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Wanted posters announced the $15,900 bounty on the brothers. Posters were distributed across the U.S. The three DeAutremont brothers destroyed a mail car and killed four men, including a Railway Post Office clerk, when they tried to rob a Southern Pacific train on October 11, 1923. After botching the robbery, the three fled the scene of the crime in a panic, leaving some items, including a pair of overalls, behind. The items left behind helped authorities learn the identities of the murderers.

The bottom portion of this wanted poster continues information on identifying each brother. Postal inspectors asked chemist Edward Heinrich to inspect the clues left behind by the robbers to see if he could tell them anything about the fugitives. Given a pair of overalls found at the crime scene, Heinrich developed a profile of a likely suspect.

Crime Does Not Always Pay

The D’Autremont Train Robbery

Most?people?think of train robberies as 19th century crimes, complete with Butch and Sundance blowing up a train car, or Jesse James and his gang taking on the evil railroad companies. However, one of the most violent and tragic train robbery attempts was in 1923. On October 11 of that year, three men, twins Roy and Ray DeAutremont and their younger brother Hugh ambushed Southern Pacific train #13 in southern Oregon, just as the train was emerging from a tunnel.

The young DeAutremont brothers and especially Ray felt they were born into a family that had been victimized by a corrupt society. It seemed only fair they follow a course of crime rather than work for a living.?Twins Ray and Roy were just twenty three when they attempted one of the most daring robberies in America. Their brother Hugh, who accompanied them, was a mere nineteen. The crime they committed in 1923 would have been laughable in its ineptitude had they not happened to kill four men during the debacle.

But what of their earlier criminal career? This too proves without doubt that the DeAutremont brothers should have stuck to a more legitimate career ? it seems that they just weren?t cut out to be criminal masterminds.

The products of a large family that lived in various Western locales, the DeAutremont twins in summer 1922, found themselves in Oregon. They were destitute and discouraged by the prospect of earning honest livings, so they decided crime was the road to a life of luxury.

The first attempted robbery took place in July 1922. The twins ? their younger brother Hugh was yet to join them ? were staking out a bank they intended to relieve of its funds.

One July day, they huddled?across the road of the bank in a bush, they studied the movements of the staff. Although it was July, the weather was cold and it was raining and their day-long vigil outside the bank was uncomfortable to say the least.

They knew that the policeman who was guarding the bank ? this was in a small one-horse town ? went home at 5.50. All they would have to do was stroll into the bank when the cop left, take the money and get away. ?They planned the robbery for the next day. They saw the policeman leave at five o?clock and made their final notes. They were anxious to get out of the cold and rain and were eager to holdup the bank the following day.

As they were preparing to leave, full of their plans for tomorrow, they didn?t see how their plan could fail. As they emerged from their foliage hideout, Roy was annoyed when a large Buick pulled up outside the bank, blocking his view. He saw three men emerge from the car and enter then bank premises.

Suddenly he realised that through the bank window he could see that the staff were holding their hands in the air. The three men emerged from the bank with their booty and sped off down the road and?disappeared. The twins figured that their plan had been perfect ? except they had left it a day late. Another gang had beaten them to it.

(From left) Ray, Hugh and Roy DeAutremont attempted a train robbery 86 years ago today that was one of Oregon?s most notorius crimes. The brothers dressed up for this photo before their trial in Jackson County in an effort to help their case. Photo: State of Oregon Archives

They then moved on to a town called Seaside, where huge July 4th celebrations were planned. The twins? logic was that a robbery would be easy in the chaos that would be brought about by the Independence Day festivities. They checked out the town?s bank. It looked promising. ?But the problem was that it was so close to the police station.

Having had a lesson from the gang who had robbed ?their? bank, Ray decided that the should steal a car. Because the police station was so near, they?d need wheels to escape. But there was one problem. Neither of the boys knew how to drive. The bank idea was abandoned. They drifted south to another community, a town called Cannon Beach. The weather had changed and it was a beautiful warm day.

Thinking that a bank was too risky without the advantage of a vehicle, they spotted a confectionery store that was doing great business. And because of the July 4th holiday, they reckoned that by the end of the day, they could rob the store and get hundreds of dollars ? maybe even a thousand. They had lowered their sights a bit because they had been relying on a bank heist, they had no money and hadn?t eaten for two days.

They decided to lay low opposite the store and attack the owner when he left with the day?s takings at closing time. They hid in a ditch right across the road ? this time thankful that the weather was warm and that it wasn?t raining. they watched as the store got busier and busier ? the owner was so run off his feet that he didn?t have time for a lunch break and the money was pouring in.

It was perfect. The man was old and they reckoned that all they had to do was wave their guns at him when he left the store for the day and he?d hand the money over. As the sun started to go down,the store owner closed the blinds. He was pleased with his day?s takings and the business he had received on that lovely sunny day. He decided it was time to go home. He gathered up the money he had taken that day, placed it in his bag and left the store, locking the door behind him.

