Never Bet the Devil Your Head
By Edgar Allan Poe             1841

     It is not my design to vituperate my friend, Toby Dammit. He was a sad dog, it is true, but he himself was not to blame for his vices. They grew out of a personal defect in his mother. She did her best in the way of flogging him while an infant -- for duties, to her well-regulated mind, were always pleasures, and babies, like tough steaks, are invariably better for beating.
    But -- poor woman! She had the misfortune to be left-handed, and a child flogged left-handedly had better be left unflogged. The world revolves from right to left. It will not do to whip a baby from left to right. If each blow in the proper direction drives an evil propensity out, it follows that every thump in the opposite direction knocks its quota of wickedness in.
     Thus it was that no matter how often and severely he was cuffed, Toby Dammit grew worse and worse. At six months of age, I caught him gnawing a pack of cards. At seven months he was in the consistent habit of catching and kissing the female babies. So he went on, increasing in iniquity until I went down on my knees, and, uplifting my voice, made prophecy of his ruin.
     Perhaps the worst of all his vices was a propensity for cursing and swearing, and for backing his profane assertions with bets. He could scarcely utter a sentence without interlarding it with propositions to gamble. However, I will do my friend the justice to say that with him the thing was a mere formula -- nothing more -- imaginative phrases wherewith to round off a sentence. No one ever thought of taking him up.
     For poverty was another vice which the peculiar deficiency of Dammit's mother had entailed upon her son. He was detestably poor. This was the reason, no doubt, that his expressions about betting seldom took a pecuniary turn. I will not be bound to say that I ever heard him make use of such a figure of speech as "I'll bet you a dollar." It was usually "I'll bet you what you please," or "I'll bet you a trifle," or else, more significantly still, "I'll bet the Devil my head."
     This latter form seemed to please him best -- perhaps because it involved the least risk. His head was small, and thus his loss would have been small, too. In the end, he abandoned all other forms of wager, and gave himself up to, "I'll bet the Devil my head," with a pertinacity and exclusiveness of devotion that displeased not less than it surprised me. I am always displeased by circumstances for which I cannot account. Mysteries force a man to think, and so injure his health.
     One fine day, having strolled out together, arm in arm, our route led us in the direction of a river. There was a bridge, and we resolved to cross it. It was roofed over by way of protection from the weather; and the archway, having but few windows, was uncomfortably dark. At length, having passed nearly across the bridge, we approached the end of the footway, when our progress was impeded by a turnstile of some height. Through this I made my way quietly, pushing it around as usual.
     But this would not serve the turn of Toby Dammit. He insisted upon leaping the stile, and said he would cut a pigeon-wing over it in the air. Now this, conscientiously speaking, I did not think he could do. I therefore told him in so many words that he was a braggadocio, and could not do what he said.
     He straightaway offered to bet the Devil his head that he could.
     I was about to reply, when I heard close at my elbow and ejaculation, "Ahem!" I started and looked about me in surprise. My glance fell into a nook of the framework of the bridge, and upon the figure of a little lame old gentleman of venerable aspect. Nothing could be more reverend than his whole appearance, for he not only had on a full suit of black, but his shirt was perfectly clean, and the collar turned very neatly down over a white cravat, while his hair was parted in front like a girl's. His hands were clasped pensively together over his stomach and his two eyes were carefully and piously rolled up into the top of his head.
     I perceived that he wore a black silk apron over his small clothes. This was a thing I thought very odd. Before I had time to make any remark, however, he interrupted me with a second "Ahem!"
     To this observation, I was not immediately prepared to reply. The fact is, remarks of this laconic nature are nearly unanswerable. I am not ashamed to say, therefore, that I turned to Mr. Dammit for assistance.
     "Dammit," I said, "what are you about? Don't you hear? The gentleman says 'Ahem!'"
     If I had shot Mr. D. through and through with a bomb, or knocked him in the head with a copy of Poets and Poetry of America, he could scarcely have been more discomfited than by those simple words.
     "You don't say so?" he gasped at length. "Are you quite sure he said that? Well, at all events, I am in for it now, and may as well put a bold face on the matter. Here goes then -- ahem!"
     At this, the little old gentleman seemed pleased, God only knows why. He left his station at the nook of the bridge, limped forward with a gracious air, took Dammit by the hand, and shook it cordially, looking all the while straight up in his face with an air of the most unadulterated benignity.
     "I am quite sure you will win, Dammit," said he, "but we are obliged to have a trial, you know, for the sake of mere form."
With a deep sigh, my friend took off his coat. The old gentleman now took him by the arm and led him more into the shade of the covered bridge -- a few paces back from the turnstile.
     "My good fellow," said the little old gentleman in black, "I make it a point of conscience to allow you this much run. Wait here till I take my place beside the stile, so that I may see whether you go over it handsomely, and don't omit any flourishes of the pigeonwing."
     Here he took his position by the stile, looked up -- and I though -- smiled very slightly, then tightened the strings of his apron, saying: "One -- two -- three -- and away!"
     Punctually, at the word "away" my friend set off in a strong gallop. I saw him run nimbly and spring grandly from the floor of the bridge, cutting the most awful flourishes with his legs as he went up. I saw him high in the air, pigeonwinging it to admiration just over the top of the stile; and, of course, I thought it an unusually singular thing that he did not continue to go over.
     But the whole leap was that affair of a moment, and before I had a chance to make any profound reflections, down came Mr. Dammit on the flat of his back, on the same side of the stile from which he had started. At the same instance, I saw the old gentleman limping off at top speed, having caught and wrapped up in his apron something that fell heavily into it from the darkness of the arch just over the turnstile.
     At all this I was much astonished, but I had no leisure to think, for Mr. Dammit lay particularly still, and I concluded that his feelings had been hurt, and that he stood in need of my assistance. I hurried up to him and found that he had received what might be termed a serious injury. The truth is, he had been deprived of his head, which, after a close search, I could not find anywhere. A thought struck me, and I threw open an adjacent window of the covered bridge, when the sad truth flashed upon me at once. About five feet just above the top of the turnstile and crossing the arch of the footpath so as to constitute a brace, there extended a great iron bar. With the edge of this brace it appeared evident that the neck of my unfortunate friend had come precisely in contact.
     He did not long survive his terrible loss. I bedewed his grave with my tears, worked a bar sinister on his family escutcheon, and for the general expenses of his funeral sent in my very modest bill. When payment was refused it, I had Mr. Dammit dug up at once, and sold him for dog's meat.