12 Lottery Nightmares and Winners Who Have Blown It All

By Martin Green | Updated on 15 Feb 2022

Is it possible to win the lottery and lose it all? Could winning the lottery be a negative experience? Can the world be a worse place now that you are incredibly rich?

Unfortunately, yes, sometimes it can! We have found multiple stories about lottery winners whose lives have changed for the worse.

Winning the lottery can be a fantastic experience with endless spending and riches. However, some of these ‘not-so-lucky’ people become totally miserable. They want to go back to their old lives and start again.

Even though these stories have negative conclusions, most lottery winners have a lot of fun along the way. They temporarily live a life that most of us can only dream of, through years of luxurious spending and incredible experiences.

Is winning the lottery really that bad for some people?

For some people, yes! Money can sometimes bring nothing but trouble and unhappiness. The weight of the world is on your shoulders and life doesn’t always change for the better.

Can winning the lottery destroy your life?

What should be the most amazing experience ever can often be short lived. Inexperience and financial mismanagement can destroy your life (even when you don’t win the lottery). 

Some people wish they had never won the lottery at all! Some people make bad mistakes and decisions. Family feuds, financial disaster and even death and murder can occur.

James Allen Hayes - The Seasoned Bandit, $19 million, California.

James Allen Hayes won the $19 million California Superlotto in 1998. With guaranteed annual payments of $684,000, life looked rosy for the security guard supervisor from Southern California.

Then the “lottery curse” set in!

His wife divorced him and took half, which was further reduced when he took a cash lump sum for $6 million. That is still a lot of money!Over the years, an uncontrollable heroin addiction after back surgery saw him whittle away $1,000 on a weekly basis.

Wrecking his Ferrari didn’t help either. Nor did the burning down of his apartment building!

Now the unbelievable part: Unable to accept his gradual demise, James started robbing banks to recuperate cash.

He threatened bank tellers with an imaginary gun on 11 different occasions and got away with cash sums. But only $40,000!

The seasoned bandit was caught by the FBI in 2017. Living in a converted garage, his life had turned into a major wreck.

Michael Carroll – The King of Chavs, GBP 9.7 million, United Kingdom

Michael Carrol is an incredible story of self-implosion. Of winning big and blowing it all.

At just 19 years of age, Michael won the equivalent of $15 million tax-free on the UK Lottery in 2002. By 2012 it was all gone and he was working as a coal carrier in Scotland. 

Over the years, Michael blew the entire fortune on alcohol, drugs, sex parties and prostitutes. He went to court 30 times for various offenses, often drunk and raising his middle finger.

Known as the Lotto Lout, some of his endeavors include:

  • Ripping a chandelier from a hotel ceiling while swinging on it.
  • Spending three months in jail on drug charges.
  • Being fined for vandalism and going to court on multiple occasions.
  • Convicted of sling-shooting ball bearings through 32 car and shop windows.
  • Ordered to stop holding demolition derbies in his junk-strewn backyard.

With no money left, Michael was interviewed by a reporter from the local press. Asked if he regretted frittering away the money, Michael responded, “No, because I have lived life”.Unfortunately, there is a lot more living left to do, Michael!

It’s not all bad news, though. His wife divorced him in 2008 for his extra-marital affairs and bad habits. But they have since got back together and remarried!

And from Michael’s point of view? “It was the best 10 years of my life for a £1.00 lottery ticket”.

A cautionary tale: Winning big when young can spell long-term disaster. The money is enormous and the highs are incredible. However, inexperience and frivolous spending can lead to lows in the years to come.

Jay Sommers, $5.8 million, Michigan

Jay Sommers was just 20 years of age when he won $5.8 million on the Michigan lottery in 1988.

He bought five cars after receiving his first payment check of $290,000. This yearly installment was gone in two-and-a-half months.

Jay spent too fast and got into financial management and taxation difficulties. He made the mistake of entrusting his finances to a friend, who frittered away the money through bad investments and shady deals.

One sunny morning, Jay woke up broke and had to take on a pizza delivery job. The worst part was when people recognized me in the street. “It was humiliating”, he said.

Jay was an inexperienced and irresponsible young man incapable of managing his new riches. After buying a Chevrolet and embarking on a career as a stock-car driver, he finished fourth out of 42 drivers at an average speed of 186 mph. The only thing going faster than him was his money!

