Toby Dammit's Never Bet The Devil Your Head

Poe begins his tale by describing how he has come under criticism because his tales do not have morals. In response to his critics, whom he refers to as "ignoramuses," Poe writes "Never Bet the Devil Your Head." The story is clearly a satire directed at these "moral mongers," who lack the intelligence to see the moral in fiction unless the author makes it obvious.

"Never Bet the Devil Your Head" is the sad history of the short life of the narrator's friend, Toby Dammit. Dammit had many vices, all of which resulted from a personal defect of his mother. Her defect was her being left-handed. As a result, she flogged her child from left to right, which is in opposition to the revolution of the world. "If each blow in the proper direction drives
an evil propensity out, it follows that every thump in an opposite one knocks its quota of wickedness in."

As a result of these frequent beatings, Toby developed a propensity for cursing and swearing, and for backing his assertions by bets.
As he was a very poor boy, Toby's bets were never taken seriously by those around him. As time went on, Toby abandoned all forms of real wagering, and began using the expression "I'll bet the Devil my head" whenever he felt the urge to bet.

One day, the narrator and Toby were walking across a covered bridge. The bridge had few windows and was therefore quite dark. Near the end of the bridge, the two encountered a turnstile. Toby insisted on leaping the stile and said he could cut a pigeon wing over it. The narrator doubted Toby's ability, and Toby then bet the Devil his head that he could do it. As soon as Toby pronounced the words of the bet, a "little lame old gentleman of venerable aspect" appeared and lay the ground rules for Toby's jump.

Finally, Toby started running and lept into the air just prior to reaching the turnstile. In the middle of the jump, Toby fell flat on his back, and the old man limped quickly away with something in his apron. The narrator rushed over to his friend and discovered that Toby had lost his head, and it was nowhere to be found. The narrator then realized that a metal bar hanging five feet over the turnstile was responsible for severing Toby's
head.

The narrator paid for Toby's funeral and sent the bill to the transcendentalists. The "scoundrels" refused to pay so the narrator had Toby's body dug up and sold for dog's meat.