The Daily Beast Podcast - Why Trump is so Epically Bad at Negotiations

Episode Date: August 19, 2025

John Bolton, Donald Trump's National Security Advisor who witnessed up close why he is so bad at making deals, joins Joanna Coles for an inside look at what it’s really like being in the room with Donald Trump. Looking at Trump's first term Putin meeting in Helsinki, where briefing papers went unread as soccer played in the background, Bolton reveals a portrait of a president who prizes optics over substance, public relations over policy. With Vladimir Putin exploiting every opening, Xi Jinping taking notes, and Trump’s envoy stumbling into Russian disinformation, Bolton exposes the dangerous mix of ego, improvisation, and manipulation at the heart of America’s foreign policy.  Hosted on Acast. See acast.com/privacy for more information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I briefed him on strategic arms issues and negotiations with the Russia while we were flying on Air Force One. He was in his cabin watching a FIFA soccer match. I had to compete for attention with that. I'm Joanna Coles. This is the Daily Beast podcast, not to be confused with inside Trump's head. That's our podcast with Michael Wolf, which goes out on Tuesdays and Thursdays. We're recording this on Monday morning as Donald Trump gets ready to meet President Zelensky. of course his band of European leaders that are traveling with him. But what can it be like to be in that room with Donald Trump? What is it like trying to brief him for such an incredibly important meeting? Well, we're going to be talking to a man who has tried to brief him, despite the fact that at the time when he was actually trying to brief Donald Trump for

the Helsinki summit with Vladimir Putin, Trump was actually on a FIFA game and not really interesting, just fascinating detail to come. But we have really no time to waste. It's a historic day and we have a president who's made it clear that he's completely uninterested in what the American intelligence community has to say because his personal relationships trump everything. So let's get into it with former national security advisor and of course ambassador to the UN, John Bolton. Ambassador, thank you so much for joining us. Go ahead and do it. We're very keen to get your experience of what an earth it can be like being in the room with Donald Trump at one of these summits. But first, I have to ask you, what was it like waking up this morning to discover the president had truth socialed about you,

saying that you're one of the reasons why this war hasn't come to an end? I'm going to quit. He said, this war can be ended now, but stupid people like Chris Murphy, obviously the senator from Connecticut, John Bolton and others make it much. much harder to do so. What is it like waking up to a truth social like that? Well, it's pretty common in my case. I'm glad the president's still thinking about me. It shows he's listening anyway. But, you know, if he can't stand to heat, he should get out of the kitchen. Obviously, you were there at the Helsinki Summit. Can you take us through what it's like trying to brief Donald Trump for a situation as complicated like this one?

Well, typically he has not read the briefing materials that are prepared, really, by the National Security Council staff with inputs from all of the affected departments and agencies. It's a pretty standard practice across almost all presidencies in the modern time. And they were laboriously put together, and I'm quite confident he read little or none of them in most cases. we tried to arrange briefings with greater or lesser success before we departed from Washington, but sometimes that was quite difficult. And probably the best example of how scattershot it was when we were flying from Scotland to Finland for the 2018 Helsinki summit, I briefed him on strategic arms issues and negotiations with the Russia while we were flying on Air Force One. he was in his cabin watching a FIFA soccer match.

So I had to compete for attention with that. And is he, like, is he, yeah, yeah, John, okay, I got it, I got it. Or is he just, does he blank you? How does he show any level of engagement on something like this? Well, it varies. Sometimes he does ask questions. There were times in his intelligence briefings that he would ask questions. but mostly he likes to talk.

There were some of the intelligence briefings where he talked more than the intelligence briefer. And I was reminded, Lyndon Johnson once said, I found that when I'm talking, I don't learn very much, but that was not an inhibition for Trump. And does he not listen

because he thinks he knows everything? Or does he like to go into a situation and assess it in the room? Well, it depends on the same. subject. In some cases, he thinks he does know a lot. He hears from all kinds of random people. Often hears things. He doesn't hear from his senior advisors and thinks he has better information sources than they have. But it's also the case that he believes in his own ability in a very short period of time to size people up. And he said frequently that he thinks that international

relations are really the personal relations between heads of state. So if he's a personal friend with Vladimir Putin or Jijun Ping. Then in his view, U.S. relations with the counterpart's state are good. And so that means that if he has a warm feeling about the person he's about to meet with, he's not really worried about specifics or further information because he figures he'll work it out with his counterpart. And if there are details that remain to be completed, others will do that work for. them. If you're Vladimir Putin and you're arriving on Friday, and you have, as we know he has,

years of being skilled at the KGB, how do you approach Trump? How do you get what you want from Trump? Well, first, Putin is always very well prepared. I first met him about six or seven weeks after 9-11. I accompanied then Secretary of Defense Donald Rumsfeld to Moscow. I was the State Department guy on that trip. And Putin had been president really only about a year and a half at that point, but he was very familiar with everything that we discussed. And in every meeting I've had with him since then, the same has been true. So he's automatically in better shape than Trump is to talk about what can be very complicated issues. And he's also now had many encounters. I think it's six or seven in-person before the Alaska summit and multiple phone calls, 25, 30 over the years.

