Read the full transcript of a conversation between Judge Andrew Napolitano and former British diplomat Alastair Crooke on Judging Freedom Podcast titled “Trump and Chaos” premiered April 14, 2025.
The interview starts here:
Netanyahu’s Shock at US-Iran Negotiations
JUDGE ANDREW NAPOLITANO: Judge Andrew Napolitano here for Judging Freedom. Today is Monday, April 14, 2025. Alastair Crooke will be with us in just a moment on Donald Trump and chaos.
I’ll stare. Good day to you, my friend, and welcome here. Before we get to your fascinating analysis of Donald Trump and chaos, let’s talk a bit about Benjamin Netanyahu and chaos. How, in your view, how stunned was the Israeli prime minister when he was sitting in the Oval Office next to the American president who announced that the United States would soon commence direct negotiations with the government of Iran?
ALASTAIR CROOKE: Yes, he was shocked. He says he knew beforehand, but it seems to me that that’s likely not true. He didn’t look as if he knew beforehand. His eyes were darting around. He was shocked. And he was shocked back at home because according to the Hebrew reports that we’ve seen, an agreement had already been reached for an attack on Iran between the US and Israel, that the plans were going forward and even a date set for this. And then so you can imagine this was a shock. Yes.
JUDGE ANDREW NAPOLITANO: You say that Netanyahu was of the view that an agreement had been reached, that this agreement involved Trump, or might it have been Israel?
Market Chaos and Trump’s Economic Reset
ALASTAIR CROOKE: I can’t tell you, but I mean, your friend Ron Dermer was a week in Washington, so I imagine he’d been around everyone that mattered during that time. And then Kurela, the head of CENTCOM, spent a couple of days down in the bunker at the Israeli Ministry of Defense preparing details. But perhaps that was when there was a date set for an attack on Iran. Anyway, for the moment, it’s on hold.
But I would say to you, you mentioned at the outset the Trump chaos, and really, I think the Iran outcome is going to depend heavily on precisely this chaos. What do I mean by that? Why am I saying the chaos is so important? Because what really spooked Trump during this period, during the time just after he announced his tariffs, according to most of this financial press, was the bond market, not the stock market, but the bond market, the debt market, because that started dropping and yields started rising quite dramatically.
This was upsetting a very delicate trade in the market called the basis trade, which is a sort of very complex, highly leveraged casino bet. And I think Bessette was so worried by that that he took his airplane and flew down to Mar-a-Lago and said, listen, you’ve got to start winding this back and got to say there’s going to be a moratorium because, if this unravels, if this basis trade unrolls, which is about a trillion dollars in the market, we’ll be back at 2008 and you’ll have a real crisis on your hand.
What happened in that crisis, what was the crucial thing that is going to affect the Ukraine war and it’s going to affect what happens in Iran, was that Trump managed to hold together the team. He was very worried at points that the chaos, the turmoil in the markets, the sort of anger about what was happening on markets was going to split his team. The team is already split. It’s quite clear that some of the coalition, the Republican coalition that was put together, that has existed so far under Trump was already fragmenting a little bit. Parts of the Republicans in the Senate were getting very anxious about what was happening to people’s share prices and everything.
What has this got to do with Iran? What has it got to do with Ukraine? Well, a lot. The most important thing for Trump, the absolute key to his position is about doing this reset of the domestic economy, about rebalancing the economy so that industrial manufacturing will be regained back in the United States. This is what his supporters want. They want the jobs back. That’s what is key about it. So this matters more than anything.
The Ukraine Plan Split
JUDGE ANDREW NAPOLITANO: All right, before we get into what—
ALASTAIR CROOKE: I was just going to finish off, just say what really split it. What we see the big split taking place was caused by Keith Kellogg. Keith Kellogg came back, presented his plan and several of the team supported him. It was one that would never be accepted by Russia. It was a very hard line, pro-Ukrainian plan that would see areas of responsibility.
It is quite clear to me that this reflects input from Starmer and Macron and the Europeans, who, as I think everyone on this program knows, are intent on destroying American normalization with Russia. They don’t want it. They want to continue the war till 2030. They want a big war in Europe.
And so what Kellogg was doing was actually saying that beyond the River Dnieper, there’s going to be NATO, British troops, French troops, whatever other troops volunteer. They will be behind the Dnieper. In front of the Dnieper, up to the contact line would be the Ukrainian forces and then there would be the Russian forces. So it was a form of separation into segments. And of course, this was completely unacceptable to Russia. He should know that. He acts very much as Ukraine’s advocate in these things.
