Those of us with even an elementary understanding of money and budgeting are often astounded to hear tales of people who have won millions from the lottery only to lose it all a few years later. Winning the lottery is a dream that is shared by most of us, but how confident are you that you could handle it? Would you buy a few nice things and live (very) comfortably for the rest of your days or would you go nuts and blow it all in short order by giving it away and squandering it foolishly on epic parties? A surprising number of once-lucky lottery winners have managed to find a way to lose it all and end up back where they started, or worse.

1. Evelyn Adams

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Most of us consider a big lottery win an extremely lucky break, but how about winning twice? That’s what happened to Evelyn Adams when she won in both 1985 and 1986. Her total take was $5.4 million, but between gambling and relatives looking for handouts, Evelyn found herself back to square one, or perhaps square zero, since that probably better reflects the amount of money she had left. Generosity is a wonderful thing, but like most things, it should be executed in moderation.