On October 11, 1923, at the summit of the Siskiyou Mountains of Oregon, Southern Pacific Train No. 13 slowed to a stop at Siskiyou Station. This was required by Company rule to test the air breaks before descending the mountain. The stop was also used to uncouple the helper engine that had been used to help the train up the steep grade and tight switchbacks. The train had only accelerated to five or six miles an hour by the time it reached Tunnel No. 13, about a hundred yards away. It was slow enough to allow three bandits to jump on board the mail car, about 12:40 in the afternoon.
The train was known was the "Gold Special," as it frequently took gold shipments up and down the West Coast. The bandits thought this train would be carrying $40,000 in its mail car, a significant enough amount to take a chance. Hugh held up the engineer and the fireman with a shotgun and ordered them to halt the train. They immediately obeyed and stopped the train, with the engine just emerging from the mouth of the tunnel. It was somewhat of a challenge since the grade of the tunnel was downhill and the train may have been moving as fast as 20 miles per hour when the robbers ordered it stopped.
Ray saw the mail clerk look out the window of the mail car, and fired at him but he missed. Hugh and Roy walked the engineer and fireman up to the front of the tunnel so they would not be injured when they blew up the mail car. Ray affixed the dynamite to the mail car. After the explosion Hugh kept a gun on the two railroad men while Roy and Ray tried to uncouple the mail car from the train.
At that time a man with a red light came toward them. It was the brakeman, Coyle O. Johnson. Hugh ordered Johnson to uncouple the mail car from the engine. But he couldn't do it because of the damage from the explosion. They ordered Johnson to go tell the engineer to pull the mail car away from the rest of the train with the engine. As Johnson turned to comply, though, Ray shot and killed him. Roy told the engineer what he wanted, but the engineer could not budge the train. They couldn't see anything in the car through the steam and smoke so
they gave up their attempts to get into it. Before they left, Roy shot the fireman, Marvin L. Seng, and Hugh shot the engineer, Sidney L. Bates. Then they fled to their hideout to or three miles northwest of the south entrance of the tunnel, without having stolen one dime.
Conductor Merritt immediately phoned the incident into the Southern Pacific agents at Ashland, Oregon. Southern Pacific phoned Chief Special Agent Dan O'Connell at San Francisco. Soon posses and National Guard troops were searching the mountains to find the culprits. Some railroad men formed their own posses to revenge their fallen comrades. But it was too late, the three men had already escaped.
Meanwhile, men at the Siskiyou station immediately refired the helper engine and backed it up to the stalled train. It hauled the train back into fresh air. At the same time, men hooked up the original engine to the mail car and hauled it down the West side of the mountain to a bypass track at White Point. The mail car was taken to the Southern Pacific Yard at Ashland where authorities found the remains of the postal clerk, Elvin E. Dougherty.
The bandits made their identification easy. As they fled the scene, Roy dropped his Colt on the railroad tracks as he ran away. Though the Colt had had its serial number scratched off there was another secret number on the gun that was easily traceable to the DeAutremont brothers. Another brother dropped a pair of tar stained overalls and a box of black paper to try to throw bloodhounds off the track. Amazingly he left a crumpled receipt for a piece of registered mail in the pocket of the overalls. That receipt made it easy to trace the DeAutremont brothers. Hugh was 19 years old at the time, and the twins, Ray and Roy, were 23 years old.
Rewards were offered and their pictures posted everywhere. They remained at large for almost four years. Over two and a half million wanted posters were circulated in the U.S. and overseas. They were printed in English, Spanish, French, Dutch, German, and Portuguese. Pictures of the dynamited car and the murdered men were printed in papers across the country. Hugh was finally picked up in Manila in the Philippine Islands in February 1927. He had enlisted in the U.S. Army under an assumed name. His picture was recognized on a poster hung in the post office near San Francisco Bay by Thomas Reynolds who knew him slightly. Roy and Ray were captured in Stuebenville, Ohio. Albert Collingsworth recognized the twins from a newspaper story about them. He told Emma L. Maynard what he thought and she passed its on to the law. The twins were using an assumed name of Goodwin. Ray had married and adopted the name while on the run. When arrested he left a wife and small child behind.
When Hugh was tried in Jacksonville, Oregon, he entered a plea of not guilty. Before the trial was over a juror died, thus a mistrial was called. Before the second trial was over the twins were arrested and brought to Jacksonville for trial. The Twins confessed to their crimes. All three brothers received life sentences at the Oregon State Penitentiary in Salem.
Sometime in the 1950s, Hugh was paroled when they discovered he had terminal cancer. He was released, but died a few weeks later. After 22 years Roy was transferred to the State Hospital because of mental breakdown where he lived until the end of his life. Ray was paroled in 1961 and took a job as a custodian at the University of Oregon and later died in a rest home
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