And he took with him Rubio, Waltz and others who said, yeah, this is right. And he contested what was going on. He was contesting what Witkoff was proposing, which was to recognize the four oblasts. As Putin has always said, that is the minimum to start anything moving towards a ceasefire.
He said that in June of 24. And he said, these four oblasts, which are already part of the territory under our constitution, which have had the referenda, they wanted to join Russia. This is the minimum.
And here is Kellogg coming out and driving a horse and cart through the whole of the process and saying, I don’t believe this will be acceptable to the Ukrainians. Well, of course it’s not acceptable to the Ukrainians. And what Witkoff was saying is not acceptable to the Europeans. They don’t want it either. And so it was setting Trump up for a big clash.
Already you can see the result of that is the talks are in trouble. Because unless Trump comes down on one side or another and he says, I back Witkoff, or if he says he backs Kellogg, he has a potential split in his group. And it’s like contagion, because that is the last thing he needs when what he wants is to keep everyone supporting his trade, his tariff policy, his devaluation of the dollar policy.
The Iran Dilemma
All of this is absolutely central to what Trump needs because he wants a normalization. But he’s got to keep his team, which involves a lot of people. They were already unhappy with Witkoff, many of them saying there was a complaint made to Waltz. Many, particularly in the Senate, say he leans too far to Russia. He’s too far gone. We can’t allow this to go on. We must stop this and we must prevent it.
This is a real problem for Trump, because he’s got to keep his support base there. They stood with him during the crisis. They’re a little unhappy. They’re very unhappy with Wyckoff and what’s happening there. I mean, this faction, not all of the Republicans, but this faction. And then there are the talks in Iran.
What is the connection? If you look at keeping the team together, 90% of the team are Israeli firsters. They’re all extreme. I don’t know what was the sort of Faustian bargain, but Trump did a deal with the most nationalist, with the hard people on Israel. So if he’s going to keep his team together, maybe the only thing is to give up Iran to them, to keep the team together, because of the economic program being his signature program.
And it’s not going that easily. There is chaos and there is a lot of unhappiness. So Iran is quite different. There is a constituency in the Republicans that wants to see the Ukraine war end and finish, even if the neocons don’t. But ordinary Americans would say, oh, well, we agree Iran mustn’t have a nuclear weapon. Most would go along with that.
So that’ll be a price. Maybe the price it will be paid. And certainly, if we find, as I somewhat expect, Witkoff comes back from Tehran and says, oh, the Iranians are putting forward a plan whereby they will reduce the amount of enriched uranium and they will allow inspections and they give undertakings that they won’t go towards weaponization. And many of Trump’s own team will say, well, look, this is just a runaround to the same old bad deal that we had that you got rid of in 2018. It’s the same deal. What’s different? Nothing’s different with that. We want something more than that. And either it’s got to be a Libya solution where we go in and we blow up the whole of the infrastructure of Iran, or we end up having to go to war with Iran.
The Bond Market Crisis and Iran’s Position
JUDGE ANDREW NAPOLITANO: So there’s a lot to unpack here. Let me stop you, Alastair. It’s a brilliant analysis. There’s a lot to unpack here. I don’t think the Trump people realize that the bond market would give them the problems that it did. The United States government cannot operate without people lending money to it called purchasing bonds. The bond yield went up to 4.5% as the current bonds out there. There are $31 trillion worth are retired and rolled over. They draw the higher interest rate. The government doesn’t even have the money to pay the interest on the bonds if they continue to go up. Trump’s people didn’t think of that.
As for Iran, I mean, why would Iran ever accept the Libya solution? They, I would think, would rather go down fighting than allow the Americans and the Israelis to come in and dismantle them and emasculate them and effectively destroy their sovereignty. Don’t you agree?
ALASTAIR CROOKE: Yes. It would be the end of Iran in the way that we’ve seen the end of Syria. I mean, it would be such a humiliation that I think then it would be a form of serious situation could take place now. They’ll never accept that. They’d never accept to be so humiliated that they risk the whole republic.
Netanyahu’s Domestic Troubles
JUDGE ANDREW NAPOLITANO: Back to Netanyahu. What kind of trouble is he in at home?
ALASTAIR CROOKE: Oh, getting deeper and deeper. Just as we speak, there are petitions going around whereby the Air Force officers and about 250 Mossad former officials, Mossad intelligence. This is not Shin Bet, this is Mossad now saying the war in Gaza has got to end and the hostages have got to be released. And we know Netanyahu is obstructing.
We are really in the most bitter confrontation taking place inside of Israel at the moment. Netanyahu is secure, but the bitterness and the sense—I mean, reservists are not turning up to serve in the army. They are refusing to serve. There’s a big shortfall. There’s a great deal of tensions about his policy of going back into Gaza again.
