Holding Up a Train by O. Henry

Note: The man who told me these things was for several years an outlaw in the Southwest and a follower of the pursuit he so frankly describes. His description of the modus operandi should prove interesting, his counsel of value to the potential passenger in some future “hold-up,” while his estimate of the pleasures of train robbing will hardly induce any one to adopt it as a profession. I give the story in almost exactly his own words. – O. H.

Most people would say, if their opinion was asked for, that holding up a train would be a hard job. Well, it isn’t; it’s easy. I have contributed some to the uneasiness of railroads and the insomnia of express companies, and the most trouble I ever had about a hold-up was in being swindled by unscrupulous people while spending the money I got. The danger wasn’t anything to speak of, and we didn’t mind the trouble.

One man has come pretty near robbing a train by himself; two have succeeded a few times; three can do it if they are hustlers, but five is about the right number. The time to do it and the place depend upon several things.

The first “stick-up” I was ever in happened in 1890. Maybe the way I got into it will explain how most train robbers start in the business. Five out of six Western outlaws are just cowboys out of a job and gone wrong. The sixth is a tough from the East who dresses up like a bad man and plays some low-down trick that gives the boys a bad name. Wire fences and “nesters” made five of them; a bad heart made the sixth.

Jim S–––– and I were working on the 101 Ranch in Colorado. The nesters had the cowman on the go. They had taken up the land and elected officers who were hard to get along with. Jim and I rode into La Junta one day, going south from a round-up. We were having a little fun without malice toward anybody when a farmer administration cut in and tried to harvest us. Jim shot a deputy marshal, and I kind of corroborated his side of the argument. We skirmished up and down the main street, the boomers having bad luck all the time. After a while we leaned forward and shoved for the ranch down on the Ceriso. We were riding a couple of horses that couldn’t fly, but they could catch birds.

A few days after that, a gang of the La Junta boomers came to the ranch and wanted us to go back with them. Naturally, we declined. We had the house on them, and before we were done refusing, that old ‘dobe was plumb full of lead. When dark came we fagged ’em a batch of bullets and shoved out the back door for the rocks. They sure smoked us as we went. We had to drift, which we did, and rounded up down in Oklahoma.

Well, there wasn’t anything we could get there, and, being mighty hard up, we decided to transact a little business with the railroads. Jim and I joined forces with Tom and Ike Moore—two brothers who had plenty of sand they were willing to convert into dust. I can call their names, for both of them are dead. Tom was shot while robbing a bank in Arkansas; Ike was killed during the more dangerous pastime of attending a dance in the Creek Nation.

We selected a place on the Santa Fé where there was a bridge across a deep creek surrounded by heavy timber. All passenger trains took water at the tank close to one end of the bridge. It was a quiet place, the nearest house being five miles away. The day before it happened, we rested our horses and “made medicine” as to how we should get about it. Our plans were not at all elaborate, as none of us had ever engaged in a hold-up before.

The Santa Fé flyer was due at the tank at 11.15 p. m. At eleven, Tom and I lay down on one side of the track, and Jim and Ike took the other. As the train rolled up, the headlight flashing far down the track and the steam hissing from the engine, I turned weak all over. I would have worked a whole year on the ranch for nothing to have been out of that affair right then. Some of the nerviest men in the business have told me that they felt the same way the first time.

The engine had hardly stopped when I jumped on the running-board on one side, while Jim mounted the other. As soon as the engineer and fireman saw our guns they threw up their hands without being told, and begged us not to shoot, saying they would do anything we wanted them to.

“Hit the ground,” I ordered, and they both jumped off. We drove them before us down the side of the train. While this was happening, Tom and Ike had been blazing away, one on each side of the train, yelling like Apaches, so as to keep the passengers herded in the cars. Some fellow stuck a little twenty-two calibre out one of the coach windows and fired it straight up in the air. I let drive and smashed the glass just over his head. That settled everything like resistance from that direction.

By this time all my nervousness was gone. I felt a kind of pleasant excitement as if I were at a dance or a frolic of some sort. The lights were all out in the coaches, and, as Tom and Ike gradually quit firing and yelling, it got to be almost as still as a graveyard. I remember hearing a little bird chirping in a bush at the side of the track, as if it were complaining at being waked up.

