The Absolute Craziest Stories Of Lottery Winners

When most people think of what they’d do if they won the lottery, they think of simple things: buying a house or car, paying off debt, maybe going on a nice trip, or investing the money for the future. Some people might even choose to donate to charity, or pay off some debts accrued by friends and family. And then, there’s a whole other breed of lottery winner…

These people accomplished the difficult task of picking the right numbers, or scratching the right ticket, and then chose to do something totally outside the box with their winnings. From funny purchases to outrageous mistakes, these stories are more than scratch-your-head worthy. If you won the lottery, is there a world where you’d spend your money like these people did…

Back To Where She Began

In 2003, 16-year-old Callie Rogers was living with foster parents in the UK and working as a shop clerk where she earned £3.60 ($5.83 US) an hour. Rogers bought a lottery ticket and ended up winning a whopping £1.9 million ($3 million US). Despite insisting that she would continue to live frugally, she bought four large homes, several new cars, and had two breast augmentation surgeries.

She also developed a penchant for sharing her money with others. She bought expensive gifts for a series of boyfriends, including a car. What led to her financial demise was an addiction issue. She estimated that she spent a quarter of a million pounds on her dangerous habit. In the end, she had to sell the homes she owned, took back the new cars, and rented a modest townhouse.

She was left with only 2% of her winnings. She picked up work as a maid. In 2012, with barely any money left and pregnant with twins, she said, “For the first time, I feel like I have everything I need.”

The Man Who Couldn’t Say No

When Billie Bob Harrell Jr., a former Pentecostal preacher working as a bag boy at Home Depot, bought a winning ticket worth $31 million in 1997, it seemed to be “God-sent,” but what would happen as a result is far from it; in fact, some would even call it ungodly.

Like many other people who won the lottery, he bought himself a few things, like a home and cars, but he ended up loaning out a lot of his money to his so-called friends and family members who came running once they heard the news of his newly gained riches.

It was no surprise that he never received any of the money back, and in less than two years of him winning, he was broke. Sadly, Harrell ended his life in 1999, only 20 months after winning the lottery.

Donating a Good Chunk Away

When Janite Lee decided to be generous with the $18 million that she won in 1993, she had good intentions, but it didn’t turn out well. She donated a good chunk of her money to government-related programs and political organizations. She even sat down with former President Bill Clinton thanks to a generous contribution. She also donated $1 million to Washington University in St. Louis, Missouri to allow them to build a new library, which was named after her.

Another chunk of her money was lost when she gambled it away. She accidentally blew about $347,000 in a year on gambling and ended up waist-deep in debt. She filed for bankruptcy in 2001.

An Attempt Was Made On His Life

William “Bud” Post is another man who fell victim to helping too many people, specifically family, after winning a large sum of money. Family members, some of whom he’d never met, were coming out of the woodwork assuming that they were entitled to some of the money. But it was his girlfriend and brother who did the most damage. When he won $16.2 million, his girlfriend sued him for some of his winnings, and she won her case.

His brother tried to hire a hitman to kill him so that he could get the money for himself. His other siblings persuaded him to make a series of bad investments that left him $1 million in debt and living off social security.

IRS and Jail-Time

When married couple Alex and Rhoda Toth won the $13 million lottery in 1990, it seemed like perfect timing because they were literally broke. Unlike many people, they opted to receive the money in payments of $666,666 a year for 20 years instead of a lump sum. They were to receive payments until 2010, and although it was a smart move, things did not go as planned.

After living it up in Las Vegas for a while, they decided that it wasn’t for them and returned home to Florida, where they bought a house and some land. 16 years later, in 2006, they were broke due to court fees. How? The winnings caused a rift in the family, leading to legal expenses.

In 2006, they were caught for tax evasion, and while awaiting trial, Alex passed away. Then, Rhoda (deceitfully) claimed that she was too sick to stand trial on her own. She was sentenced to two years prison and had to pay the IRS $1.1 million.

The Registered Offender’s Winnings

The stars seemed to align when Alex Ahsoak won approximately $500,000 in the lottery, which he was going to use to benefit his nonprofit organization, a group that helped victims of abuse. It was later discovered that Alex was a registered offender. The information wasn’t made public until he won the money.

