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He teamed up with another ex-con.

John Case was 22 years old when he arrived at the Oregon State Penitentiary on February 2, 1886. He had been sentenced in Clatsop County to serve five years on a charge of “larceny in a store.” Case was released on January 9, 1889, after serving three years, but within a year he was back behind prison walls, this time from Multnomah County serving seven years for “assault with a dangerous weapon.” He tried to hold up a mining camp single-handed but was arrested when a Chinese miner creased his skull with a hatchet.

James W. Poole arrived at the penitentiary from Douglas County, Ore., on June 20, 1890. He was sentenced to serve three years for manslaughter but won a new trial. Although Poole was acquitted of manslaughter this time around, he was found guilty of “obtaining money under false pretenses” and sentenced to serve another year. Case and Poole met before the latter prisoner was released on July 19, 1892. When Case was released two years later, the two men rendezvoused in Douglas County and spent the next year planning to rob a train. A third man also became involved.

Cow Creek Canyon was a lonely place in 1895, 30 miles south of Roseburg and eight miles south of Riddle in Oregon’s Douglas County. The mountain passes in the canyon were of such a peculiar formation, with many sharp curves, that trains had to travel at a very slow rate of speed in the dry season and even slower in the wet season. On Monday evening, July 1, 1895, there was a bright moon, but the remote canyon was pitch-black. At 10:15 p.m. Southern Pacific’s northbound train No. 15, the Oregon Express, heading for Portland, entered the canyon. The only light came from the engine’s powerful headlamp. Fireman Everett L. Gray was stoking the engine, and a stow-away hobo was helping him. Suddenly, an explosion rocked the train. Thinking it was a warning torpedo, engineer J.B. Waite applied the brakes. As the train sat idling, three masked men quickly approached it. Case collected, at gunpoint, the engineer, fireman and hobo and kept them still. Meanwhile, his two companions patrolled the sides of the cars, occasionally shooting into the air or exploding a stick of giant powder.

Case took his three hostages to the express car and demanded that express man Ralph M. Donohue open the doors. Donohue did so, but he was one step ahead of the robber; he had already removed the treasure from the local express box and hidden it under some goods. All the hostages climbed aboard with Case, who told them to keep their hands up while Donohue opened the local box. When the robber saw nothing inside worth taking, he ordered the express man to open the through safe. Donahue said he did not have the combination and, when threatened, added: “Well, you are simply wasting time. I can’t and won’t open it. The combination is not given me, just because of such occurrences as this….” Case replied, “You’re hot stuff ain’t you!” but he didn’t press the issue.

Case took his four hostages to the mail car, which mail clerk C.A. Hermann opened after the robber threatened to use explosives. Once inside, Cass demanded the registered mail. Hermann produced only three registered pouches, which seemed to be the entire lot. Case then asked for the local packages, and Hermann replied: “It’s Sunday, you know, and I haven’t many. They are scattered in those pouches.” Case went through the pouches and took out only five packages, leaving unmolested 45 other pouches that were well hidden.

Next, Case took his hostages to the first passenger car. Donohue walked ahead with a lantern, followed by the hobo carrying an empty sack. The party went through the coaches from front to back. Once the party stepped onto the rear platform of the last car, Case ordered the trainmen to the front of the train. With sack in hand, Case followed them, but then kept walking until he came upon his two partners. The three holdup men then hurried into the brush and disappeared into the darkness. Their take was calculated at about $1,000 from the mails and $520.70 from the passengers.

The Southern Pacific Railroad offered a reward of $2,000 for the arrest and conviction of each robber. In response, several posses took the field, while Sheriff C.F. Cathcart and Riddle’s constable, George Quine, rushed to the scene of the robbery. Quine, an amateur detective, began documenting evidence. At a camp near the tracks he found distinctive boot prints, one with two rows of tacks in the heels. The foot tracks led to where the robbers mounted, and the posse then followed the horse tracks to a more permanent camp. There they found the masks, which had been made from sugar sacks, and a rag from a flour sack used to bind a wound. They determined that the robbers had used giant powder sticks that were common to miners.

On July 2 Stilly Riddle rode into Roseburg and reported that three men, working at Nichols’ Station 13 miles south of Riddle, matched the description of the robbers. He said that two of them were Jim Poole and John Case, and it happened the lawmen were familiar with those two desperados. With suspects named, the posse went to search the home of Napoleon Poole, father of Jim and his brother Albert. Napoleon let the lawmen search the place, and they found sacking and string that matched what had been found at the robbers’ camp. They also discovered both Jim’s and Albert’s boots, each with heel prints that matched the peculiar double tack design. Case himself was arrested later that day and identified as the man who had gone through the coaches, as his mask of light cloth had revealed his features. The Poole brothers were also soon apprehended.

After a preliminary hearing, the three men were taken to Portland, where a five-day trial began in mid-December. On Christmas Eve, after one hour’s deliberation, the jury returned a verdict of guilty against Jim Poole and John Case but found Albert Poole not guilty. Everyone on the defense side was astonished with the verdict against Jim Poole, as the evidence against him had been weak. The judge declared, “I am frank to say that I am not entirely satisfied with the verdict.” The prisoners were returned to jail while the defense attorneys filed a motion for a new trial, and after months of thoughtful contemplation, the judge set aside the verdicts and ordered the prisoners released without bond, setting the new trial date for June 28, 1897.

Upon his release, Case made his way up the coast, stopping at several cities until he reached Tacoma, Wash. On May 23, 1897, Steilacoom, Wash., streetcar superintendent Frank Dame caught Case trying to rob a streetcar and shot him dead. Three men who knew Case positively identified his corpse. The deceased robber’s Colt revolver, serial number 13,908, was the same one Case had on him when arrested back in 1895. (The gun had been returned to him upon his release from jail.) For further confirmation, the dead man’s photo was sent to Roseburg, and indeed the Case was closed.

The evidence against Jim Poole was no stronger than it had been at his first trial, and Case clearly had been the leader of the Cow Creek Canyon train robbery. Once Case was dead, law officials decided to dismiss the indictment against Jim Poole.


Originally published in the August 2007 issue of Wild West. To subscribe, click here