The Regularity of Irregular Diplomacy
LARRY M. ELKIN, CPA, CFP®

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Larry Elkin, Certified Financial Planner (CFP®), CPA, is president of Palisades Hudson Financial Group.

If there is a “regularity” spectrum for special presidential envoys to foreign nations, I’d guess former President Jimmy Carter sits near one end and former basketball player Dennis Rodman near the other. Rudy Giuliani can go wherever you would like to put him between the two.

One thing is certain about Giuliani’s representation of President Trump’s positions on Ukraine: What some State Department employees consider his “irregular” diplomatic channel occurs so regularly in American diplomacy that its occasional absence is more irregular than its presence.

Franklin D. Roosevelt used Harry Hopkins, a social worker by training and former commerce secretary, as his chief interlocutor with the United Kingdom’s wartime government. This choice bypassed Joseph P. Kennedy (father of the future president), who was ambassador to the Court of St. James at the time. Hopkins was an advocate of arming Britain to resist Nazi aggression, while Kennedy was isolationist and openly anti-Semitic. After helping Roosevelt secure the Irish-Catholic vote to win a third term in 1940, Kennedy returned home to the United States. Hopkins continued his informal liaison to London through the war’s end. Even after Roosevelt’s death, while Hopkins was fighting the stomach cancer that shortly would cause his own death, President Harry Truman sent him on a final mission to Moscow.

Rudy Giuliani. Photo by Gage Skidmore; courtesy of Flickr.

President Richard Nixon had an experienced Washington hand, William P. Rogers, as his secretary of state. But Nixon sidelined Rogers in favor of the academic Henry Kissinger, who was Nixon’s national security adviser before eventually replacing Rogers. Kissinger negotiated the American withdrawal from Vietnam, spearheaded the diplomatic opening to China and laid the groundwork for the first Strategic Arms Limitation Treaty (SALT I) with the Soviet Union, all while Rogers headed the State Department.

Carter was an unusually hands-on president. But he still turned to a former Democratic National Committee chairman, Robert S. Strauss, to serve as his special envoy to the Middle East. Later, in a display of bipartisanship hard to imagine today, Strauss served as the last U.S. ambassador to the Soviet Union and the first to the newly reconstituted Russia under President George H.W. Bush.

Carter himself has undertaken many diplomatic missions, formal and otherwise, in an extended post-presidential career. Some, such as an ostensibly private mission to North Korea in 1994, were actually done at the behest of the U.S. government; President Bill Clinton secretly recruited Carter for the 1994 journey. Carter undertook other missions on his own, or on behalf of his Carter Center. Carter made himself such a fixture on the world stage that even when he criticizes his own country’s policies, he is hardly seen as doing anything “irregular.”

Neither of the Bush presidents were big fans of going around the State Department and its “regular” channels. Between the two Bush administrations, however, Clinton made frequent use of such impromptu representatives. Besides Carter, one of note was Richard Holbrooke, who brokered an end to hostilities in the former Yugoslavia. And within three years of taking office, President Barack Obama had no fewer than 24 special envoys attending to matters in all corners of the globe, while Hillary Clinton was nominally in charge of diplomacy as his secretary of state.

North Korea is one place where a lot of stuff has been thrown at the diplomatic wall surrounding the isolated state in hopes something might stick. Clinton used former congressman and future New Mexico Gov. Bill Richardson as a special emissary to Pyongyang. Richardson reprised the role two decades later on behalf of the Obama administration. Somewhat less regularly, flamboyant hoops star Rodman also visited North Korea on goodwill missions during both the Obama and Trump administrations, though neither Rodman nor the government have acknowledged any official coordination.

Presidents,  in short, can choose whomever they like to represent them to practically any nation, on practically any subject, at practically any time. Most do. Sometimes they choose people with experience, training or connections that make them better suited to a task than the “regular” diplomatic channels that run through U.S. embassies (in those nations where we have embassies at all). Sometimes presidents use an “irregular” option because they have greater trust in an individual outside the government to represent the president’s own views and promote his agenda.

Giuliani is a former high-ranking Justice Department official; a prosecutor who addressed corruption in government, labor and Wall Street; and a two-term mayor of New York City and former presidential candidate. He is hardly an odd choice as White House liaison to a newly inaugurated president in Kyiv. All this is quite apart from whether one believes there was anything untoward in Giuliani’s advocacy of investigations that would have touched on Democratic presidential hopeful Joe Biden and his son Hunter, who took a lucrative sinecure on the board of a Ukrainian gas company during and after Biden’s term as vice president.

At the House Intelligence Committee impeachment hearings, where Giuliani’s efforts were a major point of discussion, some State Department officers sniffed that there was something “irregular” about his back-channel diplomacy in place of that of the ambassador, Marie Yovanovitch, an Obama holdover whom Trump ultimately recalled. It is hardly surprising that the Foreign Service careerists resent such intrusion on their bureaucratic turf. More than once during the hearings, the witnesses gave the impression that they view the president as an instrument to conduct their foreign policy, rather than the other way around.

I find it hard to see why a diplomatic tool used so regularly even qualifies as irregular anymore. One can reasonably argue that Giuliani’s role as Trump’s personal attorney created real or potential conflicts between the president’s personal interests and those of the United States. Such conflicts might even have made it advisable for the president to choose someone else to convey his messages to Ukraine’s leadership. But this is also a president who has little reason to trust the bureaucracy he inherited, which has made abundantly clear that it does not trust him in return. By going around regular diplomatic channels, Trump was – arguably for a change – doing what most of his modern predecessors have done.

Looking Ahead: Life, Family, Wealth and Business After 55

Larry M. Elkin is the founder and president of Palisades Hudson, and is based out of Palisades Hudson’s Fort Lauderdale, Florida headquarters. He wrote several of the chapters in the firm’s book, Looking Ahead: Life, Family, Wealth and Business After 55. His contributions include Chapter 1, “Looking Ahead When Youth Is Behind Us” and Chapter 4, “The Family Business.”

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LARRY M. ELKIN, CPA, CFP®

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