So the KGB training is focused on helping one of their agents assess other people, judge what's on their mind, figure out ways to get to them, to achieve the manipulation that's the desired outcome. That doesn't mean in any sense I'm saying Trump was a Russian agent. In fact, sometimes the best tools for the Russians and other espionage organizations is to get people to do what they want unwittingly, which is what I think is going on here. But having had all this experience and a lot of practice with Trump, Putin can size up pretty quickly what the moments of opportunity are. And you could see as Putin approached on the red carpet to where Trump was waiting to greeting. Trump started applauding. You could see him smile.

Putin started right in. There was a lip reader who gave her interpretation of what they were saying, walking on the red carpet toward the stand where they took pictures. I don't know if it's accurate or not, but Putin engaged him very quickly. And then Trump gave him the perfect opening by inviting him to rise. in the Beast, the presidential limousine, which gave him a couple minutes totally one-on-one. And after that, we don't really know we have little bits and pieces of pictures of what happened in the conversation. But watching the press conference afterward, I came away with a pretty firm impression that Putin felt he had had a very successful meeting.

And Trump came away feeling maybe it had not been so successful. So nothing's guaranteed the round of meetings with Solicester. and the Europeans in the U.S. today will have a big impact. But if I were Putin, I would have come away from Alaska feeling very positive. Does Donald Trump have a sense of the fact he's being manipulated, do you think? Or does he just think his personality sort of conquers everything? Well, I've never heard him express any concern that he was being manipulated, not by Vladimir Putin, not by Xi Jinping, not by Kim Jong-un, not by Rechip Erdogan of Turkey,

not by almost anybody. There are two kinds of people in Trump's world, winners and losers. He's a winner. That's all you need to know. It's so fascinating. And does he get nervous or stressed before these kind of meeting? Yes, I think he does. And I think he was demonstrating some of those nerves in the morning and during the flight to Anchorage, where he was tweeting this, that, and the other thing. he was making comments to the press. I think that's the sign of somebody who's got the concern about how things are going to come out. Now, I am sure, I wasn't in the room, obviously, but I'm sure that when he came face to face with Putin, that he performed. In other words, he didn't show nerves through the meeting.

But I think he was clearly on edge before the meeting. How important are optics to him? Do the optics matter more than any? I think optics are probably more important to Trump than almost any other contemporary president. Obviously, all politicians worry about optics. There's no question about that. But Trump thinks of himself as a TV performer, and he is a TV performer. In a sense, if his whole day were on television, he'd probably enjoy that. So he's very aware of what impressions are. That's why you saw the F-35s parked on the tarmac in Anchorage. That's why you saw the beach. That's why you saw the B.

two overflight and a number of other aspects of it. So I think his assessment after the meeting was pretty well reflected in his appearance, where he could have said it was a great meeting, everything went fine, were well on the road to peace, I'm very confident, so on and so forth. That was not the three-minute performance you saw in Anchorage. Only after he had recovered in his interview with, I think, Sean Hannity, did he say on a scale of 1 to 10, it was a 10. So he had gotten his presence of mind back.

And again, since there are only winners and losers, and we know he's a winner, it was a 10. And that's what you've heard since then. But I think the first reaction before he had time to think through what the performance should look like was the real indicator of how he felt. And he didn't feel good about it. John, hold that thought. We're just going to take some ads.

And we're back with John Bolton. the former ambassador to the UN talking about what else Donald Trump. I want to come back to that in a second in his ability to sort of take defeat and spin it as victory. But when you're in the room with him and the cameras aren't on, what is he like? Is there a big difference? Well, not really. I mean, it depends, again, on the circumstances. But Trump likes to talk, as he said to me, any number of times, I'm a talker.

and so his natural default is to be talking. And I think sometimes foreign leaders have trouble getting a word in edgewise, but I don't really think his behavior is that different. People have said, you know, in the second term, he's in public behaving more offensively, more profanity, and so on. And that may be, but it's not that he's changed between his first term and his second term. It's just that in public going back even to the campaign. In public, he's just more.

more like he was in private before. He's lost not all of his inhibitions, but he's lost a lot of them. I think that's fair to say. Well, so let's talk about that. You mentioned on CNN on Friday night, that to you, he looked tired on Friday. And when you watched him walk up the steps to Air Force One, he was sort of hunched over. You can see, obviously, he's not as young as he was. He's now 79. he got his Homeland Secretary's name, Christy Noem confused with the golfer, Christy Kerr, a couple of weeks ago. He's clearly finding things harder to grasp. What are the differences you see between now and when you worked with him?

