The 5 Unluckiest Guys Who’ve Ever Won The Lottery

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If you were one of the millions of losers with a worthless Powerball ticket last weekend, count your blessings. From family betrayal to untimely death, these poor folks (well, rich folks) embody Biggie Smalls‘ lyric, “Mo Money Mo Problems.”

1. Jeffrey Dampier

Dampier seemed to be doing the smart thing by using his $20 million payday to invest in a gourmet popcorn business. Unfortunately, an affair with his wife’s sister went south and she killed him. Even if you can afford Armani suits, keeping it in your pants is the best way to avoid getting screwed.

2. Willie Hurt

Willie thought he’d never “hurt” again after winning $3.1 million in 1989, but he quickly lost it all to a cocaine addiction, a divorce and an attempted murder trial.

3. Jack Whittaker

We’re not sure why Whittaker, already a millionaire, was playing the lottery to begin with…but he won $314 million from Powerball. It was the catalyst for a series of unfortunate events: Getting robbed, DUIs, a divorce and a sexual assault allegation at a dog track. Talk about pressing your luck.

4. Michael Carroll

Michael Carroll won £9.7 million, but his real stroke of luck is still being alive after blowing his fortune on prostitutes, crack and (worst of all) investing in a soccer team. He’s currently living off £42 a week (about $63) from the government. “The dealer who introduced me to crack has more of my lotto money than I do,” he told the Daily Mail.

5. Urooj Khan

Last year Khan won a million bucks in a Chicago lottery…and a month later, died of cyanide poisoning. His family members are fighting over the money. What are the odds?

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Sean Green is a standup comedian and podcast host living in LA.