

#3 Waffle House waitress Tonda Dickerson was given a winning lotto ticket as a tip.

Edward Seward finished up his cheap meal and handed Tonda Dickerson a lotto ticket as her tip in 1999. Dickerson, a then-divorced woman in her late 20s, won $10 million dollars with the ticket. “But Tonda’s colleagues had a different idea,” The Sun reported. “They accused her of breaking a promise made to other waitresses to share any winnings from the lottery ticket handed over by Seward.” Even Seward sued her for millions.

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In a bizarre turn of events, Dickerson was allegedly “kidnapped” by her ex-husband Stacy Martin who was armed with a .22 caliber handgun. When Martin was distracted, Dickerson got the firearm and shot him in the chest. Martin was rushed to a hospital, but strangely enough, no charges were pressed against anyone for the outlandish kidnapping and shooting incident, AL.com reported. For 12 years after that, Dickerson was chased to pay $1 million in “gift taxes,” on top of hefty income taxes. It was reported that she got a job as a poker dealer at the Golden Nugget casino in Biloxi, Mississippi.

#4 William Hurt won a $3.1 million lottery jackpot in 1989 and ended up murdering a woman.

Prior to 1989, Willie Hurt was a happily married family man who was fairly well known in his community, according to reports. That all changed when he won $3.1 million in the Michigan Lottery. Within two years, Hurt separated from his wife, lost custody of his children, and blew through his fortune, thanks to his newfound addiction to crack cocaine. Hurt was arrested for the murder of Wendy Elizabeth Kimmey, 30, who was found shot in the head.

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Willie Hurt turned himself into the police in Lansing the day the murder took place. According to Ingham County Prosecutor Donald Martin, the altercation that led to Kimmey’s murder started because Hurt was enraged that they didn’t have any more crack cocaine and couldn’t find more. Not much is known about Hurt after that, however, the judge in the case ordered a psychiatric evaluation, the Associated Press reported.

#5 Callie Rogers was just 16 years old and in foster care when she won $2.3 million dollars.

What does a teenager do when they win the lottery? They spend it on boob jobs, tattoos, and luxury cars. According to The Sun, Callie Rogers is Britain’s youngest ever Lottery winner. After winning the lottery in 2003, the British girl quit her job as a checkout girl and started splashing the cash.

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Rogers lavished herself with three breast enhancement surgeries, drug-fuelled parties, and $362,000 dollars worth of designer clothes, theDaily Mail reported. In 2021, Rogers was on welfare and was given a suspended driving license after crashing her 4×4 while high on cocaine when it emerged she had blown her winnings.

The lure of the lottery is that it will magically change your life overnight, but actually winning the big jackpot could make your life a nightmare. As any of these winners-turned-losers would tell you, winning isn’t everything. Especially when you don’t have a clue what to do with all of that money. Spend your money wisely, no matter how much you have.

5 Of The Dumbest Lottery Winners Who Blew It All By Making Foolish Decisions (2024)


What is the biggest mistake a lottery winner makes? ›

7 Biggest Mistakes Lottery Winners Make
  • 2 They get confused about how much they owe in taxes. ...
  • 3 They don't wait long enough to start spending. ...
  • 5 They let it get to their heads. ...
  • 6 They quit their jobs too quickly. ...
  • 7 They don't realize it can come with some profoundly negative consequences.
Feb 23, 2024

How many lottery millionaires go broke? ›

Nearly one-third of lottery winners eventually go bankrupt within three to five years, which is more likely than the average American, according to the Certified Financial Planner Board of Standards.

Who went broke after winning the lottery? ›

William Post. William “Bud” Post was broke when he died in 2006, despite winning $16.2 million in the Pennsylvania Lottery in 1988. It didn't last long. Just one year after he hit it big, Post was $1 million in debt.

Why do most lottery winners go broke? ›

According to the National Endowment for Financial Education, 70% of lottery winners go bankrupt within a few years. Obtaining more money often leads to careless spending and the desire to get more money, and the greed can be destructive to the lives of winners and their families.