And also they are edging closer and closer to some sort of conflict in Syria where Israel is bombing right up to the airports in the center of Syria in order to make sure that the Turks can’t get them, because the Turks have announced they are going to take those areas and they’re going to establish main air bases in the center of Syria. And Israel is engaged at the moment in trying to stop them.
Netanyahu’s Legal and Political Challenges
JUDGE ANDREW NAPOLITANO: Are Netanyahu’s own legal and political woes continuing to get worse? I read an article that you published indicating that members of the Knesset, the hard right members of the Likud Party, are actually going into court where Netanyahu was on trial and disturbing the court to the point where they have to be physically escorted from the courtroom. In America, this would result in incarceration. But maybe it’s some standard operating procedure in Israel, I don’t know.
ALASTAIR CROOKE: Yes, we’ve seen this. The police are attacking the demonstrators strongly. And so some of the demonstrators are going into the court. They’ve already disrupted the Knesset. They did, if you recall, just invade some of the forces of Ben Gibir, invaded a military installation and took out people that they wanted to take out of it and stop the proceedings. So the point I’m trying to say is this whole thing is just only just holding together and without the support of Trump, this thing could come apart altogether.
JUDGE ANDREW NAPOLITANO: Netanyahu needs war to stay in power. He needs either to continue the war in Gaza, which isn’t a real war, it’s just a genocide, or he needs to start a war with Iran, with US backing, or both.
ALASTAIR CROOKE: Yes. The problem for him is the war in Gaza has become so discredited by senior military officers, by security officials, all of them are the same. And the last figures that came out from Haaretz in the English language Israeli newspaper showed that Hamas had 40,000 forces on the ground after all of this. This is not me saying that. This is the Israeli statement saying that they estimate they still have 40,000 armed forces in Gaza.
So the thing is it’s not such a winning solution for him, he wants a big win. So where can he get a win? Well, Syria is not so great at the moment. Lebanon is complicated, very complicated. So really, Iran is the thing that if he can push Trump towards it.
What I’ve been trying to say to you is that I can’t see, given what Trump said when he exited the JCPOA in 2018. He said this agreement is no good because it doesn’t deal with Iran’s missiles, it doesn’t deal with their weaponization of Hamas and Hezbollah and all of those things. That’s why I’m leaving it, and that’s why I’m putting sanctions on everybody, including the Europeans, who dealt with Iran illegally in the JCPOA.
Why the Europeans have now started, if you like, said to the Iranians, Euro 3, who are part of the JCPOA, have said to them, by the end of June, we will trigger sanctions snapback on you for failure to stay within the JCPOA limitations. So I think there will be, I’m sure, quite strong pushback on Trump if they come back with a proposal which is basically just to revert to the JCPOA, because everything they’re saying, it’s only about the nuclear program, only going to be limiting their ability to move towards a weapon. Well, all of that was in the first JCPOA, which Trump walked out of, because it didn’t deal with Iran’s conventional defense forces and didn’t deal with its proxy forces around the world.
Trump’s Tariff Policies and International Reactions
JUDGE ANDREW NAPOLITANO: How were the Trump off again, on again, off again tariffs reviewed by elites in Moscow and elites in Europe? Do they think he knew what he was doing? Do they think he got caught with his pants down over the bond market? Or do they think this is some sort of a technique to negotiate the grand reset?
ALASTAIR CROOKE: No, I think they have a very good idea what’s happened. And I think what you hear quite clearly out of Moscow, they understand that there are now divisions, quite deep divisions within the most senior elements of his own team, between those that support Kellogg’s really very sort of, shall I say blinkered and pro-Ukrainian proposal, which sees no concessions by Ukraine whatsoever, and the demand for a sort of immediate ceasefire. And Witkoff and others, who obviously is regarded as someone you can talk to and who’s intelligent and very sharp.
So where is all this going to lead? I think increasingly cautious about the whole process now. I think that’s where it’s going. They’re not only cautious about it, becoming increasingly skeptical. And that’s why I think we’re seeing the beginnings of a really major Russian advance in Ukraine taking place. The forces are amassing in parts right across the front. And I think Russia is moving to its second option, which is simply to finish off the Ukrainian armed forces in the next period, trying to take Trump with them.
But I don’t know whether he’ll feel he’s able to go with them because he needs these people. This was the deal. This was the Faustian deal with the most sort of nationalist and Israeli first as he’s got. But his main deal is to change the economic domestic system. And now this is disturbing that support. It’s actually more than that. Keith Kellogg has put an absolute spanner in the works.
