From 2017 to 2021, a string of businessmen with long, lucrative careers entered government service and left with their reputations tarnished. Rex Tillerson was a world-bestriding CEO who found himself hated by both his new boss and his new employees. Steven Mnuchin, a successful though largely anonymous moneyman, developed an image as a sloppy supervillain. President Donald Trump was arguably the paragon of the class, transforming himself from a famous personality to an infamous threat to democracy.
Gordon Sondland was one of the lower-profile but stranger examples. In 2015, he was a prospering hotelier and GOP donor in Portland. Initially a Jeb Bush supporter, he later backed the Trump campaign but bowed out amid controversies in summer 2016. When Trump won, he got back into the president-elect’s good graces with the help of a $1 million check to the inaugural committee, and in 2018 he snagged the U.S. ambassadorship to the European Union. In October 2019, compelled to appear in Trump’s first impeachment, he testified that Trump sought a “quid pro quo” in return for a White House meeting with Ukrainian President Volodymyr Zelensky. Sondland was variously portrayed as a hero, a traitor to Trumpism, or a Chauncey Gardner–like walk-on to the scandal, and the Latin phrase came to define his public image. He was fired in February 2020, two days after the impeachment ended without a Senate conviction.
Sondland reflected on the impeachment recently. “This was just a freak thing that happened, and I’m trying to use whatever notoriety I have to help advance some things that are important to me,” Sondland told me, explaining the motivation behind his new book, The Envoy: Mastering the Art of Diplomacy With Trump and the World. But the book is more interesting than the average reputation-burnishing political memoir, thanks in part to the same unvarnished tone that Sondland displayed in his testimony, but also because he is not always the most self-aware narrator. His subtitle ascribes mastery to a 19-month stint as a political appointee, and he criticizes Foreign Service officers for doing the job for the lifestyle while cheerfully admitting he wanted to be an ambassador for the lifestyle. He puzzlingly praises Trump’s “candor” when he really seems to mean brusqueness.
The world is awash in books about Trump. Many of them are either seeking to curry favor with the former president or profit off his followers or simply seeking to settle personal scores. Many more are straightforwardly critical of Trump. But Sondland is neither a full-on apostate nor a true believer, and his account is unusual for someone with direct experience with Trump who doesn’t just have an ax to grind.
Our conversation has been edited and condensed for clarity.
David Graham: You give Trump credit where you think it is due and criticize where you think he deserves it. Broadly, did you respect Donald Trump when you started supporting his campaign in 2016?
Gordon Sondland: Did I respect him?
Graham: Yeah.
Sondland: I want to make sure I understand your question. Was the question, “Does Gordon Sondland respect President Trump?”
Graham: When he was running, many Republicans were skeptical of him, and many business leaders seemed dubious. You were a Jeb Bush backer early in the race. What was your view at the outset?
Sondland: My initial view of him was [that he was] quite refreshing. Here was a guy who came out of the same type of business that I’m in. People ask me, “Why didn’t Trump have a front-loaded transition team?” People in my business are very superstitious about measuring the drapes of an office you may never achieve. I think his thought process was, Let’s win the fucking election first and then worry about who’s going to do what job. If you win, you have to govern. I can’t excuse it—he should have done it. But I understand why not—because of superstition.
I put up with a lot of Trump’s peccadilloes because I viewed Trump as a package. You get the good, the bad, and the ugly. You’re in or you’re out, and I was in until January 6. One thing that I learned as ambassador is that the world admires the way we turn over the keys to our next leader. We have these wonderful ceremonial things. Two guys meet at the White House and shake hands. The cameras are rolling. Everybody knows they hate each other’s guts, but they smile and then they get in the car together and they drive to the Capitol and one of them sits on the podium watching the other give a speech. They act like this is the best thing that ever happened, when they fucking resent the shit out of it. They leave a nice note in the drawer at the Oval Office, which I think Trump did, but he didn’t do the important parts, which were showing up at the inauguration, and he didn’t do the most important thing, which was trying his best to stop what happened at the Capitol. That really hurts the United States brand.
Graham: You write, about Trump, that “to deal with a bully, you have to stand up to him. To deal with an egomaniac, you have to feed that ego. To deal with a decision maker who sees black and white … you have to give him two options and paint one of them as obviously more attractive.” Is that a good way to run a country?
Sondland: Trump was highly effective because he could listen to very complex discussions and arguments and he could distill down to what really mattered and what really counted. The problem was an analysis always seemed to creep into every discussion, whether it was tacit or whether it was verbalized: Yes, I’m going to take care of the country, but what’s in it for me, as well? I don’t necessarily mean monetarily, but in terms of self-aggrandizement or fame or public adoration.
Graham: That seems to be the story of the first impeachment: What’s in it for me? Sure, I can help Ukraine, but what’s in it for me? I want an investigation into Burisma.
Sondland: With 20/20 hindsight, it certainly appears that way. When it comes to that specific incident, I think there was much ado about very little. The famous [Barack] Obama utterance to President [Dmitry] Medvedev about having more flexibility after the election fits neatly into that same category. I would have preferred that Trump simply had Zelensky in for a meeting without preconditions, because we thought he would really like Zelensky. We thought that once they met and shot the shit and hit it off, that would bode well for our support of Ukraine.
Graham: It seems to me that a lot of the seeds of January 6 come from the inability to hold him accountable for that. He got away with something and then he tried it again. Why am I wrong?
