Post had just $2.46 in his bank account in 1988 when he won $16.2 million in the lottery. His nickname should be Icarus, however, because Post definitely flew too close to the sun. He spent lavishly, buying planes and massive mansions. If that’s not exciting enough, his girlfriend then tried to sue him for his winnings. Still bored? His brother hired a hitman to kill him and his wife. Though the would-be hit failed, Post has since tumbled back to Earth and is dirt poor once again.