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Background photo is an image of Highway 395 on the shores of Abert Lake, made by F.J.D. John in 2016.




‘Last great train robbery’ was brutal, clumsy fiasco

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By Finn J.D. John
January 1, 2017

EDITOR'S NOTE: This column is a rewriting and thorough re-researching of a much shorter column first published in April 2009, which you’ll find here.

This is Part 1 of a 2-part series on this story. This part tells of the robbery itself; part 2 tells the story of the manhunt that followed.

Few people realize it, but modern forensic detective work — the kind showcased on the “CSI” series on television — was born in southern Oregon, back in October 1923.

Before that fateful day, there had been a few crimes solved with the help of science, including some big ones. In Portland, the evidence given by Dr. Victoria Hampton in the 1904 trial of Norman Williams for murdering his wife and mother-in-law — proving that the long silver hairs found at the crime scene were human and had been violently ripped out of the scalp before death — sent Williams to the gallows.

But stories like that were outliers. At the dawn of the 20th century, most crimes were still solved with shoe leather and intuition, the old-fashioned way.

But after 1923, it would be very clear to everyone that a new day had dawned in crime investigation. And the breakthroughs made in southern Oregon that autumn would inspire, several years later, the founding of the FBI’s legendary forensics division.


OF COURSE, FOR forensic detective work to be pioneered, a suitably horrific crime had to be perpetrated. And on Oct. 11, 1923, one was — a crime so cold and gratuitously nasty that it shocked the whole nation.

This front-page cartoon in the Portland Sunday Oregonian, run three days after the robbery, nicely illustrates the public’s attitude toward the robbers. (Image: Oregonian)

It was a train robbery — the last big train robbery in American history, in fact. It was perpetrated by three bumbling brothers: Roy, Ray and Hugh DeAutremont, the sons of a barber in Albany.

Roy and Ray were the older brothers, and they were twins. Of the two, Roy was particularly crazy, and probably led the others in the criminal enterprise; later in his life, he was diagnosed with schizophrenia and given a lobotomy.

The brothers had been sort of trying to get into the crime business since just after the First World War, when they had been caught up in the popular backlash that had followed the “Centralia Massacre” on Armistice Day 1919. The “massacre” was a gun battle that broke out between members of the International Workers of the World — the “Wobblies” — after a gunman hiding in the IWW hall opened fire on Legion members during a parade. The ensuing gun fight killed six people and utterly destroyed any respectability and effectiveness the “Wobblies” might have had, and was followed by a big law-enforcement dragnet operation. One of the “usual suspects” rounded up and thrown in jail was Ray DeAutremont — the less-crazy brother — and the experience in jail seems to have convinced him that the system was not worth saving, and that he might as well become an outlaw and grab what he could.

After his release from prison, Ray rejoined his brother and the two of them journeyed to Chicago to try to join a gang. This did not work out for them, so they returned to the Pacific Northwest, where they were joined by their younger brother, Hugh, for their second attempt to enter the world of crime: A bank robbery.

This robbery attempt was foiled by one of history’s most surprising coincidences. Just as the brothers were approaching the bank they’d picked out, a car full of gangsters pulled up in front of it, and they watched in astonishment as “their” bank was robbed by someone else, right before their eyes.

So the brothers took jobs on logging crews in the woods and started biding their time, looking for other opportunities to score.

They thought they had found one in the “Number 13 Gold Special” train. Years before, when the Gold Rush was still on, the Gold Special had carried plenty of “color” over the Siskiyous and into Oregon. The California gold fields had long since petered out for commercial purposes, but the train still had the cachet; and the brothers had some reason to believe it would be carrying something particularly valuable in its mail car on Oct. 23. So they started making their plans. And on the big day, they were ready to do the job.

