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Disrupted Diplomacy

Trump’s ambassador to the EU oscillated between focus and distraction.

Impeachment Hearing - Washington, DC
(Photo by Matt McClain/The Washington Post via Getty Images)

The Envoy: Mastering the Art of Diplomacy with Trump and the World by Gordon Sondland (2022, Bombardier Books), 272 pages.

Theodore Roosevelt famously lionized the “man in the arena” who endures blows and stays in the fight to shape public policy. Hotelier and businessman Gordon Sondland so eagerly wanted his turn in that arena that he literally paid a million dollars, delivered as a financial contribution to President Trump’s inauguration, to get himself in. By summer 2018, newly confirmed Ambassador Sondland was on a plane to Brussels to serve as Trump’s top envoy to the European Union.  


In his new book, The Envoy, Mastering the Art of Diplomacy with Trump and the World, Sondland has penned a chatty memoir that recounts not only his 18-month fast ride in government, but also shares an interesting life story, with lots of candor about his own foibles and personal misjudgments. Plainspoken and earthy, Sondland provides anecdotes on personal encounters with Trump and numerous senior officials, while also making worthy policy recommendations, most notably on how Washington can effectively retool the rusty U.S.-E.U. transatlantic alliance. 

Full disclosure: I served on Sondland’s senior staff at the U.S. Mission to the E.U., and while we were not personally close, I watched firsthand as the ambassador choreographed his unique diplomacy. The book is a fair enough retelling of what I observed in Brussels.

The author naturally desires to tell his side of the Ukraine story and the impeachment imbroglio that followed. Sondland expresses no remorse about jetting off to Kiev, although many American readers might wonder what the fuss was about Ukraine. Even before the Russian invasion, Ukraine commanded far more U.S. attention than was in our legitimate national interest. The dodgy facts that came out around the 2019 impeachment are further evidence that our country could use more foreign policy skepticism and caution.  

Trying desperately to arrange a meeting between Trump and Ukrainian President Zelensky, Sondland plunged into the Ukrainian morass, even though the president was uninterested and even scornful of that country. Sondland joined the line of Innocents Abroad trying to pick their way through Ukraine’s flimflam and corruption, which would burn Rudy Giuliani and reward Hunter Biden (at least until a new Congress starts an investigation).  

The Envoy is a remarkably candid book on the whole, but after recounting the story of the “Three Amigos” in Ukraine, the author ducks offering a real explanation for why he agreed to testify before Congress. Ambassador Sondland was a high-profile Trump partisan pulled into a dramatic political fight, but to justify his testimony, he glibly says his lawyers advised he had to respond to a Congressional subpoena.  


Other senior administration officials tied up in the same mess, such as Energy Secretary Rick Perry, on the advice of their lawyers, declined to participate in what was, after all, a partisan effort to discredit Trump. In fact, the White House actually tried to block Sondland’s testimony, about which the author has little to say.  

Sondland instead writes about letting the “truth” come out, but Adam Schiff’s Congressional hearing was all about politics, and the ambassador knew it. Without insights on what Sondland and Trump actually discussed, the reader is left to conclude that the ambassador wanted the limelight that testifying would bring. He mentions more about his un-reimbursed legal fees ($1.8 million), which Sondland believes Secretary Mike Pompeo promised the State Department he would pay, but never did. It seems only Sondland was surprised when Trump sacked him after the impeachment,

While Sondland generally criticizes his administration rivals lightly, he did not hold back when assessing John Bolton (“extremely insecure,” controlled by “ego” and “hubris”), Alexander Vindman (“Deep State” and “hatchet job”) and Fiona Hill (a “whiner” who could not “negotiate her way out of a paper bag”).  

None of that biting commentary surprises, nor does Sondland’s critique of President Trump: “His instincts were great. His execution was terrible.” But Sondland–a Bush Republican before joining the administration—holds a grudging respect for Trump’s aspirations to put relations with Europe on a transactional footing. “Trump was the first president who really took Europe to task in terms of what countries owe us,” Sondland explains. 

