TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. President Trump's national security adviser John Bolton is known as a tough-talking hawk. A new article about him in The New Yorker is titled "John Bolton On The Warpath." My guest is the author, Pulitzer Prize-winning journalist Dexter Filkins, who's a staff writer for the magazine. He's joined us many times on the show, dating back to when he covered the war in Iraq.

Bolton is President Trump's third national security adviser, after Generals Michael Flynn and H.R. McMaster. Trump was familiar with Bolton's views because Bolton had made hundreds of appearances on Fox News as a guest, and then as a paid commentator. On Fox, he'd advocated for military strikes on Iranian training camps and for forced regime change in North Korea. Earlier in Bolton's career, he served in the George W. Bush administration as undersecretary of state for arms control and international security affairs and as U.N. ambassador. He advocated for the invasion of Iraq and told Filkins he still thinks the decision to overthrow Saddam Hussein was correct.

Dexter Filkins, welcome back to FRESH AIR. So as you point out in the piece, the Trump administration has no permanent secretary of defense, no secretary of homeland security, no ambassador to the U.N. What does it mean in terms of the power John Bolton has now in his role as national security adviser?

DEXTER FILKINS: Well, the national security adviser, just by virtue of the geography of that job - it's in the West Wing. It's right down the hall from the Oval Office. It's an incredibly powerful position. You know, Bolton sees the president every morning. He sees him or he talks to him in the evening. It's just, the proximity of that job to the presidency gives the occupant of that job just an enormous amount of power. So just on its face, you know, you're in the pole position there. But I think in this administration because, you know, it's a revolving door in the rest of the government pretty much all the time - Jim Mattis, the secretary of defense, he's gone. There hasn't been - no replacement has been named so there's an acting secretary of defense. There's no ambassador to the United Nations. There's no secretary for homeland security.

So it's just kind of a big vacuum. I think it's fair to say that makes his job even bigger and gives him even more influence than you would ordinarily have. So I think in that administration, when you're talking about foreign policy, you're basically talking about John Bolton and Mike Pompeo, and that's it.

GROSS: And are they on the same page on most things, Pompeo and Bolton?

FILKINS: I think so. I think so. I had a funny conversation about Pompeo and Bolton together with an unnamed Western diplomat who knows them both. And they said, look, you know, Pompeo is really only interested in what Trump is interested in. So you can't really sit down and talk about the world with him. Bolton, on the other hand, you can talk about anything. You can talk about aid programs in Africa, and he's well-briefed. He knows about it. But Pompeo has a much more political outlook.

GROSS: So you're saying Pompeo is there to amplify Trump's views. Bolton has very strong views of his own.

FILKINS: Yes, he does.

GROSS: So the title of your piece is "John Bolton On The Warpath." I know he's a hawk. Does the piece imply that he's going to lead us into war?

FILKINS: No, but I think it fairly raises a lot of questions. And I think the basis of the piece is this, which I was kind of surprised to find - this divergence of world views between Bolton, on the one hand, who's been a hawk his whole life. He's for aggressive use of American power. He's advocated bombing North Korea. He's advocated bombing Iran. And then on the other hand, to the extent that President Trump has a world view, it is he wants to stay home. It's America first. He's pretty close to being an isolationist. He doesn't want to - you know, he doesn't want to partake in this kind of entire international architecture that was set up after the Second World War, whether it's the World Trade Organization, or NATO or EU. He doesn't want to pay for any of that stuff, and he doesn't want to get involved.

So Trump, I think it's fair to say, doesn't really want to launch new military operations. They do not see eye to eye on things. I tried to kind of, you know, figure out what it is they talk about when they get together (laughter) for that reason.

GROSS: If Trump and Bolton have such opposing world views when it comes to the possibility of military intervention or war, why would Trump choose him? Why did he choose him?

FILKINS: Well, I think there's - that's a really good question. I think there's two reasons for that. One is that, you know, I think he's, Bolton, is kind of emotionally appealing to Trump. You know, Bolton was a very highly paid analyst on Fox News. He was on there few times a week. One of the revelations is - for me was I got to look at Mr. Bolton's financial disclosure, which you're required to submit for a job like that. And yeah, there was lots of stuff in there. So I think he was being paid $600,000 a year - this is just part of his income, but - $600,000 a year to be on Fox. And so every night, he's banging away, talking tough. And I think that appeals emotionally to Trump. He's like, he's a tough guy. Plus he just sees him all the time. 'Cause they didn't really know each other very well.

