Chief Boatswain's Mate Shepherd served aboard the destroyer USS Brush (DD-745) in Korean waters. He was listed as Missing in Action when his ship struck an enemy mine near Tanchon, North Korea on 26 September 1950. He was presumed dead on 27 September 1951.

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