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Riches-to-Rags Stories of ‘Cursed’ Lottery Winners

BY SANDRA GRAUSCHOPF

Updated April 27, 2020
Many people think winning the lottery would be the answer to their prayers and the solution to all of their problems — but some winners have had the opposite experience. Despite being lucky enough to win the lottery, they later wished they’d torn up their ticket rather than redeeming it.

It may seem impossible that you could win millions of dollars and wish you hadn’t. But it’s happened often enough that the phenomenon has been dubbed the “lottery curse.”

Don’t believe it? Here are seven victims of the lottery curse — people whose “lucky” win turned sour, leading to divorce, bankruptcy, or even death.

These stories are cautionary tales, but there are plenty of jackpot winners who have gone on to put their money to good use for themselves and their communities. Read through to the end for tips on how to handle a jackpot responsibly and enjoy your winnings.
Jack Whittaker: “Since I Won the Lottery, There’s No Control for Greed”

Powerball jackpot winner Scott Gries with granddaughter Brandy, who died of a drug overdose. © Scott Gries / Getty Images
Unlike many winners, Andrew “Jack” Whittaker was already wealthy when he won the largest jackpot ever awarded to a single Powerball ticket on Christmas morning in 2002. He chose a lump sum payment instead of an annuity, so he took home $113-some million from his $314.9 lottery ticket.1

He added that to the money that he’d earned himself, working his way up from poverty to the owner of a West Virginia contracting company. When he bought the ticket, his company was doing about $15 million a year in contracts.

However, Jack Whittaker found his lottery winnings changed him more than the wealth he’d earned himself did.

Jack Whittaker did a lot of good with the money he won, setting up a charitable foundation, donating money to build churches in West Virginia, and even giving the woman who sold him the winning ticket a new house, a new car, and a pile of cash.

Nevertheless, the lottery curse hit him.

Not all states let winners stay anonymous, and Jack Whittaker’s win was widely publicized. He was deluged with people asking for money and favors.

He developed a habit of leaving large amounts of money in his car, which became widely known. One evening, when he was visiting a strip club, someone stole about half a million dollars out of his car. Later, in a separate incident, $100,000 was stolen from another car.

Furthermore, his company was hit with frivolous lawsuits from people who wanted to get access to deep pockets, costing him millions in legal fees.

Under the strain, Whittaker started to unravel. He started drinking hard and getting into fights. He’d get handsy with women and offer them money to sleep with him or take off their clothes for him.1

But that’s, by far, not the worst of it.

He enjoyed spoiling his granddaughter, Brandi. He gave her a huge allowance and four cars, but his generosity backfired when her wealth attracted a bad crowd.

A boyfriend of Brandi’s died of an overdose in a house Whittaker was developing, and Brandi was implicated. Friends wouldn’t even let her attend the funeral.

A year later, Brandi was found dead under suspicious circumstances, though the case was never solved.

The deaths had devastating consequences for his family. His daughter, Brandi’s mother, was found dead seven years after the jackpot was won. Whittaker’s wife divorced him.

Whittaker lost the people he loved and the money that he won.

“Since I won the lottery, I think there is no control for greed,” Jack Whittaker said. “I think if you have something, there’s always someone else that wants it. I wish I’d torn that ticket up.”

You can read more about Jack Whittaker’s story here: Powerball Winner Says He’s Cursed.

Curtis Sharp, Lottery’s $5 Million Man

Curtis Sharp, Jr. was famous for his lottery win and his bowler hats. Image © Andrew Paterson / Getty Images
When Curtis Sharp, Jr. won a $5 million jackpot in 1982, he was a dream come true for the lottery’s public relations department. The lottery was facing an image problem, and Curtis Sharp, Jr. was just the person they needed to spread the word that everyday people could turn their lives around by buying a ticket.

Curtis Sharp, Jr., who had been a dishwasher before he struck it rich, became known as the “Five Million Dollar Man”.

With his larger-than-life personality, his distinctive bowler hat, and the way he loved to flash his newly-won money around, he was a walking advertisement for the lottery. Parties, women, new houses, flashy cars… he lived big and became one of the lottery’s best-known winners because of it.

Unfortunately, Curtis Sharp, Jr.’s lifestyle wasn’t sustainable. He was spending more than his big yearly checks covered, and his party-hard attitude was wearing on him. The lottery curse had hit.