I think the other reason is there were - H.R. McMaster had been the national security adviser before John Bolton. And there was a kind of a pretty large group of Trump allies who had decided that McMaster had to go. They didn't like him. They thought he wasn't supportive enough of Israel and of, you know, the current leadership there. And so they pushed him out. I mean, I think it's fair to say they lobbied very hard to get him out, and they worked pretty hard to get Bolton in. So I think it was a confluence of those two things.

GROSS: What did Bolton advocate for as a highly paid commentator on Fox News?

FILKINS: (Laughter). Well, he, as I mentioned, he - and I went through a lot of stuff that he said on the air. And, you know, I think he's finding - I should say, before I answer that question - I think he's finding, you know, it's a little different when you're in power, as opposed to being out of power. But on Fox, talking tough - strike North Korea, if necessary, before they acquire an ICBM capability. Strike Iran in various, you know, various ways and in various contexts. That's, like, at a minimum. And support Israel in its kind of what I think is a covert or actually pretty hot war that's going on with Iran and Syria.

So really aggressive use of American power. But I think even more than that, not just - you know, not just dropping bombs. I think that Bolton's worldview is he's extremely skeptical of international agreements, whether they're treaties or, again, the whole kind of architecture that was built by the United States over the past 70 years. You know, whether it's NATO, or the EU, or the U.N. or the World Trade Organization, all those things which, you know, that's the world we live in. And he is - and these are, you know, treaties and commitments, and bilateral agreements, multilateral agreements. He's deeply skeptical of all those things. And he says, essentially, in - he has said this on Fox News, but he's been very articulate about it in his writing, which is, every time you sign a treaty or a multilateral agreement, you give up a little bit of your sovereignty.

And so I think he sees - his view of America is as a kind of colossus operating unilaterally wherever it wants. And, you know, if you pick up friends along the way, great. But they're not going to be your friends for long. 'Cause there's no such things as friends in the international system. There's only interests. And only interests endure. And so don't get sentimental about it. Just carry on.

And I think that it's a very unsentimental view of the world that he OK. But Trump fell in love with...

(LAUGHTER)

GROSS: ...Kim Jong Un. And I mean, they seem to have such different approaches to viewing the world, even when they agree on things, because, you know, Trump is very sentimental and very angry, you know, like, depending on what what mode he's in. But, you know, in terms of war, an aide - one of Trump's aides told you that he overheard Trump's end of the conversation with the former - his former national security adviser, H.R. McMaster. And even though he was forcing out H.R. McMaster, he called him to run ideas past him about who his successor should be. And when he mentioned Bolton, the aide said that he heard Trump say, Bolton is a hawk like you. He's going to get us into a war. So if Trump thinks that Bolton is going to get us into a war and if Trump doesn't want to get into a war, it, again, seems like it's going to be a weird ride with the two of them.

FILKINS: It's gonna be a weird ride. It is. And I think the question is, you know, what happens out there in the world - and kind of how it develops because, I think, Bolton's view is - you know, Bolton's worldview is pretty clear. I think we're seeing that kind of play out at the moment in Venezuela. But I mean, think - you mentioned North Korea. I mean, think of how - I started my piece with the scene in North Korea because I talked to a lot of people who were in Vietnam for the summit to discuss with Kim Jong Un. And so on one hand, you have the president saying, we fell in love. I can do a deal. I can make a treaty with these people. I can persuade them to, basically, disarm.

And on the other hand - and, you know, Bolton is in the room, at the table, sitting next to the president. And he has written forcefully that we need to attack North Korea. We need to bomb North Korea and destroy their nuclear capability. And so I tried to kind of - I posed that question to Bolton. I said, you know, how could you do that? You know, how could you sit down at that summit when you have been mocking every American diplomat who has done that for the past 20 years? And there you are doing the same thing yourself. And Bolton said to me, well, you know, when you take a job like this, you have to realize you're not going to win every one. You have to compromise - and, you know, perfectly reasonable answer.

