Winning the lottery seems to be the definition of lucky. In the US, you have a one in 176 million shot of winning the Mega Millions lottery. State lotteries have odds of one in 42 million. So pulling this off is pretty dramatic. Despite that, some lottery winners have made the unfortunate discovery that money doesn’t always buy happiness. A lot of times it leads to some of the worst misery you could imagine.
10. Sued Twice, Kidnapped, The Sued Again
There’s an old saying that goes “when it rains it pours” and few people have experienced that quite like Tonda Dickerson. Dickerson was working as a server at a Waffle House when a customer gave her a lottery ticket as a tip. That weekend, she won $10 million. Then trouble rolled in.
In many restaurants, tips are pooled. Dickerson’s coworkers felt that they all deserved an equal part of her win, and so they sued. She lost at first but then won on appeal because she won the lottery in Florida but lived in Alabama and gambling was illegal there.
Dickerson was then sued by the man who had given her the ticket. He claimed the waitress had promised to buy him a truck if she won. That suit was dismissed. But things were far from over.
Dickerson was divorced two years before she won the lottery. Her ex-husband tried to kidnap her. She actually managed to shoot him and then take him to a hospital afterward.
The IRS also sued Dickerson in a case they lost based on how much they felt they were owed. That seemed to be the end of her troubles, or at least the ones that happened publicly.
9. Winner Lost $5.5 Million After Buying Ticket with Illegal Funds
Most people who end up facing bad luck after a lottery win do so because of what happens after they win the lottery. Makes sense, right? Jose Luis Betancourt proved it can happen because of what you did before you won.
Betancourt had won $5.5 million from the lottery. When he went to the bank to make sure the state lottery board had transferred the funds, he didn’t get a chance to check. Law enforcement was already waiting for him and took him into custody.
Turns out Betancourt was a drug dealer and the day before he’d sold 36 grams of cocaine to an informant. Police arrested him and his lottery winnings were then forfeited as the state determined that the lottery ticket was purchased with the proceeds from crime. He tried to appeal the case but lost.
8. The Lotto Bank Thieves
There have been cases in the past of groups forming to buy every single potential number combination in a lottery draw when it’s been determined that the winnings would be more than the initial investment. But these require a large amount of money up front. How would an ordinary person do that? Two bank workers from Taiwan came up with a plan when they stole the equivalent of $6.6 million US from their work and spent it all on lottery tickets.
Their plan was as simple as it was stupid. They would steal the money, but the tickets, then replace the stolen money with their winnings. One of the robbers had successfully pulled it off alone, stealing about $25,000 and then winning enough to put it back. The robbery wasn’t one bulk heist – they stole about $1800 the first time. They didn’t win anything. At one point, they spent over $50,000 in a single day. Again, their thinking was they’d be able to double what they spent. But they won nothing. So, realizing they had seriously messed up, they chose to steal more money and run away.
Bafflingly, they then stole over $280,000 and put $215,000 back into lottery tickets. The two men were caught and sentenced to death for what was the largest bank robbery in Chinese history.
7. Life in Prison for Gaming the System
There’s a fine line between cheating and being clever, at least where money is concerned. Casinos in Las Vegas will kick you out for card counting, but is it cheating or just a helpful skill? Most people are willing to exploit an advantage if they don’t think it’s breaking rules, and maybe that’s what China’s Zhao Liqun thought.
Liqun worked at a shop that sold lottery tickets and he noticed a flaw in the way the lottery system was run. After winning numbers were announced, tickets were still being sold for about five minutes. So he started playing the winning numbers. He ended up winning about $3.7 million US before things went south.
He’d get friends and family to go cash the winning tickets, so no one grew suspicious. But suspicious they grew nonetheless and, in China, this kind of thing is taken very seriously. Courts determined he had committed fraud. The state confiscated everything Liqun owned, and he was sent to prison for life.
6. The Aussie Kidnapping
Australian Bazil Thorne won £100,000 back in 1960. In today’s money it would be worth millions so, at the time, it was remarkable. Though it seems like utter madness by today’s standards, in 1960 the newspaper printed not just the name but the home address of lottery winners right on the front page.
A former insurance salesman who had lost his job ended up kidnapping Thorne’s 8-year-old son after school. He had an expensive home and a family of his own and apparently was unable to think of a better way to make ends meet. He called the lottery winner and demanded a quarter of his money or he’d kill the boy.
