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"Holding Up a Train" is a short story by O. Henry that revolves around a clever and audacious train robbery. The tale follows a bandit who orchestrates the heist with unexpected twists and turns, showcasing O. Henry's signature wit and knack for surprise endings. As the story unfolds, themes of morality, love, and irony emerge, providing readers with both entertainment and thought-provoking insights into human nature. With its engaging characters and clever plot, the story exemplifies O. Henry's mastery of the short story format.


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Submitted by davidb on February 23, 2025


								
When the Katy Flyer pulled in not a Dalton showed up. The next station was Adair, six miles away. When the train reached there, and the deputies were having a good time explaining what they would have done to the Dalton gang if they had turned up, all at once it sounded like an army firing outside. The conductor and brakeman came running into the car yelling, “Train robbers!” Some of those deputies lit out of the door, hit the ground, and kept on running. Some of them hid their Winchesters under the seats. Two of them made a fight and were both killed. It took the Daltons just ten minutes to capture the train and whip the escort. In twenty minutes more they robbed the express car of twenty-seven thousand dollars and made a clean get-away. My opinion is that those deputies would have put up a stiff fight at Pryor Creek, where they were expecting trouble, but they were taken by surprise and “locoed” at Adair, just as the Daltons, who knew their business, expected they would. I don’t think I ought to close without giving some deductions from my experience of eight years “on the dodge.” It doesn’t pay to rob trains. Leaving out the question of right and morals, which I don’t think I ought to tackle, there is very little to envy in the life of an outlaw. After a while money ceases to have any value in his eyes. He gets to looking upon the railroads and express companies as his bankers, and his six-shooter as a cheque book good for any amount. He throws away money right and left. Most of the time he is on the jump, riding day and night, and he lives so hard between times that he doesn’t enjoy the taste of high life when he gets it. He knows that his time is bound to come to lose his life or liberty, and that the accuracy of his aim, the speed of his horse, and the fidelity of his “sider,” are all that postpone the inevitable. It isn’t that he loses any sleep over danger from the officers of the law. In all my experience I never knew officers to attack a band of outlaws unless they outnumbered them at least three to one. But the outlaw carries one thought constantly in his mind—and that is what makes him so sore against life, more than anything else—he knows where the marshals get their recruits of deputies. He knows that the majority of these upholders of the law were once lawbreakers, horse thieves, rustlers, highwaymen, and outlaws like himself, and that they gained their positions and immunity by turning state’s evidence, by turning traitor and delivering up their comrades to imprisonment and death. He knows that some day—unless he is shot first—his Judas will set to work, the trap will be laid, and he will be the surprised instead of a surpriser at a stick-up. That is why the man who holds up trains picks his company with a thousand times the care with which a careful girl chooses a sweetheart. That is why he raises himself from his blanket of nights and listens to the tread of every horse’s hoofs on the distant road. That is why he broods suspiciously for days upon a jesting remark or an unusual movement of a tried comrade, or the broken mutterings of his closest friend, sleeping by his side. And it is one of the reasons why the train-robbing profession is not so pleasant a one as either of its collateral branches—politics or cornering the market.
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O. Henry

O. Henry, the pen name of William Sydney Porter, was an American short story writer born on September 11, 1862, in Greensboro, North Carolina. He is best known for his clever, twist-ending narratives that often explore themes of urban life and human nature. His stories are characterized by witty dialogue, rich character development, and a keen observation of everyday life, illustrating the irony and complexity of human emotions. O. Henry's work has had a lasting impact on the short story genre, and he remains a beloved figure in American literature, with classic tales like "The Gift of the Magi" and "The Ransom of Red Chief" highlighting his unique storytelling style. He passed away on June 5, 1910. more…

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