But, you know, he has been utterly dismissive of the entire American effort to kind of diplomatically engage North Korea for the past 20 years to try to persuade them, peacefully, to give up the nuclear program. Bolton is right. That effort has failed. But the solution is, you know, what is the solution? Basically, the solution that he's pretty clearly advocated is war. So how does Trump get his head around all that? It's a really good question. I think the conversation that you mentioned - you're going to get us into a war. It sounds like - you know, it sounds like Trump is kind of appropriately skeptical, like, I'm going to hire this guy, but I'm going to be careful as well.

GROSS: There's one more thing about war. After President Obama won the Nobel Peace Prize, Bolton said, Homo sapiens are hard-wired for violent conflict.

FILKINS: (Laughter).

GROSS: So it sounds like he accepts war as just, like, the natural scheme of things. Like, of course, we're going to get into wars.

FILKINS: Yes, I think that's right. I mean, he - a person who worked with him for years said to me, you know, his view of life is that it's, you know, cold, nasty, brutish and short.

(LAUGHTER)

FILKINS: And I - you know, I think, you know, the world is a bad neighborhood. It is. And so, you know, the - I think that any diplomat would go into - sort of venture out into the world with a view sort of along that way. I'm going into a bad neighborhood. And I got to have - you know, I got to have my hand on my hip and be ready to draw. The question is, you know, how quickly you draw that gun.

And I think that from his writing and from, you know, years of writing, I think he's - I - you know, he has a - 600 newspaper articles or magazine articles over the years. All of his talks and speeches and his statements on Fox News and the like, he's - he indicates he'd be pretty fast on the draw. And so the question, I think, properly to be raised is, is he going to give diplomacy a chance or does he reach for that gun first?

GROSS: All right. Let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is Dexter Filkins, a staff writer for The New Yorker. His new piece is called "John Bolton On The Warpath." We're going to take a short break. We'll be right back. This is FRESH AIR.

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GROSS: This is FRESH AIR. And if you're just joining us, my guest is New Yorker staff writer Dexter Filkins. His new article is about President Trump's national security adviser, John Bolton. It's called "John Bolton On The Warpath." I asked Filkins about Bolton's role in the Trump administration's response to the mass protests in Venezuela and the effort by the Venezuelan opposition to drive President Nicolas Maduro out of office.

So as we record this, in Venezuela, there is an attempt by the opposition, by many Venezuelans, by part of the military, to overthrow President Nicolas Maduro. Venezuela has just been falling apart economically in every way. And you write that Bolton was leading the fight against Maduro, you know, in the U.S., accusing him of forming, along with Cuba and Nicaragua, a troika of tyranny in the western hemisphere. You were with Bolton in Miami when he addressed - well, tell us who he addressed. And tell us what some of the things he said.

FILKINS: Well, it's pretty amazing. I was - it was just a couple weeks ago. I was - I went down to Miami with Bolton. He addressed a convention of the surviving members of the the 2506 Brigade. And that's the now-aging Cuban veterans of the Bay of Pigs invasion - you know, the failed invasion in 1961. And so they're - you know, they're pretty hardcore anti-communist. And they love Bolton. I mean, you know, he walked into the room, and it was like they went crazy. And some of them were in wheelchairs. And they were, you know, climbing up out of their wheelchairs to applaud him.

But the - Bolton gave - and he's, you know, he's done this before - but he gave a very tough talk, first about Cuba but then sagging very quickly to Venezuela and - which, I think, ultimately, is - you know, that's topic A right now. And so he made it very clear - very clear - that Maduro has to go and that the Cubans who are in Venezuela have to go, that the Russians who are in Venezuela have to go and that the best way to do that is to change the regime.

And I talked to him about it afterwards, and he - it was remarkable, really, how blunt he was. I mean, he basically said, the Western Hemisphere - that's ours - and Russians out. And the Monroe Doctrine is alive and well. And, you know, the Monroe doctrine basically says the hemisphere is ours. But I think that what struck me there in Miami was not just what was happening in Venezuela, which is, you know, unfolding as we speak. But what was interesting to me was that - in Miami - was this was, essentially, a political speech. This was a campaign speech. And I mean an American presidential campaign speech. The - you know, if you take the Venezuelans in Florida and the Cubans and the Nicaraguans, I mean, I think you have about a million and a half in Florida. And Florida, of course, is the critical state that Trump needs to win the presidency.

