The 10 Worst Lottery Winner Horror Stories In History

The Poorest

How many of you rushed out to buy a Powerball ticket, hoping to win the $546 million prize in the recent drawing? Of course you wouldn’t be alone in that endeavor if you had. After all, it’s a dream of countless millions around the country to win the lottery. People dream of finally having the money to do anything and everything they’ve ever dreamed of and more. In fact, many experts say that simply buying a ticket is enough to increase the happiness of the purchaser because the rush of hope and fantasies bring a slice of joy to otherwise normal lives.

And as the jackpot rises higher and higher, so too do the dreams. Lottery players fantasize that by winning, they could finally travel the world, buy houses for loved ones, pay off debt… A sudden windfall of cash seems like a dream come true, a way to improve lives and finally find happiness.

But is sudden wealth really all it’s cut out to be? For the average Joe, that money likely comes with more problems than many realize. How do you invest it? Who do you trust? What do you tell people who come knocking on your door, begging for help? After all, you can’t help everyone. Then there are the legal hassles, the people who try to come after your money. In fact, it’s all a bit terrifying.

Take it from people who actually know what it’s like. People who won big, and then, instead of watching all their dreams come true, they watched their lives fall apart right before their very eyes. And for a few unlucky souls, they may have been better off if they’d never won the lottery in the first place. Heck, more than one of them might still be alive today had they never purchased that ticket.

But sadly, it’s too late for that now.

10. Thomas and Denise Rossi


Thomas and Denise Rossi were married for 25 years, and if you ask Thomas, he’d say the two had been pretty happy together. In fact, he was stunned when his wife presented him with divorce papers. Denise said she’d been unhappy for some time because her husband was always broke. The fact that she won the lottery days before she handed him the divorce papers doubtless had something to do with this.

Of course, the court never knew of the winnings, and neither did her ex-husband. The only problem was the state of California’s laws against not disclosing assets during divorce proceedings. Denise’s act of greed ended up being her downfall: The courts discovered her deception and awarded all of her winnings to her ex-husband. Had she been honest from the very beginning, she’d likely only be out half of her jackpot. But since she wasn’t – she ended up with nothing.

Of course, this isn’t as bad as some things that came about for other lottery winners. And this was partially not her own doing since she was unaware of the laws surrounding the situation. But still, this situation would leave any jackpot winner bitter and cynical.


9. Andrew Jack Whittaker

via cnn.com


When you’re already a millionaire, why would you bother playing the lottery? Probably for the same reason the rest of us do – to win. But for one particular millionaire, Andrew Jack Whittaker, that extra $315 million from a Powerball ticket appears to have done more harm than good.

After winning the big jackpot, Whittaker’s life slowly unravelled before his eyes. There were legal issues, as there almost always are with money, and there were his own personal demons like drinking and a love of strippers that helped send Whittaker down a black hole of despair. In fact, while he was visiting a strip club one night, he claims almost half a million dollars was stolen from his car. Yes, you read that right – he didn’t merely lose his car stereo or his loose change, he lost half a million dollars. Those must have been some ecstatic burglars. He later said that thieves also emptied his bank accounts.

But not only did he lose all the money he won, his life was filled with other tragedies as well. In 2004, his granddaughter died of a drug overdose and her mother – his daughter – died five years later. At the time of her death, he seemed to blame the ticket for all the bad fortune in their life. Sobbing to reporters, he said, “I wish I’d torn that ticket up.”


8. Janite Lee


If you’re like most people, at least one item on your “If I won the lottery” list is probably founding a charitable organization of some kind. Others might even say they’d give most of it to charity. Janite Lee, 60, belonged in that latter group. She spent a large chunk of her yearly $620,000 installment payments on philanthropic causes. One would think karma would pay her back for the kindness, but karma can only do so much when you’re bad at money management.

Lee later sold the rights to her annual payment for one lump sum. This lump sum buyout option seems to engender a lot of horror stories. And in Lee’s case, she did eventually have to file for bankruptcy, not even 10 years after she won $18 million.

