Siskiyou Outrage

In 1923 Portland was a modern urban city, just beginning its huge sprawl as the impact of the automobile started to be felt. Police were concerned more with Prohibition, enforcing it or breaking it, than anything else. Meanwhile a railroad tunnel south of Ashland was to be the scene of what would go down in history as the last Old West Train Robbery.

On October 12, 1923, the city awoke to headlines screaming -- Siskiyou Outrage: Fiends Murdered Four Trainmen in Cold Blood. The killers were still holed up in a mountain cave hiding from lynch mobs of outraged railroad workers and a National Guard unit that searched for them with airplanes.

On that day no one knew that it would take four years and an international manhunt to bring the D'Autremont brothers to justice. The three young brothers, Roy, Ray and Hugh got nothing from the mail car they had attempted to rob. Instead they lay in their hiding place in danger of starving or freezing to death in the cold mountain nights.

Ray and Roy D'Autremont, born in 1900, were twins that were so near identical their mother had to tie ribbons on their wrists so she could tell them apart when they were infants. Roy(right) was a deeply religious Catholic who was already beginning to show signs of mental illness.

His brother, Ray(above), had been a proud member of the Industrial Workers of the World (IWW) and had served a year in jail for criminal syndicalism during the 1919 Red Scare that followed the Centralia Massacre. Hugh(below) was a 19-year-old recent high school graduate who idolized and competed with his older brothers.

Ray and Roy, having been raised on tales of Jesse James and Harry Tracy, had been trying to start a life of crime ever since Ray's release from jail in 1921. Ray had developed a deep resentment against the capitalist "System" and had convinced his brother that they had to strike back against it.

After several unsuccessful attempts at armed robbery, including one memorable occasion when they watched a rival gang rob the bank at Yacolt, WA while they cased the place for their own robbery, the brothers were nearly ready to give up their plans and resign themselves to lumber jobs which they hated.

The strange career of Roy Gardiner, who waged a one-man war against the U.S. Post Office during the summer of 1922, changed all that for the D'Autremont twins. Gardiner lost $200 in the mail in 1920. When Postal authorities refused to even hear his complaint Gardiner robbed a mail truck in San Diego, CA of $50,000. Gardiner offered to return the money if the Post Office would give him back his $200.

The Post Office refused to be blackmailed so Gardiner declared war. Writing letters to local papers all over the West Coast, Gardiner publicized his complaint and robbed Southern Pacific mail trains of over $300,000 in a series of raids. Each time he offered to return the money if the Post Office would return his $200. Gardiner's quixotic war, which ended with his arrest in 1922, attracted a lot of attention in the press. It also inspired the D'Autremonts. They decided they would rob a train.


By the summer of 1923 the brothers, now joined by their brother Hugh who had graduated from high school in New Mexico, had decided that they would hit Southern Pacific #13.

This train, known as the Gold Special, was vulnerable as it stopped for a brake check before entering Tunnel #13, south of Ashland, at the beginning of its long ride down the mountain into California. The brothers spent several months camped in the area, staking out the train and planning their big job.

The meticulously planned job couldn't have gone more wrong. The worst problem came when they tried to blow the door off the mail car with dynamite. Ray, the only brother with demolition experience, inexplicably left the dynamite job to his brother Roy. Roy having no idea how much explosive to use blew the mail car to bits, causing an inferno that incinerated the body of Elvyn E. Dougherty, the mail clerk who had locked himself inside.

The tunnel, rather than muffling the sound of the explosion as the boys had planned, amplified the sound which was heard at the railroad camps at Siskiyou, OR and at Hilt, CA, several miles away. Rescue crews, thinking that the engine had exploded left immediately and messages for help were telegraphed to all stations along the line.

Meanwhile back in Tunnel #13 the D'Autremonts were succumbing to frustration. Brakeman Coyle Johnson was shot to death during a moment of panic. As Ray's plan fell apart before his eyes, he desperately ordered the murder of engineer Sidney Bates and fireman Marvin Seng. His brothers coldly carried out Ray's orders.

Unable to enter the mail car, because of the smoke and flames, and hearing the approach of the rescue crews, the boys fled into the hills. After a long hungry ordeal in the mountains the brothers split up. Hugh eventually joined the U.S. Army under an assumed name and shipped out for the Philippines. Ray and Roy, also taking fake names, settled in Steubenville, OH and took jobs. Wanted posters with photographs of the brothers circulated widely. Rewards of $5,300 for each brother were offered.

Army Corporal Thomas Reynolds, after returning from duty in the Philippines in 1927, recognized a wanted poster for Hugh D'Autremont and led authorities to the youngest brother. Hugh tried to deny his identity, but soon admitted who he was and was returned to Oregon to face trial. Hugh claimed that the murder charges against him were unjust. He wove fantasies about his daring escape from lynch mobs and said he was returning to Oregon to clear his name.

Meanwhile a co-worker in Ohio had recognized the twins. They were soon taken into custody and transported back to Oregon. Ray was subdued on the trip home, but Roy seemed to enjoy the attention of the press. He told wild stories of their flight through the mountains and said they were returning to help their brother clear his name.

On June 21, 1927 Hugh D'Autremont was convicted of first degree murder and sentenced to life in prison. The next day Roy and Ray decided to stop denying their guilt. They made a full confession giving the first clear explanation of the disaster their plan had become. Ray and Roy plead guilty to murder and both received life sentences.

In 1949 Roy suffered a nervous breakdown in prison and was confined in the Oregon State Mental Hospital. He was lobotomized and spent the rest of his life under supervision. Hugh was paroled in 1958, but died a few months later of stomach cancer. The governor commuted Ray's sentence in 1972. He lived until 1984 writing and painting in Eugene, OR.

One of the bloodiest of U.S. train robberies was, in the words of Hugh D'Autremont, "All for nothing."