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Jack Whittaker won one of the largest lottery jackpots ever seen, yet his story serves as an instructive tale on how not to manage such wealth. A West Virginia construction worker, Whittaker dissipated it on diner servers, strangers, and his strip club before it could all be collected in.
1. Jack Whittaker
Most people can only dream about winning big. Popping into a convenience store to purchase lottery tickets may seem like a minor act, but sometimes these tickets have proven life-altering. And while some people have seen their fortunes skyrocket after scoring the big one, others may experience heartbreak due to losing out in the end.
Andrew “Jack” Whittaker Jr won an astounding $315 Million Powerball jackpot on Christmas Night 2002, becoming the largest prize ever won from one single Powerball ticket. However, following his triumphant win, he experienced tragedy after tragedy after witnessing his home burn down and being robbed. Additionally, his granddaughter passed away.
After his win, Whittaker quickly gained notoriety for his reckless spending, gambling, and bar fights – not to mention unwanted sexual propositions from strangers. At one point, he told the Pink Pony manager he wished he’d just torn up his winning ticket, but his troubles did not end there.
2. Vivian Nicholson
Vivian Asprey, better known by her nickname Viv Nicholson, promised the media she would spend all the money won in 1961 football pools by making good on her promise: when it came time to finish it all (equivalent to over PS5 million today), she spent it all lavishly; on luxury living expenses including Harrods designer fashion, exotic holidays and cars. When she died aged 79 last year, almost all of it had vanished entirely, and she lived off a pension of less than PS2,000 each week.
Nicholson may not have been as reckless with her lottery winnings as Denise Rossi was, keeping them hidden from her husband and then quickly spending them, but she certainly wasn’t an example of fiscal responsibility. Aside from drinking too much and experiencing depression and asthma, in later years, Nicholson became a Jehovah’s Witness and attempted suicide; additionally, she wasted away the family business with her winnings and was even forced to sell off the house she built with them.
3. Callie Rogers
Not surprisingly, winning a lottery ticket can radically transform your life within moments. What may not be apparent, however, is that some winners experience difficulty with managing their newfound wealth compared to others.
Callie Rogers, Houses’ patient in Season 8’s Runaways, is one such example. After winning an unprecedented PS2.5 million lottery prize, Callie soon found herself struggling financially and living an unhealthy lifestyle despite winning such an immense sum of money. At one point, she even considered suicide, now working as a carer to give meaning and purpose back into their children’s lives.
Callie wasn’t alone in her difficulties; many fake friends joined in with the phony friend act because of Callie’s high earnings. Additionally, Callie spent her fortune on wild parties, designer clothing, and sports cars before loaning it out to individuals who never returned her money.
4. David Lee Edwards
As much as winning the lottery may seem like a dream come true, not everyone who finds themselves blessed with millions of dollars follows through happily ever after. David Lee Edwards spent all of his money within one year after becoming wealthy, spending it lavishly on an airplane called Learjet, three losing racehorses, a limousine service business, and a fiber optic installation company, as well as buying his teenage daughter Tiffani Bentleys, and various cars for herself and other vehicles in her fleet.
But his reckless lifestyle eventually took its toll, and he used up all his prize money on drugs. Together with Shawna Maddux, they became addicted to crack cocaine and prescription pills, having run-ins with police. As a result, both contracted Hepatitis from sharing needles. Once out of money, they eventually lived together in a shed covered with human waste before both passed away, aged 58 in 2013.
5. Thomas Rossi
Denise Rossi decided to keep her $1.3 million lottery win a secret from Thomas when she won it rather than sharing half with him as part of their divorce settlement agreement, which would require paying him half. When Thomas found out in 1996, however, he took her to court, and she was forced to give up every cent.
Billie Bob Harrell stands as an iconic example of how too much money can ruin lives: after winning a Texas jackpot in 1989 and spending his winnings over just two years (on gambling, reckless giving to family, and destructive investments) before eventually killing himself at only 19! Poor soul.
6. Janite Lee
Janite Lee won an astounding $18 Million lottery prize in 1993 and elected to take her money as an annuity, receiving annual payments of $620,000. As a South Korean immigrant living in St Louis, she owned a wig shop and made numerous charitable donations but soon spent it irresponsibly: leasing luxury cars and borrowing millions – ultimately leaving her bankrupt within eight years and in debt.
Alex and Rhoda Toth were one of the first lottery winners to spend down all their winnings after they won $15 million in 1990; they ultimately filed for bankruptcy after spending it on expensive items and gambling. Welsh-born Luke Pittard won $1.3 million in 2006 before finishing it all on cars, weddings, houses, and eventually working at McDonald’s flipping burgers, making just $10 an hour!
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