Deputy Woolman was shot and killed Saturday, March 25, 1911, by a prisoner in Des Moines, Iowa. Deputy Woolman was transporting the prisoner to the Inorbriate Hospital in Knoxville, Iowa 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 suspect was found not guilty by reason of insanity and sent to a mental hospital. On January 9, 1915, he was declared sane and released.

Deputy Woolman was survived by his wife and five children.

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