Department of State
Oakley joined the Foreign Service in 1957 and was assigned to Khartoum, Sudan, in 1958. He first served in the Office of United Nations Political Affairs, Department of State, and later served in American Embassies in Abidjan, Ivory Coast, Saigon, Vietnam, Paris, France, and Beirut, Lebanon. He also served at the U.S. Mission to the United Nations, and as Senior Director for Middle East and South Asia on the staff of the National Security Council.
In February 1977, he became Deputy to the Assistant Secretary of State for East Asia and Pacific Affairs. He later became U.S. Ambassador to Zaire in November 1979, and U.S. Ambassador to Somalia in August 1982. In September 1984, he was appointed Director of the State Department Office of Combating Terrorism. He again joined the National Security Council Staff on January 1, 1987, as Assistant to the President for Middle East and South Asia. He was named as U.S. Ambassador to Pakistan in August 1988, succeeding the late Arnold Lewis Raphel, who was killed in an airplane crash along with Pakistan's President, Muhammad Zia-ul-Haq.
Oakley retired from the Foreign Service in September 1991, after 34 years. After retirement, he became associated with the United States Institute of Peace. 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 October 1993, he was again named as Special Envoy for Somalia by President Bill Clinton, and served in this capacity until March 1994. In January 1995, he joined the Institute for National Strategic Studies at the National Defense University. In 2000, prior to the September 11 attacks, Paul Bremer characterized the Clinton administration as "correctly focused on bin Laden", while Robert Oakley criticized their "obsession with Osama".
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