Why is Powerball being sued? ›

Powerball and the D.C. lottery are being sued over a website mistake A D.C. resident sued after learning a $340 million winning ticket wasn't legit. His numbers matched those on Powerball's website but those were test numbers, according to court documents.

Who sued the Powerball man? ›

Man sues Powerball lottery after $340M 'win' is denied : NPR. Man sues Powerball lottery after $340M 'win' is denied In early January 2023, John Cheeks saw that the winning Powerball numbers online matched his lottery ticket. But when he tried to redeem the prize, he was told it was a "mistake." Now, he's suing.

Does winning the lottery affect your Social Security? ›

Therefore, any money received through SSDI is money a disabled beneficiary has already earned, which means unearned income such as inheritance, lottery winnings, etc. do not affect SSDI payments.

Can you retire after winning the lottery? ›

For people who earn a modest income, a $2 million lottery win might seem enough to retire on, but it's probably not. Talking with a financial advisor before quitting your job is important. If you hate your job, even a small lottery jackpot might help you transition into a career you'll enjoy more.

What happened to the lady that won $188 million? ›

Spending her winnings

McDow was convicted in April 2016 and sentenced to 10 years in prison.

Do lottery winners get divorced? ›

For women, windfall wealth (at least in the short-term) doubled their desire to divorce within two years after the win. The study noted that while a lottery win didn't necessarily cause a divorce, it accelerated the decision for women who were already unhappy in their marriage.

How long does it take for lottery winnings to hit your bank account? ›

Once the money has been collected, it usually takes five to ten business days to hit your account. Banks are often wary of handling such large transfers, and not all are equipped to handle jackpots. At the earliest, you should plan to receive your lottery winnings between three and four weeks after the draw date.

Has anyone done well after winning the lottery? ›

California. Edwin Castro won the $2.04 billion Powerball drawing in November 2022 and went the lump sum route, taking home $997.6 million, according to the California Lottery. Since then, he had purchased two multimillion-dollar homes in California, as well as a vintage vehicle.

Do most lottery winners regret it? ›

These two studies confirm what common sense would suggest: winning the lottery is usually pretty great. Stories of lottery winners whose lives were ruined by their windfall aren't representative of the experiences of most winners.

Has a lottery winner ever become a billionaire? ›

California seems to have its first lottery billionaire. The state's lottery confirmed that a gas station in Los Angeles County sold Monday night's only winning Powerball ticket, meaning someone out there is free to claim the draw's record $2 billion prize.

Do lottery winners get depressed? ›

Personal Emotional Struggles

The overnight influx of wealth can lead to significant emotional and psychological challenges. Winners may struggle with feelings of guilt, paranoia, or anxiety about their new financial status.

What not to do with lottery winnings? ›

With so much money up for grabs, here's a look at the most common mistakes individuals make when suddenly coming into a fortune.
  • Choosing a lump sum payment instead of an annuity. ...
  • Overestimating your newfound wealth. ...
  • Treating winnings like Monopoly money. ...
  • Not consulting with financial professionals.

What was the Powerball lottery mistake? ›

A man is suing Powerball organizers for $340 million after they "mistakenly posted" numbers that led him to believe he had won the lottery. John Cheeks, 60, thought he had won the Powerball lottery after seeing his numbers posted on the D.C. Lottery's website on Jan.

What are the negative effects of winning the lottery? ›

Here are three of the worst things about winning a big lottery jackpot.
  • Personal Emotional Struggles. The overnight influx of wealth can lead to significant emotional and psychological challenges. ...
  • Risk of Exploitation. ...
  • Relationship Stress.
Jun 14, 2023

Should you pay off your house if you win the lottery? ›

Pay off your credit cards, student loans, mortgage and any other debt you have, even if you have a low-interest rate. It's one less thing to think about and you can afford it. Invest prudently.

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