Major Whitehead was a member of Headquarters and Headquarters Battery, 82nd Anti-Aircraft Artillery (Automatic Weapons) Battalion, 2nd Infantry Division. He was wounded while fighting the enemy near Kunu-ri, North Korea, on 1 December 1950 and taken prisoner. He died on 10 January 1951 from his wounds, malnutrition and dysentery. His remains were not recovered. His name is inscribed on the Courts of the Missing at the Honolulu Memorial.

For his leadership and valor, Major Whitehead was awarded the Bronze Star Medal, the Purple Heart with Oak Leaf Cluster, 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.