I don't think mixing up names or things like that. I wouldn't read too much into it. Sometimes he called me Michael. People thought maybe he confused me with Michael Bolton. I think actually he was confusing me with. Michael Pompeo, the Secretary of State. Right. You don't look anything like Michael Bolton.

Your signature must have. You've seen one. You've seen them all. Whatever. But I do think, you know, at a time in that press event when he should have been upbeat, you know, I'm a winner, that's not what we got. And Putin went into that with a prepared speech,

most of it, the ending he had to put together, but he knew what he was going to say. I think Trump was winging it the whole time, which is not unprecedented, certainly. But I think that's the kind of indication when he can't put on his game face, even at a time like that, that I think shows fatigue. Do you think it matters that the First Lady isn't around as much? I mean, does he miss having support? I thought he looked very lonely walking up the steps, and you realize the mantle of the job is huge, even if you're playing it as a president on television.

Yeah, you know, I have to say, even after 17 months in the White House, I don't know enough about the relationship to comment on it. Be hard to imagine it didn't have an effect. So if you are advising President Zelensky, and we're recording this on Monday morning, if you are advising him as he comes in to talk to Donald Trump today and he's bringing his flank of European leaders, how would you advise him to approach President Trump? Very carefully, because I think this is, I think there's a little. bit of a risk here for Zelensky and the Europeans to appear to be ganging up on Trump. The scenario is that Zelensky will have a one-on-one with Trump before the Europeans get in the room, which is a point of danger. But I would be saying, look, Mr. President, you got Putin to the table in Alaska by threatening sanctions against Russia and secondary sanctions against the people

buying Russian oil and gas. That's what got him there. None of the rest of of us could have done that. Only you could do that. So please, please bear down. And if we don't get something more from Putin, some additional concessions, apply more pressure. Because it's only the pressure that you and the United States can bring. They're going to force Putin to negotiate. I think Trump's in a hurry to win the Nobel Peace Prize. I'm afraid he may not listen to that. But that's the approach I think that Zelensky needs to take. It's all due to Trump. And Trump's main point of leverage is the threat of economic sanctions. That's very interesting that you think that he might sense he's being ganged up on by the European

leaders. What advice would you give to them then as they come in after his meeting with Zelensky? Well, I would hope that there'd be a break so that they could hear from Zelensky what had happened. If they're simply, if they're meeting in the Oval Office, I'm not sure where they're going to hold the one-on-one between Trump and Zelensky, maybe it'll be in the cabinet room with some of their aides around them. But if they then bring in all the European leaders at once without any gap between the two meetings, the Europeans will not hear from Zelensky privately what actually went on in that meeting. And so Trump will tell them what went on in the meeting, which may or may not bear much relation to what Zelensky thinks happened. So that's a very dangerous point. And if any of

them begin to lecture Trump or appear to be upset about something. I just, it's not just, at that point, it's not just Ukraine that's at stake. It's the NATO alliance that might be in jeopardy. It's an astonishing moment to think of all of them coming over. In living memory, I can't think of anything quite like that. No, Trump has already, yeah, Trump has already indicated that. Only Trump could bring so many European leaders to the White House, another diplomatic crime. So how useful is his special envoy, Steve Whitkoff, who as we know doesn't have formal training as a diplomat, and his expertise is in real estate, largely in Manhattan office real estate. How useful is he in this situation?

I think it's been more of a problem than anything else. We saw another example of it on Sunday. On the Sunday talk shows, Marco Rubio, Hugh, do a very strict line. he wasn't going to get into any specifics of what was discussed between Putin and Trump in Alaska. But it was Whitkoff who offered that Trump had proposed robust security guarantees, although he got them in my mind completely mixed up with NATO Article 5 and somehow pledges of non-aggression being enshrined in Russian law. I'm not sure how all that fits together, but we'll find out soon enough. But I think the two leaders must have agreed that they,

simply we're not going to talk about details of their discussions, which, of course, neither of them did in Anchorage. So for Whitkoff to have exposed even some of the things they talk about, I think could pose a risk to Trump because it was his side that breached the agreement not to reveal details. We're just going to take a quick break for some advertising. And we're back with John Bolton, who Donald Trump truth-socialed overnight was one of the reasons that this war between Russia and Ukraine wasn't yet over because John Bolton was stupid. And also, Steve Wickoff seems slightly confused or somewhat bewildered by what had actually been agreed to.