In the ditch across the road,overcome with hunger and the warm sunshine, the DeAutremont twins were fast asleep. They awoke the next morning having missed their chance.

The twins, joined by Hugh, next decided train robbery would be a lucrative pursuit. They went to work in the woods, saved their money and equipped themselves. By summer’s end in 1923, they were ready.

The three brothers had been “tipped” by a friend employed by the railroad that Southern Pacific Train No. 13, originating in Portland and destined for San Francisco, would be passing through Southern Oregon in mid-October, 1923, with $40,000 on board.

The DeAutremont brothers worked out a grandiose plan to rob the train as it chugged its way south through the Siskiyou Mountains. They set up camp in the mountains, about a quarter mile from railroad Tunnel 13 and some 15 miles south of Ashland, several weeks before the train was scheduled to arrive. They practiced target shooting against a large Douglas fir tree and test-blasted dynamite they had purchased in town a few weeks earlier.
They also purchased a large quantity of pepper they hoped to use after the robbery to throw off the scent of bloodhounds. And they spent several hours in the sun hoping to get deep tans so that any person witnessing the heist would think they were Latinos.

After weeks of preparations, the DeAutremonts learned that Train 13 -the well-known “Gold Special” which formerly hauled gold to San Francisco would be heading through the Siskiyous on Oct. 11, 1923. The brothers hid inside Tunnel 13 — Hugh armed with a shotgun, Roy with a Colt.45 and Ray with a cache of dynamite. They knew that the train would have to stop just north of the tunnel to check its brakes – a standard requirement of all southbound trains which would soon face the steep downgrade south of the tunnel.

When the engine entered the tunnel, Hugh and Roy jumped aboard and made their way carefully up to the engine cab. They ordered Engineer Sidney Bates to stop the train when the engine cleared the south end of the tunnel. They then ordered Bates to uncouple the mail car presumably carrying the $40,000. But Bates either refused or was unable to uncouple the cars. Hugh shot and killed Bates with a single shotgun blast. Roy then fired two fatal shots into Fireman Marvin Seng, who had been travelling in the engine cab with Bates. Seng was standing on the ground next to the train, with his hands raised, when he was cut down by Roy’s Colt. 45.

Things got worse for the DeAutremonts when brother Ray, who had been hiding at the south end of the tunnel with dynamite, used too much of the explosives to blast open the door of the mail car. The resulting explosion which was heard two miles away demolished the mail car and set it on fire. The explosion also killed Mail Clerk Elvyn Dougherty, who became trapped in the burning car.
Brakeman Coyl Johnson, upon hearing the blast, figured the engine boiler had exploded and started making his way slowly through the heavy smoke and intense heat to the engine. Hugh and Roy cut him down with gunfire before he even made it.
The smoke and heat from the mail car fire made it impossible for the DeAutremonts to board the mail car. The DeAutremonts then fled, leaving death, destruction, widows and fatherless children behind. But in the process, Roy DeAutremont dropped his Colt .45 on the railroad tracks and abandoned his coveralls.

The DeAutremonts had killed four people, left several passengers cut and injured by flying glass from the explosion and fled with nothing more than the clothes on their backs and the few firearms left in their possession. To add insult to their injured egos, the brothers later learned there was no $40,000 in cash aboard the train.

This photo shows the aftermath of the explosion that?destroyed train #13, killing mail clerk Elvyn Dougherty. On October 11, 1923, Hugh, Ray, and Roy DeAutremont, stopped Southern Pacific train #13 in southern Oregon, thinking there was gold in the mail car. The three brothers used too much dynamite trying to blow open the mail car door. They destroyed the car, killing mail clerk Elvyn Dougherty and shot and killed three more train workers before escaping empty-handed.

Crime scene investigations in 1923 were based on good old-fashioned logic by street-smart law enforcement officers. As soon as responding personnel realized that engineer Sydney Bates and fireman Marvin Seng had been shot, posses formed to look for the murderers. The largest man hunt ever assembled included Southern Pacific railroad investigators, local citizens, members of the Oregon National Guard, personnel from Sheriff?s office from California and Oregon, and local police officers. All these individuals collected evidence they deemed important. A novel idea was to use airplanes to fly low over the mountains looking for suspects, a law enforcement first.

