You Win Some, You Lose Some: Lottery Winners Who Lost Everything

Google “what are the chances of winning the lottery,” and the results might just send you running for the hills. The Huffington Post puts your chances of snagging a winning ticket at one in 175 million and Forbes has urged its readers to not even try playing the lottery.

While your chances of getting struck by lightning may be greater than striking it rich in the lotto, people win big jackpots on a fairly regular basis. But what happens after someone wins the lottery is shocking. The Certified Financial Planner Board of Standards says nearly one-third of lottery winners declare bankruptcy after a big win. Whether it’s $1 million or $100 million, a lot of people are ending up far worse off after they get lucky. These are just a few of those people.

What Would You Do If You Won The Lottery?

We’ve all daydreamed about what we’d do if we won the lottery. Some of us might use our winnings sensibly, while others would live by the you-can’t-take-it-with-you motto. Read on to learn notable times that lottery winners squandered their amazing wins. You won’t believe who spent $28 million in just a few years!

He Stole His Mom’s $51 Million Lotto Ticket

When you win the lottery, it’s in your best interest to not let anyone handle the winning ticket for you. But what about your own family members? When Etta May Urquhart won $51 million dollars in May 2011, her son, Ronnie Lee Orender, signed the ticket on her behalf. Then, he got greedy.

The two had a mutual agreement that Orender would handle her money and that the winnings would be used to take care of the family. Instead, he went on a spending spree, buying four houses, 10 cars, and a boat. Etta filed a lawsuit claiming her son stole her winnings and the two settled for an undisclosed amount in 2013 — but there’s been no word on whether or not the mother and son have made up.

“I’m Going to Spend, Spend, Spend!”

In 1961, Vivian Nicholson’s husband won roughly $4 million in various football pools. But she became the subject of tabloid news when she told the media she would, “spend, spend, spend!”

It’s not surprising that with that mindset, Viv didn’t spend her winnings wisely. Instead, she decided to blow it all on constant spending sprees consisting of lavish sports cars, fur coats, jewelry, vacations. and fashionable wardrobe. Things only got worse when he husband died in a car crash in 1965 and the rest of their savings dwindled. Viv died in 2015, but not before remarrying four times and developing a bad alcohol problem.

You Can’t Trust Anyone

Lots of people pool their money in the hopes that it will increase their chances at winning big in the lotto. But when Americo Lopes and five of his co-workers won $38.5 million dollars, Lopes got greedy.

The unsuspecting coworkers gave Lopes their pooled money and trusted him to buy the tickets. Lopes did buy the tickets but when he realized the group had won, he didn’t say a word. To make matters worse, he silently collected the winnings (a cool $17.4 million after taxes) and quit his job claiming he had a foot injury. It wasn’t long before the men found out and brought Lopes to court where he was eventually ordered to split the winnings equally amongst his ex-coworkers.

Tonda Lynn Dickerson Loses $9 Million Dollars

Edward Seward was a Waffle House regular. He was so close to the employees at his Grand Bay, Alabama Waffle House that he would share his lottery tickets with them. But when employee Tonda Lynn Dickerson won $10 million from one of the tickets he bought her, she took a “finders keepers” approach.

Seward and the Waffle House crew took Dickerson to court claiming she has fraudulently misrepresented herself by agreeing to accept the ticket on the condition that she would share her earnings if she won. Since there was no contract, Dickerson won in court but eventually faced the IRS, who ruled that she owed $9 million of her winnings. We’re guessing Dickerson hasn’t been in a Waffle House since.

Janite Lee Was a Little Too Charitable

Unlike many lottery winners, Janite Lee spent the majority of her $18 million winnings on others. The South Korean immigrant won the lotto in 1993 and immediately moved her family into a million-dollar gated community. She spent the next 10 years spending the $620,000 she received annually on philanthropic efforts. Lee’s contributions were so generous she found herself invited to dinners with the likes of Al Gore and Bill Clinton.

Unfortunately, her giving nature came to end when Lee was forced to file bankruptcy in 2001. At that time she had less than $700 to her name and was a whopping $2.5 million in debt.

