Lottery Winners Who Battled The Challenges Of New Fortune

We often fantasize about winning the lottery and think up all the wonderful things we would do if millions of dollars landed in our pockets. Some dream of a private jet or yacht, and others want to live a wild lifestyle, free of all financial burden.


Unfortunately for some, there are a few people who cannot manage money as well as others – as we will soon find out. These people were caught lying, cheating, stealing, or wasting their winnings often leaving them worse off than before they won. For these unfortunate souls, it would have been best had they never bought that dreaded lottery ticket.

Stole From His Own Mother

In May 2011, Etta May Urquhart won $51 million – a lot of money by anyone’s standards. It’s always important to remain humble in these situations and make sure you set up a responsible financial plan. However, Etta May hadn’t planned on preparing for the wrath of her own son! Ronnie Lee Orender signed for the ticket on her behalf and went on a binge.

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He bought four houses, 10 cars, and a boat instead of putting the money towards caring for the family. They went to court and settled for an undisclosed amount in 2013, but it’s unclear if the family dynamics ever recovered.

‘Spend, Spend, Spend!’

In 1961, a woman called Vivian Nicholson won the equivalent of $33 million after betting in various football pools. Lucky, right? She vowed to ‘spend, spend, spend’ her winnings, which are often famous last words.

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Soon after buying sports cars, fur coats, jewelry, and traveling, she ran out of money. Her husband then died in a car crash and she remarried four times before dying of alcoholism. Ouch.

Be Careful Who You Trust

A lot of friendship groups sometimes pool together to try to increase their chances of winning the big jackpot. That’s what Americo Lopes did, alongside five of his colleagues. The good news is they won $38.5 million.

The bad news, however, lies with Lopes’ greedy nature. The five colleagues never knew they won, since he kept the result to himself. However, they had a hunch when he quit his job a few days later. Awkward.

A $9 Million Loss

Edward Seward was such a regular at his favorite Waffle House that he would often buy the staff some lottery tickets as a light-hearted sign of affection. When one of the waitresses won, however, she didn’t share his generosity.

Tonda Lynn Dickerson argued that she had never agreed to actually share the winnings, and so so tried to run away with the $10m. Although she won the court case, she faced IRS troubles and ended up giving 90% of it away.

Too Much Charity

Janite Lee experienced the American Dream when she won the lottery soon after moving to the US in 1993. Originally from South Korea, she moved her family into a gated community before giving the rest away.

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She had a fine life, dining with the likes of President Bill Clinton and Al Gore – until she lost attention and went bankrupt. By 2001, she had less than $700 to her name. We hope she bought some good legislation first.

Cheating the System

Amanda Clayton used to rely on food stamps to eat each day. When she won $1 million, however, it would have been a good time to stop relying on the government.

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She never told them – and kept using them – before being charged with fraud. She was given a 9-month probation sentence but passed away due to a drug overdose before she finished it.

Divorce And Betrayal

When Denise won the lottery, she figured it was a perfect time to leave her husband. After 25 years of marriage, she filed for divorce. Who needs deadweight, right?

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Well, turns out Thomas Rossi was smarter than she thought, and after he realized she was leaving him for money the divorce settlement entitled his to all of it.

Sip and Snort Your Winnings

There’s always a chance that winning the lottery will lead to a life of debauchery and partying. For Michael Carroll, he thought his $13 million would be enough to last a lifetime of partying. He drank, smoked, and snorted his money for five years, living a care-free and wild life.

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It would all end badly, however, after he ran out of money after just five years and ended up in prison (twice!). Today, he is a shortbread packer and earns $260 a week.

Robber Turned Winner

In 2006, Timothy Elliot was arrested for robbery in Cape Cod. His sentence was probation, which including not being allowed to gamble or buy lottery tickets.

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He defied the court and ended up winning $1 million. The judge let him keep the money, since “It was the purchase of the ticket that violated his probation, not the fact that he won.”

Death by Lotto

2006 seemed to be a bad year overall for lottery winners. When Abraham Lee Shakespeare received $30 million from a jackpot in Florida, he was rightfully over the moon. He decided to do the wise thing and invest his money in business ventures and try to grow his fortune in a responsible way.

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Three years after his win, Abraham went missing. Soon after being reported as a missing person, he was found under a slab of concrete – shot and killed by his own business partner.

Inheriting a Debt

When Bud Post won his $16.2 million fortune in 1998, he spent $300,000 immediately on gifts and investments. He wanted to enter the food and liquor space, buying a license, leasing a property, and becoming a businessman. After seven failed marriages, he generally stayed to himself.

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After his win, friends kept begging him for loans, ex-partners would try to sue him for his fortune, and his own brother tried to have him killed. When Bud died in 2006, he was $1 million in debt.

What’s Crazier Than Losing Money Once? Doing It Twice.

