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.
9 Andrew Jack Whittaker
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.
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.
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.
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.
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.
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.
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.
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.
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.
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