Taking Advantage Of The System

Amanda Clayton won $1 million but kept using the food stamps that the government issued her every month. She was charged with fraud and given nine months probation. She passed away due to a drug overdose before her probation was even up.

“People who win the lottery lose perspective on normal things in life,” wrote Don McNay in the Huffington Post. “They start to think that rules don’t apply to them. In Amanda’s case, she thought she could outsmart the welfare people and do serious drugs without consequence. Wait until you read about how one guy blew almost $13 million on cocaine, partying, and girls.

Denise Rossi Takes Selfish To A New Level

When Thomas Rossi’s wife, Denise, left him unexpectedly after 25 years of marriage, he was confused and devastated. It wasn’t long before he found out Denise had won $1.3 million in the lottery just a week before she decided to part ways. Thomas brought her to court and he was awarded every single penny of her lottery winnings.

Experts often suggest that lotto winners claim their reward anonymously in states where that is allowed but that doesn’t mean it’s a smart idea to not inform your spouse about those winnings. Denise was selfish and in the end, it was her husband who walked away as the big winner from this lottery prize.

Michael Carroll Enjoyed Life In The Fast Lane

Michael Carroll hit it big back in 2002 when he won a lottery in Britain for a cool $12.89 million USD. But as we’ve discovered with many of our lottery winners — he was not very smart with his money. Cocaine, partying, girls and other expensive purchases put him right back where he started only five years after his big win.

Since then, he has been sent to jail twice (once for driving without proper license plates and one for catapulting steel balls from his van at other cars while drunk). Despite losing millions he claims he has no problem with where his life is now. “I get £204 every week for ­packing and stacking shortbread and cookies and I love it,” he said. “I treasure those wages more than any £9 million fortune.”

Callie Rogers Life Turned Into a Series of Tragic Events After She Won Millions at 16 Years Old

Callie Rogers was just 16 years old when she won £1.8 million (approximately $2.3 million in U.S. dollars). Within a decade, almost all of her winnings were gone and her life has been a series of tragic events.

Almost immediately after her big win, the fame made it difficult to live a normal life. She found herself surrounded by “friends” who were only interested in her money. Tempted by her hefty bank account, she spent huge sums of cash on vacations, cars, and plastic surgery. Now in her thirties, Callie is a mother and has a young son, Blake, who has cerebral palsy. Blake’s condition has left him unable to walk, talk, or swallow properly, and will likely need care for the rest of his life. Of all of Callie’s financial regrets, she says, “It’s my one big regret that the money isn’t here for Blake. He loves sensory stimulation. If I had that money, I’d give him the biggest sensory room you could buy.’ She certainly should have been able to.”

The Banker Robber Turned Millionaire

What happens when a convicted bank robber wins the lottery? Timothy Elliott got to find out! In Elliot was the winner of a $1 million lottery scratch-off ticket, which he bought for 10 bucks at a gas station.

In 2006, Elliott was arrest for unarmed robbery in Cape Cod and placed on five years probation. Under terms of his probation, he was not allowed to “gamble, purchase lottery tickets or visit an establishment where gaming is conducted, including restaurants where Keno may be played.” Fortunately for Elliott, who is also mentally disabled, the judge let him keep the money saying, “It was the purchase of the ticket that violated his probation, not the fact that he won.” You won’t believe the next story about a mother and son who both won the lotto!

The Lotto Cost Him His Life

In 2006, Abraham Lee Shakespeare took home a $30 million jackpot in Florida. However, just three years after his win, he went missing. He was later found under a concrete slab. Devastatingly, he had been shot, killed, and buried by his own business partner, Dee Dee Moore, who had befriended him after his win.

This story gets even crazier though. In June 2017, Abraham’s mother, Antoinette Andrews, won $1 million dollars with a scratch-off ticket. Antionette reportedly spends $100 a day on lottery tickets according to the Daily News, but this time it finally paid off. This doesn’t stop her from worrying about people taking advantage of her though. “I’m a little scared,” she told The Ledger. “It still doesn’t seem real.”

