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Almost nothing is known about his military career, except for his most famous flight, which was when he and Lt. John A. Macready flew the 1st non-stop cross-country flight.
He won the prestiguous Mackay Trophy 2 years in a row in 1922 and 1923, both times with Lt. Macready.
He served in the USAF and 5 of its 6 predecessors!
(In lower photo, he is on the right, Macready is on the left.)
His DFC citation:
Awarded for actions during Peace Time Awards
The President of the United States of America, authorized by Act of Congress, July 2, 1926, takes pleasure in presenting the Distinguished Flying Cross to First Lieutenant (Air Service) Oakley G. Kelly, U.S. Army Air Service, for extraordinary achievement while participating in an aerial flight. Lieutenant Kelly, with First Lieutenant John A. MaCready, departed from Michel Field, Long Island, New York at 12:36 p.m. on 2 May 1923 in the Army transport Airplane T-2, on a nonstop transcontinental flight. They encountered practically every hazard of flying and displayed remarkable ingenuity, skill, and perseverance in over coming the many handicaps imposed upon them by the elements and the mechanical equipment used by them. They arrived at Rockwell Field, Coronado, California. At 12:26 p.m. on 3 May 1923, thus successfully completing the first transcontinental nonstop flight in the history of aviation.
General Orders: War Department, General Orders No. 4 (1928)
Action Date: May 2 - 3, 1923
Service: Army Air Forces
Rank: First Lieutenant