Soon after, Ahsoak was attacked while he was walking down a street. He was hit repeatedly in the head with a pipe, leaving him severely injured.

Not Needing The Money

When Jack Whittaker won $315 million, he didn’t need the money, as he already had a little over $1 million because of his contracting firm. He used some of the money to build churches, and he donated 10% of his winnings to charities, and then he started a family. Not too long after, Jack was robbed, losing approximately $500,000 from his car parked outside of a strip club.

The worst of it was when his granddaughter, who he’d been giving a weekly allowance of $2,100, overdosed on substances that were funded by his money. He later said that he wished he’d torn up the ticket.

Dollar Signs Make You Go Crazy

Most people have good intentions when they win large sums of money, as was the case with Jeffrey Dampier, who won $20 million in the Illinois lottery a few years ago. He invested some of it in a gourmet popcorn store called Kassie’s Gourmet Popcorn, but some of his family members weren’t very happy to be left out of the winning circle.

His brother and sister-in-law, who had dollar signs in their eyes, shot Dampier seven years after he won the money. They were later caught and convicted of murder and were sentenced to life in prison.

The $200,000 Loan

In 1993, Suzanne Mullins won $4.2 million in the Virginia Lottery, which she decided to split with her family. After that and taxes, she split the payments into 20 annual payments, which didn’t leave her with much money for herself. She was left with less than $50,000 in annual payments a year, clearly not enough to maintain a millionaire’s lifestyle.

Five years later, she took out a loan of nearly $200,000, using her winnings as collateral. Mullins was later pursued when she owed more than $150,000 from the loan.

Violating The State Asset Disclosure Law

Denise Rossi had been married to Thomas Rossi for 25 years when she played and won $1.3 million in the California Lottery back in 1996. The first thing that she did when she won was to ask him for a divorce, and she never told him that she had hit the jackpot.

Thomas learned the news a few years later when he opened a letter addressed to his ex-wife, asking if she wanted to take her winnings in a lump sum rather than in annual payments. Taken aback, he decided to sue. In 1999, a judge declared that Denise Rossi had violated state asset disclosure laws, which led to her ex-husband receiving all of the winnings.

During a 2004 interview with People magazine, while he was collecting approximately $50,000 a year, he said, “If it wasn’t for the lotto, Denise and I would probably still be together. Things worked out for the best.”

The Perfect Marriage

To the outside world, Lara and Roger had a wonderful marriage… that is, before they won $2.7 million in the lottery. Like most who win the lottery, they spent a fortune living it up. They went on expensive trips to exotic destinations around the world. Then they bought a luxury car, and finally, they spent over one-third of their fortune on the house.

Disaster struck in 2010 when a fire destroyed their million-dollar home. Roger then left Lara, ending their 14-year marriage.

Rags To Riches

Single mother Sharon Tirabassi got the break of a lifetime in 2004 after scoring the winning numbers in the Ontario Lottery and Gaming Corporation. She won just over $10 million, and it was a real rags to riches story. She spent quite a bit of money on big houses, expensive cars, and wild parties.

In less than ten years after winning the money, she had spent it all. It didn’t take long for her to go back to working part-time and living in a rented apartment.

Needing Surgery

Construction worker Americo Lopes’ story was sketchy from the onset, and he should not have been surprised by what happened to him next. When he won the lottery, he didn’t tell any of his coworkers, and it was this action that caused him to lose most of the winnings. It turns out that the winning ticket was purchased by him and his colleagues, who had split the cost of the ticket with him.

He quit his job, claiming he needed foot surgery and not telling any of them about the money. When they eventually found out, they sued him. He was ordered to split his winnings.

Going To His Head

When Gerald Muswagon won $10 million while playing the Super 7 jackpot in Canada in 1998, no one expected that his fairy-tale would turn into a horror movie. The attention from his big win instantly went to his head, and he spent much of his money on cars, parties, and property.

After burning off the cash within a few years, he had to take a summer job on a friend’s farm in order to make ends meet and feed his six children. Muswagon took his life a few months later.