In the meantime, he wrapped the boy’s head in a scarf to stop him from crying and put him in the trunk of his car. The next time he checked on him, the boy was dead. Officials were unclear if there was some kind of head trauma or suffocation that officially caused his death. It was argued that he’d had no “real” intention of killing the boy at all because he needed him to get the money, but his intentions obviously didn’t amount to much. The killer was caught and sent to prison while laws were changed to allow lottery winners to remain anonymous, but it’s doubtful any of that was much comfort to the Thornes.
5. The Meth Trafficker
In 2015, Ronnie Music Jr. picked up a scratch ticket at his local store and hit the jackpot to the tune of $3 million. Unlike some winners, he didn’t squander his winnings and then turn to crime. He turned to crime immediately.
Music invested a chunk of his winnings into a meth ring run out of a prison. The drug trafficking operation was a multi-state endeavor and authorities said music was tied to drug cartels, white supremacists and even the Bloods gang. Although he ended up cooperating with law enforcement, he still got 21 years in prison for his involvement. That was actually a light sentence for the crimes he was accused of, which also included firearms offenses. The federal guidelines listed 27 years as a minimum.
4. James Hayes Won Big Then Started Robbing Banks
Most of us will never know what it’s like to have millions of dollars. Would you buy a mansion? Cars? Vacations? All of the above? You can imagine how addictive that money would be. So what would you do if you lost it all?
Jim Hayes won $19 million, which seems like it should have been more than enough to live on comfortably for his whole life.But Hayes, like so many other winners, spent too much too fast. He bought million dollar condos and six Lamborghinis. He took extravagant trips. He also got addicted to heroin.
In 1998, at age 35, Hayes won the lottery. He spent and spent some more. He borrowed against the money he hadn’t given yet and. Eventually, it all caught up with him. Three herniated discs saw him turning to prescription pain pills. By 2007, he had to file for bankruptcy. He lost access to his winnings, which were taken to offset his debt. He moved into a cheap apartment, which later burned down.
By 2017, Hayes had turned to bank robbery. He robbed 11 banks over five months. Since he had no record and he didn’t use a weapon, he was only sentenced to 33 months in prison.
3. William Post’s Brother Put a Hit on Him
William Post likely thought he had solved all of his problems when he won $16.2 million back in 1988. Within five years, he was talking about how no one realizes what a nightmare having money truly is. And if anyone would know, it was Post. After he won, his brother put out a hit on him to try to kill him.
Post was sued by his former landlady with whom he’d had a deal to share winnings before he won. The court ordered him to give her a third, but Post was not able to comply. He’d fallen into a dangerous habit of wasting his annual payments on extravagant and useless items. He bought a car lot for one of his brothers, a restaurant for another, and a plane for himself despite having no pilot’s license. He kept accumulating debts and then buying more useless junk.
He ended up auctioning off his 17 remaining yearly payments to get out of debt, then spent most of that money on more junk like a sailboat, two more houses, and cars. When he passed away in 2006 he was living on disability.
2. The Fortune Cookie Powerball Winners
Any time you order Chinese food, you get a fortune cookie and every fortune cookie has a lucky number. Odds are that fortune was written by the CFO of WonTon Food Company. The numbers are pretty much random. But they turned out to be a windfall for Powerball players in 2005. On March 30, 110 different players matched the first 5 of 6 numbers.
The jackpot was an impressive $13.8 million dollars. Unfortunately, the fortune cookie numbers were a single digit off. That meant most of them only won $100,000, with a handful getting $500,000 for putting an extra dollar on their ticket.
1. The Not-So-Timely Divorce
On December 28, 1996, Denise Rossi won $1.3 million playing the lottery. Eleven days later, she filed for divorce from her husband and, in the interim, she neglected to mention her little windfall. Her plan was to start life fresh and single and rich. And hey, anyone who wants a divorce should be able to file for one whenever they like. But, as Rossi soon learned, you can’t do it when you’re hiding millions of dollars.
Despite being married for 25 years, Rossie admitted in court filings she hid the win because she didn’t want her husband getting his hands on the money. It was two years before her ex-husband discovered she’d even won and then sued her. The court was not sympathetic to her greedy plight and accused her of fraud or malice by violating disclosure laws.
The judge ordered her to pay her husband 20 annual payments of $66,800. That works out to just over $1.3 million. In other words, she forfeited everything she’d won. Rossi went on to appeal the decision and lost.