Dumbest Lottery Winners Of All Time

Ever find yourself clock-watching at your 9 to 5, only dreaming what it might be like to win big on the lottery? It's hard to believe, but the grass isn’t always greener on the lotto winner’s side. From those who excessively splurged their cash on the finer things, to those whose fraudulent and immoral schemes saw their millions melt away, here are some of the dumbest lottery winners of all time!

Denise and Thomas Rossi

They say that trust is the foundation of any relationship, and without it you have nothing. This exact sentiment became a literal reality for our first lotto winner, as her deceit left her penniless. It was 1996 and Denise and Thomas Rossi had been seemingly happily married for the last 25 years. However, much to Thomas’ surprise, one day, Denise suddenly wanted a divorce.

And while perhaps Thomas’ snoring or untidiness might’ve been a contributing factor like other failed marriages, there was a vital piece of information Thomas didn’t know that had set their marriage on the rocks. Just 11 days before filing for divorce, Denise and her pals pooled together and won $6.6 million on the California state lottery, with Denise secretly pocketing $1.3 million.

It seems plausible to imagine that Denise was already unhappy in her marriage and thus saw her winnings as an escape route. Whatever the case, the divorce was finalized, and Thomas was left none the wiser about his now ex-wife’s winnings the entire time. But here’s the crux: when finalizing a divorce, both parties are legally required to declare their financial position, as to determine alimony payments.

Having just become a millionaire, Denise knew that if she declared it, she’d have to share a portion of it with Thomas. So, she just didn’t declare it. 2 years after the divorce, Thomas, who was still in their marital home, received a letter addressed to Denise, regarding her lottery winnings.

‘What lottery winnings?!’ he initially thought, but before long, the proverbial penny dropped, and the pair were back battling it out in court. Ultimately, the court found Denise guilty of fraud and declared Thomas as being entitled to the FULL sum of her winnings! It may seem like a harsh punishment, but let this be a lesson, folks. Honesty is always the best policy. Or just make sure to change all your mailing addresses after your big lottery win!

Christina Goodenow

In 2005, Oregon woman Christina Goodenow won $1 million on a scratch card lottery ticket. But strangely, this didn’t trigger the big celebration you might imagine. As a matter of fact, there was something rather shady. Christina didn’t want anyone to find out about her win. So much so, she specifically requested that lottery officials keep it on the down low.

Meanwhile, though, the local police department was tracking down suspicious activity on the credit card of a woman who’d passed away a year prior. This ultimately led them to Christina, who, it turned out, had actually been using her then-boyfriend’s dead mom’s credit card to buy things, including her winning lotto ticket, technically making it a dead woman’s winnings!

In her reckless swiping of the credit card, Christina had incurred $12,000 of debt, which she attempted to pay off with her lottery winnings. But, alas, despite now having plenty of money, her fraudulent credit card usage led the police right to her, and Christina was charged accordingly with forgery and theft.

While Christina insisted that she’d used her own cash to buy the ticket, she was stripped of her winnings, which were given to the local police department. She was also sentenced to a month behind bars, and given 2 years of probation. Hopefully, during Christina’s short time in the slammer, the police at least spent some of her winnings on a few nice things to spruce the place up.

Washing Machine Ticket

In 2021, a US woman, who remains anonymous, won $26 million in the lottery. It was an incredible stroke of luck in fact, for perspective, you’re 250 times more likely to be crushed by a meteor than you are to win the lottery. But the winning ticket was, unfortunately, where this anonymous woman’s luck ended.

She accidentally put her winning ticket in the washing machine! Ultimately, after a full cycle, the woman’s fortune became nothing but a squidgy, crumpled, illegible piece of paper. In her desperation, she returned to the store where she’d bought the ticket from and requested surveillance footage that would show her buying the winning ticket.

But unfortunately, it wasn’t enough for the lottery company to grant her winnings. According to them, the only way to cash in a lost or destroyed ticket would be by having a picture of it, front and back. Let this be a reminder that nothing good has ever come of doing laundry!

Evelyn Adams

Statistically, winning the big-time lottery is virtually impossible, with jackpot odds coming in somewhere between 1 in 170 million and 1 in 292 million depending on what lottery you play. However, one woman defied all statistics when she won the lottery not once, but twice!

It was October 1985 and regular lotto lover, Evelyn Adams from New Jersey, won an astonishing $3.9 million. But, even with enough cash for a lifetime, she continued playing the lottery, and just 4 months later scooped an additional $1.4 million! Evelyn was now sitting on $5.3 million. However, this massive fortune wouldn’t last long.

Evelyn was initially responsible, opting for annual payments of $218,000, rather than the lump sum. She invested in her daughter’s education, as well as businesses, such as her own music store. But ultimately, these ventures failed, and her money began to dwindle.

