8 Lottery Winners Who Ended Up Losing Big

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If you have ever seen the television show Lost, then you are familiar with the curse of the winning lottery ticket. While the show is fictional, the curse is something some people think is very real. Here is a list of people who claim that winning the lottery was one of the worst things to ever happen to them.

Name: Callie Rogers

Age when won: 16

Amount: £1,875,000 ($2,846,812 USD)

Callie Rogers was a British lottery winner who, in 2003, won a national lottery jackpot of £1,875,000 (around $2,846,812 USD). At the time, she was just 16 years old with a full time job working at a local co-op.

Press Association

In an interview with The Telegraph after her win, she told them she was going to enroll back into school, spend some time traveling, and help her family. However, things quickly took a turn for the worse as Rogers spiraled downward into a spending frenzy.

By 2009, she had spent most of her money, was in an abusive relationship with a man who got her addicted to partying, had two kids, attempted suicide several times, and had to move back in with her foster parents.


After her downfall she luckily began to find solace in the important things in life. Rogers is in a new, healthy relationship, is a mother of three, works three jobs while in school studying to be a nurse, and says that even though she is poorer, she is the happiest she has been.

Name: Michael Carroll

Age when won: 19

Amount: £9,736,131 ($14,400,000 USD)

Michael Carroll was a (mostly) normal 19-year-old living in the United Kingdom making his wages by working as a garbage man when he won the lottery in 2002. Carroll had a history of trouble, however, and had to pick up his winnings while wearing a police-ordered electronic monitoring ankle bracelet. His trouble was really just beginning as the money began to change Carroll into an even bigger hooligan who consistently made headlines as the “Lotto Lout” for his outrageous behavior.


He had a large party habit and wasn’t shy about it, which lead to a jail sentence in 2006. He bought a mansion in a ritzy area and would terrorize his neighbors by driving a catapult down the street, launching rocks into cars and storefronts. He also threw insane parties that included backyard demolition derbies. He caused so much trouble that he was in court over 30 times in a three- year span.

By 2012, the lifestyle caught up with him and he was living on unemployment and selling his possessions to get by.

Simon Price / Mirror

Carroll now resides in Scotland and has been living clean, working in a cookie factory making around $300 a week, but says, “I treasure those wages more than any £9 million fortune, I’ve only got one chance left—I’d have been dead in six months if I’d carried on that lifestyle”.

Name: Lee Ryan

Age when won: 32

Amount: £6,527,880 ($10,000,000 USD)

Lee Ryan served time in 1986 for stealing cars and would stay up at night dreaming of being a millionaire. “My cellmate warned me to be careful what I wished for,” he said in an interview, “The money was cursed.” Less than 10 years later, Ryan won the lottery in 1995. At the time, he was awaiting trial for handling stolen cars. Once he won, his sentence came through and he had to serve 18 months in prison. He was the first British lottery millionaire to end up in prison.


The ticket was split with his wife at the time, Karen Tyler. After their win, they moved with their three children to a million-pound mansion in the country and bought a fleet of cars, including a Bentley, a Ferrari, Porsche, and BMW, two Ducati superbikes, a small plane, and a helicopter.  

The Sun

By 2010, he had been divorced twice, lost all his money, and was sleeping on park benches or in cemeteries. These days he has slowly built a new life; he works as a cameraman and rents a flat in South London. He says that even with the poor outcome of winning the lottery, if he had never won the money to begin with, he would have most likely ended up in prison for life as he would have continued on the path as a criminal.

Name: William “Bud” Post III

Age when won: 48

Amount: $16,200,000

When Post won the lottery in 1988, he was on disability with just $2.46 to his name. He had pawned a gold ring to get $40 worth of lottery tickets and within those was the winning one.


In the first two weeks of collecting his first of 26 installments of his winnings (nearly $500,000), he spent more than $300,000. He bought a restaurant for his brother and sister (and a liquor license), a used car lot for another brother, and a small airplane. Within three months he was $500,000 in debt. This kind of downfall continued on for years.