Sondland: I don’t know that you are wrong, but if the goal of the impeachment was to find facts and make a case that a duly elected president of the United States should be removed from office—and I’m dubious about the second one—then the committee should have run the entire process in a far more Watergate-like way where there was no dispute that the minority and the majority had a fair shot.
Graham: When you uttered that phrase quid pro quo in your testimony, did you anticipate how potent your use of that phrase would be?
Sondland: I just had a quid pro quo a couple of hours ago: I went into a restaurant, they gave me food, and I gave them my Amex card. Big fucking deal. What I was trying to say in that testimony was, Do you guys want to know if a quid pro quo occurred? Yes, it did. Here was the quid pro quo. There’s a lot more information that came to light after the fact, but at the time, the quid pro quo that I was describing was the first requests that came back from Trump, allegedly through [Rudy] Giuliani: We want that old investigation that got shut down to be restarted. That’s not a big ask, because Zelensky campaigned on eradicating corruption. Do it publicly. Give a press conference, put out a press release, go on CNN, I don’t really give a shit. Just do one of those things and I’ll give you a meeting in the Oval Office. Then, of course, more ornaments started getting hung on the tree: Now we want to specifically focus on Burisma and Hunter Biden, and then the military aid. All of that came through Giuliani. We had no idea whether it was Trump telling Giuliani to tell us or whether Giuliani made it up out of whole cloth. I still to this day don’t know.
Graham: Many people look at Trump as a president who praised Vladimir Putin, who was disinterested in Ukraine, at best, and who weakened Ukraine. Why do you think Trump would have done a better job of keeping Putin from embarking on this war?
Sondland: The conventional wisdom in dealing with Putin or with Kim Jong Un or with Xi Jinping was to stand up at the White House briefing room and issue the same old tired condemnations. Trump said, That clearly doesn’t work. They just laugh. So how do I approach this a little differently? Taking a page out of my private-sector experience, I’m going to praise the shit out of the guy, which is going to confuse him. He’s going to think I’m either crazy or maybe I really am his friend. Then in private, I’m going to threaten him within an inch of his life, and say, “You even touch Ukraine, I’m going to bomb the shit out of you like you’ve never seen before.” Putin—this is my own speculation—thinks that Trump is just crazy enough to do that. I don’t think he believes for one second that [Joe] Biden or Obama or others would have done it.
Graham: Where do you see the war in Ukraine going?
Sondland: I wish I had a crystal ball. I do think the nuclear threat is a real threat. If President Putin even pops off a tactical nuke, I hope he understands how severe the response is going to be. That might be a conventional response, but it will be devastating to his people and his equipment. If he doesn’t get taken out by his own people, I don’t know how you can continue to govern after that.
Graham: There’s a debate among Republicans in Congress now about cutting aid to Ukraine. Do you think that would be a mistake?
Sondland: It would be a huge mistake. This is where I vehemently disagree with my friends on the further-right side of the Republican spectrum. I’m not an isolationist. My parents are Holocaust survivors. I’ve advocated privately and publicly that we should put our foot down on the gas. When I hear my friends that are further right than I say, “Why do we need that? We should be spending the money here”—I can’t disagree with that more. The good news is, I think the same leadership of the Republican Party, starting with Leader [Mitch] McConnell, feels the same way.
Graham: You write that businessmen understand something that career government employees don’t about how to get things done. Yet we see a lot of people who are very successful in the business world go into government and then really struggle or flame out. Why?
Sondland: I know it’s such a cliché, so forgive me, but there truly is a deep state: a vast permanent bureaucracy that is not going anywhere and has the minute-by-minute control of all organs of the federal government, regardless of which Cabinet agency. There are some incredibly hardworking, smart, well-intentioned people in that bureaucracy. But the State Department has people posted all over the world who enjoy an incredibly interesting life on the taxpayers’ dime. They journey from country to country; they live in very nice government-furnished housing; their kids all go to private schools, and usually the best private schools. They spend a lot of time worrying about the journey and not the destination and the objectives.
In a private company you have employees that are there to do what leadership tells them to do. There are certain bounds that are dictated by HR and by the laws, but if they don’t want to get on board with the mission of the company, they’re either counseled and worked with or they’re invited to leave. By definition, that’s not the case necessarily in the federal government.
Graham: You’re critical in the book of Foreign Service officers, but you also praise Marie Yovanovitch and Bill Taylor and Kurt Volker, all of whom came up through that system.
Sondland: It’s like any other meritocracy. The Bill Taylors and the Marie Yovanovitches were the cream and rose to the top. The reason they rise to the top is very similar to the U.S. military. When you talk to four-star generals, they’re not just the best killers in the Army. They’re some of the smartest people in the Army. That’s how they rise to that level. I saw a few examples of the future Masha Yovanovitches. I did whatever I could to help them in terms of writing them positive recommendations and so on. But by and large, there’s a lot of people there that could care less about achieving an objective. They just love the lifestyle.
Graham: Why did you want to be an ambassador?
Sondland: I started in politics as a volunteer in 1988 for [the campaign of] President George H. W. Bush. Along the way, I met a lot of people who had the opportunity to serve as U.S. ambassadors to all kinds of different countries. These are people, if you take their ambassadorship out of their CV, they led incredibly interesting and full lives as businesspeople or otherwise and did some really cool shit. Yet they will tell you, to a person, this is the most interesting thing they’ve ever done in their life. After hearing this over and over and over again, I decided, Shit, I want to do this. This sounds great.
Graham: Did you find that to be true?
Sondland: Without question, and I’d do it again in a heartbeat.
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