Offbeat Oregon History

It was a typical balmy August evening at the Oregon State Penitentiary. The bell had rung for supper, so inmates were streaming out of their cells and heading toward the dining hall for the evening meal, as they always did.

But on this particular evening, four prisoners hung back from the throng, and when the last prisoner had rounded the corner out of sight, they doubled back, hurrying into the cell that had been assigned to one of their number. Working feverishly with an auger stolen somehow from the prison’s shops, they cut a hole in the roof and pulled and boosted each other up through it.

One of the most legendary jailbreaks in Oregon history had just started, and the die had been cast that would lead to the men’s doom. It was August 13, 1925; not one of the four prisoners would live to see 1929.

The prisoners were Bert “Oregon” Jones, a notorious highway robber from southern Oregon; James Willos, a burglar from Umatilla County; Tom Murray, a Lane County man serving 20 years for assault with a deadly weapon; and Ellsworth Kelley, a bank robber just starting a 20-year sentence for aiding in a previous prison break.

(By the way, Ellsworth Kelley the bank robber was not related to Ellsworth Kelly the artist, the mid-century painter of large-format works of modern abstract art famous for bright colors and hard edges.)

Prison breaks, or attempted ones, were surprisingly common in 1925. A new prison administration, appointed by Governor Walter Pierce, had been installed the previous year, and Pierce had stocked the place with political appointees with little real experience running a prison.

One exception was the warden, A.M. Dalrymple, who had worked for Oregon State Penitentiary before. Dalrymple, though, was kind of an exception that proved the rule: He’d been fired from that job with the approval of then-Governor Oswald West, who publicly disparaged him as “white-livered.” Dalrymple had almost immediately moved to prove West right by relaxing discipline and ordering all the guards to avoid shooting prisoners during escape attempts. After word about that got around, as you can imagine, busting out of the joint became almost a popular pastime for the inmates.

Indeed, all of the men but Willos had made an escape the previous year. In that attempt, they had unlocked a door with a key Kelley had made in the prison shop; then sawn through the bars on a basement window, climbed a guard tower while the watch was being changed, leaped off the high wall, and run to the road, where they had commandeered a car from a motorist driving by. They’d gotten away but had only managed to elude the posses for a few days.

This time, they hoped to slip through the dragnet and get clear of the state. Their goal was to get back east.

On this occasion, Tom Murray was leading them to the outside, but their escape plan was “Oregon” Jones’s brainchild — or so the others later claimed, for reasons that will soon become clear.

The four of them hurried to the edge of the roof and tied off a length of rope that they had carefully spliced together from bits collected here and there over the previous months. Then, one by one, they stealthily descended. At the bottom of the wall, they split and ran around the cell block, two on each side, making for turnkey James Nesmith’s office … where the guns were stored.

As they crossed the yard, Warden Dalrymple, on his way back from dinner, saw Murray. He hurried toward the turnkey’s office, then stopped short — two of Murray’s colleagues were between him and the office, both armed with shanks made from files. He turned and ran back to his residence to grab his shotgun.

Meanwhile, the convicts had made it to the turnkey’s shop and burst in. The plan had been to make Nesmith open the gun locker at knifepoint, but “Oregon” Jones, in a moment of enthusiasm, had broken the turnkey’s jaw with his fist and now he was out cold on the floor. So Ellsworth Kelley bashed in the door of the cabinet with a piece of furniture, and they all helped themselves.

Two of them then opened fire on the north guard tower, raking it with bullets. The guards in the tower shot back, but they were at a huge disadvantage; rifle bullets passed right through the tower walls, whereas the turnkey’s office was made of stone.

When the guns stopped speaking from the north tower, the men left the office and ran for it, clambering over the wall, and making for the outside.

As they did so, Warden Dalrymple arrived with his shotgun and sent both barrels after one of the fleeing forms. The runner was seen to waver, but it was a long-distance shot, and didn’t have enough stuff to stop him.

But then John Davidson, a wall guard, arrived on the scene with his rifle. With this he shot Bert “Oregon” Jones as he came off the wall, hitting him in the leg and immobilizing him. Jones waved the others on, and after that, he apparently shot himself in the head.

So then there were three, running through the twilight, making for the trees.

They ran directly to the Oregon State Hospital, or the Insane Asylum as it was then called, where they came into a significant spot of luck: A yellow taxi had just pulled up to pick up a patient who was being discharged.

Soon they were on their way in the commandeered cab. Behind them, they left the bodies of the North Tower guards, James Holman and J. Sweeney, with a third guard, Lute Savage, seriously wounded. As they fled, the other inmates in their cells whistled and shouted and rattled their bars in support.

The three survivors made their way to a farm just outside of New Era, where they threw themselves on the mercy of the farmer there, C.L. Newman. It’s not clear whether Newman was part of the New Era Spiritual Society commune at New Era, but he probably was, because he took a very Mount of Olives Discourse-inspired approach with the convicts, taking them in and feeding them and letting them rest peacefully. He didn’t report the convicts’ visit until well after they were on their way, which let him in for some bitter words from local officials. Newman, though, bluntly replied that he was not going to put his family’s safety at risk by taking sides in a quarrel that he saw himself as having no part in, between the state and the prisoners.

