Robert Ivey began his military career in 1938 when newly-elected Congressman Lyndon Baines Johnson gave his first appointment to Navy Service Academy to Henry Ivey in thanks for campaign assistance in the election. Transferring to West Point, he graduated from the U.S. Military Academy at West Point, Class of 1942. After World War II selected as one of the first officers to be sent to law school at Army expense and graduated from University of Virginia Law School and served in various legal assignments until selected to become personal legal advisor to General W. C. Westmoreland, with whom he served six years culminating in his selection as the senior military advisor to the joint Allied and U.S. Headquarters in Vietnam. He retired in 1972 as a U.S. Army Colonel.