And he famously refuses to go into the meeting with a note-taker or anybody from the American team. How does that impact the conversations he's having? I think there's no doubt that somebody that inexperienced in these kinds of negotiations and so utter lacking in knowledge about Russia, Ukraine, Europe, Iran, nuclear weapons, Gaza, who knows all the things he's been involved in, is himself very vulnerable to manipulation. And we've seen clear examples of that in Witkoff's various meetings with Putin, where Putin has given him information that was basically propaganda, for example,

that Russians had the remaining Ukrainian forces that had penetrated into Kursk province, completely surrounded and they were in danger of being wiped out, which was not true at the time. Putin said that to Whitkoff. Whitkoff obviously said it to Trump, and Trump then said it publicly. So I think Putin is delighted to receive Whitkoff in Moscow because it gives him another opportunity to manipulate somebody who's obviously personally very close to Trump. So, John, what is Xi Jinping thinking as he's sitting watching this? Well, I think he's saying that Putin has been able to get the magic back, and he's saying that Trump is on the verge of giving way. That at least is the appearance, if in fact he's pushing for Zelensky to accept seeding the rest of the Donets province. And in Beijing's view, that is a sign that if the U.S. is not willing to defend,

against aggression in Central Europe, because it's too far away and our interest aren't great enough, then surely it's not going to be willing to defend against aggression against Taiwan or in the South China Sea or elsewhere along China's Indo-Pacific periphery. So I think that all gets factored in. This is not a crisis whose effects are limited to Europe. Everybody else around the world is watching to see how Trump performs. So how seriously do you take Trump's statement that she told him, I will not invade Taiwan while you are president? I think he made that up. I think Trump made that up. I think he makes up things and that's one of them. Who's going to prove him knows? The Chinese are not going to comment on that. And if Xi Jinping did say it to him, I wouldn't believe him.

Well, so the other thing I was going to ask you is that Donald Trump obviously lives in a world where people bring him good news. actually does the juxtaposition of that work with something like the conversations that are happening today, which really does impact the future of Europe, the future of the free world? Well, Trump is thinking about the Nobel Peace Prize, and he believes if he says things often enough, he can bend others to his belief, that the reality becomes irrelevant once you enter into Trump world. And so I think we'll see a performance of that. there will be such a performance behind the scenes.

We'll see how it works when they all come out of the meeting. And what do you think his chances are of getting a Nobel Peace Prize? I think his chances are pretty remote. I think although he claims to have stopped six wars and six months, if you look at them piece by piece, he may have made incremental contributions in several of them. But even if you took all of them together, it wouldn't amount to that much.

I think he's pinning his hopes on Ukraine. And I think he's a long way from getting it. John, incredibly interesting to talk to you. Thank you very much. Well, thanks for having me. What a perfect moment to hear from John Bolton, a man who has been in the room. And I find his detail of being on Air Force One with Donald Trump

as they're heading to the Helsinki Conference for a meeting with Vladimir Putin. And he's having to compete with FIFA on the television for the president. attention. And also his description, which Michael Wolfe has often given us, that Donald Trump sees people as one of two kinds, is completely binary. You're either a winner or a loser. And he is such a winner that he doesn't need to prepare. So it'll be very interesting to see who wins coming out of today's meeting. President Zelensky and the European leaders and possibly NATO, or whether or not as John Bolton, hinted at Putin, Putin actually is a very important. It's a

playing this exactly the way the Russians want it to go. And China is sitting and watching with enormous interest. If you have been, thank you for joining us. Don't forget to subscribe. You can leave us a comment on YouTube. You can subscribe on YouTube and you can subscribe on Spotify, Apple, wherever you get your podcasts. Thank you to our producer, Devin Roderino, our logistics and researcher, Anna von Erson, and our editor. And don't forget, as the first lady would have us be every day, be Beast. Want more great listens? Check out our comedy podcast, The Last Laugh,

and our star-studded The Daily Beast podcast at the Daily Beast.com slash podcasts. If you enjoyed this episode, consider becoming a Daily Beast subscriber. Subscribing is the best way to feed the beast and support all of your podcasts as we cover what might become the darkest timeline. Head to the DailyBeast.com slash membership slash podcast and sign up. up today.