I made the fireman get a lantern, and then I went to the express car and yelled to the messenger to open up or get perforated. He slid the door back and stood in it with his hands up. “Jump overboard, son,” I said, and he hit the dirt like a lump of lead. There were two safes in the car—a big one and a little one. By the way, I first located the messenger’s arsenal—a double-barrelled shot-gun with buckshot cartridges and a thirty-eight in a drawer. I drew the cartridges from the shot-gun, pocketed the pistol, and called the messenger inside. I shoved my gun against his nose and put him to work. He couldn’t open the big safe, but he did the little one. There was only nine hundred dollars in it. That was mighty small winnings for our trouble, so we decided to go through the passengers. We took our prisoners to the smoking-car, and from there sent the engineer through the train to light up the coaches. Beginning with the first one, we placed a man at each door and ordered the passengers to stand between the seats with their hands up.

If you want to find out what cowards the majority of men are, all you have to do is rob a passenger train. I don’t mean because they don’t resist—I’ll tell you later on why they can’t do that—but it makes a man feel sorry for them the way they lose their heads. Big, burly drummers and farmers and ex-soldiers and high-collared dudes and sports that, a few moments before, were filling the car with noise and bragging, get so scared that their ears flop.

There were very few people in the day coaches at that time of night, so we made a slim haul until we got to the sleeper. The Pullman conductor met me at one door while Jim was going round to the other one. He very politely informed me that I could not go into that car, as it did not belong to the railroad company, and, besides, the passengers had already been greatly disturbed by the shouting and firing. Never in all my life have I met with a finer instance of official dignity and reliance upon the power of Mr. Pullman’s great name. I jabbed my six-shooter so hard against Mr. Conductor’s front that I afterward found one of his vest buttons so firmly wedged in the end of the barrel that I had to shoot it out. He just shut up like a weak-springed knife and rolled down the car steps.

I opened the door of the sleeper and stepped inside. A big, fat old man came wabbling up to me, puffing and blowing. He had one coat-sleeve on and was trying to put his vest on over that. I don’t know who he thought I was.

“Young man, young man,” says he, “you must keep cool and not get excited. Above everything, keep cool.”

“I can’t,” says I. “Excitement’s just eating me up.” And then I let out a yell and turned loose my forty-five through the skylight.

That old man tried to dive into one of the lower berths, but a screech came out of it and a bare foot that took him in the bread-basket and landed him on the floor. I saw Jim coming in the other door, and I hollered for everybody to climb out and line up.

They commenced to scramble down, and for a while we had a three-ringed circus. The men looked as frightened and tame as a lot of rabbits in a deep snow. They had on, on an average, about a quarter of a suit of clothes and one shoe apiece. One chap was sitting on the floor of the aisle, looking as if he were working a hard sum in arithmetic. He was trying, very solemn, to pull a lady’s number two shoe on his number nine foot.

The ladies didn’t stop to dress. They were so curious to see a real, live train robber, bless ’em, that they just wrapped blankets and sheets around themselves and came out, squeaky and fidgety looking. They always show more curiosity and sand than the men do.

We got them all lined up and pretty quiet, and I went through the bunch. I found very little on them—I mean in the way of valuables. One man in the line was a sight. He was one of those big, overgrown, solemn snoozers that sit on the platform at lectures and look wise. Before crawling out he had managed to put on his long, frock-tailed coat and his high silk hat. The rest of him was nothing but pajamas and bunions. When I dug into that Prince Albert, I expected to drag out at least a block of gold mine stock or an armful of Government bonds, but all I found was a little boy’s French harp about four inches long. What it was there for, I don’t know. I felt a little mad because he had fooled me so. I stuck the harp up against his mouth.

“If you can’t pay—play,” I says.

“I can’t play,” says he.

“Then learn right off quick,” says I, letting him smell the end of my gun-barrel.

He caught hold of the harp, turned red as a beet, and commenced to blow. He blew a dinky little tune I remembered hearing when I was a kid:

Prettiest little gal in the country—oh!
Mammy and Daddy told me so.

I made him keep on playing it all the time we were in the car. Now and then he’d get weak and off the key, and I’d turn my gun on him and ask what was the matter with that little gal, and whether he had any intention of going back on her, which would make him start up again like sixty. I think that old boy standing there in his silk hat and bare feet, playing his little French harp, was the funniest sight I ever saw. One little red-headed woman in the line broke out laughing at him. You could have heard her in the next car.

