Look Who’s Screwed Up: The Unluckiest Lottery Winners You’ve Ever Heard of!

Unlucky Lottery Winners: They Won to Lose

No truer words have ever been spoken (rapped?) than those written by Notorious B.I.G. in his song, Mo Money, Mo Problems:

I don’t know what they want from me
It’s like the more money we come across
The more problems we see

When we think about winning the lottery, the first thoughts are often about luxury and security. We imagine how we’d spend the cash, ensure long-term financial stability, and provide for our families. Rarely do we consider the problems that might arise, like people coming out of the woodwork seeking handouts or the life-altering consequences of sudden wealth.

But as these stories prove, money doesn’t always bring happiness. For some, it brings betrayal, loss, and even tragedy. Let’s dive into some of the unluckiest lottery winners ever. Brace yourself—these cautionary tales show that hitting the jackpot isn’t always a dream come true.

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Mark Gardner: Betrayed by His Closest Ones

Mark Gardiner, who won half of a £22.6 million prize in 1995, learned the hard way that money can reveal the true nature of people around you. Shortly after his win, his adoptive mother, who had previously disowned him, sold a fabricated story about him to the press. Friends and acquaintances surfaced, hoping to take advantage of his newfound wealth, and one even leaked his personal information to the media, branding him a “lottery rat.”

It didn’t end there—Mark’s fiancée couldn’t handle the pressure and the constant attention. By 2004, the couple had divorced. His story is a harsh reminder that even those closest to you may not have your best interests at heart when money is involved.

William ‘Bud’ Post: Living on Food Stamps

In 1988, William Post won $16.2 million in the Pennsylvania lottery. What started as a dream quickly spiraled into a nightmare. Post’s spending was out of control from day one, blowing his first lottery check on a restaurant spree, a car lot visit, and even buying an airplane. Within a few years, he was embroiled in lawsuits, including one from his landlady (and ex-girlfriend), who claimed a share of his winnings because she had given him the money to buy the ticket.

Things only got worse when Post’s own brother hired a hitman to kill him for the money. Though the plot failed, it was the final nail in the coffin of his fortune. Post died in 2006, deep in debt, living on food stamps—a tragic end for someone who once held a life-changing jackpot.

Jeffrey Dampier: Betrayed by His Own Family

Jeffrey Dampier’s story is a grim illustration of how even those you trust most can turn against you. After winning a $20 million jackpot in 1996, Dampier generously shared his wealth with his family, opening a gourmet popcorn shop in Tampa, Florida. He even supported his sister-in-law, Victoria Jackson, with whom he had an affair.

But things took a dark turn when Victoria and her boyfriend, Nathaniel Jackson, decided to rob Dampier. They kidnapped him, and under pressure from Nathaniel, Victoria shot him in the back of the head. Both were sentenced to life in prison. Dampier’s generosity and trust were ultimately met with betrayal and tragedy.

Jack Whittaker: The Cursed Good Samaritan

Jack Whittaker became an overnight sensation in 2002 when he won $315 million in the Powerball. Known as a businessman and a devout Christian, he initially seemed like the perfect winner—donating millions to churches and his local parish. Unfortunately, the publicity and sudden fame invited a flood of lawsuits—at one point, Whittaker faced 460 legal claims against him.

His generosity was also exploited when he was robbed multiple times, losing nearly $650,000 in cash. But the most heartbreaking tragedy came when his granddaughter, who he had hoped would inherit his fortune, died from a drug overdose at just 17. Shortly after, Whittaker also lost his daughter. What started as a life-changing win ended in sorrow and despair.

Lara and Roger Griffiths: From Millionaires to Bankrupt

Lara and Roger Griffiths seemed to have it all when they won £1.8 million in 2005. The couple bought a luxurious home, expensive cars, and indulged in lavish holidays. Roger even pursued his dream of recording a music album. But their fortune quickly dwindled due to poor financial decisions, and their relationship fell apart under the strain.

The final blow came when a fire destroyed their mansion, leaving them with nothing. By the time their money was gone, so was their marriage. Lara and Roger’s story shows how fast money can slip away when there’s no plan for managing it.

Denise Rossi: Divorce for All the Wrong Reasons

Denise Rossi thought she had the perfect plan when she won $1.3 million in the California lottery in 1996. Instead of sharing the news with her husband, she filed for divorce to keep the winnings for herself. But karma came knocking when her ex-husband, Thomas, discovered her secret during the divorce proceedings. The court ruled that Denise had violated state asset disclosure laws, awarding Thomas all of her winnings.

Her attempt to hide her fortune backfired spectacularly, proving that deceit doesn’t pay off—even when millions are at stake.

Evelyn Adams: Double Trouble

Evelyn Adams defied the odds and won the New Jersey lottery twice, in 1985 and 1986, for a combined total of $5.4 million. With luck on her side, it seemed like a dream come true. But Adams quickly became a regular at Atlantic City casinos, where she lost her winnings through gambling.

By the early 2000s, she was broke and living in a trailer. Despite her double win, Adams serves as a cautionary tale that no amount of luck can overcome poor money management.

Curtis Sharp Jr.: Partying Away the Millions

In 1982, Curtis Sharp Jr. became famous as the “lottery millionaire” after winning $5 million in the New York lottery. Known for his flashy lifestyle and big personality, Curtis became a media sensation, showing off his winnings with flashy cars, jewelry, and wild parties.

Unfortunately, Curtis’s lavish lifestyle caught up with him. After multiple marriages and extravagant spending, he eventually lost everything. Curtis later admitted that he had wasted his fortune and wished he had been more responsible with his winnings.

Michael Carroll: The Self-Destructive King of Chavs

Michael Carroll, a former garbage man, won £9.7 million in the UK’s National Lottery in 2002. Carroll, known as the “Lotto Lout,” spent his winnings on drugs, cars, parties, and even demolition derby events. He gained notoriety for his bad behavior, earning himself a criminal record and several stints in jail.

By 2010, Carroll had blown through his entire fortune and was back to working as a garbage man. Reflecting on his win, he said that it had “ruined” his life. Carroll’s story illustrates how quickly life can spiral when money is spent without caution.

These stories reveal that winning the lottery is not always the golden ticket it seems to be. For some, sudden wealth brings problems that far outweigh the rewards. If anything, they serve as reminders that while winning may change your life, it doesn’t guarantee happiness. Play smart, plan wisely, and be prepared for the challenges that come with striking it rich.