[1] Born in Dallas, Texas, Oakley graduated in 1948 from Connecticut's South Kent School and spent four years as an Intelligence Officer in the US Navy.

He again joined the National Security Council Staff on January 1, 1987, as Assistant to the President for Middle East and South Asia.

[3] However, he also took office at a time when U.S.-Pakistan relations were becoming strained over the Pakistani nuclear weapons program, which Oakley believed was being used to force concessions from the United States, and a cut-off in U.S. aid to Pakistan because of the invocation of the Pressler Amendment.

In December 1992, he was named by President George H. W. Bush as Special Envoy for Somalia, serving there with Operation Restore Hope until March 1993.

In 2000, Oakley claimed in an interview with the Washington Post that the Clinton administrations "obsession with Osama" was making Bin Laden stronger.

[6] In Cairo, during June 1958, Oakley married fellow Foreign Service Officer Phyllis Elliott who, under then-prevailing rules, was obliged to resign.