About 2 miles south of Tunnel 13, a cabin was found which showed evidence of recent habitation and was thought to have been used while planning the holdup. This became a second focus of the investigation. Several other campsites were discovered that appeared to have been used during the escape. Examination of case records in the sheriff?s office of Jackson County, Oregon, reveals the following partial list of the evidence collected from the tunnel:

  • One colt automatic pistol 45 caliber
  • One pair of ?Pay Day? brand bibbed overalls
  • Detonating machine
  • Fuse wire and cap
  • Several 45 caliber shells
  • 12 gauge shot gun shells
  • Some of the evidence collected from the cabin and campsites included:
  • One towel from cabin near tunnel
  • One union suit from cabin near tunnel
  • Three brown canvas blanket bags
  • One scorched coat
  • One valise
  • Two cans
  • One pair of gloves, leather
  • One pair socks, from cabin near tunnel
  • Three pieces of wire and bone from cabin fireplace
  • Two gun wipers cloth
  • The beginning of?Forensic Science in the US

Once the evidence had been collected, cataloged and compiled, the State and Federal law enforcement authorities knew precisely how the crime was committed, but had no clues as to who the criminals were. With four men murdered and mangled car remains, it was maddening to the authorities that this crime couldn?t be solved. Therefore, they decided to send the evidence to a 42 year old chemistry professor at the University of California at Berkeley who had had some success in helping Southern Pacific railroads with minor train robberies. His name was Edward Oscar Heinrich.

The investigation was headed by Chief Agent Dan O’Connell. In a few weeks, Heinrich informed them that their ?coverall man? was white, light complexioned, had light-brown eyebrows, a mustache, medium-brown hair, and was near 5-feet, 10-inches tall. He was a logger in the Pacific Northwest, left-handed, and very meticulous about his appearance. The man smoked and when caught, Heinrich said he would probably be wearing a new jacket and a bowler hat. When Roy D?Autremont finally was caught, he was smoking a cigarette and wearing the jacket and hat. Wizard Heinrich, determined that the ?dirt? discovered on the overalls was not oil or grease, as the police had thought, but fir pitch from Douglas fir needles peculiar to the Northwest. The man with the coveralls was left handed, since in swinging with his left hand, his right-side pocket would face the tree and collect wood chips, as found in that pocket. In a breast pocket, Heinrich discovered fingernail clippings, rolled-up cigarette butts, and mustache wax that indicated that this person was a vain man. The definitive clue found was a crumpled up, mail receipt, deep in a pencil pocket, and signed by Roy D?Autremont. The address was in ?Lakewood, N.M.,? where the brothers and their divorced mother had lived in 1920,?leading to the identification of three Oregon d’Autremont brothers as suspects.

California criminalist, Edward Heinrich, examine soiled overalls found nearby. Using primarily botanical evidence, Heinrich identified them as those of a woodsman.

In the early 1920s, crime labs existed only in Europe. The world-famous FBI crime lab was not founded until 1932. Therefore it must have been a bold move for law enforcement personnel to submit evidence to a university professor in 1923. Professor Heinrich used meticulous scientific processes to examine the evidence and his analyses yielded surprising results. Until recently, the only available information about Professor Heinrich?s conclusions were the sketchy news reports of the day.

In the analysis associated with the Siskiyou train robbery Professor Heinrich conducted handwriting comparisons, examined latent fingerprints, bullets, cartridges, fibers, hairs, stains, blood, etc., and conducted serial number restoration on the recovered handgun. Thus, he used most of the techniques that are still used today to deduce how and who committed the crime.

Heinrich was able to link a .45 caliber gun found at the crime scene with Ray through serial number restoration. Hair recovered from the ?Pay Day? bibbed overalls place Roy at the crime scene and it was established that Hugh was at the planning cabin by analyzing the handwriting on sale receipts for supplies. After the media publicized Heinrich?s deductions, he was often referred to as the ?Wizard of Berkeley? or the ?Edison of crime detection?.

The DeAutremont brothers stole this detonator and dynamite from a construction company to use in the train heist.

Finding these bits and pieces of evidence was easy; finding the DeAutremont brothers was something else. Although U.S. Postal officials spent a half million dollars circulating wanted posters, containing pictures of the three brothers, all over the nation and in several foreign countries, it took nearly four years to track them down.

What followed with wanted circulars posted around the world was said to be the most intense manhunt ever. Ray and Roy spent the next three years in constant fear that they would make a fatal slip, saying something that would tie them into that unsolved train robbery attempt in Oregon. To avoid recognition, Ray bleached his hair white and both he and Roy grew bushy moustaches. Yet, they were constantly looking over their shoulders, fearing that someone was spying on them.?Hugh DeAutremont joined the U.S. Army in hopes of avoiding capture, changed his name to James C. Price (purportedly using the name “James” in honor of his boyhood idol, Jesse James) and was sent to the Philippine Islands.?His two brothers traveled in different directions for awhile before reuniting and moving to Ohio. They both got jobs in a Steubenville, Ohio, steel mill, under the assumed last name of “Goodwins.” Ray took the name “Elmer Goodwins” and Roy, “Clarence Goodwins.”

