Deputy Sheriff Clarence Woolman was shot and killed by a prisoner in the Kirkwood Hotel, at 400 Walnut Street, in Des Moines, Iowa.

He was transporting the prisoner to the State Hospital for Inebriates, in Knoxville, and had stopped in Des Moines for the night. As Deputy Woolman slept in a hotel bedroom his prisoner took his gun from his pocket and shot him three times. The prisoner then walked to a saloon at 3rd and Court Avenue and shot and killed the bartender.

The prisoner was the former police surgeon for the Council Bluffs Police Department.

The man was found not guilty by reason of insanity and sent to a mental hospital. On January 9th, 1915, he was declared sane and released.

Deputy Woolman had served with the Pottawattamie County Sheriff’s Office for seven years. He was survived by his wife and five children.