And they love nothing more than, you know, the Cuban exiles there, particularly the older ones. They love nothing more than to hear a table-pounding speech about how we're going to roll back the lefties in the hemisphere. And they were loving it, and they were eating it up. And I think the whole discussion - the whole speech was about foreign policy. But it kind of struck me as, first and foremost, a domestic political speech, again, as these events are unfolding in Venezuela.

GROSS: OK. But you're right. With the 2020 elections looming, the prospect of appealing to voters may create a strong temptation to launch a military intervention. You're talking about a military intervention in Venezuela.

FILKINS: Yes. And I - you know, the administration's been very clear about it. I mean, Bolton was - I asked him directly. And he could have said no. He said - to the contrary - he said all options are on the table. And he said that to get the Russians out, we got to change the regime. So I think - you know, I think Maduro - yeah, Maduro's finished. It's just a question of time because this administration is not going to permit Maduro to stay. And so I think - you know, we're watching this unfold in Venezuela right now. It's just really - I don't want to say it's a matter of time because, of course, events could unfold in any number of ways. But this administration is strongly behind the uprising in - and between - behind Juan Guaido, the - who's leading the opposition.

GROSS: So if we do any kind of military intervention in Venezuela, are we, in some ways, in conflict with Russia?

FILKINS: Definitely. I...

GROSS: I mean, like, a military conflict.

FILKINS: Well, I think that - I think we're a long way from a military intervention - we're a long way. I mean, the administration is foursquare behind Juan Guaido, the opposition leader. And they're supporting him in every way. And it's impossible - I mean, I don't know the facts on the ground, but it's hard for me to imagine that Guaido would be calling for an uprising in the way that he is without at least the tacit approval of the United States and without the tacit approval of the White House.

But the - I think that our objective is to push the Russians out of the hemisphere and make it clear, once again, you know, a la the Monroe Doctrine, that this hemisphere is ours. And I think - I - you know, Putin's probably watching all that very carefully. I doubt we're going to come into conflict - armed conflict with any Russians. But I think that - but the objective of the White House is to clear the Cubans and the Russians from Venezuela and the Maduro regime as well.

GROSS: Bolton has been tweeting a lot. He's been directly tweeting the people of Venezuela to overthrow Maduro. He's been tweeting leaders of the Maduro administration to leave, that, you know, like, you know what the right thing to do is. Leave.

FILKINS: Yes.

GROSS: And I'm wondering if that sounds kind of unprecedented to you. I mean, I know Twitter is kind of new in the world of diplomacy. But to directly address not just the people of Venezuela but the leaders of, you know, Maduro's administration or regime, depending on how you want to look at it, and tell them to leave.

FILKINS: Yeah, I think it is remarkable. The national security adviser is - typically and historically is not someone who gets out in the public and bangs the drum. And Bolton is doing that, you know, with his tweets, with his political speeches. He's really, really vocal, and he's really out front. And that's remarkable.

GROSS: My guest is Dexter Filkins. He's a staff writer for The New Yorker, and his new article is titled "John Bolton On The Warpath." We'll talk more about John Bolton after we take a short break. And our TV critic, David Bianculli, will review the new Netflix dark comedy series "Dead To Me," about two women dealing with grief issues played by Christina Applegate and Linda Cardellini. I'm Terry Gross, and this is FRESH AIR.

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GROSS: This is FRESH AIR. I'm Terry Gross. If you're just joining us, we're talking about President Trump's tough-talking, hawkish national security adviser John Bolton. My guest Dexter Filkins is a staff writer for The New Yorker. He's written a new article about Bolton called "John Bolton On The Warpath." Bolton is President Trump's third national security adviser after Generals Michael Flynn and H.R. McMaster. Trump was familiar with Bolton's views because Bolton had made hundreds of appearances on Fox News as a guest and then as a paid commentator. On Fox, he'd advocated for military strikes on Iranian training camps and for forced regime change in North Korea.

So you just grabbed John Bolton as a ferocious critic of Iran. And when he moved into his office as national security adviser in the Trump administration, he hung a framed copy of Trump's executive order nullifying the nuclear agreement with Iran. I'm sure President Trump liked that because it was his order. But did you see it when you interviewed Bolton? Did you see it framed...

FILKINS: Yeah. Yeah, he gave me a little - you know, he gave me a little tour around the office, and that was the first thing he pointed to. He said, you know, this is the executive order nullifying the agreement with Iran. Very - he was very happy about that.

