5. Callie Rogers
The teenager girl who spent all her money on clothes, parties and silicone
Callie Rogers was once the world’s luckiest teenager. At the tender age of 16, Ms. Rogers won £1.9million lottery. That was, at the time, about $3 million. Now it’s all gone. The ecstatic girl spent her winnings on vacations, homes, shopping, friends, and even a couple of breast improvements. Six years and two attempts of suicide later, Rogers is a 22-year-old single mother of two. She now works as a maid to sustain herself and her family. She is paying off debt induced by her spending.
4. Janite Lee
The Missourian who gave away her money to politics, education and the community and ended up with nothing left
Sometimes, even good intentions can get wildly out of hand — as was the case for Janite Lee, the 52-year-old woman, who landed an $18 million payout from the Missouri Lottery back in 1993. The South Korean immigrant immediately began to contribute chunks of her wealth to various educational programs, community services and political organizations. Besides the usual million-dollar house and cars, Lee reportedly donated more than $1 million to Washington University, where her namesake reading room commemorates the occasion. She reportedly donated $277,000 to Democratic political candidates, earning herself meals with Bill Clinton, Al Gore, and even the President of South Korea. She didn’t stop there. $30,000 went to the family of a South Korean church pastor who passed away. The St. Louis Korean American Association received a house from her. Another Korean adoption-related association also benefited. Lee’s philanthropy was expensive. But combined with her gambling habit—she lost $347,000 in a single year—bank loans, and credit card debt, it harkened disaster. She filed Chapter 7 bankruptcy in 2001.
3. “Jack” Whittaker Jr
The once biggest lottery winner who lost $114 million in four years
On December 25, 2002, West Virginia building contractor Andrew Jackson “Jack” Whittaker Jr. won $315 million in the Powerball multi-state lottery, at that time the largest jackpot in history won by a single person. At the time, he was the president of a successful contracting firm called Diversified Enterprises Construction. 55-year-old Whittaker was living a successfully comfortable American life complete with a net worth of over one million dollars, a well rounded family, great job and healthy grandkids. After winning the prize, he famously pledged 10% of his winnings to various Christian charities and created the Jack Whittaker Foundation with another $14 million.
Whittaker did some good, but his bad deeds make his story. He was arrested twice, once for drunk driving and once for threatening a bar manager. A woman sued him after he groped her at a dog racetrack. Thieves took $545,000 in cash from Whittaker’s car while he was visiting a strip club. About a year later, thieves again stole $200,000 from his car. Caesars Atlantic City sued him for bouncing $1.5 million in checks. His wife divorced him. Then, there were the dead bodies. In 2003, Whittaker’s granddaughter’s boyfriend was found dead of an overdose inside Whittaker’s home. His 17-year-old granddaughter, whom he had been giving a $2,100 weekly allowance, fatally overdosed months later, at a different location. His daughter—mother of the dead granddaughter—died this year of as-yet-undetermined causes. When reached for comment, Whittaker, now with no family and no fortune, said “I wish I’d torn that ticket up.”
2. Ken Proxmire
The machinist who won $1 million, went into car business and bankrupt in 4 years
Ken Proxmire was a machinist when he won $1 million in the Michigan lottery. He moved to California and went into the car business with his brothers. Within five years, he had filed for bankruptcy. “He was just a poor boy who got lucky and wanted to take care of everybody,” explains Ken’s son Rick. “It was a hell of a good ride for three or four years, but now he lives more simply. There’s no more talk of owning a helicopter or riding in limos. We’re just everyday folks. Dad’s now back to work as a machinist,” says his son.
1. Evelyn Adams
The woman won the lottery twice and now lives in a trailer
Everyone knows the odds of winning the lottery once are astronomical. But Evelyn Adams beat those odds — twice. The New Jersey resident hit the jackpot in 1985 and 1986 to the sum of $5.4 million. But Adams was a heavy gambler. And with Atlantic City being located in New Jersey, it wasn’t long before Adams had lost all her money. Twenty years later, Adams is broke and living in a trailer.
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