Winnings: $5.4 million (in two separate jackpots)
Time until bust: 15 years
You’d think someone lucky enough to win the lottery twice would respect its sanctity. Evelyn Basehore hit a $3.9 million Pick Six jackpot in 1985 and then won $1.4 million in the same game just five months later, beating odds set at 1 in 15 trillion. But she couldn’t rein in her spending habits. She gave away much of it to friends; much of the rest went to support her hefty gambling habit at the slot machines in Atlantic City. “Winning the lottery isn’t always what it’s cracked up to be. Everybody wanted my money. Everybody had their hand out,” she told Bankrate after she went bust around 2000 and moved into a trailer park in Brick, N.J. She recently admitted to the New York Post that she still plays the lottery from time to time. Can lightning strike thrice?