Transcript of ‘Judging Freedom,’ 27 August edition

Transcript submitted by a reader

https://www.youtube.com/watch?v=TI2k2jbku8c

Napolitano: 0:32
Hi everyone, Judge Andrew Napolitano here for “Judging Freedom”. Today is Wednesday, August 27th, 2025. Professor Gilbert Doctorow will be here in just a moment on Trump’s confusing signals. But first this.

0:49
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1:59
Professor Doctorow, good day to you, my friend, and thank you very much for joining us and for accommodating my schedule.

In the past week, President Trump on his own Truth Social has written that Ukraine is doomed to lose the war unless it can get offensive and attack Russia, in a Truth Social that we have been posting, you can see it right there. He also authorized the delivery of 3,000 E-ROMs, offensive missile weaponry that can travel 280 miles. That’ll take about six weeks for them to get there. And just yesterday, he said he has something very severe in mind for Russia if President Putin doesn’t sit down at the same table in the same room at the same time with President Zelensky. What kind of signals is he sending to the Kremlin?

Doctorow: 2:54
Well, they’re not good ones, but I don’t see any sense of alarm coming out of Russia. They’re rather calm about this. Mr. Trump changes his– he pivots this way and pivots that way, in accordance with domestic American politics and where he sees the greatest threats to his position.

In this sense, Mr. Trump is not a great departure from other presidents and from the American political establishment for whom the rest of the world are just props. The only thing that counts in foreign policy is domestic policy. And that dictates many things. I was asked earlier today about the American initiative in the United Nations to reinstate the sanctions against Iran.

3:51
And in Tehran, they’re very upset about this. They take this, shall we say, personally? My point is, there’s nothing personal about it. If Mr. Trump sees himself under threat for one or another issue, however unrelated it is, for example, to Iran, then he will take action on Iran.

And if it’s the most convenient and less costly thing that he can do to flex muscles and to prove that he is macho and still in control of everything.

Napolitano: 4:27
I realize that you and I agree that he is often driven by his own personality and his own ego. He doesn’t have the moral or ideological or value-laden sense of some of his predecessors. But what is to be accomplished by these threats? How can he expect the Kremlin to react positively, or do they just dismiss it as, “Oh, there he is changing his mind again, he doesn’t mean it, he’ll back off, what can he possibly do to us?”

Doctorow:
I think it’s the second situation. We don’t know what back channels there are, what messages are being sent by Washington to the Kremlin to reassure them that this is not going to be what it looks like. If it is what it looks like, then we have World War III. So then we all should be quite excited about it. What I mean is that the Russians have made definite threats, what they will do to the suppliers of long range missiles that are being used against them deep inside the Russian Federation.

5:40
And this would be in direct, this shipment of these 3,600, whatever it is, medium-range, oh, 480 miles is pretty good. If that is used as the Ukrainians would normally use it to destroy civilian infrastructure, to kill ordinary Russians and not to attack military posts, then the Russians will have to, if they want to follow through on their red lines, attack Washington.

So I don’t believe this is going to happen. He’s making sounds and he’s silencing critics of one kind or another, maybe in relation to his policy on Gaza. It’s hard to say exactly what is motivating him.

But I would go a little bit in variance with what you said about his ego. I don’t think he’s ego-driven. I think it is policy-driven. But it is political threats that he’s responding to. They are real threats. And he responds in what seems to be illogical and unrelated manners.

Napolitano:
Here’s his threat yesterday, Chris, cut number two.

Trump: 6:50
I want to see that deal end. It’s very, very serious, what I have in mind, if I have to do it. But I want to see it end.

I think that in many ways he’s there. Sometimes he’ll be there and Zelensky won’t be there. You know, it’s like, who do we have today? I got to get them both at the same time. But I want to have it end.

We have economic sanctions. I’m talking about economic, because we’re not going to get into a world war. I’ll tell you what, in my opinion, if I didn’t win this race, Ukraine could have ended up in a world war. We’re not going to end up in a world war.

And it will not be a world war, but it will be an economic war. And an economic war is going to be bad. And it’s going to be bad for Russia. And I don’t want that.

Napolitano:
–done a damn thing to dial back the violence. If anything, it’s accelerated in the past eight months.

Doctorow: 7:49
Well, this brings us to the point. I think the hidden message from Moscow is what he said to Netanyahu months and months ago. But in Netanyahu’s case, it didn’t serve his interests. His interest is to keep the fight going, but to keep in, to stay in power. Mr. Putin doesn’t have a problem staying in power. He doesn’t need a war to stay in power. So the issues are a little bit different, but Trump’s behavior towards them both is the same: get it over with fast. And frankly speaking, the Russians are getting it over with much faster than they were before Mr. Trump made his threats.

