Vicious and Inept
The DeAutremonts and the Railroad
Vicious indeed, and that was on their good days. The DeAutremont brothers, Hugh, Ray, and Roy, are in the running for the title of all-time worst scum in the robbery business. They are also among the stupidest, which is saying quite a lot, considering their short career and the host of formidable competitors for the designation.
Born in Iowa and Arkansas, they ended up as West Coast boys. Their father was a barber in Eugene, Oregon, and the elder boys turned their hands to lumberjacking. The two older DeAutremonts, twin brothers Ray and Roy, were twenty-three; Hugh was only nineteen.
When young Hugh graduated from high school in 1923, he joined Ray and Roy out in Silverton, Oregon, where the brothers worked for four months or so until the Big Money beckoned and they embarked on their dubious claim to fame: They decided to hold up Southern Pacific train number 13, the so-called “Gold Special,” running between Portland and San Francisco. Once upon a time, it had in fact regularly carried very large shipments of gold. The brothers thought it still might. Then their little holdup would make them rich, a fine payday for very little work.
It turned out instead to be not only one of the last train holdups on record, but also one of the bloodiest of all time.
At least one brother, Ray, had spent some time as a “Wobblie,” a member of the radical and violent International Workers of the World (IWW). His Wobblie membership got him nothing but some reformatory time, which obviously didn’t teach him anything, but maybe it did provide a little graduate schooling from the pros.
He made his trip to stir after an Independence Day celebration turned very bad indeed. The city of Centralia, Washington, was having a parade in which the American Legion was proudly marching, and every building in town was flying the Stars and Stripes . . . except the building occupied by the radical International Workers of the World.
It’s unclear just what happened next, but it is certain that when the legionnaires reached IWW headquarters, they were stopped, and gunfire erupted almost immediately. Three legionnaires died in the fusillade, and one Wesley Everest ran out the back door of the IWW building only to find the river in his way. He turned and shot down the nearest legionnaire and then inexplicably gave himself up and was promptly taken to jail.
But that night Centralia suffered a total blackout, and when the sun came up the next morning, Wesley was found suspended from a bridge, full of bullets. That made five dead, Wesley and the four legionnaires, and the great state of Washington had had quite enough of the IWW. What followed was a series of mass arrests, and one of those swept up was Ray DeAutremont.
Ray unadvisedly announced that he was proud to be a Wobblie, and while he was in jail, he and another prisoner tried an escape attempt and bungled it. That got him another year behind bars.
That didn’t improve his temper once he was released, and so he conspired with twin brother Roy to pick up some easy money by robbing people. That didn’t work out either; the brothers’ inept planning was already starting to show.
First it was to be a bank, and Ray and Roy watched their target an entire day in a chilly drizzle, which turned into a downpour later. They were still lying in wait, huddled together, when a big Buick pulled up in front of the bank, and a real holdup followed before their very eyes . . . only it was the men in the Buick doing the robbing. Ray was minded to intervene—sort of a “we were here first” notion—until Roy reminded him that their guns were empty.
Next they traveled south, looking for opportunity. They found it, or thought they did, in little Cannon Beach, Oregon. They chose a shop as a target and worked out a plan to rob the owner when he left at the end of the business day with the receipts. Trouble was, they went to sleep in the ditch from which they were going to jump the shop owner and woke only after their target had gone home.
Curses! Foiled again!
There were other problems also impeding their career in crime, among them the fact that neither Ray nor Roy knew how to drive a car. And in this dismal winter of 1922–23, there was little work to be had, which heightened Ray’s already well-developed feeling that an oppressive world was against him. Roy worked as a barber, but he had eye trouble and was afraid of going blind.
Somewhere about now the brothers began to talk about a really major crime, and the planning began. In the summer of 1923, little brother Hugh left his mother’s home in New Mexico and returned to be with Ray and Roy.
Hugh had done well in high school, both academically and athletically. Still, he fell in with his brothers’ planning for the criminal big time. It was to be nothing less than a railway express car, a bonanza that would keep them in deep clover for the rest of their lives. This was perhaps a bit ambitious, since they had so far been a flop at planning even the simplest stickup.
They began by buying a used Nash automobile and adding a pile of ammunition, at least one shotgun, one or more .45 pistols, and some other equipment, including three rucksacks to haul away all that loot. They hit a construction site and stole dynamite, blasting caps and wire, and an exploder.
The next step was to find a safe base of operations, and they made do with an abandoned shack that provided at least some shelter. They passed their days figuring out how to use the dynamite and practicing their marksmanship, until they decided they were at last ready. Almost.
They had the odd notion that the Nash would be dangerous getaway transport, so they added another strange, additional complexity. Hugh would drive their car into Eugene and stash it in their father’s garage. Then, after the robbery was complete, Hugh would ride the rails back to Eugene, collect the car, and pick up his brothers.
So the grand plan—such as it was—started into action and immediately hit a snag. Actually, it was a cow it hit, an unfortunate animal Hugh managed to run into on his way to Eugene. That stopped the execution of the brothers’ plan for a few days, until the car could be repaired.
Meanwhile, Ray and Roy had indulged in some practice boarding a train, in the course of which Roy managed to injure one knee. They did get back to the cabin hideout, and there they had a last-minute conference with Hugh, in the course of which they apparently tried to talk the younger brother out of going along on the robbery. Hugh was determined, however, and so the die was cast.
After all this preparation, the brothers boarded train number 13 near Siskiyou station, not far from the border between California and Oregon. There was a tunnel at that point—also numbered 13—but apparently the brothers were not superstitious enough to make their big score someplace else.
