Never Bet the Devil Your Head is a lesson on using figurative expressions, almost along the lines of another Poe story called Loss of Breath. The narrator describes an acquaintance by the name of Toby Dammit that makes a habit of using the figurative expression of "I'll bet the devil my head". He uses so freely that anything he does involves betting the Devil his head. One day he is overheard saying this by an old man who takes him up on the bet.
Good old Toby Dammit invites the challenge to jump over a turnstile on a bridge. While soaring through the air over the turnstile, Toby manages to hit a thin piece of metal and literally loses his head. The old man then seems to disappear.
I rate this short story a 3.5 out of 5. It was quite entertaining and makes you think twice before using common expressions that may be too much of an exaggeration. Don't use figurative language if you can't handle the literal.