In 2001, she only had $700 to her name. If that was the end of the story, however, she may not be worse than she was before the lottery. But alas, it doesn’t end there. Lee was also in debt to the tune of over $2.5 million, leaving her in worse shape than she would have been had she never won the lottery in the first place.


7. Callie Rogers


In America, you can’t play the lottery until you’re 18 years old. And if you ever wondered why that might be, consider the case of British teen Callie Rogers. Rogers won $3 million in July 2003 when she was only 16-years old.

That kind of money comes with a lot of responsibility, more than many of us can possibly imagine. But poor Callie ended up getting a harsh lesson in what wealth can do to a person – and especially to their friends. As many of us would like to do, Rogers spent hundreds of thousands of dollars pampering her loved ones, buying them presents like cars and homes, and taking them on lavish trips.  Of course, Rogers indulged her own desires as well, spending money on breast implants and designer clothing – the types of things you’d expect a 16-year old girl to splurge on.

But in 2009, young Rogers was already facing bankruptcy, her dream-life coming to a crashing halt. All the pressure was a bit too much for the teen, who has reportedly attempted suicide twice since winning big and developed a drug problem. Now with all the money gone, she actually hopes to find happiness in poverty. She works three jobs and lives with her mother.


6. William Post III


The story of William Post III sounds almost like a fairy tale, at first. Post grew up in an orphanage, and when he struck it rich, he was surviving on disability payments. Before his big win, had less than $3.00 in his checking account.

Sadly for Post, winning $16.2 million ended up causing him even more problems.

In interviews, he’s insisted that he was happier when he was poor. And when you look at the months following his win, it’s easy to see why. He not only fell victim to his own poor spending habits – something that many lottery winners struggle with since they’re not used to having large sums of money just handed to them – but like many on this list, tragedy also struck shortly after he was handed the first check.

In the first three months alone, he blew through half a million dollars, the amount of his first annual payment, and ended up in debt for another $500,000. But that’s not even the worst of it. Post’s own brother hired a hitman to try and kill both Post and his wife. Other relatives were almost as destructive, convincing Post to invest the money in terrible business ventures.

It all ended up with Post filing bankruptcy and spending time in jail for firing a gun at a bill collector. Not the ending any of us would hope for, that’s for sure.


5. Ibi Roncaioli


Many of the people on this list lost money, homes and even their marriages, but not many ended up losing their lives thanks to their lottery winnings. But Ibi Roncaioli story is one like no other.

Dr. Joseph Roncaioli was charged with murder in the poisoning of his lottery winner wife, Ibi. He claims he was merely trying to numb her arms to take her blood for some health tests, but there were needle marks all over her body and a large amount of painkillers in her system.

After his wife’s death, he was in for an unpleasant surprise of his own, however. When he went to the family’s safe where they kept the money, he found that it was all gone. His wife had illegally signed bank documents, transferring all the winnings over to her sole possession – and she’d handed out large amounts of that money to her three children, only two which her husband knew about.


4. Billie Bob Harrell Jr.


You know the saying “money doesn’t buy happiness?” Sure, most of us scoff at the concept. But if ever there were a story that proves that there may be something to the old saying, this just may be it. Billie Bob Harrell Jr. was like most of us, and when he won $31 million in the Texas Lotto in 1997, it seemed like the world was his oyster.

Prior to winning big, Harrell and his family were mostly broke as he moved between low-paying jobs. And when that first payout hit, well, he did what many of us would do – he quit his job at Home Depot, took his family on a vacation to Hawaii, donated tens of thousands of dollars, bought houses and cars for his loved ones and even donated almost 500 turkeys to the poor. Nothing unusual so far, right?

Well, with large sums of money comes greed, of course, and in this case it was the greed of others that started to get to him. Harrell had to change his phone number repeatedly because strangers were calling him left and right, asking for donations. On top of it all, he made a bad deal with a company that gives lottery winners a lump sum payment in exchange for their yearly winnings – never a good thing to do, it seems – losing out on a ton of money.