Eventually, though, the convicts did have to move on. So, after writing an account of the breakout in which they claimed “Oregon” Jones had done all the killing and pledged never to be taken alive, they left Newman’s farmstead, Eden, aiming to get far enough away to make a clean break.

Near the town of Bingen in southern Washington, Murray, the leader of the crew, wanted to go east; but Kelley and Willos thought north was a better option. So the gang split up.

Murray drifted into a trainyard in Centralia, where he started looking for a morally flexible drifter who might help him pull a holdup to get some traveling money.

He found one in Phillip Carson, a 26-year-old hobo from Portland … or so he thought. Carson paid to rent a cheap hotel room in which they could plan the job and told him he knew an experienced stick-up man who would help for a cut of the take. Then, Carson went to get his friend … from the local police station. One of the cops on duty, C.D. Pilling, quickly changed into civilian clothes and came back with him.

Soon, Carson was introducing Murray to Pilling, and a few minutes later Pilling and Murray had hatched a full plan to knock over a nearby roadhouse.

Then Carson and Pilling went out to hire a car, and returned with George Barner, the mayor of Centralia, behind the wheel of his own car.

Needless to say, Murray never made it to the roadhouse for the stick-up. Back he went to Salem in careful custody to face his reckoning.

But he never received it. On May 10, 1926, as it became increasingly clear that he was headed straight to the gallows, Murray hanged himself in his holding cell.

By that time, the other two were back in custody as well. Ellsworth Kelly and James Willos got off to a bad start on their own when sticking around Bingen to try to raise traveling money, they burgled E.G. Lewis’s general store. The haul was pitiful — about $18 — but they helped themselves to some of the merchandise as well. This, though, turned out to be a huge mistake, because they stole new shoes for themselves, and left the packaging behind … which is how police learned that whoever robbed the store wore the same size shoes as two of the escaped prisoners from Oregon ….

They then broke into the town marshal’s house, not realizing that he was still inside and asleep. Luckily for everyone involved, he did not wake up. They stole some money, tried and failed to steal the marshal’s car, and continued on their way. Farther down the road they found an Overland sedan, which they managed to start, and in which they fled.

But they wouldn’t get far in it. The next day, a posse of Multnomah County cops driving to Bingen saw a track of freshly smashed-down foliage leading off the highway through the brush into a deep canyon. Leaving their car on the road, the four of them stealthily followed the trail on foot to where the car was parked out of sight of the road, and both convicts were sitting on the ground in front of it with sandwiches in their hands. Their surprise was complete and they were back in Salem almost before Murray was.

In his suicide note, Murray tried to save the other two from the noose by claiming he had shot one guard, “Oregon” Jones had shot the other, and Kelley and Willos hadn’t even fired a gun. He needn’t have bothered. Under the law, when an illegal operation ends with innocent blood spilled, every member of the criminal conspiracy is considered just as responsible as every other member.

It took some time; convictions were appealed, and the Supreme Court even had to weigh in. But in the end, it was all for nothing, and finally, on April 20, 1928, both Ellsworth Kelley and James Willos were hanged.

The 1925 prison break had a big effect on the state prison. Warden Dalrymple, as mentioned before, had been given the job for political reasons, and he was paired up with J.V. Starrett as the state parole officer. Starrett was actually on the Ku Klux Klan’s payroll (he was a Kleagle or something like that) and had done a yeoman’s job getting out the “Klown vote” to elect Pierce as governor; the position of parole officer had been his reward.

But like a lot of people to whom membership in a gang of secret vigilante terrorists was appealing, Starrett was always hungry for more power and contemptuous of rules. By 1925 Starrett and Dalrymple were openly feuding and everyone at the prison, guards and prisoners alike, had learned how to play them off against each other.

That, of course, all came to a screeching halt after this bloody fiasco. Both Dalrymple and Starrett were given their walking papers, along with five guards who “retired early,” and the prison was taken over by Warden J.W. Lillie, former sheriff of Gilliam County. Order was restored, and the next time a disturbance broke out — a food-fight in the dining hall that escalated into a 200-man riot — Warden Lillie himself ran to the scene with a gun and fired over a dozen shots into the crowd, critically wounding at least one man.

The Oregon State Pen was always a pretty awful place. But under Lillie, it became, at least, a little more predictable and less dangerous to its neighbors.

(Sources: A Cycle of Crisis and Violence: The Oregon State Penitentiary, 1866-1968, a master’s thesis by Joseph Willard Laythe published in 1992 by Portland State University; archives of Roseburg News-Review and Oregon Statesman: March 1924, August 1925, May 1926, April 1927, April 1928; correspondence with Peter Bellant of Portland)

Finn J.D. John teaches at Oregon State University and writes about odd tidbits of Oregon history. His book, Heroes and Rascals of Old Oregon, was recently published by Ouragan House Publishers. To contact him or suggest a topic: [email protected].