They knew that all trains were required to slow far down and finally to stop just north of the tunnel’s mouth to check their brakes before starting the long descent southward. The tunnel would be, they thought, the perfect place for the newly minted DeAutremont gang to attack the train.
The brothers had gone to a great deal of trouble in preparing for their big payday. In addition to marksmanship practice, they had tried out part of their store of the dynamite, too, although they had the misfortune of having no railroad car on which to practice. They had even gone to the trouble of preparing to evade pursuit by obtaining a large quantity of pepper and sacks soaked in creosote to throw off trailing bloodhounds.
They had heard, maybe from an accomplice, that the train was carrying some forty thousand dollars, a substantial sum in the autumn of 1923. And so they had their eyes on number 13’s express car; even the greenest train robber knew that’s where the money traveled, if there was any on board (ironically, this time there wasn’t). But the express agent inside, like so many courageous men in his business, refused to open the car.
The brothers—vicious but not very bright—responded with dynamite, a charge so heavy that it blew out the whole front of the car and set a fire so intense that the robbers could not get in to collect the bonanza they thought was inside. The gutsy agent died, either in the explosion or in the fire, and the brothers had gotten nothing.
Tragically, when the brakeman ran forward toward the fire, thinking the boom had been a boiler explosion on the engine, the DeAutremont boys shot him down; and finally, apparently out of pure meanness, they murdered both the fireman and the engineer while they were standing helplessly with their hands raised.
In a later statement, one brother matter-of-factly admitted they killed at least two of the train crew to prevent possible identification. Maybe the brothers’ motive was to eliminate any witnesses against them, maybe it wasn’t. But it did something far more dangerous to them; what it certainly did was launch a dogged, relentless pursuit.
The blast had been deliberately set off inside the tunnel to muffle the noise. It didn’t. The roar was heard in a Southern Pacific maintenance camp just across the California border.
And so the law gave chase, but they had a lot of ground to make up. The brothers unwittingly helped their pursuers a good deal: They managed to leave lots of evidence behind; the question their pursuers had to solve was what to make of it. There were a couple of backpacks—no need for them, there being no gold to carry, a pistol, the exploder, and a pair of stained coveralls. Without these, the law would almost certainly have come to a dead end; after all, the brothers, save Ray, had no criminal record, and even his connection with real crime was minimal. But the wanton murders changed the situation.
Now forensic analysis was virtually unknown in those distant days, but Edward Heinrich, a chemistry professor at the University of California, did a surprisingly sophisticated analysis of the evidence, and this is what he found: One of the men you’re after is a lumberjack, he said; he has Douglas fir needles in the pockets of his overalls, and the position of the pitch stains on the overalls show he is left-handed. A bonus the detectives discovered was a piece of faded paper in one overall pocket. The professor managed to bring out some writing on it, and behold! It turned out to be a registered mail receipt for mail from one brother to another. The lawmen were assembling a fairly clear picture of the robbers.
The pistol’s serial number led back to the store whence it came, and there officers found a receipt, with which they traced the Colt back to the buyer. He’d used an alias, but the investigating officers found that the buyer, “William Elliott,” was none other than Ray DeAutremont. An express tag further identified the brothers, and the hunt was on.
There was lots of other evidence, too, including Hugh’s grandiose nom de crime, “J. James,” which led investigators to the hotel in which Hugh had stayed. The Nash also pointed to the brothers (once it had served as evidence it became a police car), and there were also various letters and an insurance policy sent to still another brother.
Meanwhile, the brothers had hidden out in their primitive shack. When the food began to run low, Ray elected to go down to civilization to pick up the Nash and get some news. It was not good. There were wanted posters—complete with pictures—all over Ashland and Medford; he concluded that he could not safely get to Eugene and turned back without the car.
Once he had shared his bad news with his brothers, they elected to leave their hideout and run for it; and so, at the end of October 1923 they set out in miserable winter weather, without proper gear, trying to make it to the coast. They gave that notion up when they saw the extent of the search still under way and instead headed south through driving snow for the California line. In the end they split up, agreeing to meet on New Year’s Day five years thence at a YMCA in New York.
They wouldn’t make it.
They had about four years of freedom left, with much wandering and nothing of the good life. The railroad detectives in particular stuck to their trail like burrs on a hound’s tail. They were not about to give up.
Hugh enlisted in the army under an alias, serving in the Philippines, but even there he was finally run to earth after another soldier noticed that he resembled one of those DeAutremont boys. Hugh was worth a little more than five thousand dollars to his informant, which sure beat corporal’s pay. Wanted posters sometimes get wonderful results.
The other two brothers saw a lot of the rest of the United States, including Michigan, Ohio, and West Virginia. But at last the inevitable happened, and a coworker recognized Ray and Roy for who they were. By this time Ray had married and had a child, with a second on the way. It had been a love match, at least for the lady, and so Ray had managed to badly damage some more lives.
In the end the brothers had some luck, more than they deserved. Hugh had long since been tried and convicted, and now Roy and Ray stopped protesting their innocence . . . they had already admitted their identity. The court’s sentence for all three was prison for life.
Roy finally drifted off into a land of his own. Episodes of violence in prison finally led to a trip to a mental hospital and a prefrontal lobotomy. The surgery did indeed fix the violent behavior, but it did a good deal more. He spent the rest of his days as a vegetable, finally dying in a nursing home at age eighty-three.
Hugh was finally paroled after thirty-one years in prison; he lived only a few months as a free man before cancer got him. Ray was finally paroled at the age of sixty-one, after serving thirty-four years behind bars. He died in 1984.
It hadn’t been much of a life for any of them. For the DeAutremonts, for those who loved them, for the railroad men and their families, it had all been a terrible waste, as badly bungled a criminal enterprise as any in history.
They had at least set a sort of criminal record.