Tough Lessons from Lottery Winners Past

Winning the lottery is all fun and games, until the bank runs dry.

Winning the Lottery is All Fun and Games, Till the Bank Runs Dry

How many of you out there have ever dreamt of winning an enormous, multi-million dollar lottery prize? I’d be willing to bet most of you have. Anyone who has bought a lottery ticket has surely considered what they would spend all that money on if they ever struck it rich.

The list often starts out the same. We would buy a new house, or pay off an existing mortgage. We would buy a new vehicle. Maybe even two of them – one for practical purposes, and one for joy riding. Most of us would designate a portion of the money to help out others, either paying off the debts of family, granting cash to loved ones, and/or donating some to a worthy charitable cause.

These are the things most of us say we will do if ever that fateful day comes. Sometimes, we throw in college funds for the kids or grand-kids. We may even promise to invest a large portion, ensuring our wealth continues to grow for generations to come. But just as our dreams of becoming a lottery winner are usually only fantasies, for many people who actually win the prize, those honorable intentions go up in smoke.

When Winning the Lottery Isn’t All Fun and Games


Once a player wins the lottery, we don’t usually hear anything more about them. They go on to live their lives, for better or worse. The only cases we hear about far down the line tend to be those with extreme endings, and unfortunately, those extreme endings are rarely good.

There are at least two dozen tales of “riches to rags”, in which lottery winners suffered a terrible fate. These are some of their stories…

Fast and furious financial burn…

By far the most common reason for ruin is burning through all of the cash in a fast and furious reign of exotic purchases. Luxury homes, sports cars, personal jets and yachts, elaborate vacations – the most expensive things life has to offer can drain millions in just a few months time.

Evelyn Adams was once considered one of the luckiest women in the world, winning a pair of lottery jackpots in 1985 and 1986, worth a combined $5.4 million. She spent it nearly as fast, spending, gambling and giving it away. She now lives in a trailer.

Gerald Muswagon blew through the $10 million he won in 2011, spending it on himself and a fast-growing list of ‘friends’ who showed up nightly at his new party house. A few years later he was broke, working on a farm to support his girlfriend and six children. In 2018, he hung himself in his parents basement.

Sharon Tirabassi won Canada’s $10.5 million Lotto Super 7 jackpot in 2004, and managed to sift through the entire sum in just two years. She paid no attention to dollar signs, by anything and everything her heart desired. Countless homes, cars, vacations and handouts later, her seemingly bottomless barrel of wealth dried up. In 2013, she was back to riding the bus to work to suport her children.

The young and the reckless…

Mickey Carroll and Callie Rogers are two of the youngest lottery winners of all time. Mickey was 19 when the young Brit collected his £9.7 million winnings in 2002. He tore through the cash so fast, he earned the nickname ‘Lotto Lout‘. Most of it was spent partying with drugs and prostitutes. The rest was lost on exorbitant material purchases.

Callie suffered a similar fate in 2003 when she won £1.8 million. She was only 16 at the time. Excessive partying, plastic surgery and lavish purchases left her penniless. In August 2019, she was calling for the UK to raise the age limit for lottery ticket sales, and despite now making just £12k/yr as a caregiver, says “I am the the happiest I have ever been.”

Generous to a fault…

Every lottery winner in history has been bombarded by friends and family, all hoping for (if not demanding) a hand out. It’s one reason so many winners find their families torn apart. You’re either too stingy, and everyone hates you, or you’re too generous, and the money disappears.

Jack Whittaker, Janite Lee and Billie Bob Harrell Jr. all fell into the latter category.

Whittaker won a $314 million Powerball jackpot in 2002. He was a generous man all his life, and once he had the ability to help so many people, he couldn’t stop himself. Jack was passing out huge stacks of cash to family members, friends, strangers, the local church, and leaving king-sized tips for everyone from diner waitresses to strippers.

Lee’s story was similar, following an $18 million haul in 1993. She gave to charities, social causes, education and political campaigns. She was originally receiving annuities, but changed her agreement to a lump0sum for the remainder. By 2011, she was $2.5 million in debt and filing for bankruptcy.

