1. Jack Whittaker — $315 Million (2002)
Jack Whittaker was already a millionaire when he won the $315 million Powerball jackpot on Christmas Day 2002 — the largest single-ticket jackpot at the time. He took the lump sum of $114 million after taxes and famously said he wished he'd torn up the ticket.
Within two years, Whittaker had been robbed multiple times (including $545,000 stolen from his car at a strip club), sued by multiple parties, and was drinking heavily. His granddaughter Brandi Bragg, whom he adored and showered with money, died of a drug overdose at age 17 in 2004. Her boyfriend had died of a drug overdose months earlier.
Whittaker's wife left him. His home was destroyed in a fire. He was sued by Caesars Atlantic City for bouncing $1.5 million in checks. He later told reporters he wished he'd never won. By most accounts, he went through the entire $114 million in under a decade. He passed away in 2020.
The lesson: money doesn't fix pre-existing problems. Whittaker was generous to a fault and had substance abuse issues before the win. The money amplified both.
2. Abraham Shakespeare — $30 Million (2006)
Abraham Shakespeare won $30 million in the Florida Lottery in 2006. He was 42, a truck driver's assistant who could barely read. Over the next few years, he gave away and was swindled out of most of his winnings by people claiming to be friends, business partners, and romantic interests.
In 2009, a woman named Dee Dee Moore befriended Shakespeare, claiming she was writing a book about people who took advantage of lottery winners. In reality, she was doing exactly that. Moore systematically drained Shakespeare's remaining funds, eventually transferring his house and assets into her name.
When Shakespeare confronted Moore about his missing money, she shot and killed him in April 2009, then buried his body under a concrete slab in her backyard. She sent texts from his phone to family members to cover up his disappearance. His body was found in January 2010.
Moore was convicted of first-degree murder and sentenced to life without parole in 2012. Shakespeare's story is the darkest lottery cautionary tale in American history — a man murdered for money he'd already lost.
3. Evelyn Adams — $5.4 Million (1985, 1986)
Evelyn Adams beat astronomical odds by winning the New Jersey Lottery twice — $3.9 million in 1985 and $1.4 million in 1986. The combined $5.4 million (worth about $15 million in today's dollars) should have set her up for life.
Instead, Adams gambled most of it away at Atlantic City casinos. She was also generous to a fault, giving large sums to family and friends who came out of the woodwork after her wins. By the early 2000s, she was living in a trailer park.
In interviews, Adams was remarkably honest about what happened. She described being overwhelmed by requests for money and unable to say no. The gambling was an escape from the pressure. Without financial advisors, a trust, or any plan for the money, it simply evaporated.
The lesson: two jackpots don't make you financially literate. Without professional help, even multiple wins can't outpace poor money habits.
4. William 'Bud' Post III — $16.2 Million (1988)
Bud Post won $16.2 million in the Pennsylvania Lottery in 1988. Within a year, his landlady and former girlfriend sued him for a share of the winnings (and won). His brother hired a hitman to try to kill him, hoping to inherit the money. Post was arrested for firing a shotgun at a bill collector.
Post went through the entire fortune in spectacularly poor ways: buying a restaurant, a used-car lot, and a twin-engine plane (he couldn't fly). He owed $1 million to the IRS by 1993. He declared bankruptcy and eventually died in 2006 while living on a $450/month disability check.
Post's most famous quote: 'I was much happier when I was broke.' His brother's murder-for-hire plot was real — the brother was convicted and sentenced to 20 years. Post's story shows how family dysfunction and sudden wealth can be a literally lethal combination.
5. Billie Bob Harrell Jr. — $31 Million (1997)
Billie Bob Harrell Jr. won $31 million in the Texas Lottery in 1997. He was a devout church-going father of three who had recently been laid off from his Home Depot job. The win seemed like divine intervention.
Harrell was incredibly generous — buying cars for friends, paying off strangers' bills, donating heavily to his church. He and his wife moved into a mansion. But the constant stream of people asking for money took a toll. His marriage fell apart. He made a disastrous deal with a company that gave him a lump sum in exchange for his annual lottery payments, receiving far less than the payments were worth.
Less than two years after winning, Harrell died of a self-inflicted gunshot wound. He was 47. His last words to a friend were reportedly: 'Winning the lottery is the worst thing that ever happened to me.'
Harrell's story is especially painful because he was by all accounts a good person who used the money generously. But generosity without boundaries, combined with predatory financial 'deals,' left him worse off than before he won.
6. Michael Carroll — £9.7 Million (2002)
Michael Carroll was 19 years old and wearing an electronic ankle tag for a previous offense when he won £9.7 million in the UK National Lottery in 2002. He became a tabloid fixture almost immediately, earning the nickname 'the Lotto Lout.'
Carroll spent lavishly on drugs, gold jewelry, demolition derbies on his property, and parties. He reportedly spent £2,000 per day on crack cocaine. He bought a mansion and trashed it so thoroughly that it was condemned. He was banned from multiple pubs for antisocial behavior.