GROSS: So why did he hate the deal so much?

FILKINS: That's a good question. I think - somebody told me in my piece that Bolton has a kind of anal obsession with Iran which is, like, not explicable. I think Bolton would - in his defense, he would say - in fact, I asked him this question. I said, why are you obsessed with Iran? And he said, because of nuclear weapons. That's why I think about Iran. And his aide said to me, the first thing John thinks about when he wakes up in the morning is how to protect the American people from the threat of nuclear weapons, and so - which is, you know - none of which is unreasonable.

I think that when they - but their view of Iran is just very, very dark, and it's much darker than the Obama administration - the view that the Obama administration had. The Obama White House basically saw Iran, and they thought, OK, look. These guys are doing bad stuff all around the world. They're not particularly nice people, but we can make a deal with them. And we can make a deal that's verifiable and which will be in everyone's interests. We can try to stop their very, you know, deliberate progress towards acquiring a nuclear weapon. And the rest of it - you know, we just hold our nose. And that was, like, the Obama view.

And I think the Bolton view - and it's not necessarily Trump's view, but the sort of - Bolton represents a huge part of Washington that believes that Iran is a - is not just a serious threat, but cannot be trusted to make a deal. And basically, the regime there has to be changed, as well. And I think - they don't really say that publicly. They're not allowed to use the words regime change. But they're trying to cripple the economy, and I think they're making a lot of progress on that front.

So I think that - cancel the nuclear agreement on one hand, and crush the economy on the other. And let's see where that goes. As one of - as a, let's say - a senior administration official said to me, if we cripple the economy - which I think we can do - and the Iranian people decide that - in their anger that they want to get rid of their government, well, you know, good luck to them. And I think that's kind of where we are. That's the White House policy towards Iran right now.

GROSS: But, you know, somebody else told you that the Obama administration sanctions were to punish the Iranian regime, but these new sanctions are punishing the Iranian people. And people express to you in the piece the fear that the sanctions are so tight they will lead to war with Iran, as opposed to a regime change.

FILKINS: Well, I think that's one of the fears. The - I think one of the things that the United States kind of bureaucracy, I should say - the kind of - the experts in the government have learned over the past decade or so is just how sweeping American sanctions can be, particularly with regard to financial controls and financial sanctions. The United States essentially controls the international financial system.

And so if the right restrictions in - put in place, you can - which I think we're seeing now in Iran - you really can cripple an economy. And so what the Trump administration is trying to do with Iran right now is basically shut down as completely as possible their ability to export oil. And that's - you know, that's, like, 90% of their government revenue. It shut down their ability to export oil and then basically drive the economy to collapse. And I have to say they're making a lot of progress in that regard.

The - I think when they - when Trump came into power, the Iranians were exporting something like 2.9 million barrels of oil a day. They're now below a million. And they're going to - the Trump White House is going to keep pushing that lower. Inflation is just - is galloping Iran. Unemployment is very, very high.

So they're doing - I think they're achieving their objective, which is - at the moment, which is to cripple the Iranian economy. What comes out of that - you know, that's kind of anyone's guess. The - you know, they think - they believe, I think, pretty strongly that they can essentially foment an uprising or foment a collapse of the regime. I'm - you know, a lot of people I talked to are pretty skeptical that - you know, yes, they can collapse the economy, but does that necessarily take us where we want to go? Does that necessarily change the regime?

And - 'cause, like, the regime - you know, the people at the top - they're always the last people to suffer. They're always going to eat well, and they have, you know, their bank accounts abroad. So - and, you know, we know that the Iranian regime is willing to kill as many people, kill as many Iranians as they need to to stay in power, as we saw in 2009. So where does this all go? Unclear, but they think they can - yeah. If we make the Iranian people miserable enough, they will rise up.

GROSS: Let's talk about John Bolton's background. He was in the George W. Bush administration, first as undersecretary of state for arms control and international security affairs, then as U.N. ambassador. He was a controversial pick for U.N. ambassador. He never got out of committee, but he managed to get the position anyways. So refresh our memory about how he managed to become U.N. ambassador.

FILKINS: Well, it's pretty amazing. It really is because it - when Bolton was nominated to become ambassador to the United Nations - first of all, the - it was in the middle of the Iraq War. So it was, you know - it was a pretty ugly time, and there was a lot of anger against the White House. And so they nominated their - you know, their most vocal hawk to go to New York. And in the months leading up to the invasion of Iraq, there was a Brazilian diplomat who worked for the - what's called the Chemical Weapons Convention, which is like every - virtually every country in the world is part of.

