The four convicts prepared for their escape by cutting a hole through the roof over the north wing of the cell house. Later, when the cell doors
opened to allow inmates to march to the mess hall for the evening meal,
the four instead climbed to the top of the cell block. They went through the roof and walked above the main office where they fastened a rope and climbed down a brick wall to the front of the administration building. During this time they remained completely hidden from the view of all guard towers. The group ran to the turnkey's office which held an arsenal of all guns not in use by guards.
The violence began when the four surprised the arsenal guards, captured the arsenal and took all of the guns and ammunition they thought they would need for the escape. The convicts began to fire at the guards at posts one and seven who returned fire. Guard John Sweeney was shot through the head and killed instantly on post one. Guard J.M. Holman suffered a wound while on post one and was moved by another guard to the west outside of the base of the post. Guard John Davison, who had already fought with the convicts in the turnkey's office, rushed to tower one and armed himself for an opportunity to fire on the four who had taken cover.
The convicts then succeeded in capturing post one. They jumped to the ground outside of the west wall where they immediately shot and killed Guard Holman. The misfortunate Holman had been sitting on the ground suffering from wound he had already received. From his position of advantage in tower one, Guard Davison shot Bert "Oregon" Jones, the leader of the outlaws, through the hip as he jumped to the ground. According to statements made by guards and later accounts from the escaped convicts, Jones then shot himself in the head. Convict Thomas Murray was also wounded in the arm and hand during the escape. Guard Lute Savage was shot just below the heart by one of the convicts as he approached tower one from the west. Another guard, James Nesmith, was overpowered by the convicts and suffered numerous injuries including a broken jaw.
Guard Davison continued to fire on the remaining three escapees as they ran to the nearby Oregon State Hospital. The group managed to commandeer a vehicle and sped out of Salem in the darkness. They drove to a thickly wooded area near Silverton.
Posses numbering more than 150 men combed the countryside for the escapees. Governor Walter Pierce was quoted in the newspapers as saying "While I have no longing to see men hung, I would be pleased to come out here and witness the execution of these fellows if they are caught." Former Governor Oswald West was quoted in several Portland newspapers criticizing Governor Pierce and Warden A.M. Dalrymple. He blamed them for poor security at the penitentiary and mismanaging the search for the convicts. At one point he was reported to have issued a challenge to the governor and warden to join him in the search for the escapees.
Kelley, Willos and Murray eluded posses for more than 10 days. Kelley and Willos were captured together near Goldendale, Washington. Murray was captured in Centralia, Washington and returned to Salem. Newspapers portrayed him as a dangerous criminal and the ring leader of the escaped men. Bert "Oregon" Jones' body was transferred to a local funeral home awaiting transfer to his home town of Grants Pass. Newspapers reported approximately 7000 curiosity-seekers came to view his body.