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Unidentified officials pose with the wreckage of the mail car blown up by the DeAutremont Brothers in a bungled attempt to rob it on Oct. 11, 1923. (Image: Smithsonian Institute)


THE HEIST STARTED at the summit of the Siskiyous, as the train crossed the border into Oregon. It had to slow at the summit for a brake check just before going into a long tunnel — Tunnel 13, coincidentally enough — and when it did, Roy and Hugh jumped aboard the engine. Wasting no time, they leveled their weapons — a sawed-off shotgun for Roy and a .45 automatic for Hugh — and ordered the engineer, Sydney Bates, to stop the train right at the end of the tunnel. This was, it seems, to prevent passengers from seeing what was going on. (Ironically and tragically, it was to be Bates’ last day on the job; he was scheduled to start his retirement the very next day.)

Once the train was stopped, the brothers were joined by Ray, who had been waiting at the end of the tunnel with a box of dynamite stolen from a mining operation, just in case it might be needed to open the mail car.

As it turned out, it was needed for that. The mail clerk, when he saw what was happening, barricaded himself inside the car and refused to open the door; so the brothers packed dynamite around the door and touched it off.

Unfortunately they had no idea what they were doing. The amount of dynamite they used wrecked the end of the car, filled it with smoke, and instantly killed the mail clerk, Elvyn Daugherty. And although they were now able to get in, it didn’t do them much good; there was mail scattered everywhere, they couldn’t see through the smoke, and the fire was spreading quickly.

Back in the train, of course, the passengers were starting to panic. The train had stopped suddenly while they were still in the tunnel; then a huge explosion had rocked the car and probably broken out some windows, and the tunnel had started to fill with smoke and fumes. They were trapped in the tunnel like rats.

This plunger-type detonator, found at the scene of the crime, was stolen from a work site for use in the robbery. (Image: Smithsonian Institute)

One of the train’s brakemen, C. Coyle Johnson, started fighting his way through the smoke and flames to the front, trying to find out what was wrong. Unfortunately for him, he made it. Emerging from the fiery tunnel mouth, he startled the robbers, who wheeled and opened fire on him. Down he went, dead.

At this point, the brothers apparently switched their plan from “salvage something from this mess” to “escape at all costs.” They ordered engineer Bates and fireman Marvin Seng to uncouple the engine from the mail car, apparently planning to have the engine take them down the mountain away from the scene of the crime; but the explosion had damaged the couplers, so it could not be done.

So the brothers simply gunned the two survivors down in cold blood. Sydney Bates and Marvin Seng were simply shot in the head as they stood there with their arms in the air, because the brothers wanted no witnesses left on the scene. And then they ran, dragging creosote-soaked sacks behind them to fool the bloodhounds.


THE BROTHERS HID out in a cabin in the woods for about a week and a half, waiting for things to settle down a bit. While they were hiding out there, they noticed an unusual amount of activity in the air; in 1923, very few airplanes were actually in operation, but it suddenly seemed like every plane on the West Coast was flying low over the Siskiyous.

But they didn’t figure out what those planes were doing until Roy hopped a freight train to Ashland to pick up some supplies. Sitting in a diner with a cup of coffee and a newspaper, he looked down and saw a photograph of himself and his brothers there, on the front page.

The manhunt was on. It had been on since a few days after the robbery, when authorities had turned to a university professor for help in figuring out who the robbers had been. And it was in the course of that manhunt that the modern science of forensic detective work was born. We’ll talk about all that in Part 2 of this story, next week.

(Sources: Trail, Pepper & al. “Tunnel 13: How Forensic Science Helped Solve America’s Last Great Train Robbery,” Jefferson Public Radio,; Joers, Lawrence E.C. “The Siskiyou Train Robbery,” Great Moments in Oregon History. Portland: New Oregon Publishers, 1987;

TAGS: #DeAutremontBros #TrainRobbers #Tunnel13 #Manhunt #SiskiyouPass #Dynamite #IWW #GoldSpecial #Albany #Timber #DumbCrooks #MostWanted #BankRobbery #SydneyBates #ElvynDaugherty #CoyleJohnson #MarvinSeng #PepperTrail #LawrenceJoers

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