It's like 189 countries, including the United States. It basically bans chemical weapons, but it also - if you become a signatory to that convention, there's a mandate for a kind of automatic, you know, independent inspections to make sure that you're not, you know, violating the treaty - that you're not manufacturing chemical weapons.

So this Brazilian diplomat who was working for the Chemical Weapons Convention, I think in The Hague, was negotiating with Saddam Hussein's government to join the Chemical Weapons Convention. And the Iraqis were basically - the Iraqi government indicated a willingness to join. And I think, in fact, they may have for a time actually joined and - whereupon, there would have been automatic chemical weapons inspection.

So I interviewed Bustani. And again, this is 2002. It's, you know, in the run up to the invasion. And if you think back to that time, in 2002, kind of a lot of people had a sense that kind of that was the direction that the Americans were going. And it wasn't a huge mystery. So Bustani told me, I thought that if I could engage the Iraqi government and I could send these inspectors in, they could go in and they could determine - because we didn't think that they had a chemical weapons production capability - we could basically show that, and we could maybe help stave off an invasion - and say, look, the Iraqis don't - they let us in. They don't have chemical weapons.

And so he was working towards that end and, I think, you know, pretty earnestly. And again, in the run-up to the war - so one day after the Iraqis had indicated that they were willing to sign and willing to come on board and allow inspections, John Bolton turned up in his office in The Hague and, you know, closed the door and sat down and said, I'm here at the request of Vice President Cheney. And we would like you to resign.

And Bustani was kind of stunned, as he described to me. And he said, I refused. I - and then he said Bolton threatened him and threatened his family. And he said, look; we want you to quit. We know where your daughters live. We know where your sons live. We know where your wife lives. It's time for you to go.

And Bustani told me, I was shocked, but I stuck to my guns. And I said, no. You know, I'm not afraid of you. And so the United States then - Bolton left, went home. He denies this, of course. But he - Bolton went home. The United States kind of orchestrated - all of this is public record, but the United States orchestrated kind of Bustani's firing. They called for a special gathering of the 189 member states. They kind of, you know, lobbied very hard for him to be removed, and he was.

GROSS: If the story is correct - I mean, I know...

FILKINS: Yes.

GROSS: ...Bolton denies saying this. But if the story is true, that he actually threatened Bustani and said, look; we know where your wife and your children are...

FILKINS: Yeah.

GROSS: ...That's really Mafia talk.

FILKINS: Yeah. Yeah, that's - I think Bustani said the same thing to me. I mean, he said, I felt like I was in a movie - like a Mafia movie or something. You know, like, let's assume for a second it's true. Yeah. Maybe that's what, you know, hardcore sharp-elbowed diplomats do behind closed doors. I doubt it, but it seems kind of shocking if it's actually true.

GROSS: Let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is Dexter Filkins, a staff writer for The New Yorker. His new piece is about President Trump's national security adviser, John Bolton, who was George W. Bush's U.N. ambassador, and in between was a paid commentator on Fox News.

Let's take a short break. We'll be right back. This is FRESH AIR.

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GROSS: This is FRESH AIR. And if you're just joining us, my guest is Dexter Filkins. He's a staff writer for The New Yorker. His new piece is called "John Bolton On The Warpath." John Bolton is President Trump's national security adviser.

Let's talk about Bolton's background. In 1985, Bolton joined the Reagan Justice Department. And there, he helped shepherd in the Supreme Court nomination of Robert Bork. He did not get confirmed in the Senate. And as you say, that began the era of fiercely partisan high-court nominations. I think Bork went on to found or co-found the Federalist Society...

FILKINS: Yeah.

GROSS: ...The group of very conservative, you know, lawyers.

So what were Bolton's priorities back then? Do you know?

FILKINS: Again, he's been a conservative his whole life. If you go back - when Bolton got out of law school, he was an assistant to his Yale law professor Ralph Winter. And Ralph Winter was a very well-known figure in the conservative intellectual movement. And when Bolton got out of law school, he joined up with Winter. So he's just in his 20s. They take this - what turns out to be a landmark Supreme Court case, Buckley v. Valeo, in - which was the first big lawsuit - kind of the precursor to Citizens United - it was the first big lawsuit that challenged restrictions on campaign spending and giving. And they won.