William “Bud” Post Was In Debt When He Died

In 1988, William “Bud” Post won a massive $16.2 million lottery. He was quick to spend $300,000 on gifts and investments like a liquor license, a Florida restaurant lease, a used car lot, and a mansion. Post lived a reclusive life, was estranged from most of his siblings and had been married seven times already when he won the lotto.

Soon after his win, unfortunate things started happening to him. Relatives begged him for cash, an ex-girlfriend sued him and his own brother even tried to have him killed. By the time he passed away 18 years after his big win, he was $1 million in debt and had been living off food stamps.

From Millionaire To Living In the Trailer Park

Not only did Evelyn Adams win the lottery twice, she did it back-to-back in 1985 and 1986. Her wins totaled over $5.4 million dollars, but that didn’t last long. Adams blew through her winnings spending millions on herself, bad investments, gifts for family and gambling in Atlantic City… lots and lots of gambling.

Today, Adam is broke and resides in a trailer park. Perhaps she should have kept the attitude she had after winning the first time. Regarding her first big win, she said, “Why should I let this upset my life? It was a big change and a phenomenal event. At the same time, I was very much in shock. I said I just couldn’t let my life go upside down.”

Sign Willie Hurt Up For Millionaire Etiquette 101

In 1989, Willie Hurt won a lottery that totaled $3.1 million. However, his life would soon go down the drain. Only two years after his win, Hurt would be divorced, had lost custody of his kids and was charged with attempted murder. He also developed a terrible addiction to crack cocaine, which consumed most of his winnings. Another story of someone not handling their new found money correctly. There should be classes people who win the lottery have to take before they are allowed to accept their money. We’ll call it Millionaire Etiquette 101.

Luke Pittard Is Lovin’ It?

In 2006, Luke Pittard won almost $2 million in the lottery. However, he spent most of his winnings in record time on things like lavish vacations, a house, and a wedding. In fact, a year and a half after winning the lottery, he was back to flipping burgers at McDonald’s. He says he is happy as his leftover winnings collect interest, but no doubt he wishes he would have spent it more wisely. As long as he’s happy, that’s all that matters. Unfortunately, some people who lose their money are so miserable and feel so trapped that they take their own lives, like the next winner on our list.

Billie Bob Harrell Jr.’s Tragic Decision

Billie Bob Harrell Jr. was a preacher who hit it big in 1997 when he won a lottery worth over $30 million. But this kind man’s problem was that he just couldn’t say no to anyone. Soon after winning his massive fortune, all his money was gone. He later got divorced and committed suicide.

Naturally, being a preacher, you would expect some generosity but just how many people did he refuse to turn down? Enough to lose all that money in a very short period of time. The man in our next entry not only lost his winnings but had to return to work a year after winning the lottery. The next story might make you cry.

Gerald Muswagon Learned Money Doesn’t Equal Happiness

In 1998, Gerald Muswagon won a Canadian lottery and took home a cool $10 million. Fast forward seven years and he had blown every single penny of his winnings by partying way too much. Muswagon was so unhappy with how he spent his winnings and how his life had turned out that he decided to hang himself in his parent’s garage in 2005.

“This difficulty that Gerald experienced was considered to be a major factor for his suicide in 2005,” reported euro-millions. “After spending almost every penny of his fortune, Gerald was forced back into work. He got a job doing the heavy lifting on minimum wage just to support his girlfriend and six children.”

Lisa Arcand Lives Luxuriously

After winning $1 million in the Massachusetts lotto in 2004, Lisa Arcand bought a big house, enjoyed fancy vacations, and opened up a restaurant. Being foolish with her low lump-sum, Arcand eventually had to close down her failing restaurant and was flat broke just three years after she won the money. If you think about it, three years with a million dollars isn’t that bad. After inflation, it’s crazy that $1 million doesn’t seem like all that much these days. Let’s just hope she enjoyed herself on those vacations!

She Lived A Charmed Life…Until The Money Ran Out

Sharon Tirabassi is the epitome of the generic win big, spend big, lose big situation we often see in lottery winners. After receiving $10 million in 2004, she lived the high life to the fullest for 10 years, buying a huge house, nice cars, and expensive clothes. After riding in the fast lane and spending all of her money, however, Sharon is back to riding the bus and working her part-time job.