The posters were effective: Hugh was detected and arrested while serving in the army in the Philippines in February 1927. Ray and Roy reunited and traveled to Ohio where they adopted aliases Elmer (Ray) and Clarence Goodwin. Ray married 16-year-old Hazel to add to his disguise. Again, wanted posters did their job, and the twins were captured in Steubenville OH in June 1927 and extradited to Jacksonville OR where brother Hugh was now being tried on four counts of murder and several of interfering with a mail train. Heinous crime these capital murders were, public sentiment of “string ’em up!” was moderating, and prosecution and defense began bargaining to spare Hugh’s life.

Agreement was reached just about the time the twins reached Jacksonville from Steubenville – if Hugh would confess, the penalty would be life in prison, not death. Eager to save their lives, Ray and Roy sought this same deal.The day following their arrests, Ray and Roy DeAutremont waived extradition and agreed to return to Oregon to face charges.?To be nearer “her boys,” mother Belle sold her store and home in New Mexico and bought a boarding house in Salem, just down the street from the penitentiary.

On June 24, 1927, the three murderous DeAutremonts were manacled and taken by train to the Oregon State Penitentiary in Salem.?Sheriff Jennings and his son and Chief Deputy, Louis, travelled to Ohio by train to return the brothers to Oregon. The DeAutremonts found themselves travelling in style, in a Pullman Suite usually reserved for celebrities, politicians and other dignitaries.

Along the way, curious on-lookers would turn out at train stations all across the country to catch a glimpse of the notorious train robbers.

They arrived in Jacksonville, Ore., on June 21 –the final day of brother Hugh’s second murder trial. (His first ended in a mistrial after one of the jury members died.) The jury found Hugh guilty as charged of the four murders, although he had entered a plea of not guilty and had maintained his innocence all the way through the 12-day trial.
Convinced they could fare no better in a jury trial, Ray and Roy DeAutremont both pleaded guilty to the murder charges on June 22, 1927. All three brothers were sentenced to life imprisonment and were sent to the Oregon State Penitentiary .on June 24, 1927.

Authorities found the detonator (center) in the brush above the tunnel.

The three brothers spent the next three decades behind bars and were even described by some prison officials as “model prisoners.” Hugh published a prison publication called “Shadows,” which won two national awards. And Ray was a frequent writer for “Shadows.”
Ray and Roy shared a cell at the prison for a while until Roy gradually became mentally ill. It took six prison guards to subdue Roy after he went berserk and began wrecking all of his cell furniture. He was later sent to the Oregon State Mental Hospital where doctors performed a prefontal lobotomy. The operation successfully subdued Roy DeAutremont, but robbed him of most of his mental faculties.

“Ray had devised the whole thing — it was his get-rich quick scheme,” observed Medford-born Noreen Kelly McGraw, an attorney now living in Portland. She represented Hugh A’Autremont when he applied for parole in 1957. She later represented Ray for a short time.

As she understood the story from her discussions with Hugh and Ray, they never intended to harm anyone. In fact, the two brothers expressed deep regret for the deaths, she said

“Ray talked Roy and Hugh into the proposition,” she said. “They planned to dynamite the mail car. They didn’t think anyone would be riding in it. There was so much smoke and confusion after they blew it up. “They thought they’d get all this money and they didn’t get anything,” she added. “That’s what’s so crazy about it.”

Not only were the brothers poor criminals, they also had no expertise when it came to dynamite, she said. “They were clueless (in Ashland*)– let’s face it,” she concluded.

In the “pen,” Hugh and Ray made the best of life and gained respect from many inside and outside prison walls. Hugh learned the printing arts, took correspondence courses from the University off Oregon in Eugene and edited and published the penitentiary newletter “Shadows.” Through interesting dealings, he was paroled in 1958 and preparing to meet a fiance who had worked with him in printing for years. Smoking and cancer caught up with him: he died in the San Francisco veterans’ hospital in March 1959 just weeks after leaving prison walls.

Roy went insane while in prison. He was transferred to a mental hospital, where he was given a lobotomy. The procedure was not as successful as hoped – he calmed right down but became pretty much a vegetable. No longer a threat, he was paroled in 1983 and moved to a foster care home. He died in 1983. ?Ray DeAutremont, who had been described as a model prisoner, was paroled in 1961, on the anniversary of the robbery. His sentence was commuted by the governor of Oregon in 1971. He died in 1984, at the age of 84.

Ray argued that life is predestined. As much as he might regret his ghastly crime, fate prevented his living any other way. Many argue that there is no predestination – that we all have alternatives to select and choices to make.

This crime, typical of those in which unforeseen events lead the perpetrators to panic and to murder, helped to establish criminology and particularly botanical studies as valid scientific disciplines. Its investigation and solution also remain models of scientific crime detection.

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