Not only that, but she was very generous in her donations to friends and family some of which were merely loans that were never repaid, as people took advantage of Evelyn’s wealth. What certainly didn’t help, though, was that Evelyn couldn’t seem to curb the habit that had gotten her the money in the first place: gambling.

Over time, Evelyn became a regular at Atlantic City’s casinos, ultimately betting away her very last dime. And by 2012, she had nothing. There isn’t much reportage on what happened next, though news outlets claim she now lives in a trailer park.

In fact, a recent picture of Evelyn seems to show her in some kind of food service work uniform, not looking particularly happy. And, in all honesty, having won the lottery TWICE and still lost it all, who can blame her for not being full of smiles?

José Antonio Cua Toc

You might think you can trust the people in your life, but when it comes to money, trust no one. Something our next lotto winner learned the hard way. Back in 2010, José Antonio Cua Toc went to the local store on his boss’ behalf and decided to buy himself a lottery ticket, important to note: with his own money. This lottery ticket turned out to be worth $750,000!

Naturally, José was overcome with excitement, but he quickly realized there was a slight issue, he was an illegal immigrant to the USA from Guatemala. Fearing that declaring his lottery win would lead to questions, and thus his deportation, he put his trust in his boss, Erick Cervantes, to cash the cheque.

As a sort of quid pro quo, the pair decided that they would share the winnings. But, as Erick publicly cashed in the cheque, he was overcome with greed and refused to give José his share. José was furious and eventually decided to lawyer up. The case went to trial, and just in the nick of time, the store where José had purchased the ticket came forward and provided surveillance footage of him doing so.

With José proven to be the rightful recipient, he was awarded the full sum of money, though the media attention this attracted left him at risk of deportation. While there have been no public updates regarding whether Jose was ultimately deported, the worst part is all this could’ve been avoided.

Turns out, Georgia law doesn’t require lottery winners to prove their citizenship to claim their prize. A quick Google search and José would’ve known this, without getting his boss involved and subsequently risking losing it all and being deported.

Jack Whittaker

$314 million is a lot of money. In fact, with the USA’s average life expectancy of 76 years, that’s enough cash for a person to spend $11,319 every day of their life! However, one West Virginian man, Jack Whittaker, chomped through that sum in just 4 years after winning the lottery in 2002.

His first mistake was that he had a habit of keeping large amounts of cash in a suitcase in his car ($545,000 in cash, to be precise). Needless to say, this quickly caught the attention of burglars, who broke in and stole it. And that was just one break-in; more cash was stolen in similar circumstances.

When asked why he’d keep cash in his car, Jack cockily retorted, "Because I can". To his merit, he was also extremely charitable and not just to burglars. He reportedly pledged 10% of his fortune to various Christian charities and even built a multi-million dollar church in West Virginia.

He also created his own charity, The Jack Whittaker Foundation, which provided food and clothing to low-income families. He was so generous, or arguably ridiculous, that he once drove his Lamborghini through his neighborhood, throwing cash out to strangers!

That isn’t to say, though, that he didn’t indulge in the cash himself. While he initially claimed that the money wouldn’t change him, the reality is that just a week later he would blow $50,000 in one night’s festivities.

His most troubling habit, though, would be gambling. An addiction so severe that it’s reported one casino sued him after gambling $1.5 million that he couldn’t actually afford to pay. And so, within 4 years of winning the cash, Jack was penniless.

In the meantime, Jack’s marriage had broken down, and several other family members had fallen into the trap of all the tragic excesses extreme, sudden wealth could bring. By the time the money was all gone, Jack was quoted as saying he "wished he’d torn the ticket up".

To make matters worse, his house burnt down in 2016, long after his money had dried up. His increasingly tragic story came to an end in 2020, when he passed away from an unspecified illness, though he is now immortalized as a cautionary lottery tale, if ever there was one.

Lara And Roger Griffiths

Money often comes hand in hand with greed, ultimately putting people’s relationships to trial. And when Roger and Lara Griffiths won the UK lottery back in 2005, they were soon left broke in several definitions of the word.

The couple married in 1997 and were seemingly content. Things began to change, though, in 2005, when they struck £1.83 million on the lottery. They promptly indulged in an £800,000 house, a £28,000 Porsche Carrera, and a £24,000 Lexus 4x4, so it’s clear to see that they quickly developed a taste for the finer things in life.

These purchases alone had chomped up nearly half their fortune, and that’s not counting cash splashed on tattoos, cosmetic surgery, and lavish designer shopping sprees. Their fortune continued to dwindle through flashy vacations to Dubai, New York, Rome, London, and Monaco, where they’d reside in the most luxurious 5-star hotels.