Then Jim held them steady while I searched the berths. I grappled around in those beds and filled a pillow-case with the strangest assortment of stuff you ever saw. Now and then I’d come across a little pop-gun pistol, just about right for plugging teeth with, which I’d throw out the window. When I finished with the collection, I dumped the pillow-case load in the middle of the aisle. There were a good many watches, bracelets, rings, and pocket-books, with a sprinkling of false teeth, whiskey flasks, face-powder boxes, chocolate caramels, and heads of hair of various colours and lengths. There were also about a dozen ladies’ stockings into which jewellery, watches, and rolls of bills had been stuffed and then wadded up tight and stuck under the mattresses. I offered to return what I called the “scalps,” saying that we were not Indians on the war-path, but none of the ladies seemed to know to whom the hair belonged.

One of the women—and a good-looker she was—wrapped in a striped blanket, saw me pick up one of the stockings that was pretty chunky and heavy about the toe, and she snapped out:

“That’s mine, sir. You’re not in the business of robbing women, are you?”

Now, as this was our first hold-up, we hadn’t agreed upon any code of ethics, so I hardly knew what to answer. But, anyway, I replied: “Well, not as a specialty. If this contains your personal property you can have it back.”

“It just does,” she declared eagerly, and reached out her hand for it.

“You’ll excuse my taking a look at the contents,” I said, holding the stocking up by the toe. Out dumped a big gent’s gold watch, worth two hundred, a gent’s leather pocket-book that we afterward found to contain six hundred dollars, a 32-calibre revolver; and the only thing of the lot that could have been a lady’s personal property was a silver bracelet worth about fifty cents.

I said: “Madame, here’s your property,” and handed her the bracelet. “Now,” I went on, “how can you expect us to act square with you when you try to deceive us in this manner? I’m surprised at such conduct.”

The young woman flushed up as if she had been caught doing something dishonest. Some other woman down the line called out: “The mean thing!” I never knew whether she meant the other lady or me.

When we finished our job we ordered everybody back to bed, told ’em good night very politely at the door, and left. We rode forty miles before daylight and then divided the stuff. Each one of us got $1,752.85 in money. We lumped the jewellery around. Then we scattered, each man for himself.

That was my first train robbery, and it was about as easily done as any of the ones that followed. But that was the last and only time I ever went through the passengers. I don’t like that part of the business. Afterward I stuck strictly to the express car. During the next eight years I handled a good deal of money.

The best haul I made was just seven years after the first one. We found out about a train that was going to bring out a lot of money to pay off the soldiers at a Government post. We stuck that train up in broad daylight. Five of us lay in the sand hills near a little station. Ten soldiers were guarding the money on the train, but they might just as well have been at home on a furlough. We didn’t even allow them to stick their heads out the windows to see the fun. We had no trouble at all in getting the money, which was all in gold. Of course, a big howl was raised at the time about the robbery. It was Government stuff, and the Government got sarcastic and wanted to know what the convoy of soldiers went along for. The only excuse given was that nobody was expecting an attack among those bare sand hills in daytime. I don’t know what the Government thought about the excuse, but I know that it was a good one. The surprise—that is the keynote of the train-robbing business. The papers published all kinds of stories about the loss, finally agreeing that it was between nine thousand and ten thousand dollars. The Government sawed wood. Here are the correct figures, printed for the first time—forty-eight thousand dollars. If anybody will take the trouble to look over Uncle Sam’s private accounts for that little debit to profit and loss, he will find that I am right to a cent.

By that time we were expert enough to know what to do. We rode due west twenty miles, making a trail that a Broadway policeman could have followed, and then we doubled back, hiding our tracks. On the second night after the hold-up, while posses were scouring the country in every direction, Jim and I were eating supper in the second story of a friend’s house in the town where the alarm started from. Our friend pointed out to us, in an office across the street, a printing press at work striking off handbills offering a reward for our capture.