The year after he won the lottery, he left his wife for a lover and had a huge wedding. Five years later, his second wife had divorced him, too. He was drinking hard, to the point where he’d pass out outside of his new girlfriend’s house. And the money had run out. He had to borrow money from his first wife.

Luckily, his story has a happy ending. After a drunk-driving incident, Curtis Sharp, Jr. found God. He stopped drinking, stopped partying, cleaned up his act, and became a minister.

But he still buys lottery tickets.

You can read more about Curtis Sharp, Jr. in Matthew Sweeney’s book, “The Lottery Wars” or online here: Country’s Most Famous Lottery Winner Is Now Living Off His Pension, Social Security Checks.

William Post III: “Nobody Realizes the Nightmares”

William Post III’s win from the Pennsylvania Lottery should have been a dream come true. Instead, he became a victim of the lottery curse. Image (c) William Thomas Cain / Getty Images
If you had less than $3 in your bank account, would you buy a lottery ticket? Maybe not, but William Post, III, known to his friends as Bud, went a step further than that. He pawned one of his few possessions for $40, then spent the entire amount on lottery tickets.

Foolish or not, his gamble paid off. One of those tickets won him $16.2 million from the Pennsylvania lottery.

You might think the man who had been little more than a drifter would have an easy life from the moment he won on. But the truth was that after cashing in his win, Post’s life took a sharp turn for the worse.

“Everybody dreams of winning money, but nobody realizes the nightmares that come out of the woodwork, or the problems,” he said.

How could that happen?

Post spent his money wildly. The majority of the first yearly installment of his winnings, which totaled over $400,000, was spent in the first two weeks. After a year, he was half a million dollars in debt.

His girlfriend sued him, claiming they had agreed to share the money if he won. When she won her court claim, he couldn’t pay, so his lottery payouts were frozen.

He had to declare bankruptcy, and he only managed to hold onto about $2.6 million, which he immediately spent.

He was arrested for assault after firing a shotgun at a man who was pestering him for money.

Even worse, his brother hired a hitman to kill him and his wife so that he would inherit the money (he was on wife number six at that point).

Thirteen years later, this lottery curse victim died alone and penniless, living off of welfare payments.

You can read the whole story here: William ‘Bud’ Post III; Unhappy Lottery Winner.

Powerball Winner Willie Seeley: ‘The Drama Is Nonstop’

Willie Seeley’s lottery win went from a dream come true to an annoying curse — quickly. Image (c) Montaplex
When “Wild” Willie Seeley and 15 of his co-workers formed a lottery pool that won a big jackpot in August of 2013, it seemed like a blessing. But it only took a few weeks for Willie Seeley to feel he had been hit by the lottery curse.

The lottery pool, known as Oceans 16, bought a ticket that was one of three to win a $450 million Powerball jackpot. At a press conference, Willie Seeley said that he and his wife were, “happy, happy, happy” and planning to spend their days fishing, hunting, and relaxing.

But it didn’t take long for the downside to winning a lottery jackpot to appear.

It’s hard to go fishing when you are being followed by reporters and camera crews clamoring for an interview or an appearance on a reality TV show. And distant relatives and complete strangers coming to your house to ask for handouts made it hard to relax.

Plus, it was a shock to realize that after splitting the jackpot three ways (three winning tickets were sold), then splitting the remainder among the 16 members of the lottery pool, not even $4 million was left over after taxes.

$4 million was enough for the couples to buy new vehicles, help their families, and quit their jobs, but not the never-worry-about-money-again windfall it had seemed at first.

Only weeks after their initial exuberance, Willie Seeley and his wife were bemoaning the lottery curse. “There are days I wish we were back to just getting paid every two weeks. You have to change your whole way of life, but we didn’t want to change the way we lived.”

Read Willie Seeley’s full story here: Powerball Winner ‘Wild’ Willie Wants His Old Life Back.

Lottery Winner Abraham Shakespeare: Murdered for His Money

Filling out a lottery ticket led to Abraham Shakespeare’s murder. Image (c) David Joyner / Getty Images
After winning $40 million from the Florida Lottery in 2006, Abraham Shakespeare was more than generous with his money. Although he gave money to nearly anyone who asked, his kindness didn’t give him immunity to the lottery curse.

