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
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 any-body 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
We selected a place on the Santa Fe 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
The Santa Fe 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
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
"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
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
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 --
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 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
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,
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
gamed 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
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.