He became estranged from his family, was sued by his ex- girlfriend (who was the one who originally used Post’s money to buy the lottery tickets), and ended up having to pay her one-third of all his future payments; he also had a crumbling mansion he couldn’t afford to fix. In 1996, he sold the house for $65,000 (he paid over $350,000 for it) and auctioned off his remaining 17 payments.


By 1997, he spent almost all the money he had received from the auction ($2.65 million) on material items like cars, boats, houses, and bikes, and was arrested for shooting at a debt collector. By the end of his life, Post was living on $450 a month disability.

Name: Sharon Tirabassi

Age when won: 26

Amount: $10,569,000

Sharon Tirabassi won the Ontario lottery of over $10 million at 26 years old; by 35 she was broke. She says it wasn’t hard to do after buying things like “a big house, fancy cars, designer clothes, lavish parties exotic trips, handouts to family, loans to friends.”


These days she is solidly working class, riding the bus, and living in a rented home. She was smart enough to leave a trust for her six children, which they’ll receive when they are 26; other portions of the money were divided among her family as soon as she cashed in. She gave a million to her parents, around $450,000 to each of her four siblings, and helped friends in debt.

Barry Gray / Hamilton Spectator

She wasn’t used to having any money—as a child, she grew up in shelters her whole life and was just off welfare when she won the money. One day she woke up and realized she only had $750,000 left and decided it was time to get back to the real world.

Name: Andrew “Jack” Whittaker

Age when won: 55

Amount: $315,000,000

Jack Whittaker was already a multimillionaire when he won the lottery in 2002 worth $315 million dollars. At the time, it was the largest Powerball jackpot ever won by a single ticket.


At first he was ecstatic and planned to be smart and diligent with the winnings. He gave around 10 percent to Christian charities, donated $14 million to his own foundation, and even gave the cashier who sold him the winning ticket a $123,000 house, a new truck, and $50,000 in cash. However, the curse of winning the lottery caught up to him and within a few years he had lost most of the money and was plagued by personal and family hardships.

In 2003, was robbed of $545,000 while in his car; a year after that his car was broken into again and thieves stole close to $200,000 in cash. Then family tragedy hit with the passing of his granddaughter’s boyfriend in his home; shortly after, his own granddaughter passed away. Her mother, Jack’s daughter, died a few years later.

Jeff Gentner / Associated Press

By then, Whittaker alleged he was broke and being sued by a casino for $1.5 million dollars in bad checks. In 2016, his Virginia home was destroyed in a fire. He was quoted saying to reporters, “I wish that we tore the ticket up.”

Name: Gerald Muswagon

Age when won: 35

Amount: $10,000,000

In 1998, Gerald Muswagon won the Super 7 jackpot of $10 million dollars off a single $2 ticket. Within a 24-hour period after receiving his money, he began buying new cars for family and friends, a house, and fancy electronics.


He tried to start a business called Gerald’s Logging, which soon failed. Muswagon was losing money quickly while he was partying his days away. He served three months in jail after leading police on a high speed chase in 2000; he was again arrested in 2002 and once more in 2005.

By then he was almost completely broke and had to pick up a job doing manual labor for minimum wage in order to support his girlfriend and six kids.


Unfortunately, Muswagon took his own life in October 2005, largely due to the highs and lows of winning the lottery and then losing it all.

Name: Billie Bob Harrell Jr.

Age when won: 47

Amount: $31,000,000

Billie Bob Harrell Jr. was nearly broke and constantly moving between low-paying jobs while struggling to support a wife and three children. Then, in 1997, he thought his prayers were answered when he won $31 million in the Texas lotto. Everything started out great: he quit his job at Home Depot, took his family on a vacation to Hawaii, donated money to his church, and bought homes and cars for his friends.


But then things started to get troublesome; strangers started asking for money so often he had to change his phone number four separate times. Following unwanted attention, he wanted to just get his money but since he opted for the annual installments (25 checks for $1.24 million each) he couldn’t do that, so he found a company that buys out your winnings and gives you a lump sum. The sum they offered was much lower than the total he had won but he took it anyway.


The spending continued and so did the strain of the this newfound money, causing him and his wife to divorce less than two years after the win. Within a couple months of the divorce, Harrell was found dead after taking his own life.

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