The Trip of a Lifetime

Born and raised in Wales, United Kingdom, Luke Pittard was going about his daily life when he won $1.9 million in 2006 after shooting for the prize. At the time of his win, he was working at McDonald’s, but quickly gave his boss notice after scoring big. But it didn’t last very long…

The money was spent on a trip to the Canary Islands, a home, and a wedding. A year and a half later, he returned to his job at McDonald’s.

Adopting a New Lifestyle

Back in 1961, Keith Nicholson won just over three million dollars while playing Britain’s football pools. It didn’t take long for the millionaire lifestyle to get to his head, and he and his wife Vivian quickly adopted a life of luxury. They bought cars, a home, and hundreds of designer clothes.

Four years later, in 1965, Keith died, leaving his poor wife behind. Vivian had to declare bankruptcy after being slammed with a huge tax bill. She passed away in 2011 after struggling for years.

Trust No One

Abraham Shakespeare was described as illiterate at the time that he was living in Florida. Suddenly, he found himself $30 million richer, and after his friends and family found out, they all wanted loans. As expected, they never paid any of it back. Within one or two years, most of the money was gone, but that was just the beginning of his trouble.

Abraham met Dorice Moore, who seduced him into cutting certain people out of his life. In doing so, she took a slice of his $30 million pie for herself. A few months later, when Abraham disappeared without a trace, people began to fear the worst, and they had every reason to…

His body was found under a block of concrete in the backyard of the home Dorice recently bought with Abraham’s money. She was sentenced to life without parole.

Losing Out… Big Time

This story is a little different in that these people were unable to claim their winnings. In 2001, Martyn and Kay Tott were faced with a problem after recognizing that they had the winning numbers to a $5 million jackpot. At first, they were ecstatic before noticing that the ticket was missing.

Luckily, Martyn remembered the store, date, and time when he bought the ticket. With that information, he went to the headquarters of the lottery corporation, but there was one major problem: the rules of the corporation stated that a person must make a claim for the lost ticket in a period of 30 days.

Unfortunately, weeks had gone by, so they were unable to claim it. The couple was left knowing that they were missing out on $5 million.

Extensive Investigations

Urooj Khan lost it all in one day. He was a dry cleaner from Chicago at the time he won the $1 million lottery on July 19th. The next day, he was found dead, and at the time, it was believed to be due to natural causes, but extensive investigations proved otherwise. The medical examiner’s investigation revealed that the 46-year-old man was poisoned with cyanide.

The main suspects of the murder were his parents, but his widow and stepdaughter could also be on the list of suspects, as the two opposing teams entered into a legal battle for the money. The person is still on the loose.

Ruining His Life

When Willie Hunt won a $3.1 million jackpot, it ruined his life. Unfortunately, he was already addicted to a certain illegal substance, and by giving him $3.1 million, nothing good was ever going to result from it. He was also right in the middle of divorcing his wife. This made him use even more, driving him insane.

One evening after taking a dose, Hunt accidentally shot a woman while at a motel. Unfortunately, she succumbed to her injuries, and Hunt was convicted of the crime, and was later sent to prison.

Creating a Women’s Wrestling TV Show

After winning over $35 million at just 19 years old, Jonathan Vargas decided that he wanted to support women’s wrestling. The best way that he knew how was by purchasing a TV production company and using it to produce a TV show called “Wrestlicious,” which featured attractive, scantily-clad women wrestling in staged fights.

While the show only lasted one season, several of the female wrestlers featured on it made a name for themselves. Many of them went on to work for the WWE, IMPACT, and other major wrestling promotions.

Paying For a Secret Child and Murder

Ibi and Joseph Roncaioli were already very well-off when Ibi won $5 million. Ibi didn’t tell any of her family about her winnings, and she later sent approximately half of her winnings to a child she’d had in a previous marriage- a child her current husband had no idea existed.

Joseph was suspected of ending his wife’s life after finding out about the winnings, and her subsequent use of the money. He spent seven years in prison for his crimes.

Starting an Illegal Ring

When Ronnie Music Jr. won $3 million from a scratch-off card, like many people, he chose to start a business with the funds. Unfortunately, that business was buying and selling certain illegal substances along with his business partners. He and his co-conspirators tried to sell over $500,000 worth of the substance on the streets of the city where he lived.

As expected, someone called the police, and Music was caught. He eventually got 21 years in federal prison for his unsound investment decision.

