The Pacific Northwest Forum
Volume V, Number 1, Pages 23-27
Winter, 1980

The Great Oregon Train Holdup

Glenn Aplin

Associate Professor of Education, Glenn Alpin, writes about a famous train holdup in the Siskiyou Mountains of Southern Oregon. Professor Aplin taught history in various Oregon schools before coming to Eastern Washington University.

At the crest of the Siskiyou Mountains in southern Oregon, Southern Pacific Train Number Thirteen, southbound, carrying 115 passengers and mail, slowed down to enter Tunnel Thirteen.(1) As it entered the three thousand foot long tunnel, two men jumped aboard, unnoticed, and moved from the coal-tender to the engine cab. The train was easy to board at this place because it was moving slowly for two reasons. It had just stopped to unhook its "Helper" engine, needed to. pull it over the summit, and regulations required the engineer to test the brakes before the long down-hill run. Ominously enough, Tunnel Thirteen was the regular place for this crucial test.

The desperate young men, Roy DeAutremont, twenty-three years of age, and Hugh DeAutremont, nineteen, and only five months out of high school, had planned their crime well. On the date, October II, 1923, the train, called the "Gold Special," was said to be carrying between forty thousand and a half million dollars in its mail and express car. The two DeAutremont brothers surprised Engineer Sidney Bates and Fireman Marvin Seng when they appeared out of the tunnel darkness and, at gunpoint, gave orders to stop the train with the locomotive extending out of the south end of the tunnel. The first rail car behind the locomotive tender was the mail and express car, and connected to it were the passenger cars. The DeAutrements' plan was an ingenious one. They would blow open the mail car door with dynamite, while it was still inside the tunnel, thus muffling the sound of the explosion. They hoped that the few men at Nearby Siskiyou Station would not hear the sound. Thus, the authorities would be less likely to apprehend them. Then they could uncouple the mail car from the rest of the train, pull it out of the tunnel, using the locomotive, and loot it at will, without having to injure anybody.

When the locomotive stopped just outside the south end of the tunnel, Ray DeAutremont, the third brother, was waiting with the dynamite and detonator. He handed the dynamite to Roy, in the locomotive cab, who took it back to the mail car and attached it to the door. The three DeAutremonts, the engineer, and the fireman then left the tunnel and Roy pressed down the detonator handle, filling the air with smoke and debris. This was the great blunder of the robbery, for in attaching too large a dynamite charge to the mail car door, Roy blew up the mail car, its contents, and the mail clerk, Elvyn Dougherty. The DeAutremont boys had now committed murder.

Realizing that their plans were now going awry, the DeAutremont brothers became excited. Roy took the fireman, Marvin Seng, into the tunnel to uncouple the mail car from the train, so it could be pulled out of the tunnel by the locomotive. While they worked unsuccessfully to open the coupling, brakeman Coyle Johnson came through the smoke and told them the locomotive needed to pull the mail car forward to uncouple it from the passenger cars behind it. Roy sent the brakeman out to tell his brothers, but Ray and Hugh DeAutremont, seeing the brakeman appear out of the smoke, panicked and shot him, fearing others might be with him.(2)

Meanwhile, Hugh took the engineer, Sidney Bates, into the locomotive cab to pull the mail car out of the tunnel, but the engine's wheels spun and couldn't move the wrecked mail car. Then Ray and Roy tried to enter the mail car, but they found it to be a wrecked hulk, full of smoke and steam, which their flashlight beams couldn't penetrate.

