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Old West-style Train Robbery

It was early summer, 1914, and an Oregon & Washington Railway Navigation Co. passenger train was just passing over the summit of the Blue Mountains, between LaGrande and Pendleton. The crewmen were running the train slow, checking the brakes for the long downhill run ahead. Meanwhile, three men at the back of the train were checking their guns.

A train robbery was about to go down — one of the very last Old West-style train robberies ever. And before it was over with, it would turn into one of the very last Old West-style six-shooter gunfights, too. These three desperados couldn't seem to catch a break. First they robbed the wrong train; then it turned out to contain a dangerously competent lawman behind a big six-shooter; and finally, someone stole their getaway car.

Clarence Stoner didn’t much look like outlaw royalty. He had a mild, earnest, boyish face, and his relatives all considered him the last person they’d ever expect to become a train robber. But he was a cousin of two of the West’s most notorious desperados, Hugh and Charles Whitney, and a member of Butch Cassidy’s Wild Bunch gang in his home state of Wyoming. He was now out in Oregon and running with a close friend of his cousins, a gambler named Charles Manning and an outlaw sheepman from Kentucky named Albert Meadors.

In late July, Manning got word that Train No. 5 on the O.W.R.N. line, Chicago to Portland, would be carrying a significant sum of cash in the express car. So he got together with Stoner and Meadors and proposed that they do the job. As a place to do it, Manning picked a remote spot between Kamela and Meacham, at the summit of the Blue Mountains. At this remote place, Manning knew, the train would have to slow down and check its brakes. When it did, the three of them would be ready.

The Oregon Railroad and Navigation Company (OR&N) was a railroad that operated a rail network of 1,143 miles of track running east from Portland, Oregon, United States to northeastern Oregon, northeastern Washington, and northern Idaho. The railroad operated from 1896 as a consolidation of several smaller railroads.

OR&N was initially operated as an independent carrier, but Union Pacific (UP) purchased a majority stake of the line in 1898. The line became a subsidiary of UP titled the Oregon–Washington Railroad and Navigation Company in 1910. In 1936, Union Pacific formally absorbed the system, which became UP's gateway to the Pacific Northwest.

The outlaws bought a getaway car, a brown sedan of unknown make (although it was apparently not a Ford, since it wasn’t black). Manning also obtained enough dynamite to breach the express car — he anticipated that the clerk would barricade the door as soon as he learned the train was being robbed, to protect the strongbox. Finally, all was in readiness. The three desperados traveled to the Kamela station, bought tickets, boarded at the rear. The train rolled on westward, up the side of the mountain toward its date with destiny.

As the train neared the summit of the pass, it slowed down, which was the outlaws’ signal. Out came the guns, and starting at the back of the train, they simply collected all the train crew members and marched them forward. Manning pulled the emergency stop, the engineer slammed on the brakes and there the train sat, poised a few dozen yards beyond the crest, at the start of a miles-long, winding 2.5-percent downhill grade — airbrakes locked on. Stoner went forward and collected the engineer and fireman. At gunpoint, he marched them back and locked them in the baggage car.

The first big shock of the day came moments later, when Manning approached the express car and demanded entry. To his surprise, the clerk let him come right in rather than barring the door and refusing. Once inside, he immediately learned why: There was no money inside. Because of a printer’s error on the timetables, the train was carrying the wrong number. He and his friends were robbing the wrong train.

To Rob A Train Traveling Through Southern Oregon

Back in 1923, three men attempted to rob a Southern Pacific train that was traveling through southern Oregon. The mail car was supposed to have over $40,000 worth of gold inside, as well as any cash that was in the mail. According to reports, right as the train was entering a tunnel, two of the three men jumped the engineer of the train with hopes of taking control.

The third man was tasked with getting into the mail car, which at the time was secured by giant locking doors. Knowing this, the men stole some explosives from a nearby construction site with intentions to blow the heavy doors open so they could reach the gold.

However, none of the men had experience with explosives and instead of using a small amount and working their way up, they drastically overshot the amount needed and ended up blowing the entire railcar to bits. Inside the mail car was the railway mail clerk, Elvyn Dougherty, and he, unfortunately, did not survive the blast.

Now it wasn’t just armed robbery they were on the hook for, there had also been a murder. To make matters even worse, the mail car did not have the gold the men had expected to find. Not thinking clearly, the three men decided they couldn’t leave any witnesses and decided to shoot most of the employees on the train. The train’s engineer, brakeman, and fireman all were killed by robbers before they fled the scene.

