He was attached to the battleship USS New Mexico two months later and participated in the patrol cruises with the Pacific Fleet before he was ordered to Naval Air Station Pensacola, Florida for flight training in September 1929.

He served as test and transport pilot for government officials and also held additional duty as Naval Aide to President Franklin D. Roosevelt at the White House.

[5][1] He subsequently returned to Washington, D.C. and was attached Bureau of Aeronautics, where he headed Plans Division consecutively under rear admirals John S. McCain Sr. and DeWitt C. Ramsey and received Navy Commendation Medal for his service.

Riley was ordered to Pearl Harbor, Hawaii in early January 1945 and assumed command of escort carrier USS Makassar Strait.

He was transferred to the staff, Commander First Carrier Task Force under Vice Admiral Frederick C. Sherman as operations officer by the end of July 1945.

[8][5][1] Following the War, Riley was attached to the staff of Joint Army-Navy Task Force One under Vice admiral William H. P. Blandy as Deputy Air Commander and took part in the Operation Crossroads, nuclear weapon tests at Bikini Atoll in mid-1946.

He was subsequently ordered to Washington, D.C., where he joined the Strategic Plans Section in the office of the Chief of Naval Operations under Admiral Louis E. Denfeld.

He sailed for a tour of duty in the Mediterranean in April 1953 and visited Spain, and took part in the NATO Exercise Black Wave with Deputy Secretary of Defense R. M. Kyes on board as an observer.

Riley served in this capacity during the Cuban Missile Crisis in October 1962 and received Navy Distinguished Service Medal at his retirement on February 28, 1964.