But of course, their expensive taste came at a cost, and it was a bitter one, considering that by 2013 it wasn’t just their finances in ruin, but their marriage too. So, who’s to blame? According to Lara, it was Roger and his reckless spending which catalyzed their decline, with him pumping money into becoming a rockstar.

Apparently, he spent around £25,000 on reforming his old college band for a self-funded recording project. A pipedream that proved unsuccessful, considering the band’s first single, released in 2006, sold just 600 copies.

Roger, on the other hand, points the finger at Lara for their marriage falling apart, claiming she "liked handbags and spent a lot of time at Louis Vuitton". You don't have to be a marriage counselor to see that these two were both as bad as each other! They were soon left with nothing but divorce papers, and by 2013, Roger was broke and living alone in a tiny cottage with, he claimed, only £7 to his name.

Michael Carroll

"With great power comes great responsibility", though it seems lottery winner Michael Carroll, from Norfolk, England, didn’t quite get the memo when he splurged his £9.7 million fortune on complete and utter mayhem! Michael had a bit of a sketchy childhood and was known to be something of a local menace. So much so, at just age 13 he was sent to Hollesley Bay Prison for shoplifting.

By 2002, he was working a steady job as a garbageman. Little did he know, that he would soon be trading in piling trash for stacking cash! At just age 19, a very lucky win left him sitting on a lottery fortune of £9.7 million, or around $11.6 million, though this would dwindle into nothing at an almost impressively rapid rate.

So, what exactly did Michael spend his millions on? Initially, he indulged in a £325,000 mansion, near a lake where he could enjoy fishing. But beyond that calm, placid seeming purchase, things soon descended into sheer chaos. Michael has estimated that, in the space of a few years, he spent £300,000 on parties and £230,000 on adult refreshments for said parties.

A further £400,000 was spent on luxury cars that he would race, and subsequently give the demolition derby treatment, in his backyard. £3 million would cover the costs of various other indulgences, such as jewelry and investing in the Rangers Football Club. But worst of all was his costly daily breakfasts; no toast, eggs, or bacon, but instead a habit of the Colombian variety that reportedly cost him £2,000 a day.

To top it all off, Michael liked to fill his day with important business “meetings” with women of the world’s friendliest profession. Professional huggers, let’s say. In fact, he claims to have met with 4,000 professional huggers in just 10 years! Despite all this lavish personal expenditure, though, Michael claims that more than 50% of his winnings were spent on friends and family.

Not surprisingly, Michael’s millions soon dwindled. And just 4 years after winning, the BBC reported that he was headed towards bankruptcy. By 2010, Michael was desperately looking to raise funds by selling his beat-up mansion, but having been wrecked by his parties and cars tearing up his personal destruction derby site, the house struggled to sell.

Finally, by 2013, the former big shot had splurged every last penny, bringing his chaotic misadventure to a bankrupt end. Shockingly, even though he now finds himself back to doing tough manual labor jobs to pay the bills, he said he has absolutely no regrets. According to Michael, it was the best decade of his life.

Amanda Clayton

According to the Social Security Administration, some 65 million Americans were relying on welfare in 2021. It’s a great system to help those in need of it. However, from time to time, the system is taken advantage of even, it seems, by millionaires.

Back in 2011, Amanda Clayton was a struggling single mom, relying on welfare. But the tide was about to change when she won $1 million in the lottery. Only, even in the face of such a windfall, Amanda was overcome with greed. So, every month, she continued to collect her food cheques worth $200!

In her defense, Amanda claimed that because she was still technically unemployed, she was entitled to welfare. But what she failed to realize, is that welfare is based on income and not necessarily employment status.

Sure enough, her fraudulent doings were eventually uncovered, resulting in her arrest and a 9-month probation. Not just that, but she was also ordered to pay back $5,500 that she’d Illegitimately claimed in the form of food and medical assistance.

Lottery Winner Food Stamps AMANDA CLAYTON by Denniskirby1

Wrongdoings aside though, Amanda’s tale ended in tragedy. Just 1 year after her win, Amanda sadly passed away at 25 years old, another victim of some of the vices that sudden, large amounts of money can often make people susceptible to. It’s a sad story and a more serious reminder that winning the lottery isn’t something to be taken lightly, no matter what stories like Michael Carroll’s might seem to imply.

Bud Post

Between his mother passing away young and his father putting him in an orphanage at 8 years old, Bud Post from Pennsylvania didn’t exactly have the best start in life. In adulthood, he would go between jobs, including working as a cook and even truck driving for a traveling circus. But his already varied life was about to get a whole lot crazier in 1988 when he won $16.2 million in the lottery!