Abraham Shakespeare, $16.9 million, Florida

In 2006, Abraham Shakespeare and a friend stopped at a convenience store to purchase some lottery tickets. After winning the Florida jackpot, Abraham agreed to a payout of $16.9 million.

Generously, he bought a home in North Lakeland, plus properties for his cousins, and also paid off some of his friends’ debts. But as an uneducated and inexperienced man, he was out of his depth.

His entourage of newly found friends helped him waste away his new-found riches. Down to his last $2 million, Abraham was introduced to Dee Dee Moore, who offered to write a book about his life and tell his story. She became his financial advisor and advised him to cut away from his friends and stay at home.

After his parents reported him missing, his body was found under a concrete slab in the backyard of an acquaintance. Dee Dee Moore was formally charged with first degree murder on February 19, 2010.

Jeffrey Dampier, $20 million, Florida

In 1996, Jeffrey Dampier won the Illinois Lottery Jackpot worth $20 million.

He moved to Tampa Bay, Florida, and invested some of his money in a business called Kassie’s Gourmet Popcorn.

After getting divorced and splitting the winnings 50/50, he met his future wife Crystal Jackson. He also had a close relationship with Crystal’s two sisters, Victoria and Terri. He took care of their finances for the less-than-innocent motive of having an affair with Victoria!

However, Victoria was dating another man, Nathaniel. After learning about Dampier’s riches, a mixture of jealousy and green envy set in.

In 2005, Dampier was murdered by them both in an undoubted mixture of jealousy and greed.Victoria fired a single shot into Dampier’s skull, killing him instantly.

Now in prison, she wishes she had never set eyes on the money at all!.“It is a curse”, said Crystal Jackson.

Urooj Khan, $1 million, originally from India

Urooj Khan died from cyanide poisoning just weeks after winning a $1 million scratch-off lottery in 2012.

Originally from India, Khan was the owner of multiple dry-cleaning businesses in Chicago. Although not the biggest winner in history, Khan’s $1 million scratch-off win raked in a tidy $424,449.

Initially ruled as death from natural causes, the coroner later determined that his death was from poisoning after further tests.

No one has been arrested in connection with the murder, which saw Krooj violently coughing up blood. Five years later, police are still no closer to solving the case.

Not so true fact: Up to 70% of lottery winners are falsely reported to go broke within seven years! Some of these people die through illness, murder or suicide. Many others go broke through over-indulgence, overspending and compulsive addictions.

William “Bud” Post III, $16.2 million, Pennsylvania

William Post won half of the Pennsylvania lottery jackpot in 1988, netting $16.2 million.

In 1989, Post’s brother tried to obtain an illegal inheritance. He hired a hitman to murder Post and his sixth wife. The attempt failed and he was arrested.

Things got progressively worse. In a dispute over lottery tickets, a judge ruled that Post had to pay a third of his winnings to Ann Karpik. Post refused and had his lottery payments frozen until the case could be resolved.

In 1998, he was arrested for refusing to serve a short prison sentence for an assault conviction.

Post declared bankruptcy, suffered from bad health and was unable to control his spending. He alienated himself from most of his family and died not long after receiving a $558 social security disability check.

Evelyn Marie Adams, combined $5.4 million, New Jersey

Evelyn won the lottery twice in both 1985 and 1986 for a combined total of $5.4 million. However, she was a compulsive gambler! She spent as much as $100 per week on lottery tickets alone.

The joy of winning was short-lived and she disliked being recognized when she went out. And while many people were happy for her new-found wealth, others were resentful.

By 2012, all of her lottery winnings were gone! She lost it at gambling tables in Atlantic City casinos, through frivolous spending, poor judgment and unsuccessful business deals.

Not so fun fact. A Michigan man was found dead with a $45,000 US lottery ticket in his wallet. This was one of the most unfortunate boating accidents on record!

Andrew “Jack” Whittaker, $113.4 million, West Virginia

On Christmas Eve 2002, Andrew Whittaker bought $100 in lottery tickets when the jackpot reached $100 million. He won and took home $113.4 million after taxes.

Incredibly, Andrew already had a net worth of $17 million as the president of a contracting firm in West Virginia!

Problems soon started though! In 2003, a group of thieves broke into his car and made away with $545,000!

