Winnings: $16 million
Okay, Bud Post died in 2006 – so we can’t tell you exactly what he’s up to. But when your own brother tries to kill you, you deserve a spot on this list.
Post led a tragic life from the start, as an orphan who had to work a series of odd jobs to make ends meet. You would think winning the lottery meant his luck would change, right? Wrong.
His landlady threatened him into giving her a third of his winnings, he bought an airplane that he didn’t know how to fly, and his own brother hired a hitman to murder him – with the money that Post had given him. Ironic, right?
While the murder attempt was unsuccessful, Post did not live a happy life. He was married and divorced a whopping seven times, and went into debt after his extravagant purchases on cars and houses. The cherry on top? He shot a gun at a bill collector and served a sentence for assault – eventually dying alone and penniless at age 66.