I have been asked what we do with the money we get. Well, I never could account for a tenth part of it after it was spent. It goes fast and freely. An outlaw has to have a good many friends. A highly respected citizen may, and often does, get along with very few, but a man on the dodge has got to have “sidekickers.” With angry posses and reward-hungry officers cutting out a hot trail for him, he must have a few places scattered about the country where he can stop and feed himself and his horse and get a few hours’ sleep without having to keep both eyes open. When he makes a haul he feels like dropping some of the coin with these friends, and he does it liberally. Sometimes I have, at the end of a hasty visit at one of these havens of refuge, flung a handful of gold and bills into the laps of the kids playing on the floor, without knowing whether my contribution was a hundred dollars or a thousand.

When old-timers make a big haul they generally go far away to one of the big cities to spend their money. Green hands, however successful a hold-up they make, nearly always give themselves away by showing too much money near the place where they got it.

I was in a job in ’94 where we got twenty thousand dollars. We followed our favourite plan for a get-away—that is, doubled on our trail—and laid low for a time near the scene of the train’s bad luck. One morning I picked up a newspaper and read an article with big headlines stating that the marshal, with eight deputies and a posse of thirty armed citizens, had the train robbers surrounded in a mesquite thicket on the Cimarron, and that it was a question of only a few hours when they would be dead men or prisoners. While I was reading that article I was sitting at breakfast in one of the most elegant private residences in Washington City, with a flunky in knee pants standing behind my chair. Jim was sitting across the table talking to his half-uncle, a retired naval officer, whose name you have often seen in the accounts of doings in the capital. We had gone there and bought rattling outfits of good clothes, and were resting from our labours among the nabobs. We must have been killed in that mesquite thicket, for I can make an affidavit that we didn’t surrender.

Now I propose to tell why it is easy to hold up a train, and, then, why no one should ever do it.

In the first place, the attacking party has all the advantage. That is, of course, supposing that they are old-timers with the necessary experience and courage. They have the outside and are protected by the darkness, while the others are in the light, hemmed into a small space, and exposed, the moment they show a head at a window or door, to the aim of a man who is a dead shot and who won’t hesitate to shoot.

But, in my opinion, the main condition that makes train robbing easy is the element of surprise in connection with the imagination of the passengers. If you have ever seen a horse that has eaten loco weed you will understand what I mean when I say that the passengers get locoed. That horse gets the awfullest imagination on him in the world. You can’t coax him to cross a little branch stream two feet wide. It looks as big to him as the Mississippi River. That’s just the way with the passenger. He thinks there are a hundred men yelling and shooting outside, when maybe there are only two or three. And the muzzle of a forty-five looks like the entrance to a tunnel. The passenger is all right, although he may do mean little tricks, like hiding a wad of money in his shoe and forgetting to dig-up until you jostle his ribs some with the end of your six-shooter; but there’s no harm in him.

As to the train crew, we never had any more trouble with them than if they had been so many sheep. I don’t mean that they are cowards; I mean that they have got sense. They know they’re not up against a bluff. It’s the same way with the officers. I’ve seen secret service men, marshals, and railroad detectives fork over their change as meek as Moses. I saw one of the bravest marshals I ever knew hide his gun under his seat and dig up along with the rest while I was taking toll. He wasn’t afraid; he simply knew that we had the drop on the whole outfit. Besides, many of those officers have families and they feel that they oughtn’t to take chances; whereas death has no terrors for the man who holds up a train. He expects to get killed some day, and he generally does. My advice to you, if you should ever be in a hold-up, is to line up with the cowards and save your bravery for an occasion when it may be of some benefit to you. Another reason why officers are backward about mixing things with a train robber is a financial one. Every time there is a scrimmage and somebody gets killed, the officers lose money. If the train robber gets away they swear out a warrant against John Doe et al. and travel hundreds of miles and sign vouchers for thousands on the trail of the fugitives, and the Government foots the bills. So, with them, it is a question of mileage rather than courage.

I will give one instance to support my statement that the surprise is the best card in playing for a hold-up.

Along in ’92 the Daltons were cutting out a hot trail for the officers down in the Cherokee Nation, Those were their lucky days, and they got so reckless and sandy, that they used to announce before hand what job they were going to undertake. Once they gave it out that they were going to hold up the M. K. & T. flyer on a certain night at the station of Pryor Creek, in Indian Territory.

That night the railroad company got fifteen deputy marshals in Muscogee and put them on the train. Beside them they had fifty armed men hid in the depot at Pryor Creek.

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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