If you do the math, that equates to spending $1 million dollars a year. 10 years of living the lavish life isn’t horrible but she could have been set for life if smart money management was involved. That’s more money than the majority of people in the population will ever get to experience!

Lou Eisenberg Now Lives Off Social Security

After winning $5 million in 1981, Lou Eisenberg became reckless with his money, taking extravagant trips, gambling, and buying property all over the world. The result? He was flat broke by the time 2001 came around. After receiving $120,000 checks in the mail for 20 years, the now 81-year-old resides in a mobile home living off of social security and pension checks for $1,000 a month.

While living it up for 20 years isn’t that bad, the trend we are seeing is none of these lotto winners know how to stretch their earnings. This next story might give you crippling anxiety.

He Lost His Winning Lottery Ticket

Losing all of your money after you win the lottery is bad enough, but that pales in comparison to what Ian Galtress did. Galtress purchased two lottery tickets and one was a single number off from winning the fortune, which meant the other ticket was the winner. The problem, however, was that he couldn’t find the winning ticket and missed out on over a million dollars. Oops?

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

Murdered For Money

In an awful and sad story, Urooj Khan never even got to see or spend the $1 million he won in the lottery in 2012. Planning to expand his dry-cleaning business, Khan would have received a lump-sum of $424,500 but was sadly poisoned and murdered just one day before he got the check in the mail. They never found the suspect.

“I keep getting the same answer — they are looking for a witness. How long is it going to take?” Khan’s older brother, Imtiaz, said in his thick Indian accent during an interview last week at his west suburban home. “Who could be the witness?”

Ibi Roncaioli’s Double Life

After winning a $5 million lottery in 1991, Ibi gave $2 million of the earnings to a child that she conceived with a man that was not her husband. When her spouse found out about her secret spawn he poisoned her with painkillers and was found guilty of manslaughter.

Another story of deceit. This just goes to show you can’t trust many once you unexpectedly receive a ton of unexpected cash. This is often why experts say you should claim your prize anoymously if your state allows that type of prize to be awarded for lottery winnings.

Marva Wilson Learned You Can’t Trust Anyone

After winning $2 million in the Missouri lotto in 2012, Marva Wilson was scammed out of almost all of her money. A woman named Freya Pearson pretended to be her friend and said she would help Wilson put a lien on her house and do her taxes. Instead, Pearson convinced the new millionaire to transfer more than $400,000 of her winnings into a bank account for a non-profit she had set up.

With her winnings gone, Wilson says Pearson duped her out of the money she was going to use to send her grandkids to college, repair her home, and invest in her life savings. Pearson didn’t get off guilty free and was sentenced to five years in prison for fraud, money laundering, and tax evasion. You won’t believe how this next couple spent $13 million in just 15 years.

$666,666 A Year Was An Omen

Struggling parents of six, Alex and Rhoda Toth, won a staggering $13 million in a lottery in 1990. After knowing poverty for so long, the family had hoped to spend the money wisely but got carried away with fancy cars, lavish trips, and gambling. They blew through all of their money in just 15 years. Even worse, the couple committed fraud by filing a false tax return. Alex passed away from various health issues, and Rhoda served three years in prison. Perhaps the omen of their annual payments —$666,666 for 20 years — was a sign of what was to come.

Money Ruined Their Marriage

This happily married couple received $2.76 million after winning the lottery in 2005 and rose straight to the top with their two daughters. Spending the money on extravagant trips, cars, and clothes, they eventually got too wrapped up in the fast lane and ended up losing their marriage when Lara thought Roger was cheating on her. After just six years, the couple lost everything they had won and a devastating house fire sent their debt over the top. This is yet another couple that could have used a class to set them on the straight and narrow path with their lottery winnings.

