Rudolph Giuliani didn’t hide the fact that he was investigating whether Ukraine interfered in the 2016 U.S. presidential race. Yet most media have treated Giuliani’s efforts as sneaky and suspect because he acted at the personal behest of the president and not as an official representative of the bureaucracy. The New York Times, for example, claimed Giuliani was conducting “a shadow foreign policy campaign.”
In fact, presidents since George Washington have turned to individuals without formal government positions to pursue foreign policy interests and objectives. Private citizens, often acting as special envoys, have helped negotiate issues ranging from trade to war. While critics deride such efforts as “back-door,” “secret,” or “shadow” undertakings, many presidents have found it useful to dispatch people they trust, who can think and operate outside the constraints of official channels in handling delicate matters.
Personal envoys who aren’t official diplomats have always rankled the State Department, which sees itself as holding a monopoly on forming foreign policy and negotiating to secure American interests (even if its workings aren't completely transparent, as with Secretary of State Hillary Clinton's private email setup, to take a recent notable example). Foggy Bottom doesn’t view its role as simply fulfilling the president’s druthers, which can be frustrating for a president. So it’s no surprise that President Trump might feel the need to do an end-run around State, a department he trusts perhaps even less than it trusts him.
Giuliani’s freelancing has been characterized by many Republicans as an effort to get at the truth. Democrats and most media describe his actions differently – as “unlawfully wielding political influence,” a blatant conflict of multiple interests, representing not only the president but also “clients with cases to plead before the Justice Department.”
Whether such conflicts are unlawful will perhaps be sorted out. But potential conflicts are a standard hazard of freelance diplomacy. An example that is both typical and extreme: In February 1978, President Carter sent not just a private envoy to Cuba but one who had significant personal business interests in normalizing relations between Washington and Havana. The unofficial diplomat was Carter’s old Georgia friend and booster, J. Paul Austin, the CEO of Coca-Cola.
According to “Back Channel to Cuba” by William LeoGrande and Peter Kornbluh, Austin had already been to Havana in the summer of 1977 where he “met with Fidel Castro to discuss the possibility of opening a Coca-Cola bottling plant in Cuba” – a literal instance of what was jokingly called “Coca-Cola diplomacy.”
Carter used Austin in part because official government entities were busy trying to further their own policy agendas instead of promoting the president’s goals. “I asked Paul to go down as my emissary,” Carter said to LeoGrande and Kornbluh. “I felt that this would be a good way for me to have a direct assessment of what Castro’s commitment was.”
Austin overdid it. He proposed to Castro not only a summit in the United States but that the Cuban dictator come join the Carters for Christmas in Plains. A Carter-Castro Christmas never came off, and the affair left official officials rolling their eyes. “It was a good lesson not to rely on non-professionally trained people to conduct private negotiations,” recounted Carter’s national security adviser, Zbigniew Brzezinski, “because there was a real disconnect between what the guy was sent to talk about and what he came back with.”