On Christmas morning 2002, Andrew Jackson ‘Jack’ Whittaker — a West Virginia construction-company owner who was already a self-made millionaire — won a Powerball jackpot of $314.9 million, at the time the largest single-ticket jackpot in American history. He took the lump sum of about $114 million after taxes. Within a few years he had been robbed, sued, arrested, and bereaved, and he later said he wished he had torn the ticket up.
Whittaker was not the stereotypical hard-luck winner. He ran a successful water-and-sewer pipe business, employed more than a hundred people, and was worth several million dollars before the win. That made his unraveling all the more striking: it was not naivety or poverty that undid him, but the sheer scale of the money and the way it warped everyone and everything around him.
The money made him a target. He was robbed of hundreds of thousands of dollars left in his car outside a strip club; he was hit with lawsuits and accusations; and the people closest to him suffered most. His granddaughter Brandi, on whom he lavished cars and cash, died of a drug overdose at seventeen in 2004, her body found wrapped in a tarp; her boyfriend had died in Whittaker’s home months earlier. Whittaker’s daughter, Brandi’s mother, later died as well.
By the end of the decade Whittaker said the money was gone and the lawsuits had consumed what the thieves and the spending had not. ‘I wish I’d torn that ticket up,’ he told reporters. He died in 2020, his fortune and most of his family gone — the most famous American example of the ‘lottery curse,’ and a case where the curse was less supernatural than the predictable result of a vast, sudden, public fortune landing on an ordinary life.
Abraham Shakespeare was a barely literate laborer who rode as a truck driver’s assistant in central Florida, owing back child support and living hand to mouth, when he bought a Florida Lotto ticket on a work trip in November 2006. It won a $30 million jackpot, and he took the discounted cash option of roughly $17 million. Almost immediately the money made him a destination: relatives, acquaintances, and total strangers came asking, and Shakespeare — a soft-touch who reportedly found it nearly impossible to say no — gave much of it away.
Into that swirl of need stepped Dorice “Dee Dee” Moore, who approached Shakespeare in October 2008 saying she wanted to write a book about how the lottery had brought him misery and hangers-on. Instead, prosecutors said, she methodically stripped him of what remained. She set up a company, Abraham Shakespeare LLC, took control of his accounts and real estate, and moved his assets and money to herself — prosecutors said she withdrew about $1 million and bought luxury vehicles, and had his home transferred to a company she controlled.
Shakespeare was last seen alive in April 2009. For months Moore told family and investigators he was alive and simply hiding from the people who wanted his money, even sending text messages from his phone and paying others to suggest he was in contact. On January 27, 2010, his body was found buried under several feet of dirt and a newly poured concrete slab behind a home connected to Moore in Plant City, Florida; he had been shot twice in the chest.
Moore was arrested on February 2, 2010, and charged with first-degree murder; on December 10, 2012, a Hillsborough County jury convicted her. She was sentenced to life in prison without the possibility of parole, plus a 25-year minimum for using a firearm in a violent felony. Shakespeare’s case is the starkest entry in this catalogue: not a slow squander or a self-inflicted ruin, but a man killed for a fortune that a predator decided was easier taken than earned.
William “Bud” Post III had bounced through life as a cook, a truck driver, and a carnival worker, and in February 1988 he had about $2.46 in the bank when he pawned a ring to buy Pennsylvania Lottery tickets. One of them won $16.2 million, paid as an annuity of 26 annual installments of about $497,953. Within roughly three months he was reportedly some $500,000 in debt; within a few years the fortune was effectively gone.
The money detonated his relationships. A former landlady and onetime romantic acquaintance, Ann Karpik, sued him claiming they had agreed to share any winnings, and a court awarded her a substantial portion of the jackpot. Post’s own brother, Jeffrey, hoping to inherit, hired someone to kill Post and his wife — a plot that was uncovered and led to the brother’s arrest. Post spent heavily and badly, sinking money into a used-car lot, a restaurant or lease venture, an airplane, and property, much of it with relatives.
