From Rags to Riches to Rags Again: 21 Winners Who Lost It All

Powerball winner David Edwards and his fiance, Shawna Maddux, pose in front of their new home and luxury car Wednesday, Nov. 14, 2001, in Palm Beach Gardens, Fla. Edwards won $27 million after taxes in the Powerball lottery, and he has given a chunk of his winnings – $700,000 so far – to those who need it. (AP Photo/Tony Gutierrez)
When I was a repo man, one of my more unusual assignments was repossessing a Cadillac from a recent $1 million lottery winner.

While investigating to determine where the vehicle was hidden, I learned that when the annual lottery checks arrived she quickly spent them partying, leaving her without enough to make her car payments. One night, I drove her car away while she slept.

It’s tough to say how often lottery wins have happier endings. Given the many national lotteries around the world and the 44 state lotteries in the U.S., there have probably been thousands of $1 million-plus winners, and some of them must responsibly manage their winnings.

But sadly, some lottery winners lose it all very quickly.

It’s too easy to find one tragic real-life case after another. Here are 21 of the worst. And what if you win big in the lottery someday? What mistakes should you avoid? The lessons are pretty clear, and they’re right there in the stories if you pay attention.

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