Detective Woolsey was shot and killed by a suspect who attempted to rob him. Detective Woolsey was headed home around 6:00 pm and stopped to speak to a woman on the Third Street viaduct. He noticed a man and a boy approaching them. As the man passed he stuck a gun in Woolsey's abdomen as the boy went through their pockets. Detective Woolsey drew his gun on the man but his the hammer fell on a bad round. The suspect fired shooting Detective Woolsey in the abdomen. Detective Woolsey fired again striking the suspect in the head and in the shoulder. Detective Woolsey fell to the ground firing at the boy as he ran away. Detective Woolsey died a few minutes later. The suspect, Walter R. Warren, also died from his wounds. The 17 year-old suspect, Charles "Chubb" Hardin, was apprehended the following day. On December 13th, Hardin was sentenced to twenty years for second degree murder for his part in the killing of Detective Woolsey. The charge was reduced from first degree murder to second degree murder and Hardin immediately entered his plea of guilty.

Detective Woolsey was a seven-year veteran of the Joplin Police Department. He was promoted to detective on October 11, was shot three days later, and just returned to work a week before he was killed. Detective Woolsey was survived by his wife. Interred: Forest Park Cemetery.