Damaged mail from the holdup

Courtesy of Southern Oregon Historical Society

Ray and Roy, realizing that all was lost, decided that they must leave no witnesses, and then walked back to the locomotive. Roy shot the fireman and Hugh shot the engineer.(3) They fled to a pre-arranged spot in the mountains where they made their last plans. They agreed to separate and meet again, five years later, at the Empire State Building in New York City. This never happened, and events later proved that there was no money or gold in the mail car on that fatal day. Ray, Roy, and Hugh DeAutremont had planned their escape well, for it was over three years before they were caught. Southern Pacific Railroad detectives and United States Postal authorities soon identified the names of the holdup men, but locating them came only after hundreds of thousands of "Wanted" posters had been distributed world-wide in several different languages.(4)

Hugh had enlisted in the army, using an assumed name, and was arrested in the Philippines in February, 1927. Four months later Ray and Roy were apprehended in Steubenville, Ohio, where they both had settled down. Ray had married and had one child.

Ray DeAutremont

Courtesy of Southern Oregon Historical Society

In the trial which followed, Ray, Roy and Hugh DeAutremont were found guilty of murder and sentenced to life imprisonment in the Oregon State Penitentiary in Salem. The trial was held in the Jackson County Courthouse in Jacksonville, Oregon. This building is now the home of the Southern Oregon Historical Museum, and the historic "trial courtroom" is the location of a permanent DeAutremont Trail display.(5)

After the trial, Southern Pacific Railroad trainmen were keenly disappointed at the verdict of life imprisonment for the prisoners. They vowed to sound their train whistles every time they passed the state penitentiary as a reminder to the brothers of the four men they had slain. Many people feel that the continuing sound of these train whistles was the cause of Roy DeAutremont going insane while in prison.

Many people have speculated about the reasons for the holdup and murders. The most logical ones being with speculation about their childhood on a worn-out farm near Artesia, New Mexico. The boys hated the poverty of their childhood and later tried various types of employment, none of which were very rewarding. Ray, eventually moved into the Pacific Northwest and joined a politically radical organization called the Industrial Workers of the World, better known as the "Wobblies." In Vancouver, Washington, he was one of hundreds of the "Wobblies" who was arrested and sent to jail. He unsuccessfully tried to escape and was given a one year term in the Washington State Reformatory. After his release from prison he communicated his feelings of radical social protest to his brothers, and they began to plan a life of crime. This eventually led to the "holdup in Tunnel Thirteen" and its bloody aftermath.

Hugh DeAutremont, the youngest brother, became a printer while in prison and won several national journalism awards for his magazine, "Shadows." When paroled in 1958, he sent for his finance, married her, and settled down to the life of a newspaper printer. Tragically, however, fate intervened, and within six months of his prison discharge, he died of cancer. Fate had assigned him an especially short period of true freedom during his life-time. This included the first four months after his high school graduation and the last six months of his life.

The last of the brothers, Ray, was freed from prison by Oregon Governor Tom McCall in 1972. At that time McCall stated, "I was proud and happy to have the opportunity to do it. We should base our corrections program on reformation rather than punishment. "

Today, at the age of seventy-eight, former train robber Ray DeAutremont lives quietly in Eugene, Oregon, actively pursuing a variety of interests. He is a prize-winning painter of landscapes and modern art and teaches Spanish at the Eugene Senior Citizens' Center. He reads philosophy, Steinbeck, and the Bible. He attends church twice a week at the local Baptist Church and is a favorite with children. He spends much of his time reading and is eager to improve himself. In the words of the director of the Senior Citizens' Center, "He is a nice, sincere person, dedicated to helping others. "

In these days of crisis and uncertainty, Ray DeAutremont's present life is an illustration of man's ability to grow and find contentment through reaching out to help others.


(1)Bert Webber, Oregon's Great Train Holdup. (Fair-field, Wash: Ye Galloon Press 1974), p 1.

(2)Hugh DeAutremont, "Confession," Archives, Southern Oregon Historical Museum, Jacksonville, Oregon. (copy in possession of writer).

(3)Edward D. Culp, Stations West, The Story of the Oregon Railways, (Caldwell, Idaho: Coxton Printer., 1972, p. 33.

(4)DeAutremont, "Trial Collection," Archives, Southern Oregon Historical Museum. Jacksonville, Oregon.