Though many of his tales have morals, so few of Poe's stories start with the idea that they are meant to be moralistic as is the case with Never Bet the Devil Your Head. In this story, the narrator showcases his friend, Toby Dammit, who is a man of low morals and often makes bets against the devil. One day, while on a bridge, Dammit sees a turnstile and bets the devil his head that he can make it that far. An old man goads Dammit into making the leap – and the cost is about what you might expect.