But if that weren’t bad enough, his personal life started to fall apart. His wife, Barbara Jean, left him less than a year after he won. He told his financial advisor that “Winning the lottery was the worst thing that ever happened to me.” Sounds hard to believe, doesn’t it? Well, apparently it was true. Harrell was found dead inside his home about 20 months after the win. Cause of death? A self-inflicted gunshot wound.


3. Urooj Khan


It’s a story that sounds like it came straight out of a crime novel. Urooj Khan, an immigrant from India living in Chicago, had all but given up on gambling until one day, he randomly bought a scratch off ticket. That ticket would end up being worth $1 million.

Khan was ecstatic, even giving the clerk he brought the ticket from $100, saying he’d give him more, but that was all he had on him at the time. Khan chose to take his winnings as a lump sum payment, which came in at just under half a million after taxes.

The day the check arrived, Khan had dinner with his family, including his wife, his daughter from another relationship and his father-in-law. Khan’s wife made a lamb curry to celebrate. Later that night, before he could even cash the check, Khan became incredibly ill and died at the hospital. At first, his death was ruled to be due to natural causes, a hardening of the arteries.

It wasn’t until his brother pressed for an autopsy that they discovered something more sinister – it appeared that Khan may have died from cyanide poisoning.

His wife and daughter ended up splitting the winnings.


2. Abraham Shakespeare


This winning lottery ticket couldn’t have been sold to a nicer guy. Abraham Shakespeare was an American laborer who won big with a lottery ticket he bought on a whim.

Shakespeare apparently struggled with holding onto the cash, but unlike some people who merely blow their winnings on extravagant luxuries, Shakespeare apparently helped people whenever he could. In fact, he gave a large chunk of the money away before his life took a turn for the worse.

According to the mother of one of Shakespeare’s sons, people were always hounding him for money. People would show up at the house, begging to stay with him, and often he’d let homeless people stay with him as well.

And it very well could have been that kindness that got him killed. Shortly after winning the lottery, he was befriended by Dee Dee Moore. Dee Dee offered to help him manage the rest of his winnings, but instead the woman stole from Shakespeare. At first, when Shakespeare went missing, she told everyone that he ran away from those begging for his money, and she also sent text messages from his phone. The text messages were red flags because according to his family, Shakespeare was mostly illiterate.

Investigators discovered Shakespeare’s body under a concrete slab at a home that Moore put under a boyfriend’s name, and everything came crashing down. Though Moore didn’t go down without a fight; she tried to blame drug dealers and even her own 14-year old son for Shakespeare’s death.

On December 10, 2012, Dee Dee Moore was convicted of first degree murder and sentenced to life in prison without parole. And what about the winnings? They were all gone, leaving nothing for Shakespeare’s children. The year their father died, they didn’t even have enough money for Christmas presents or shoes – items that Shakespeare took care of when he was alive.


1. Jeffrey Dampier


Winning $20 million should be the start of a wonderful new chapter in one’s life. Or so you would think. For Jeffrey Dampier, his winnings helped him launch his own gourmet popcorn business, along with the ability to buy gifts for friends and family. This included his sister-in-law, Victoria, with whom he was having an affair…

It seems Dampier should have thought twice about spoiling his beloved mistress, as she wasn’t feeling so benevolent herself. Victoria and her boyfriend, Nathaniel, decided to rob Dampier, since apparently the gifts he was buying for her weren’t already enough. They bound his hands and feet together, and this is where the robbery took a gruesome turn.

Nathaniel reportedly turned to Victoria and told her, “Shoot him or I’ll shoot you.” Choosing to save her own skin, Victoria shot Dampier in the back of the head, killing him.

All of this over some money. It almost makes you wonder if winning the lottery isn’t all it’s cracked up to be. Or if you do get lucky, perhaps you should be sure to surround yourself with people who don’t have a desire to take it all away from you.