Pushing Her Luck

When Evelyn Adams won the lottery, she believed herself to be the luckiest person in the world. Why? Because she won the lottery twice within the space of two years. The odds of one person winning the lottery once in their lifetime are quite low, so she was right to believe that she was lucky.

Her total payout was almost $6 million in hand, and she decided to try her luck again, this time in Atlantic City. Unfortunately, she gambled away everything she’d made and now lives in a trailer park with no assets.

Investing in a Football Club

John McGuinness loved football (or soccer to Americans) for many years before he hit the jackpot. After winning nearly 10 million dollars in a lottery in 1996, he invested a hefty sum of it in the Livingston Football Club, living out his dream of being heavily involved in his favorite sport.

Unfortunately, the investment went poorly, as it turned out that the club’s former director lied to him, costing him over 4 million dollars. To say he was heartbroken is a gross understatement.

Derbies and Other Things

Michael Carroll, perhaps the most famous lottery winner in the UK, reportedly spent nearly $3,000 a day purchasing illegal substances to fulfill his needs. And while he did buy a house like many lottery winners often do, he also purchased several luxury cars and designed a home-made racetrack for them.

He destroyed multiple vehicles, some say during his binges, and eventually had to sell his home after losing nearly all of his $15.8 million in winnings. The lottery probably made his life worse than it was before.

Renovating a School

Here’s a charming story: Gloria Mackenzie, having won the biggest ever Powerball prize at the time, found herself with nearly $600 million. After sharing the wealth with her friends and relatives, she discovered her old high school would have to shut down if it didn’t receive some essential repairs.

So she got some of her money together and decided to help. The school needed $1.8 million, and Gloria donated a cool $2 million to help her old school return to its former glory.

Building a Water Park

John Kutey, along with six other people, won a $319 million Mega Million lottery in 2011. With his nearly $30 million share, he and his wife knew exactly what to do. They spent a quarter of a million dollars installing a huge spray park at the site where a local pool had been.

They then donated another $200,000 to build a water park in New York. They said the park was in honor of their parents. They had a really healthy chunk to spend on themselves afterward.

Brewing Whiskey

Peter Lavery took home 10 million pounds after winning a UK lottery. He decided to invest half of it in a whiskey distillery in Belfast. He was an avid fan of this particular kind of alcohol and thought that not only could he learn more, but there was also a chance to make some really good money too.

Lavery’s distillery has been a lucrative investment, paying him back in spades! He probably has more money today than he started off with when he won the lottery.

Paying For Implants

This purchase might not seem so crazy, but there’s a twist: the implants weren’t for the person who won! When Sarah Cockings won over $4 million in 2005, she believed the win should be shared with her friends and family. That included paying for breast augmentation for both of her sisters! It was something the two wanted but did not save up for yet.

She also bought luxury cars and took fabulous holidays with her family, who she credits for keeping her grounded. That’s definitely one way to spend $4 million.

Creating a Trust

Louise White bought a rainbow sherbet at a Stop N Shop right before she purchased her winning ticket. At 81 years old, she found herself with nearly $340 million in winnings (she never thought she’d actually win). But initially, she didn’t know what she would do with all that money at her age.

Doing the smart thing with her money, she created “The Rainbow Sherbet Trust” in honor of her lucky dessert, which would benefit her family after she passed away.

Legalizing a Certain Substance

Bob Erb had bought lottery tickets for over 40 years before finally striking it rich and winning $25 million in 2012. He kept it simple when it came time to spend the money, continuing to work as a seasonal construction worker, and donating most of his wages to a local food bank.

However, he also allocated $1 million in winnings towards legalizing cannabis, and celebrating “420 Day,” an (unofficial) annual celebration of cannabis that takes place on April 20th.

Getting New Knees

Tony and Greta Dodd were dancing for joy when they won nearly $4 million. Greta, 67, had always been a huge fan of line dancing but had to stop due to severe joint issues. She had been suffering with those problems for years at that point, and it severely affected her wish to hit the dance floor once more.

Her husband also suffered from joint pain, and both of them decided to invest in new knees. The new joints let Greta take up dancing again and helped the couple enjoy a more active lifestyle.