Amazingly, Evelyn Adams won the lottery twice. Back-to-back in 1985 and 1986, she amassed a $5.4 million fortune. Much like others in this story, her money didn’t last long: she blew a lot of her finances on gambling in Atlantic City and a series of bad investments.

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She now lives in a trailer park, where she often reminisces about the advice she gave herself the first time she won. “Why should I let this upset my life? It was a big change and a phenomenal event. I said I just couldn’t let my life go upside down.” Perhaps she’s waiting for ticket number 3?

An Expensive Drug Habit

Another unfortunate example of people turning to drugs after their jackpot. In 1989, Willie Hurt won $3.1 million, most of which ended up in his nose.

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After two years, he was divorced, separated from his children, and charged with attempted murder.


Two years after Luke Pittard won $2 million, he ended up back in his same job flipping burgers at McDonald’s. After spending his winnings on a fancy wedding, lavish vacations, and a new house, he could no longer afford to live a life without a job to pay the bills.

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It’s not all doom and gloom, though. Luke is still happily married and says he enjoys his job, and even kept a bit of his fortune that collects interest. As long as he’s happy, healthy, and stable, who cares, right? Good for him.

Winnings of a Preacher Man

What happens when you give a generous person the chance to change the world? Billie Bob Harrell Jr. won $30 million and suddenly attracted the attention of everyone in his local community. As a preacher, people often traveled to see him and tell him their problems, knowing there was a way he could help.

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The problem is, he helped too much. He gave away almost all his money to other people and had to return to work only one year after collecting his winnings. Still, this may be the most altruistic person on our list.

Money Doesn’t Bring Happiness

1998 was a bad year for Gerald Muswagon, who won a whopping $10 million in the lottery. He didn’t know it at the time but it set forth a series of events that would end his life.

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First, he partied too much. There was the normal behavior of indulging in drugs, drink, and women. Then, faced with the realization he would have to return to work to support his girlfriend and six children, he noticed how his relationships had all disintegrated. Seven years after winning his fortune, he hung himself in his parents’ garage.

Living Luxuriously

After winning a ‘modest’ $1 million in 2004, Lisa lived her best life. She bought a house, went on vacations around the world, and even opened up her very own restaurant. Life was good – for about three years.

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Lisa had opted for the lump sum option and had quickly found she had run out of money. Her business was a failure, her house was too expensive to run, and she had run out of money.

Live Large, Run Dry

10 years is a long time to live a rich lifestyle, but it must hit hard when it all comes to an end. For how that must feel, we can always ask Sharon Tirabassi. This lottery winner received a lump-sum of $10 million in 2004, and has since returned to her life of riding the bus and working part-time.

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She blew her fortune on extravagant purchases, but it’s nice to know she got to live a good life while it lasted.

Spending Time

The disadvantage of receiving monthly payments means you may not plan for the time those checks stop coming. After Lou Eisenberg won $5 million in 1981, he opted for the installments of $120,000. The problem was that he always knew there was another check coming so he didn’t bother to save.

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Problems started when the last check was cashed and he realized he had spent all his money. Today, he lives off social security where he receives $1,000 a month. Quite the change from his lottery days!

Losing The Ticket (And His Mind)

Losing your money when you have it is bad enough, but losing a winning ticket before it’s cashed is probably the worst thing you can do. Ian Galtress lost a ticket worth $1 million.

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“It’s ruined my life. I’ve lost lots of weight. I’m not sleeping because of the anxiety.” He spent 20 months after ticketgate living with a defeatist mindset. “I’ve got this permanent feeling of anxiety and nervousness in my stomach. I just can’t switch off.”

The Poisoned Winner

Urooj Khan couldn’t believe his luck when he saw his winning numbers appear on the television one night. He realized it would change his life forever. Tragically, he never got the chance to receive his winning check of $1 million as he was poisoned just days before it arrived in the mail.

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His plans of expanding his laundry service were cut short and police are still looking for the suspect. There are no ideas what happened to his fortune.

Cherish Anonymity

Another shameful example of how the fame you could receive with a lottery win can kill you. When Ibi received $5 million in 1991, she gave 40% of it to the child she conceived with a man who was not her husband. When her current spouse found out, he murdered her.

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Be careful who you trust – you never know who will turn their back on you after coming into large amounts of money.

Trust No One!

Poor Marva Wilson. In 2012, the Missouri native won $2 million and had every intention of providing financial support for her grandchildren as they attend college.

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Unfortunately, she was scammed by someone who claimed to be an accountant who ran away with all her money. Thankfully, he was caught and sent to prison for five years on charges of fraud, tax evasion, and money laundering. Good!

The Youngest Winner Makes The Youngest Loser

At 16 years old, Callie Rogers became one of the youngest lottery winners in history. Even though she vowed to hire an account and prioritize her family’s well-being with her $3 million fortune, a young girl can always be tempted by the eyes of a man.

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This man, it seems was a deadbeat. Her new boyfriend accessed the fortune so they could party and support his children. Youth is wasted on the young, indeed.

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