Winning the lottery and becoming an instant millionaire sounds like a dream come true for most people. However, some lottery winners have found that sudden wealth and fame can quickly turn into a nightmare if not handled properly. There have been several cases of big lottery winners who ended up in jail not long after hitting the jackpot.
The Curse of Winning the Lottery
Lottery winners gaining instant millionaire status often find that money does not solve all of life’s problems. In fact, quick wealth can sometimes exacerbate issues like substance abuse, mental illness, dysfunctional relationships and poor financial management skills. Without proper planning, guidance and discipline, major lottery winners can quickly squander their fortunes and wind up worse off than before they won.
There are several psychological and interpersonal factors that contribute to lottery winners making poor life choices and ending up in legal trouble:
- Feeling undeserving of the money and having low self-esteem
- Money causing tension, envy and jealousy among family and friends
- Being unprepared for media attention, solicitation and fraud attempts
- Overspending and making reckless financial decisions
- Indulging in too much luxury “stuff” like cars, homes, jewelry
- Getting involved in drugs, alcohol and other addictions
- Feeling bored, empty and purposeless without having to work
Without diligent money management skills and a solid support system, coming into great wealth can disrupt lives and lead to criminal behavior. Some big lottery winners spend much of their winnings and then turn to crime to try to maintain their wealthy lifestyles.
Major Lottery Winners Who Went to Jail
Here are some of the most notable cases of big lottery winners who ended up behind bars after hitting it big:
Jack Whittaker – $314 Million Powerball Winner
In 2002, West Virginia businessman Jack Whittaker won what was at the time the largest single Powerball jackpot of $314.9 million. At the time, he was already worth over $17 million from his construction company.
Whittaker quickly fell victim to vices and irresponsible behavior. He was arrested for drunk driving multiple times, was sued for bouncing checks to casinos, got embroiled in legal issues over strip club visits, and had over $500,000 stolen from his car. Within four years Whittaker had spent most of his fortune on luxuries and legal issues.
In the ensuing years, Whittaker faced even bigger problems. Several members of his family died due to drug overdoses, likely linked to his lottery winnings. In 2009, Jack Whittaker ended up serving a year in jail on drug charges after being busted for possession of illegal narcotics.
Willie Hurt – $3.1 Million Michigan Winner
In 1989, Willie Hurt won $3.1 million in the Michigan state lottery. Less than two years later, he was arrested for cocaine possession and sentenced to life in prison without parole under Michigan’s strict drug laws at the time.
Hurt had descended deep into crack cocaine addiction following his lottery win. Despite winning millions, he was spending hundreds per day on crack and eventually turned to crime to support his habit after burning through his fortune.
The judge at Hurt’s trial said winning the lottery was the worst thing to ever happen to him based on how quickly his life spiraled out of control. He spent over 20 years in prison before finally being granted parole in 2010 at age 72.
Callie Rogers – Britain’s Youngest Lottery Winner
In 2003, Callie Rogers became Britain’s youngest ever major lottery winner when she took home £1.9 million (around $2.5 million USD) at age 16. Too young to handle such a vast fortune, Rogers quickly spent lavishly on alcohol, vacations, gifts, cosmetic surgery and drugs.
Within just a few years Rogers had reportedly spent all her money and was left with large debts. In the years after her lottery win, she was arrested for assault, pled guilty to drunk driving, and received treatment for addiction issues.
Rogers said she thought winning the lottery at such a young age ruined her life. She was unable to finish school, didn’t know how to responsibly manage money, and suffered anxiety due to fame and constant requests for help.
Louise Woodward – Nanny Who Won £9.7 Million
Louise Woodward was an 18 year old nanny in the UK when she was convicted of shaking an infant baby to death while working in Boston in 1997. Following appeals of her murder conviction and public outcry, she was released after less than 300 days in jail.
When Woodward returned to Britain, she eventually won close to £10 million (around $13 million USD) through a lawsuit and lottery winnings. However, the lottery winnings reportedly made her a target for blackmail.
In 2008, Woodward was arrested and spent a week in jail for assaulting someone during an altercation. The man she assaulted allegedly had information on her lottery win and tried to blackmail her for £50,000.
Ibi Roncaioli – Poisoned Her Husband for Winnings
Toronto woman Ibi Roncaioli won $5 million in the early 1990s while secretly battling cancer. Wanting to prevent her husband from gaining the lottery fortune after her death, she sought to leave the money to her family instead.
In order to freely change her will, Roncaioli fatally poisoned her husband with antifreeze, leading to a painful slow death. Her plan quickly unraveled as evidence pointed to her as the prime suspect. She was convicted of manslaughter and spent two years in prison.
The lottery winnings ended up being fought over in court by her widower’s family and her own siblings for years. The darkly ironic case showed the twisted lengths grieving and desperate lottery winners may go to control their prizes.
