Wilson enlisted in the Maryland National Guard as a private in 1916 and served with it on the Mexican border and the Western Front during World War I before transferring to the United States Army Air Service.

Wilson became a leading theorist who embraced the doctrine that strategic bombing was the most important aspect of air power.

The doctrine which Wilson expounded later became the basis for AWPD-1, the Army Air Forces' strategic war plan developed in 1941.

In February 1945, Wilson was present at the Battle of Iwo Jima as an official Army Air Forces observer.

After the war, Wilson served as a member of the Gerow Board, which examined the military educational system and instituted a series of long-lasting reforms.

It was based at Eagle Pass, Texas, and, like most National Guard units, supported but did not directly participate in the Pancho Villa Expedition, although it did occasionally cross the border into Mexico.

[13] In France, Wilson once again applied for training as an aerial observer, in response to an appeal from American Expeditionary Forces (AEF) headquarters.

[16] He was assigned to the 186th Aero Squadron at Weißenthurm (Weissenthurm) in May 1919,[17] returned to the United States in July, and was discharged from the Army on 15 August 1919.

[2] Wilson married Edna Taggert, the older sister of the wife of his best friend in Anniston, in a ceremony in her home in Pittsburgh.

[2] On return to the United States in 1929, Wilson was posted to the Air Corps Tactical School at Langley Field, Virginia as an instructor.

However, Wilson rejected those parts of Douhet's doctrine that called for mass bombing of cities to break the morale of the enemy.

[26] The formulators of industrial web theory were relatively young junior officers, nearly all of them former reservists commissioned during or immediately after World War I.

They viewed war in the abstract and admitted that they had no conclusive proof of their theories,[27] but firmly believed that air power would dominate future warfare, after certain technological limitations had been overcome.

Wilson was one of the nine key advocates, all instructors at the Tactical School, who became known as the "Bomber Mafia": Wilson, Walker, Major Odas Moon (who died in 1937), and future generals Haywood S. Hansell, Laurence Kuter, Muir Fairchild, Robert Olds, Robert M. Webster, and Harold L.

[28] They espoused the doctrine in testimony to the Howell Commission on Federal Aviation in 1934,[25] where it was used as an argument supporting the creation of an independent air force.

[30] Wilson accepted the argument, most forcibly advanced by fellow instructor Kenneth Walker, that fighter aircraft did not have the range or speed to accompany bombers and probably could not shoot them down.

[32] He considered the course to be a waste of time, "devoted in large part to the minutiae of ground officers' duties" and "devoid of serious recognition of the airplane as an instrument of war.

Kenney had specifically requested General Henry Arnold to send Wilson to replace his chief of staff, Air Vice Marshal William Bostock, an RAAF officer.

[41] Wilson took the long way back, visiting the other war theatres in India, China, the Middle East, Italy and England.

[43] In February 1945, Wilson was present at the Battle of Iwo Jima as an official Army Air Forces observer.

Discharged on the grounds of disability with the rank of major general, he retired to Carmel, California,[50] where he wrote and published his memoirs, entitled Wooing Peponi, in 1973.