Born in Macon, Missouri on November 4, 1891 Orlando Ward, at the age of 18, entered the United States Military Academy (USMA) at West Point, New York in 1909, graduating five years later (after being held back due to problems with the French curriculum) on June 12, 1914, shortly before the outbreak of World War I in Europe, as a second lieutenant in the Cavalry Branch of the United States Army. Among his fellow graduates included Frank W. Milburn, Jens A. Doe, Vicente Lim, Carl Andrew Spaatz, Ralph Royce, James L. Bradley, Brehon B. Somervell, Harry C. Ingles, Harold R. Bull and John B. Anderson who, like Ward, would all become general officers.