Soundman First Class Middleton was a veteran of World War II, serving submarine duty in the Pacific. During the Korean war, he was a member of the Destroyer USS Ernest G. Small. He was Killed in Action when his ship struck an enemy mine near Hungnam, North Korea on 7 October 1951.

Middleton was awarded the Purple Heart, the Combat Action Ribbon, the Korean Service Medal, the United Nations Service Medal, the National Defense Service Medal, the Korean Presidential Unit Citation and the Republic of Korea War Service Medal.