Picking Up a Pair of Slippers

John Baxter won 1 million pounds but simply couldn’t think of anything to spend it on. After the 63-year-old wracked his brain for something to buy, he finally decided to purchase a pair of slippers for his wife at the local Tesco. People thought it was absolutely hilarious when he told them.

When asked what his next major buy would be, he gave an equally funny response. He told the press that his next big purchase was going to be a stainless steel sink.

Buying Property on The Moon

When David Copeland won almost 1 million pounds in the UK lottery, he bought a car and champagne to celebrate. But that wasn’t all he bought, as he had some very peculiar dreams. His more unusual purchases included an acre of property on the moon, as well as property on Venus and Mars.

With space exploration getting more popular and discussions of colonies on Mars popping up in the media, Copeland’s early investment might pay off! No word on how much he has left.

Establishing a Foundation For The Arts

Roy Cockrum took home $115 million after taxes were deducted in 2014, a sum of money that happened to be the largest prize ever won in the Tennessee Lottery’s history. The former actor and monk decided to give much of his winnings to a foundation to support performing arts around the US.

He credits his father with his money management strategy: “Tithe a tenth, save a tenth, and spend the rest wisely.” There’s no word on whether he regrets his decision or not.

Buying a Tumble Dryer

Ever a practical couple, Barry and Roberta’s first purchase after winning a cool million dollars was a tumble dryer. Very practical, seeing as how that’s all they thought they needed. The couple tries to live simply and spend their money wisely, referring to a period in their life where they had to scrape for funds just to get by as the reason.

Roberta’s tumble dryer cost only 220 dollars! Based on news received about them, they still have most of their winnings saved away for a rainy day.

The Five Million Dollar Man

In 1982, Curtis Sharp, Jr., a dishwasher for several years, won a $5 million jackpot and soon became known as the “Five Million Dollar Man.” He soon became a walking advertisement for the lottery. He spent much of his money on parties, women, houses, and cars, but his lifestyle was not sustainable.

He was spending more than his yearly payout checks covered. He left his wife for his lover, whom he married in a huge ceremony, but he soon realized that the lottery curse had hit. She divorced him, and he began to drink hard and soon had to crawl back to his first wife to ask to borrow money.

Luckily, his story has a happy ending. After a drunk driving incident, Curtis Sharp, Jr. found religion. He stopped drinking, stopped partying, cleaned up his act, and became a minister. But he still buys lottery tickets.

Too Many Handouts

When “Wild” Willie Seeley and 15 of his co-workers formed a lottery pool that won a big jackpot in August of 2013, it seemed like a blessing. But it only took a few weeks for Willie Seeley to feel he had been hit by the lottery curse. The lottery pool, known as Oceans 16, bought a ticket that was one of three to win a $450 million Powerball jackpot.

At a press conference, Willie Seeley said that he and his wife were “happy, happy, happy” and planning to spend their days fishing, hunting, and relaxing. But it didn’t take long for the downside of winning a lottery jackpot to appear. It’s hard to go fishing when you are being followed by reporters and camera crews clamoring for an interview or an appearance on a reality TV show.

And distant relatives and complete strangers coming to your house to ask for handouts made it hard to relax. Plus, it was a shock to realize that after splitting the jackpot three ways (three winning tickets were sold), then splitting the remainder among the 16 members of the lottery pool, not even $4 million was left over after taxes.

$4 million was enough for the couple to buy new vehicles, help their families, and quit their jobs, but not the never-worry-about-money-again windfall it had seemed at first. “There are days I wish we were back to just getting paid every two weeks. You have to change your whole way of life, but we didn’t want to change the way we lived.”

The Deadly $31 Million

Billy Bob Harrell, Jr. had fallen on some very hard times after an unsuccessful attempt to become a minister. When he won $31 million from the Texas Jackpot, it seemed he had finally found a way to support his family (maybe his dream) and put his money troubles behind him.

He was very generous with his winnings, helping his family, his church, and needy parishioners. But the requests for money didn’t stop coming. His bad investments and the constant demand for more, more, more from outsiders put a strain on his family. His marriage ended, and other family members were at odds with each other.

He said, “Winning the lottery was the worst thing that ever happened to me.” He died less than two years after his miraculous lottery win.