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Diggins then enlisted in the Aviation Section, Signal Corps, U.S. Army and was first stationed at Rich Field, Waco, Texas, where he completed a course of flight training as a Military Aviator, then took training in night bombing at Ellington Field, Houston, Texas until January, 1918. At that time he was commissioned and assigned to the 92nd Squadron, American Expeditionary Forces stationed at Littlehampton, England to fly missions over the English Channel for the protection of Britain against German Zeppelin airship raids. On June 19, 1912 Diggins was granted F.A.I. Pilot License No. 1739 while in England. 

After World War I Diggins returned to Chicago where he founded and became President of the Diggins Aviation Company and School of Aeronautics. He quickly developed this into a sizable business, employing several instructors and using war surplus training planes at Midway Field. This school was in operation until mid 1923, during which time about 400 students were graduated. Many of them went on to become prominent in the aviation industry.

During this period Diggins also pioneered in putting the airplane to work in overall useful ways and was credited with making the first air-express flight, from New York to Chicago, in May 1921. In this type of activity he made numerous flights to distant cities carrying special air express and light freight shipments. He also ferried many notable passengers on business flying trips and did considerable aerial photographic work in the Chicago area. 

In 1923 Diggins sold the business to Yackoy Aircraft Company of Forest Park, Illinois. From 1923 to 1925 he was Sales Manager of the Morcantille Finance Corporation of Los Angeles, California, then in 1925 he joined Western Air Express where he remained until 1927. At that time he became Traffic Manager for Transcontinental Air Transport and served in that capacity until T.A.T. merged with Western Air Express in 1931 to form T.W.A. He then went into business for himself at Los Angeles. 

Diggins returned to his former home town, Harvard, Illinois, in 1934, and about 1937 retired to a dairy farm nearby where he made his home until he passed away at the Harvard Community Hospital on May 13, 1959, at age 72. He was survived by his wife. He was a co-organizer of the National Aeronautic Association and a member of the Early Bird, the Professional Pilots Association, and the 

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