The legal and financial wreckage compounded. Post was convicted of assault after firing a shotgun at a debt collector who came to his mansion, and he eventually declared bankruptcy. The annuity that might have provided a steady income for life had been borrowed against, litigated over, and squandered, and he ended up living on Social Security and food stamps — the man who had won $16.2 million reduced again to public assistance.
William Post died on January 15, 2006, at age 66, of respiratory failure, in the Pittsburgh area. He had said more than once that he was happier when he was broke. His case became one of the foundational “lottery curse” stories in American journalism precisely because nearly every failure mode arrived at once: predatory litigation, a murderous relative, reckless spending, and a slow slide back into poverty.
Billie Bob Harrell Jr. was a devout Pentecostal man who had struggled to provide for his wife, Barbara Jean, and their three children, working at one point as a stocker at a Home Depot in the Houston area after a series of job losses. In June 1997 his Quick Pick ticket won a $31 million Lotto Texas jackpot, paid as an annuity of 25 annual installments of about $1.24 million. For a man who had felt the shame of not being able to support his family, it seemed like an answered prayer.
Harrell’s first instincts were generous and characteristic of his faith. He gave heavily to his church, bought vehicles and homes for relatives, paid off debts, and famously bought turkeys for the poor. But the giving and the requests quickly outran even a multimillion-dollar annuity, as family, friends, fellow congregants, and strangers pressed him for more, and he found it agonizing to refuse.
Under mounting financial pressure, Harrell made a deal with Stone Street Capital, a company that buys future annuity payments: he traded roughly ten years of his installments — worth about $6 million in face value — for a lump sum of about $2.25 million, a transaction that compounded his losses. The strain corroded his marriage, and he and Barbara Jean separated. He reportedly told a financial adviser that winning the lottery was “the worst thing that ever happened to me.”
On May 22, 1999 — roughly 20 months after the win — Billie Bob Harrell Jr. died by suicide at his home. His story is one of the most sobering in this catalogue not because of crime or spectacular excess, but because generosity, social pressure, a predatory financial deal, and a collapsing marriage combined to crush a fundamentally decent man in less than two years.
In 2006, Sandra Hayes was a Missouri state social worker and single mother of three from Florissant, near St. Louis, living on less than $26,000 a year when she and a dozen co-workers shared a $224 million Powerball jackpot. Her portion, taken as a lump sum after taxes, came to roughly $6 million. By the financial measures of this catalogue, that should have been the end of the story — a hard-working public servant lifted into security and comfort. Hayes did not gamble it away, did not get robbed or sued into ruin, and did not go broke. She paid off her debt, put the rest into savings, and remained financially stable.
What she lost instead were people. In the book she later wrote, ‘How Winning the Lottery Changed My Life: Windfall, a Blessing or a Curse,’ and in interviews, Hayes described a relentless siege by relatives and friends who turned predatory once they learned of her money. ‘I had to endure the greed and the need that people have, trying to get you to release your money to them,’ she said. ‘That caused a lot of emotional pain. These are people who you’ve loved deep down, and they’re turning into vampires trying to suck the life out of me.’
Her account is valuable precisely because it is the comparatively happy-ending case. Hayes is proof that a windfall need not destroy a person’s finances — she kept her money and managed it carefully. But she is equally proof that the lottery curse is often social rather than financial: the same money that secured her future cost her relationships she had assumed were unconditional, and forced her to defend her boundaries against the very people she had expected to celebrate with.
Hayes did not retire the instant she won; she stayed in her social-services job for about a month afterward. Her measured, deliberate handling of the prize is part of why she survived it. Yet she has been candid that the emotional toll was real and lasting, and her central message to new winners is sober: that they are, as she put it, ‘in for the ride of their life,’ and that the hardest part is not the money but the people it changes around you.