Trump’s Stance on the Ukraine War
JUDGE ANDREW NAPOLITANO: I want to play for you a clip from the president on Air Force One last night, Sunday night, Palm Sunday evening, as he was flying from his home in Florida back to Washington, D.C. and I want to ask you about his repeated statements that the war in Ukraine isn’t his war, it’s Biden’s war.
[VIDEO CLIP STARTS]
UNIDENTIFIED SPEAKER: Do you have a reaction to Russia’s Palm Sunday attack on Ukraine?
DONALD TRUMP: Oh, I think it was terrible. And I was told they made a mistake, but I think it’s a horrible thing. I think the whole war is a horrible thing. I think the war is for that war to have started is an abuse of power.
[VIDEO CLIP ENDS]
ALASTAIR CROOKE: They made him, and you were told.
JUDGE ANDREW NAPOLITANO: They made a mistake unintentionally. I believe it was. Look, you’re going to ask Deb. This is Biden’s war. This is not my war. I’ve been here for a very short period of time. This is a war that was under Biden. He gave him billions and billions of dollars. He should have never allowed. If he had any brain, which he didn’t have and doesn’t have, and now it’s being proven. He wouldn’t have allowed that war to start. I would have absolutely not. That war would never have taken place. But remember this, this is Biden’s war. I’m just trying to get it stopped so that we can save a lot of lives. They happen to be Ukrainian and Russian lives. But all I want to do is get it stopped. Legislation providing for US Military aid to Ukraine says at the discretion of the president, Donald Trump could stop this with a phone call. He could stop it this morning. Why do you suppose he hasn’t?
ALASTAIR CROOKE: Because of the divisions. Because there is a strong component and one that seems to be gathering strength, which is saying that Trump and Witkoff are leaning too much, are taking sort of Putin’s speaking points and using them. I mean, it’s all nonsense. These have been. The Russian position has been outlined so clearly all of this time. There’s no doubt about it. This is not something that came up. It’s been there well before Trump took office.
But he has his friend who’s doing the work, I mean, a lot of work, trying to build trust with the Russians. But there’s now a gathering sort of force against that. And that’s why he’s trying to distance himself from this and say, it’s not my war, it’s Biden’s war, which is something Bannon told him to do from the beginning. Steve Bannon said, you know, this will end up, you’ll end up owning it if you go down the route of supplying it.
And that’s what Putin has asked for specifically. He said, look, if you want to get the thing moving, stop the intelligence sharing, stop giving weapons to Ukraine, then we can talk about some sort of acceptable administration, UN administration of Ukraine that would allow elections to take place and a new government to form. But so far, he doesn’t move on those things, and so nor does therefore Russia. And the thing falls into stasis, entropy.
JUDGE ANDREW NAPOLITANO: Here’s what Ukrainian President Zelensky said last night on 60 Minutes about this. This is Scott Pelly, the 60 Minute anchor doing the translating.
[VIDEO CLIP STARTS]
SCOTT PELLY: Sadly, Russian narratives are prevailing in the U.S. how is it possible to witness our losses and our suffering, to understand what the Russians are doing and to still believe that they are not the aggressors, that they did not start this war? This speaks to the enormous influence of Russia’s information policy on America, on US politics and US Politicians.
[VIDEO CLIP ENDS]
JUDGE ANDREW NAPOLITANO: Not sure where he thinks he’s going to ingratiate himself with the President of the United States with that.
ALASTAIR CROOKE: Well, the gun sights were quite clearly pointed at Witkoff. There’s no doubt about that. That’s the person he claims is too close, who’s taking Russian speaking points and delivering them back to Washington. And he’s interfering indirectly into the policy making of Trump by this.
I imagine Trump is not a fool, he’s smart. I guess he sees this, exactly what he’s doing and how. The Europeans, who’ve been desperate to try and sort of get some sort of token NATO force inside Ukraine have persuaded Keith Kellogg to go along with this idea and to have them sort of sitting there as a sort of reassurance force for the future. It’s a tripwire force is what they want because they want the war to go on.
JUDGE ANDREW NAPOLITANO: Right, Alastair, thank you very much. Boy, we’re all over the place today and I appreciate the breadth of your knowledge and your patience in allowing me to take you from Iran to Ukraine to Israel to American monetary policy. Thank you my friend.
ALASTAIR CROOKE: All the best to you and to you. Thank you.
JUDGE ANDREW NAPOLITANO: Thank you. And coming up later today at 10:00 in the morning Eastern, Ray McGovern at 11:30, Larry Johnson at 1:00 our friend Kevork Almasian who used to be in Syria but is now elsewhere in the Middle east will be giving us the latest on Syria. And at 3:00 Scott Ritter, Judge Napolitano for judging freedom.
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