DeAutremont Brothers

Oregon's most famous train robbery also turned out to be one of the most badly-bungled non-robberies in the nation's history.

But it made instant, international "celebrities'' out of the DeAutremont brothers -- 23-year-old Ray DeAutremont, his twin brother Roy, and theft younger brother Hugh, 19.

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. They panicked and fled into the woods. But in the process, Roy DeAutremont dropped his Colt .45 on the railroad tracks and abandoned his coveralls.

The DeAutremonts had killed four persons, 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.

Authorities who arrived at the scene shortly after hearing the dynamite blast found Roy's handgun and coveralls. They found a hidden serial number on the gun and learned it had been sold to a "William Elliott," a name used by Roy DeAutremont. Investigators also found a receipt for registered mail sent to Lakewood, N. M., and signed by Roy DeAutremont. Hair taken from the coveralls also matched the hair found on one of Roy's sweaters later found at his father's house in Eugene. And Roy's signature on the mail receipt matched the handwriting of "William Elliott" on the gun sale records.

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.

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."

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, on the other hand, felt relatively safe-- serving his country several thousand miles away in the South Pacific. But a fellow Army soldier, who had been transferred back to the States and stationed at the Army prison on Alcatraz Island (before it became a federal penitentiary) in early 1927, recognized his old Army buddy James Price from a picture on a wanted poster, above the name Hugh DeAutremont. He contacted his commanding officer, who in turn notified Army officials in the Philippines.

After several hours of intense questioning, Hugh DeAutremont revealed his true identity, but steadfastly denied any knowledge of the train robbery. In March, 1927, he was sent to the Alcatraz Island military prison where he was held in custody until Jackson County Sheriff Ralph Jennings arrived in the Bay Area by train to take the robbery suspect back to Oregon. DeAutremont was lodged in the Jacksonville City Jail.

Back in Ohio, Hugh's two brothers were getting restless. Fearing the law was closing in on them, they decided to flee to Mexico. But before they could leave, a fellow employee at the Steubenville, Ohio steel mill recognized them from a wanted poster and notified postal authorities and the U.S. Bureau of Investigation -- later renamed the Federal Bureau of Investigation.

Authorities laid a trap for the two brothers. They put out notices that there were better paying jobs at another steel mill on the outskirts of Steubenville and made sure Roy DeAutremont knew about it. When Roy turned up looking for the job, he was arrested. He later admitted his true identity, but like his younger brother Hugh, denied any involvement in the Oregon train robbery.


Next, authorities went to Ray DeAutremont's home and informed his wife that Roy had been injured in a steel mill accident. She awakened Ray and told him. He was arrested moments after leaving his house.

The day following their arrests, Ray and Roy DeAutremont waived extradition and agreed to return to Oregon to face charges. 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.

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.

Hugh DeAutremont, who had become terminally ill with cancer, was paroled from prison on Nov. 24, 1958, and died less than three months later in San Francisco.

Roy DeAutremont died in 1983 at a Salem care center. Ray, who was paroled in 1961, worked several years as a custodian at the University of Oregon in Eugene. He became a free man in 1971 when the late Gov. Tom McCall commuted DeAutremont's two consecutive life sentences.

The last surviving DeAutremont brother died Dec. 20, 1984 at a Eugene care center at the age of 84.

Lynch Mob Justice

In frontier Oregon, vigilante justice frequently prevailed over "law and order." It was generally shoot now and ask questions later, a time when the prevailing attitude toward thieves, robbers and murderers was hang 'em from the highest tree, rather then try 'em in a court of law.

The Oregon gold rush of the mid 1800s spawned several outlaw gangs which would hide out along stagecoach roads and along railroad tracks, waiting for the next shipments of gold to pass.

Because most town Marshals had their hands full trying to keep peace and order on the street, stage lines took it upon themselves to hire the best stage drivers and best shots around to ride shotgun. One of the best stage drivers of the time was Jack Montgomery, a tall, strong man capable of driving a team of six horses through narrow, treacherous mountain passes at full speed.

Montgomery was constantly in demand, but never more so than that May day in 1857 when he was summoned to the office of the Oregon and California Stage Coach Line in Jacksonville. A Wells Fargo Express Co. official told Montgomery there had been a huge gold strike in the mountains of Southern Oregon and Wells Fargo needed him to transport a half-millon dollars in gold from Jacksonville to Portland.

The Wells Fargo officer said highwaymen might find out about the shipment and could be waiting along the regular stagecoach roads between Jacksonville and San Francisco, the usual destination point for mail and gold shipments in Northern California. Wells Fargo planned to send the big gold load to Portland by stage and then have it shipped to San Francisco.

A large stagecoach was specially-built for the Portland run, a coach so big it would take a team of 10 horses to pull it. The coach would be transporting a full load of passengers to Portland -- the better to divert suspicions about the giant gold shipment. At least that was the hope of Wells Fargo.

The job paid $250. Montogomery didn't have to think twice before accepting the offer.

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