Before he reached age 30, T. Ross Milton led vast armadas of American heavy aircraft on some of World War II's most famous bombing missions. Born in 1915 at Schofield Barracks, Hawaii, this future combat leader grew up in an army family. A colonel's son, he enlisted in the regular army in 1934 and later was appointed to the U.S. Military Academy at West Point. Graduating in 1940, Milton entered flying training and then earned his pilot's wings in 1941. In the spring of 1943, after flying the Consolidated LB-30 Liberator (B-24) on submarine hunting patrols from Langley Field, Virginia, he went to England as the operations officer of Eighth Air Force's 351st Bombardment Group (BG).
Flying the Boeing B-17 Flying Fortress, he gained experience running the gauntlet of Axis flak and fighters, and in June became Deputy Commander, 91st BG. On 12 August 1943, he led 22 B-17s of his group against a German refinery at Gelsenkirchen. On 12 October, after confusion over the English Channel, Milton took lead of a force of 291 B-17s that, in two waves, dropped more than 2,800 bombs on industry in Schweinfurt. Deep in Germany without fighter escort, 60 B-17s were lost and over 600 airmen were killed, wounded or missing-in-action. On 6 April 1944, Milton led 730 B- 17s and B-24s on the historic, first successful daylight raid on Berlin.
He ended the war as Commander, 384th BG. Following the war, Milton went on to serve as Chief of Staff, Combined Airlift Task Force during the Berlin Airlift. Later he served as Director of Operations of the newly created Military Air Transport Service, and then was appointed Executive Assistant to the Secretary of the Air Force. From 1958 to 1965, Milton served in the Pacific. As a brigadier general, he commanded the 41st Air Division in Japan, and then as a major general, led Thirteenth Air Force from the Philippines. In 1963, he became Deputy Chief of Staff, Plans and Operations, Pacific Command, and then in 1965, moved to Tactical Air Command as Chief of Staff.
Promoted again in 1967, Milton served for 6 months as USAF Comptroller. He crossed the Atlantic to Belgium in 1969 for duty as Deputy Chairman, NATO Military Committee. Later, promoted to general, he became the US representative to the committee. Retired in 1974 from an illustrious career that spanned nearly 40 years, General Milton received many awards and decorations including the Purple Heart, Silver Star, Distinguished Flying Cross with three oak leaf clusters, and from allies; the British Distinguished Flying Cross and the French Croix de Guerre. Milton's name is well known today as author of numerous articles in Air Force magazine and other journals.
In the Mighty Eighth War Diary, the noted British aviation historian, Roger A. Freeman, writes "in the great 1943-44 air battles between the Luftwaffe and the Fortresses there was one air leader who time and time again was fated to be in the van. The resilience of Theodore 'Ross' Milton was remarkable... every time he led the Wing, he would inevitably wind up in the front position... "Whether enroute to Schweinfurt in October 1944, or to Oschersledben in January 1944, when faced with determined fighter attacks, Freeman notes, "the Wing nevertheless ploughed through and bombed the target..."