With just $2.46 to his name beforehand, it seemed like this was Bud’s big break. However, it would only bring on more hardship because Bud just wasn’t all that smart. His winnings were in the form of a repeated annual payment of $500,000 within 2 weeks, he’d already spent 2 thirds of his first year’s payment on a restaurant, a plane, and a used car lot, to name but a few items.

It’s reported that just 3 months into his win, he was, somehow, $500,000 in debt! Thankfully, these debts could be settled when he received the next year’s payments, but the same pattern of debts began to emerge each year, each time worse than the last. Not just that, but a little further down the line, Bud’s then-girlfriend, Ann Karpik, claimed that she was entitled to half of the fortune.

That's because back when he was broke, Bud had pawned a ring for $40. With that money, he’d asked Ann to go buy 40 lottery tickets. One of those 40 was the big winner. According to her, they’d agreed to split the winnings. While Bud denied this, the court ultimately awarded Ann a third of his winnings!

If that wasn’t enough, Bud’s life was also in danger what with his estranged brother hiring an individual with a very particular set of skills to take Bud out of the picture, hoping to inherit his money in the process.

Fortunately for Bud, the attempt failed. Despite all the setbacks, Bud still found time to indulge in cars, a boat, and property. However, by the late 90s, he was facing yet another legal battle, this time for getting into a rather unpleasant altercation with a debt collector. By this point, Bud was onto his 6th wife, a number which eventually grew to 7, with each divorce taking another huge chunk of his assets with it.

After his debt collector-related legal battle, Bud found himself with a 6 to 24-month prison sentence, which he refused. A bold strategy, for sure, but not necessarily a smart one. Eventually, after 6 years of avoidance, he was arrested on a $260,000 sailboat. By the time his sentence was served, Bud was completely broke, reportedly living off a $450 per month disability cheque not to mention, over a million dollars in debt!

Marva Wilson

Just the thought of being a millionaire might be enough to make most people’s mouth water, but 65-year-old Marva Wilson was a lot calmer and more measured than most when she pocketed a tasty $2 million in 2008.

The Missouri grandmother actually planned to use some of the money to put her granddaughter through college and allow herself just $30,000 a year to spend. But little did she know she would become the victim of an elaborate scam that would diddle her out of $480,000!

It all began in 2010 when Marva crossed paths with Freya Pearson, an unemployed single mom relying on welfare. As scammers so often do, Freya appeared kind and personable, and she and Marva quickly became good friends. But Freya had an ulterior motive.

She began convincing Marva to withdraw funds from her lottery winnings and donate them to her non-profit charity, “Recidivism at Work”. Freya built up a picture of the charity as providing support to prevent at-risk young folks with criminal records from reoffending and helping them find work.

But the charity was nothing but a front, the money was just lining Freya’s pockets. But with the unfortunate naivety of a good-hearted and generous older soul, Marva blindly agreed to donate to ‘Recidivism At Work’ and all in all was swindled out of $480,000. Having fooled Marva, Freya would begin indulging in gambling, traveling, expensive cars, and designer clothes.

Eventually, this escapade left Marva bankrupt, and as financial authorities unraveled the paper trail, Freya was caught. In 2017 she was sentenced to 5 years of jail time with no parole, and charged with wire fraud, money laundering, and tax evasion. The scariest part is that she’s probably been let loose now and, ironically, there might be some recidivism.

Callie Rogers

It’s estimated that the human brain doesn’t fully develop until around age 25 And, as we saw with Michael Carroll, winning the lottery as just a teen can have disastrous outcomes. Britain’s youngest lottery winner, 16-year-old Callie Rogers, is an example.

The year was 2003 and Callie Rogers became the lucky winner of £1.8 million. Like many a lotto winner, she assured she wouldn’t "go wild and spend loads". Predictably, though, this didn’t exactly turn out to be true.

In the next few years, she reportedly splurged £300,000 on designer clothes, splashed out on endless lavish parties, hefty donations to friends, family, and romantic partners, plus thousands on cosmetic surgeries.

Callie was having fun, some might even say a little too much, seeing as she was reported as being broke by 2009. This quick rise and fall left her living back with her mom, taking on cleaning jobs just to make ends meet.

Similar to other lotto winners though, Callie claims to be much happier without the money, with it causing her severe anxiety and leading her to many of those same vices lottery winners often encounter. However, since losing it all, she hasn’t exactly stayed out of trouble.

Despite now being a mother of 4, training to work in social care, in 2020 she was given a 22-month driving ban as a result of driving while in a less-than-suitable state of mind. During her arrest, she was said to be irate and even attempted to break out of her cuffs. Not such a smart move. But, considering how she lost her millionaire status through unchecked, reckless extravagance, it was a fairly in-character move all the same.

I hope you were amazed at the dumbest lottery winners of all time! Thanks for reading.