Billie Bob Harrell Jr won the Lotto Texas for $31 million and immediately began donating fantastic sums of money to his church and individual members of the congregation. Combined with purchase of new homes and cars for he and his wife, and all of their family members, the money was gone, and his marriage over, within just two years. Harrell Jr. was so distraught, he committed suicide.

Lottery money – the root of all poison…

Suicidal tendencies are the only reason some lottery winners turn up dead. Ibi Roncaioli and Urooj Khan were both poisoned after their would-be-fortunate windfall.

Ibi won a $5 million jackpot in Canada in 1991. She and her husband were already doing well; he being a gynecologist. But after the win, Ibi became a reckless problem gambler and alcoholic. In 2003, she dies. In 2008, her husband, Dr. Joseph Roncaioli, was convicted of her murder. The horrid tale that finally emerged was that Mr. Roncaioli poisoned his wife after discovering her expensive double life.

Urooj Khan’s fate was similar in as much as he died of a lethal dose of poison in 2012. However, his fate between winning the lottery and dying was entirely different. In fact, the Chicago businessman dies just weeks after he won – before he received a single dollar of his $1 million winnings. At first, his death was reported to be natural causes, but his family insisted on an investigation into the 46 year old man’s sudden demise. An autopsy found the true cause to be cyanide poisoning. His murder case remains unsolved.

Drug addiction leads to destitution…

Having a sudden and seemingly endless supply of money can certainly lead to irresponsible behavior. Sometimes that behavior can harm more than the lottery winner’s finances. Drug abuse is unfortunately and exceptionally common. When it stems from, and/or leads to, addiction, it can be all the more devastating.

In 1989, when the crack cocaine epidemic was as its worst, Willie Hurt won the Michigan Super Lotto for $3.1 million. He was already suffering from an addiction to the drug, and having access to so much money only fueled the problem. Within two years, his life was in shambles. He was penniless, undergoing divorce proceedings, and fending off a murder charge after allegedly killing a woman during one of many drug and alcohol binges.

In 2001, Kentucky resident David Lee Edwards won the Powerball for $27 million. He and his wife were so excited, they literally blew through $1 million a month for the first year. It was irresponsibly innocent at first – exotic cars, a mansion, a personal plane. Five years later, these materialistic things no longer satiated their appetite. Both fell into a deep drug addiction from which they never recovered. In 2013, at just 58 years of age, David died alone in the care of hospice.

Death and deception…

Sometimes, it takes a monumental shift in one’s circumstances to reveal who they really are. The truth isn’t always pretty. That’s what happened when these people won the lottery.

In 1996, Thomas Rossi was a happily married man – or so he thought. One day, out of nowhere, his wife, Denise Rossi, demanded an immediate divorce. Shocked and utterly confused by her marital discontent, he soon found out that 11 days earlier, Denise had won an $11 million lottery. She was hoping to divorce Rossi quickly enough to keep all the cash for herself.

The Pennsylvania Lottery paid out $16.2 million to William ‘Bud’ Post in 1988. He also suffered from the unfortunate irresponsibility of greed, buying anything and everything he desired all at once. Another chunk was lost to his long-time girlfriend, who successfully sued him for her fair share after he dumped her in favor of the cash. His own brother hired a hitman to kill him hoping to inherit a portion of the money. Post lost it all. He was $1 million in debt within a year, and according to the most recent reports, is now a product of the welfare system.

Then there’s Jeffrey Dampier, winner of a $20 million Illinois Lottery jackpot in 1996. He wasn’t a terrible investor at all. In fact, following he and his wife’s amicable divorce and 50/50 split of the winnings, he remarried, moved to Florida and opened a very successful popcorn business. Jeffrey was very generous with his new wife’s family, ensuring they never went without. He was especially helpful towards her younger sister Victoria, who he subsequently began having an affair with. Eventually, Victoria grew tired of Jeffrey – but not his money. In 2005, Victoria’s new boyfriend came up with a plan, and she was all too willing to help. She called Jeffrey, faking car trouble to lure him to a secluded road. There, she and her beau demanded he turn over his wealth. When he refused, they murdered him.

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