David Lee Edwards

After splitting a $280 million Powerball with friends, David Lee Edwards bought whatever his heart desired. Spending $1 million on cars, $600,000 on real estate, $78,000 on a single watch, $4.5 million on a fiber-optics installation company, and $1.9 million on a jet. He also bought various expensive medieval weapons, which helped leave him penniless. In just one year, he blew through $12 million dollars and had to foreclose on his house, all while he and his wife faced multiple run-ins with the police. Edwards died due to complications from hepatitis a as a result of his drug problems.

You Truly Can’t Buy Happiness

Jack Whittaker’s story might be the saddest of all on our list. When he won $314.9 million in the Powerball, it was, at the time, the largest sum ever won by a single person in American history. But after winning, he had several run-ins with the law and a string of personal tragedies.

His bad luck began a year after his win and is hard to believe. Not only was $545,000 stolen out of his car, but his granddaughter’s boyfriend overdosed and died in Whittaker’s mansion. Soon after his granddaughter succumbed to the same fate and Whittaker turned to drinking over the loss of his granddaughter. He faced a series of lawsuits amidst DUIs and gambling debts before his daughter passed away in 2009. To add insult to injury, Whittaker’s uninsured home burned down in a fire in December 2016.

The Twice-Lotto Winner With a Gambling Problem

Evelyn Basehore won $3.9 million in 1985 and just five months later hit the jackpot in the same game to add another $1.4 million to her personal bank account. After spending like crazy, gambling much of her money away in Atlantic City slots, and giving money to family and friends, the New Yorker was broke in just 15 years and now lives in a trailer in Brick, New Jersey.

By the looks of this picture, at least she made the most of her earnings. She sure did flaunt what she had and wanted everyone to know.

Did He Deserve the Money?

As an “in denial” sex offender, Alec Ahsoak donated his $500,000 winnings to his non-profit organization that helped victims of sexual abuse in 2009. It wasn’t until he won the huge cash prize that the Alaskan community realized that Ahsoak had been convicted for sexual abuse of a minor in 1993 and again in 2000. Although Alec did not deserve the money, the matter was considered an incident of bad luck and the money was still donated to the charity. Even though his actions before winning were vile, he would have been better off if he kept winning a secret.

Freddy Topous Tries To Cover Up His Wrongs

Freddy Topous Jr. won $57 million in 2008. After being released from prison in 2006, He was bestowed with a $33 million lump-sum but must live with the fact that he will remain on the sex offender list until 2024. The Michigan local was charged with committing a criminal sexual assault with the intent to commit penetration. Although he still has the money, his dignity is a thing of the past that he will never get back. Apparently, karma is not always out to level the playing field for people who really don’t deserve to win massive lotteries. The next story shows exactly why you need a prenup.

A Prenup Would Have Been A Good Idea

Juan Rodriguez was struggling to get by with $0.49 cents in his account before winning $149 million in the lottery. The luck-struck Colombian ended up losing half of his winnings to his wife when she decided to divorce him right after he claimed the massive prize. Even if you are getting married without a penny in your pocket, it’s not a bad idea to sign a prenup. With that being said, the take home before taxes was still $75.45 million each. They might not be together any longer but he was probably better off on his own if his wife only cared about the money and not their relationship.

Jose Antonio Cua-Toc’s Biggest Fear

As an illegal alien, 27-year-old Guatemalan worker Jose Cua-Toc gave his $750,000-winning lottery ticket to his boss out of fear of being deported. Cervantes apparently stole the ticket after Cua-Toc bestowed it in his trust, but eventually lost it in court to his employee after being sued over the theft. “The jury did not have any law to go on regarding whether the ticket belonged to the person who purchased it or the person who provided the money to purchase it,” The Telegraph wrote. Ultimately, jurors decided that the ticket was Cua-Toc’s because he made the purchase.” His fear got the best of him but in the end Cua-Toc won the big battle over his lotto winnings.

Stuart Donnelly’s Stressful Life

As Scotland’s youngest lottery winner in history, 17-year-old Stuart Donnelly celebrated his win with his mother and father over a glass of Coca-Cola since he was not old enough to drink champagne. He soon became known as one of the most generous winners, giving a large donation to a local hospital and helping friends and family financially.

