Lieutenant Milford Trail died of a heart attack following a struggle with a suspect.

On January 26, 1965, Detective Lieutenant Trail and Captain Charles Webster went to pick up a juvenile who had escaped from the state training school for boys in Boonville just after 1 pm. The boy was booked at 1:40 pm after a scuffle which lasted several minutes.

Lieutenant Trail became ill after returning to the police station and was rushed to a doctor's office. He was later taken by ambulance to the hospital, where he was pronounced dead at 2:20 p.m.

Lieutenant Trail joined the police department on April 1, 1943. He was survived by his wife, Margaret. Interred: New Hope Cemetery, Elsberry, MO.