Indeed, the main value of the book is not that it offers yet another retelling of the Ukraine impeachment, but that Sondland shines a light on his efforts to push back against outdated practices in the U.S.-E.U. relationship, in which Washington, out of habit, accommodates Europe’s interests instead of adapting to new trade and national security realities.

Sondland argues convincingly that across a range of issues undergirding the transatlantic alliance, from defense-burden sharing, to market access imbalances, to energy policy and data privacy regulation, Europhile U.S. policymakers too often conceded to our European cousins. “We treat the E.U. as if they have some child-like innocence,” the author writes, “but in reality, the French and Germans and others are wicked smart, manipulative and self-interested.”  

Although Trump gave little advance consideration to Sondland’s nomination, the ambassador turned out to be a very good fit for the administration, at least in the initial stage when he concentrated on his core E.U. portfolio. Always looking to make a big splash, the brash Sondland threw himself into his diplomatic duties, plunging into a number of technical portfolios, while happily fencing with skeptical, even hostile, Europeans officials.  

It took Sondland’s thick skin and outsized ego to engage a city of Eurocrats more anti-Trump than even their counterparts back home. E.U. politicians, senior officials, diplomats, and virtually all elite opinion-makers considered Trump and his representatives to be an American plague unleashed on the old Continent.

For background, there are in fact three U.S. ambassadors in Brussels: one to Belgium, one to NATO, and one to the European Union (both NATO and the E.U. are headquartered in Brussels). Since the E.U. has become, for better or worse, a de facto supra-state for 27 European countries, its policy influence is enormous, with the major continental powers jockeying to forge Europe’s complicated priorities.  

Like no other diplomatic posting in Europe, the U.S. ambassador to the E.U. has the daunting task of advancing America’s interests in Brussels, where lobbying is opaquer and more multidimensional than even in Washington. Curiously, in his burning ambition to become a U.S. ambassador, Sondland appeared hazy on what a prize the E.U. assignment was (he was willing to take Luxembourg!), but he proved a quick study, determined to influence policy, and not be content with diplomatic ceremonies. 

Affable and approachable, Ambassador Sondland would reach out to any significant interlocutor, in Europe or America, and he gained a reputation as a formidable U.S. representative. Winning friends was harder, but mustering considerable charm, Sondland tried to balance being Trump’s outspoken envoy while also being a great admirer of Europe (he is the son of immigrant German-speaking Jewish parents, who knew the old continent before the war). 

The author makes a convincing case that political appointee ambassadors, committed to their policies and armed with strong people skills, are the most effective proponents for any administration that wants to advance its initiatives abroad. Indeed, no career Foreign Service Officer could have matched Sondland’s commitment to advancing Trump’s approach to Europe.  

Sondland prodded reluctant U.S. career diplomats to do things differently, but while skeptical of State Department’s bureaucratic ways (he particularly scorned cable writing), he treated staff fairly and was often even personally generous (for example, paying the costs of an embassy coffee shop out of his own pocket). He did take a certain mischievous glee in upending stuffy diplomatic practices, but his efforts were calculated to move an agenda forward. He never hesitated to question business-as-usual activities.

For example, Sondland convinced Trump to nix the State Department’s long-standing plans to construct a massive and expensive new Mission compound on the far outskirts of Brussels. He also blew past protocol to bring senior European and Trump officials together (with mixed results but impressive effort). He threw out plans for a modest U.S. national day event, instead organizing a massive celebration that brought comedian Jay Leno and his Vegas monologue to Brussels.  

Leno’s humor was largely lost in translation, and the dubious celebration began Sondland’s unwise courtship of Ukrainian President Zelensky (also a comedian and in attendance at the event), which would eventually all crash and end in Trump’s first impeachment. The ambassador should have stayed focused on his core U.S.-E.U. portfolio, as his real mission—modernizing the transatlantic alliance—has yet to be achieved.