The detonator they used to blow up the mail car was left behind, as well as a few clothes which should have led the bloodhounds directly to their location. However, that’s not how it worked out. The men managed to elude authorities for quite some time.

Southern Pacific made a decision to bring in a highly specialized investigator, Edward O. Heinrich, who was often referred to as “The Edison of Crime Detection”. Heinrich focused more on the small details, similar to what they do in current investigations. He apparently immediately asked to see the clothes left behind that police had already checked over multiple times.

From the clothes, he was able to determine there was a substance on them that was produced by a very specific Fir tree that was commonly found on clothing worn by Lumberjacks. This discovery alone cut down the possible suspects nearly by half. He also found a strand of hair that helped him determine the approximate age of one of the assailants.

But it was a small scrap piece of paper that he found that would ultimately lead him to the identities of the three men. Apparently, the scrap was a piece of a mail receipt that pointed directly at the DeAutremount Brothers, twins Ray and Roy and their teenage brother Hugh.

It took almost 5 years to locate all three men, but by March of 1927, they were brought to justice. Each man plead guilty and was sentenced to life in prison.

Hoping to salvage something for their efforts, the robbers now turned their attention on the passenger cars. Leaving Stoner to guard the captured train crew, Manning and Meadors started going down the rows robbing each passenger in turn. This turned out to be a bad plan. Because inside the passenger cabin, sitting in the back row, was Morrow County Deputy Sheriff George McDuffy.

McDuffy waited for a moment when both Manning and Meadors were distracted, then stood up and pulled his revolver, apparently planning to arrest the two at gunpoint. Manning, the gambler, rolled the dice, whipping his pistol around to shoot. This was not a good idea. As it turns out, Deputy McDuffy seems to have been something of a gunfighting ninja. Manning never had a chance.

Both weapons fired at about the same time. Manning’s shot hit McDuffy high in the chest, inflicting a wound that would have been very serious or even fatal if the bullet hadn’t hit a metal pencil case and pack of cards in McDuffy’s breast pocket. McDuffy’s shot went straight through Manning’s heart, and the officer followed it up with a second shot within inches of the first and a third shot that hit the outlaw in the head — all this from an old-school single-action six-shooter firing black-powder cartridges.

McDuffy’s three shots had filled the car with smoke. Manning was dead before he hit the ground, and Meadors couldn’t see well enough to return fire even had he been inclined to do so. So instead, he took advantage of the smokescreen to cover a hasty retreat. He leaped off the train and ran into the bushes, closely followed by Stoner. The two of them got away with just $750 worth of loot.

When the two hard-pressed robbers got back to where they had cached their car, they seem to have found a third and final unpleasant surprise waiting for them. Some accounts of this robbery say there was a fourth man who was waiting by the car for them. If so, that fourth man double-crossed them, because the next day the two of them were arrested trudging along the railroad tracks twenty miles from the scene, trying to make it to La Grande on foot. The car was never seen again. “I am mighty glad to come in and have it all over with,” Meadors told the cops, after he was lodged in the county jail. “That is exactly the way I feel about it,” Stoner agreed. “This is the first time either of us was ever in any trouble of this kind before in our lives.”

For Stoner, it was the last time. After he was released from prison, he settled down and led a perfectly normal and successful life. He worked hard, bought a farm in Idaho, raised a family and never talked about his previous career, even to his children. After moving back to Oregon, he died in 1974 in Newport at age 91.

Meadors was another story; for him, the train robbery was the beginning of a life of crime punctuated by stretches of hard time. Pardoned out of the joint in 1918, he was back in again the following year after getting caught burgling a house in Missouri. He spent the next 20 years filling up his rap sheet with more burglaries, bootlegging charges and even a manslaughter rap. He changed his name several times, and disappeared from the records in the late 1930s.

Deputy McDuffy was hailed as a hero — not just for foiling the robbery, but for saving the lives of everyone on board the train. M.J. Buckley, the general superintendent of the railroad line, told the Morning Oregonian that the air brakes on a stationary train of that weight, on such a steep grade, would only hold for 15 or 20 minutes. So the whole time the robbers were on board, the clock was ticking, and the only people who could do anything about it were locked in the baggage car. “It would have been impossible to hold a train like that on that grade without losing some air,” Buckley said. “As soon as the air begins to leak the brakes don’t hold long, and had the train ever started, nothing in the world could have stopped it. It would have torn down the hill and at the first curve undoubtedly would have left the rails and plunged over the mountainside.”

By Finn J.D. John. Train robbery turned into on-board gunfight with the law. Offbeat Oregon History. September 15, 2013.


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