His granddaughter’s boyfriend was found dead in Whittaker’s home in 2004 after overdosing on drugs. Two months later, his granddaughter was also found dead on the property of a friend.

Court cases and gambling issues ensured, with multiple checks bouncing for millions of dollars.

In 2009, Ginger Whittaker Bragg, the mother of his granddaughter was also found dead.

Although Whittaker remained financially stable, disaster struck on many occasions. In 2016 his home was engulfed in fire and burned down. It was not insured.

Alex and Rhoda Toth, $13 million, Florida

Alex and Rhoda had financial woes, but in 1990 they won the $13 million lottery jackpot!

The money went straight to their heads. They lived in expensive hotels and gambled huge sums of money away in Las Vegas. Eventually, they returned to Florida, bought property and settled down.

The spending spree didn’t end there though! They continued frittering away their money. When Alex Toth died in 2008 he faced major tax fraud charges. They were living in dreadful conditions and couldn’t afford to pay the electricity bill.

Unbelievably, Rhoda Toth was sentenced to two years in federal prison after her husband’s death. She firmly believes that winning the lottery was the worst thing that ever happened to her.

This couple became dizzy with fame and had no money management skills.

Billie Bob Harrell Jr., $31 million, Texas

When Billie Bob won $31 million on the Texas lottery in 1997 he thought his problems were over. They were not!

The stress of suddenly becoming rich was too much! He attracted unwanted attention and had to change his phone number several times.He made financial mistakes and separated from his wife.

Just 20 months after his landslide win, Billie Bob locked himself away and fired a shotgun into his chest. He was dead!In his own words, “winning the lottery is the worst thing that ever happened to me”.

Some people win the lottery but get nothing at all

Here is a sad story to round off. 

Martyn and Kay Tott from the UK who won £3 million on the UK Lotto, but lost their ticket!

The Camelot Group confirmed the legitimacy of the lost ticket, but decided to pay nothing because the winning claim was made after the required 30-day deadline.

No words can describe the heartbreak. "It drains the life out of you and puts a terrible strain on your marriage. It was the cruelest torture imaginable", reflected Kay Tott.

At the end the couple agreed they should split because the marriage was over.

The Youngest Winners and Tragedies

Winning a huge lottery jackpot can be even more cataclysmic when you're just a teenager. You have a small amount of life experience to draw on to moderate your newly acquired spending power.

Without guidance there is no perspective, plus the sometimes incorrect belief that you will be rich forever. This can be a wave of euphoria that is difficult to accept when it's all over.

Callie Rogers, GBP 1.9 million, United Kingdom

Callie Rogers from the United Kingdom was only 16 when she won the lottery. She won GBP 1.9 million in 2003. Tax free!

She quickly spent the cash.

  • £11,500 on breast implants
  • £85,000 on luxury sports cars
  • £250,000 on cocaine
  • £300,000 on clothes
  • £180,000 on a new bungalow
  • £76,000 to buy her mother's house

This endless spending craze caught up with her in the end. She tried to commit suicide in 2013, with just £2,000 left in the bank.

Stuart Donnelly, GBP 2 million, United Kingdom

Also from the UK, Stuart Donnelly won GBP 2 million in 1997. But his spending rapidly spiraled out of control.

He abandoned his home town, education and studies to live the life of luxury. Even though he gave money away to good causes and bought luxurious properties, Stuart became more and more reclusive. He was unable to handle the unwanted attention.

In 2010, Stuart was found dead at home at just 29 years of age!

Summary

For some people, winning the lottery is not the positive experience that they imagine it to be. It would be better to not win anything and remain none the richer. These people find it difficult to handle the pressure and expectation of suddenly having so much cash.

Good money management is the key to winning big and keeping hold of your fortune. Unfortunately, many people have no idea how to do this. Or are too young to handle it. They instead choose to spend wildly without thinking about the long-term consequences. They don’t think about the back-to-earth letdown after such a euphoric experience.

Fortunately, these people are in the minority. Most people have positive life-enhancing experiences. Read rewarding stories in our Lottery Success Stories and Winners Who Are Still Rich.

Remember to be sensible if you win big. Take some time out and try to get away from your newly acquired attention. Next, get some financial advice and carefully plan your next move. Once the foundations are in place, spend and live the dream!

For additional perspectives and more in-depth information, the biggest lottery winners of all time are listed in our article Who Are The Biggest Lottery Winners Ever?