[1] Oakes is an engineer by training (at one point in the series, he is hired by an architectural firm), and Anthony Trust, ahead of Black at both Greyburn and Yale, recruits him for the Central Intelligence Agency in his senior year, 1951.
Blackford's missions with the CIA involve various top-secret Cold War enterprises arranged by the Agency's highest ranking individuals and American presidents alike.
Oakes' personal life is somewhat hectic because of his constant globetrotting for the Agency, as he can never seem to find ample time to settle down with Sally, who yearns for the day when Blackford will retire from the CIA.
Their respective worldviews are quite dissimilar, Oakes being conservative, and Sally, a liberal feminist who studied and teaches Jane Austen and admires Adlai Stevenson.
While always holding Sally close to his heart, Oakes still finds plenty of time to pursue romantic conquests across the globe, often mixing work with pleasure.