Biggest Lottery Scams Leading to Prison Time
Some lottery winners have deliberately carried out major frauds and scams designed to con people out of money. The most ambitious plots have led to long prison sentences for these unscrupulous characters:
Eddie Tipton – Employee Who Rigged Lotteries
While working as an IT specialist for the Multi-State Lottery Association from 2003 to 2015, Tipton covertly installed software code that allowed him to predict winning numbers on certain days of the year. He conspired with his brother and other associates to “win” lottery prizes by playing numbers he knew would hit.
Tipton successfully scammed five state lotteries out of over $2 million in winnings over several years. When the scam was discovered, he was sentenced to up to 25 years in prison. The elaborate fraud shook public trust in lotteries and led to increased oversight.
Louise Loraine-Tooth – Faked £2.5 Million Scratchcard Win
In 2018, UK woman Louise Loraine-Tooth pretended she won £2.5 million on a scratchcard lottery ticket in order to borrow money from friends and family. She convinced over 20 people that she would repay them once she received her lottery winnings.
When her fake scratchcard win was inevitably exposed as a scam, she was arrested for fraud. Loraine-Tooth pled guilty to nine counts of fraud and was sentenced to three years in prison for the elaborate con job.
Mirlande Wilson – McDonald’s Worker’s False Claim
After a winning Mega Millions ticket was sold at a Maryland McDonald’s in 2012, employee Mirlande Wilson falsely claimed she purchased the winning ticket. She even held a press conference before coming clean that she lied.
Wilson was sentenced to a year in prison for her false claim after being convicted on charges of conspiracy and theft. Prosecutors believed she was trying to scam McDonald’s out of some of the prize money through her fake story.
Tragic Stories of Lottery Winners Gone Astray
While greed and criminal intent have led some lottery winners astray after hitting it big, others simply fell victim to personal demons and the weight of newfound wealth and attention.
Here are some of the most tragic and cautionary tales of lottery winners who lost their way:
Jeffrey Dampier – Millionaire Murdered by His Sister-in-Law
Chicago native Jeffrey Dampier won $20 million in the Illinois Lottery in 1996. He used some of the money to help family members start businesses. Tragically, this act of generosity led to his murder.
In 2005, Dampier was kidnapped and murdered by his sister-in-law and her boyfriend. The sister-in-law, Victoria Jackson, had grown bitter and resentful that Dampier wouldn’t give her more money. She and her boyfriend were convicted of murder and sentenced to life.
Abraham Shakespeare – Slain by Woman Who Took His Winnings
Abraham Shakespeare won $30 million in the Florida lottery in 2006. Just two years later he was murdered at age 42 by Dorice “Dee Dee” Moore, a woman who befriended him after his lottery win and took control of his remaining $1.8 million.
Moore siphoned off Shakespeare’s money into her own accounts, leading him to sue her. Before the lawsuit could proceed, Moore fatally shot Shakespeare and buried his body. She was found guilty of first degree murder and sentenced to life without parole.
Urooj Khan – Died of Cyanide Poisoning After Mega Millions Win
A day after collecting his $425,000 Mega Millions prize in 2012, Chicago businessman Urooj Khan died unexpectedly. An autopsy later revealed he had ingested a fatal dose of cyanide poison.
Police launched a homicide investigation and later alleged Khan’s wife tried to cash the lottery check shortly after his death. No one has ever been charged for Khan’s murder, and the motive remains unknown.
William Post – Bankrupt Within a Year of Winning $16.2 Million
William “Bud” Post won $16.2 million in the Pennsylvania lottery in 1988. Believing the windfall would change his life forever, he made lavish purchases like a horse farm and airplane.
However, within just one year Post had gone broke and declared bankruptcy. Far from solving his problems, the lottery money led to costly divorces, lawsuits, and a kidnap attempt. Post said winning the lottery ruined his life, causing him nothing but grief.
Preventing Lottery “Curse” Through Financial Planning
These tragic and troubling stories show that winning the lottery can sometimes bring out the worst in people. Lack of preparation for sudden wealth, underlying issues, and not maintaining a disciplined lifestyle can lead to disaster.
While coming into money through sheer luck can be destabilizing, there are ways for lottery winners to prevent disasters:
- Seek experienced legal and financial advice before making big moves
- Live below your means and make conservative investments
- Don’t immediately quit jobs or make drastic lifestyle changes
- Avoid freeloaders looking for handouts
- Keep charitable giving anonymous and within your budget
- Maintain structured daily routines and humility
- Surround yourself with positive trusted people
- Make lifestyle changes gradually
With the right discipline and support team, even the biggest lottery winners can avoid the “curse” and build stable lives. While luck plays a big role in landing a jackpot, making wise choices is key to lasting success.
Conclusion
Winning a massive lottery prize can be a life-changing event full of amazing possibilities. However, some winners have managed to quickly squander their fortunes and even end up behind bars.
Lack of preparation for instant wealth, poor money management, substance abuse, greed, and fraud have led some lottery winners down the wrong path. Their cautionary stories serve as lessons that money alone cannot solve deep personal issues.
While coming into great wealth through sheer luck can be destabilizing, lottery winners who are disciplined, responsible, and surround themselves with good support have the best chance of building lasting success and fulfillment.