Abraham, a high-school dropout and convict who couldn’t even read, won the lottery when he stopped at a convenience store with a coworker and gave the coworker a couple of bucks to buy tickets.

His troubles started almost immediately. His coworker took Shakespeare to court, accusing him of stealing the tickets and the jackpot from him Shakespeare won the suit, but his troubles didn’t end there.

So many people were asking Shakespeare for money that he said, “I’d have been better off broke,” and “I thought all these people were my friends, but then I realized all they want is just money.”

Then he met Dee Dee Moore, who said she wanted to write about his experiences. She also said she’d help manage his money. When he agreed, she immediately started spending it on herself, buying herself a Hummer and a Corvette, for example. She even took possession of his home.

But apparently, stealing from Shakespeare wasn’t enough for Moore, who killed Shakespeare and buried his body under concrete slabs at her boyfriend’s house.

She took extreme lengths to try to make it seem as if Shakespeare were still alive, sending fake texts and attempting to bribe his family to say they had seen him.

Moore’s crime was discovered and she was convicted of first-degree murder. Nevertheless, Shakespeare would have been better off sticking to the $5 he had in his pocket when he bought his winning lottery ticket.

You can read more about Abraham Shakespeare’s life and death here: Abraham Shakespeare, Wikipedia.

Billy Bob Harrell Jr.: Committed Suicide Only 2 Years After $30 Million Win

Billy Bob Harrell Jr.’s lottery win seemed like a godsend, but it became a curse. Image (c) Michael Melford / Getty Images
Billy Bob Harrell, Jr. had fallen on hard times after an unsuccessful attempt to become a minister. When he won $31 million from the Texas Jackpot, it seemed he had finally found a way to support his family and put his money troubles behind him.

He was very generous with his winnings, helping his family, his church, and needy parishioners. But the requests for money didn’t stop coming.

His bad investments and the constant demand for more, more, more from outsiders put a strain on his family. His marriage ended and other family members were at odds with each other.

He said, “Winning the lottery was the worst thing that ever happened to me.”

On a day when he was scheduled to go to dinner with his ex-wife, Billie Bob Harrell, Jr. decided he’d had enough. He put a shotgun to his chest, pulled the trigger, and killed himself. He died less than two years after his miraculous lottery win.

You can read Billie Bob Harrell, Jr.’s full story here: Billie Bob’s (Mis) Fortune.

Jeffrey Dampier, Jr.’s $20 Million Lottery Win Led to His Murder

This Lottery Curse Victim’s Win Led to His Murder. Image (c) Jan Stromme / Getty images
Many lottery curse victims fall on hard times because they overspend or flaunt their money, but Jeffrey Dampier, Jr. seemed to be doing everything right after winning $20 million from the Illinois lottery.

Dampier moved to Tampa Bay along with his parents, his second wife, and her family. He invested in a popcorn business that he named after his daughter, and the business thrived.

But despite paying for an apartment, a car, holidays, and more for his sister-in-law, Victoria, and her boyfriend, the two of them hatched a scheme to get their hands on Dampier’s money.

Victoria asked Dampier to come to her apartment to help her with car trouble. When Dampier arrived, her boyfriend tied him up and they stole thousands of dollars in cash from him.

The couple then took Dampier into an alley and shot him in the back of the head with a shotgun, killing him.

The crime didn’t pay off, however. Victoria and her boyfriend are each serving life sentences for murder, kidnapping, and other charges.

You can read about the case here: Sister-in-Law, Boyfriend Arrested in Businessman’s Slaying.

You Don’t Have to Be a Lottery Curse Victim!
Although these lottery curse stories make it seem like winning money is the worst thing that could happen to you, remember that the media loves a riches-to-rags story. Lottery curse stories are often blown out of proportion.

There are ​many more big winners who treat their money responsibly and have a wonderful experience after winning. For some examples, see these interviews with PCH Winner Natalie Bostelman and HGTV Dream Home Winner Don Cruz.

Don Cruz is sometimes cited in news articles as a big winner who lost it all, but he had a great time with his huge prize ​and cherishes the memories that he has.

Remember that most lottery winners don’t make big news because they handle their money responsibly and use it to enjoy an easier life.

Want to know what steps to take to avoid becoming a victim of the lottery curse, should you ever win big? Check out my article, How to Win the Lottery Without Losing Your Shirt.