By 2012, Carroll was broke and working in a cookie factory for £200 per week. He later worked as a coal delivery man. To his credit, Carroll has been remarkably philosophical about the experience in later interviews, saying he doesn't regret it and that he had a great time while the money lasted.
Carroll's case is a textbook example of what happens when a teenager with no financial framework suddenly gets nearly £10 million. No one — no bank, no advisor, no family member — intervened effectively.
7. Andrew Jackson Whittaker Jr. — Not to Be Confused
Wait — didn't we already cover Jack Whittaker? Yes. But his story is so instructive that his full legal name, Andrew Jackson Whittaker Jr., appears in court records from over a dozen lawsuits filed by or against him after his 2002 win. Let's look at a different kind of horror story instead.
Janite Lee — $18 Million (1993): Janite Lee won $18 million in the Missouri Lottery and became a celebrated philanthropist. She donated to Washington University, the Democratic National Committee, and multiple charities. Politicians courted her. She was invited to presidential dinners.
But Lee was spending far beyond even an $18 million budget. She donated millions without accounting for taxes on her remaining payments or her own living expenses. By 2001, she had filed for bankruptcy with over $2.5 million in debt. The charities that had celebrated her moved on.
Lee's story is different from the others — she wasn't reckless or irresponsible in the traditional sense. She was genuinely generous and wanted to make a difference. But she never understood the math: lottery winnings paid in installments are worth far less than the headline number, and giving away principal without professional financial planning leads to insolvency.
8. Callie Rogers — £1.9 Million (2003)
Callie Rogers was 16 years old — the youngest UK lottery winner at the time — when she won £1.9 million in 2003. She was a shop worker living in foster care in Cockermouth, Cumbria.
Over the next several years, Rogers spent the money on cosmetic surgery, drugs, gifts for boyfriends, and multiple houses. She attempted suicide three times. By 2013, she told the Daily Mail she was down to £2,000 and was actually happier for it.
Rogers has become an advocate against allowing teenagers to play the lottery. The UK subsequently raised the minimum age for National Lottery play from 16 to 18 in 2021 — a change Rogers had publicly supported.
Unlike many other lottery horror stories, Rogers's has a relatively hopeful ending. In later interviews, she described rebuilding her life, working as a carer, and raising her children. She's spoken publicly about how the money destabilized her during a period of her life when she had no emotional or financial tools to handle it.
9. Urooj Khan — $1 Million (2012)
Urooj Khan won $1 million on an Illinois instant scratch-off ticket in June 2012. After taxes, he received about $425,000. He told friends he planned to invest in his dry-cleaning business. One day after the check was issued, Khan was dead.
His death was initially ruled natural causes. But his family pressed for a deeper investigation, and a toxicology report revealed lethal levels of cyanide in his blood. Khan had been poisoned.
The case became a homicide investigation. Khan's widow and other family members were considered persons of interest, but as of 2026, no one has been formally charged with his murder. The case remains officially unsolved. His $425,000 check was never cashed.
Khan's case is uniquely disturbing because the prize was relatively modest — $1 million pre-tax. It wasn't a mega-jackpot that attracted worldwide attention. Someone in his life decided that $425,000 was worth killing for.
10. Alex and Rhoda Toth — $13 Million (1990)
Alex and Rhoda Toth won $13 million in the Florida Lottery in 1990. Rather than live large, the Toths tried to hide from the IRS. They moved to Las Vegas, failed to file tax returns, and attempted to conceal their winnings through various schemes.
The IRS eventually caught up with them. Alex was charged with tax evasion and spent two years in federal prison. Rhoda died before the case was fully resolved. The Toths owed millions in back taxes and penalties.
Their story is a reminder that the government always gets its cut. Lottery winnings are taxable income — there's no hiding from that. The Toths turned a $13 million blessing into a criminal conviction and family destruction because they tried to avoid the one thing that was unavoidable.
What These Stories Teach Us
The patterns across these 10 stories are remarkably consistent:
1. No financial plan. Almost none of these winners had a trust, a financial advisor, or a spending plan before the money started flowing. If you win, the first three calls should be to a lawyer, a CPA, and a fee-only financial advisor — before you tell anyone else.
2. Going public too soon. Most US states require winners to be publicly identified, but some allow anonymous claims. If you can stay anonymous, do it. The requests, scams, and manipulative relationships that follow a public win are a recurring theme in every story above.
3. Generosity without boundaries. Multiple winners were kind, giving people who simply couldn't say no. Generosity is admirable, but without a budget and a trust structure, it becomes self-destructive.
4. Pre-existing issues get amplified. Money doesn't create problems — it magnifies the ones you already have. Substance abuse, family dysfunction, financial illiteracy — all of these get worse with sudden wealth, not better.
For a detailed guide on what to actually do if you hit a jackpot, read our complete guide to what happens when you win the lottery. And for information on verified winners and their stories, visit our lottery winners page.