Although he was happy with his winnings, Stuart said the money was stressful too. “It was very hard to deal with all the attention I got,” he said. “I even had people camping outside my house. It put a huge strain on me and my family.” Sadly, he passed away from natural causes as just 29-years-old although some speculate it was due to stress.

She Won the Lottery And Then Sued

Jane Park is a 21-year-old woman from Edinburgh who won $1.25 million in the lottery when she was just 17. What did a teenager do with all that money? Park underwent extensive plastic surgery, traveled the world, purchased a custom purple Range Rover and bought two homes. She then claimed that the money ruined her life and sued the UK’s National Lottery. She claims they should never have awarded someone so young with so much money. In an interview with the UK Mirror, she stated, “I wish I had no money most days. I say to myself, ‘My life would be so much easier if I hadn’t won.’”

Jonathan Vargas’ Questionable Investments

Vargas was only 19-years-old when he won just over $35 million on the lottery. He decided to blow most of his money on an all-female wrestling promotion called “Wrestlicious,” which fizzled out after only a year in operation. This and other bad investments led him to lose all his money in only a few years and he is now broke.

Crazy investments brought to lottery winners by family, friends, and complete strangers, are often cited as one of the main reasons lottery winners go broke. The more money these lottery winners take home, the crazier their investments often become if you look at their track records.

Suzanne Should Have Hired a Financial Advisor

When Suzanna Mullins won $4.2 million the lottery, she chose to get yearly payouts as opposed to a lump sum. But when she found herself in debt, she took out a loan for $198,000, knowing she would get another payout soon. However, when the rules of the lotto changed, she found that she could switch to the lump sum. She did so, and without paying back her debt. The company who gave Mullins the loan sued her and won $155,000 which left her broke. If she would have spent a little bit of her winnings on a financial adviser there’s a very good chance Mullins would never have lost all of her money so quickly.

The Biggest Losers

Don’t you hate when you lose something valuable like a wallet or credit card? Well, imagine if you lost a winning $5 million lotto ticket like these two knuckleheads. Since the couple had purchased the ticket six months prior to the lotto announcement, it was misplaced and they never recovered the lost proof of their potential wealth. Due to overwhelming depression after losing his one-way ticket to riches, Martyn became obsessed with proving his winnings and eventually lost his wife, Kay. With so much money on the line, we can’t even begin to imagine the thoughts that went through Martyn’s head.

Gough Gets Greedy

After winning $9 million in the lottery in 2005, struggling baker Keith Gough experienced the greed and gluttony that is oftentimes foolishly followed with a lottery win. Gough became an alcoholic, a gambler, and lost his wife during his seemingly wealthy period of struggle. He eventually passed away due to his fight with alcohol addiction.

With crippling alcohol and drug addictions, severe depression, and marital problems, we can understand why many people don’t play the lottery, even if it has the very slim potential to make them rich beyond their wildest dreams. The next guy on our list won $20 million and then lost his life to a foolish decision.

Jeffrey Dampier

Jeffrey Dampier lost not only the $20 million that he won playing the lotto, he so lost his own life due to foolish choices. The Tampa, Florida winner chose to spend his newly found fortune on a gourmet popcorn making business, Kassie’s Gourmet Popcorn, and on gifts for family and friends. After cheating on his wife with his sister-in-law, Victoria Jackson, Jackson decided to rob and kill Dampier with her boyfriend, Nathaniel. Talk about karma! And talk about a plot twist! This too could have been a story of greater purpose but poor decisions seem to weigh heavy on people who were completely broke and then won a big lotto prize.

She Donated $700,000 To A Pastor, Then He Sued For More

Marie Holmes was working multiple jobs, struggling to make ends meet for her and her four children — so when she won a cool $188 million in the Powerball she thought all of her problems were solved. After receiving her winnings, she bought her mother a home in Seattle, purchased a business for her fiance to run, and donated $700,000 to a local pastor, Kevin Matthews, to help build a retreat center. But soon after, Matthews sued the lotto winner, claiming that Holmes had said she would give him upwards of $2 million. He also claimed the emotional stress of the situation caused him to up his intake of depression meds. In the end, there was no contract between the two so the judge threw the case out.