And essentially, it was Buckley v. Valeo - landmark case - it established essentially that money and political contributions is essentially political speech. And that ultimately led to rulings like Citizens United, which have basically just unleashed, you know, as we now have the system - we now have this massive flood of private money into our campaigns.

And that was the beginning. And Bolton was involved in that when he was just in his 20s. And he was involved in the Bork nomination. And he was involved in the Iraq War. So you can just chart his career, and it takes you through the whole rise of the Republican establishment as we now know it.

GROSS: Is there anything I left out of the interview...

FILKINS: Yeah.

GROSS: ...That you reported that you think is really important and you want to share with...

FILKINS: Well...

GROSS: ...Us before we have to move on?

FILKINS: Yeah. Yeah, I would do - I think there's one. You know, Bolton has aggressively advocated attacking North Korea for years. And I had a conversation with - Larry Wilkerson was chief of staff to Colin Powell. And Bolton was essentially advocating, you know, preemptive war with North Korea in the early 2000s - like, after 9/11. He was going around saying, they've got this nuclear program. We have to act now and take them out.

And it was so disturbing to Wilkerson that - and there's a scene in the piece where he said, we arranged - we had to find a way to shut him up. And he said, we arranged for a briefing for Bolton. So we brought him into the room - he and Richard Armitage, who was the deputy secretary of state - and we gave him a briefing on what would happen if we went to war with North Korea. And as Wilkerson said to me - he said, it's, you know, tens of thousands of casualties. And they kind of laid it out. He said, we laid it out for John - like, how many South Koreans would die, how many Americans would die - there's 200,000 Americans in Seoul - how many Japanese would die, how many Chinese would die.

And he said, I'll never forget what Bolton said to me. He looked at me, and he said, are you finished now? You clearly do war. I don't do war. I do policy. And I think that for Wilkerson, you know, that really stunned him. And I think their - you know, their relationship has never been the same since. But there was - that it was - it struck him as a very cavalier attitude towards going to war and having a war like that.

And I just - one more thing about North Korea - I remember when I was on the plane of secretary - then-Secretary of Defense Jim Mattis. This is in 2017. And the subject of North Korea came up. And he said, if there was a war, a war with North Korea would be bloodier than - it would be a bloodier war than anyone alive has seen. That's how bad it would be. I mean, he got very sober very fast. And so that struck me as a pretty remarkable moment.

GROSS: And I guess a question that we're left with is, you know, there's a difference between recommending policy and being responsible for pushing us into a military conflict with devastating consequences and tens of thousands of deaths. Would Bolton go to the point where tens of thousands of deaths were kind of, you know - that he'd be responsible for the action that led to it? Is he...

FILKINS: Well, that's - yeah. That's a really good point. Look. I - it's one thing to be a highly paid commentator on Fox News and to say, we should bomb North Korea. We should bomb Iran. We - you know, we need to take action. Regardless, you know, go forward. Damn the torpedoes. That's one thing. But when you're actually, you know, in the cockpit and it's - and you're flying the plane and it - you got to drop that bomb yourself, it starts to look a little bit different.

And I think - I don't know. I mean, I think this brings us to Bolton in Vietnam, sitting next to President Trump, sitting across the table from the North Korean leaders on - and negotiating the - their nuclear weapons. It's - you never could've imagined that John Bolton, who has made fun of and mocked, you know, every American diplomat who has ever done that - he's sitting there in the same chair himself, doing exactly the same thing.

And I - he didn't say it in quite that way to me, but I think you can imagine that you can't - you can't be - you can't speak as freely and as loosely when you're the national security adviser, as opposed to when you're a commentator on Fox News. And I think he's finding that out right now.

GROSS: Well, Dexter Filkins, it's always great to talk with you. Thank you so much for coming back to FRESH AIR.

FILKINS: Thank you, Terry.

GROSS: Dexter Filkins is a staff writer for The New Yorker. His new article is titled "John Bolton On The Warpath." After we take a short break, our TV critic David Bianculli will review the new Netflix dark comedy series "Dead To Me" about two women dealing with grief issues, played by Christina Applegate and Linda Cardellini. This is FRESH AIR.

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