Raised in South Carolina,[2] Robertson graduated from the United States Air Force Academy in 1968. During his 33-year career he has held a variety of operational and staff positions, including command at the squadron, wing and numbered air force levels. In previous assignments he served as director, personnel plans, Headquarters United States Air Force; vice director, the Joint Staff, Joint Chiefs of Staff; vice commander, Air Mobility Command, and commander, Fifteenth Air Force. A command pilot, he has logged 4,700 hours in airlift, tanker and bomber aircraft, including 150 combat missions as a gunship pilot in Vietnam. Robertson retired on December 1, 2001.
August 1968 – August 1969, student, undergraduate pilot training, 3550th Student Squadron, Moody Air Force Base, Georgia
April 1970 – April 1971, AC-119K gunship pilot, 18th Special Operations Squadron, Da Nang Air Base, South Vietnam
May 1971 – June 1974, B-52H co-pilot, aircraft commander, instructor pilot and flight examiner, 17th Bombardment Wing, Wright-Patterson Air Force Base, Ohio
October 1975 – August 1977, aide and executive officer to the vice commander in chief, Headquarters Strategic Air Command, Offutt Air Force Base, Nebraska
August 1977 – March 1980, FB-111A commander, flight commander and assistant operations officer, 528th Bomb Squadron, Plattsburgh Air Force Base, New York
March 1980 – May 1982, plans and programming officer, Strategic Forces Division, Directorate of Programs and Evaluation, Deputy Chief of Staff for Programs and Resources, Headquarters U.S. Air Force, the Pentagon, Washington, D.C.
May 1982 – June 1984, FB-111A commander, 529th Bomb Squadron, later, assistant deputy commander for maintenance, 380th Bombardment Wing, Plattsburgh Air Force Base, New York
June 1984 – July 1985, student, National War College, Fort Lesley J. McNair, Washington, D.C.
July 1985 – June 1986, executive officer to the Air Force vice chief of staff, Headquarters U.S. Air Force, the Pentagon, Washington, D.C.
June 1986 – July 1987, assistant for general officer matters, Deputy Chief of Staff, Personnel, Headquarters U.S. Air Force, Washington, D.C.
August 1998 – December 2001, commander in chief, United States Transportation Command, and commander, Air Mobility Command, Scott Air Force Base, Illinois