Napolitano: 8:29
Yesterday, President Zelensky said he would never voluntarily surrender the oblasts in the Donbas region or Crimea. It sounds ridiculous. But is he free to make those concessions? Or would he do so at the peril of the loss of his life?

Doctorow:
Oh, I think it’s the latter case. I think the Russians are solving that predicament for him. The way they are progressing now, along the whole front, taking every soft spot they can, even if it’s not in Donetsk, even if it’s not moving closer to the Dnieper, they are taking territory and position, making emphasis on position. They moved into and took one or two towns in the new oblast for them, the Dnepropetrovsk oblast. We know about that area because there the only use of Oreshnik was to destroy a factory, military factory, heavily fortified and underground factory in Dnipro. Dnipro is the Ukrainian word for Dnepropetrovsk. And this area is of symbolic importance, the same way that taking Kramatorsk and Slavyansk in Donetsk oblast, is symbolic, because that’s where the– that was the cradle of the Russian Renaissance, the resumption of spirit and self-confidence that came in 2014.

10:07
So this Dnepropetrovsk is more than a physical acquisition, it is a symbolic acquisition, because that is the home base of Kolomoisky, the oligarch who from the start financed the Azov battalion, who financed a lot of the dirty operations against Russia.

Napolitano;
Right.

Doctorow:
And was one of the wealthiest men controlling, owning the most important bank in the country and owning the airline and calling all the shots. Well, that’s where he came from. So this is a territory, if they move on Dniepropetrovsk, they are going at the jugular of the…

Napolitano:
What actually happens or changes on the ground when the Russians take a village Does the government of the village change? Do the police in the village change? Does everybody go back to speaking Russian? Or are these takeovers of villages, which we’ve never heard of here in the US, just symbolic or part of the pathway toward the Dnieper River?

Doctorow: 11:21
It is more than symbolic. It’s clearing the way for reconstruction and for resettlement. There aren’t too many people in those towns that are taken, to greet the incoming Russian soldiers. Very few have remained behind, because they were under threat of being shot by the Ukrainian soldiers for not evacuating with them. So there are very few people in their cellars or whatever who are there to toss flowers to the incoming Russian soldiers.

The main task that the Russians have is demining. And they send in their specialists to remove the mines, because everything is mined after the Ukrainians leave a village. Well, I say village; most of these places they’re conquering really are hamlets. Maybe they have two, three, 500 inhabitants. They’re not a village in the sense that you had in mind.

And they don’t have mayors and high officials. But this is very important. Mr. Putin yesterday had his meeting one-on-one with the governor of Kherson oblast. And this is an area that is highly contested.

The Kherson city, the capital, is on the right bank, that is say the west bank of the Dnieper. It is under Ukrainian control. It was evacuated by the Russians as untenable. They had to cross the river to supply it.

But most of that, Kherson oblast is in Russian control on the east side of the Dnieper. And they were discussing the vast reconstruction program that’s now ongoing, building 600 kilometers of new asphalt roads and all kinds of infrastructure. And taking each of these little hamlets and villages is extending the territory in which Russia will restore normal living conditions, rebuild housing, and so forth. So it’s more than symbolic that when they take these, they’re preparing to move in immediately to restore normal living in these places.

Napolitano:
And who pays for this reconstruction? The Russian Federation, or is it private investments, or is it BlackRock in the U.S.? Who’s paying for it?

Doctorow: 13:41
It is multiple layers of the Russian government. You have cities in Russia like Moscow, which have city-to-city brotherly relations with this or that town, the same thing as St. Petersburg, and they put up their own laborers, their own equipment and so forth, to do construction work and then to build new housing for the returnees.

You ask which language they speak. Almost everyone in these territories speaks Russian. The idea they’re– or they’re bilingual, Ukrainian, Russian. Let’s not confuse the language with the ethnicity. There are ethnic Ukrainians, if you can define that, who are Russian speakers. That was the predominant language in the region where they were living. So that is not really an issue.

Napolitano: 14:38
Right.

Doctorow:
Even on Ukrainian television, you have a lot of officials who are interviewed and are speaking Russian. That was the language.

Napolitano:
Isn’t it illegal, even criminal, under Ukrainian law to speak Russian?

Doctorow:
It is. But practicality says if you want them to say something, they’ll say it in a language they can speak.

Napolitano:
Right. Foreign Minister Lavrov says no Putin-Zolensky meeting without an agenda. What does that mean?

Doctorow:
Well, they have an agenda. It’s a negation of the agenda by Zelensky. As soon as he got back home following his trip to Washington, he was saying that in no way will we accept surrender of territory. And that put a big “nyet” on the whole logic of the meeting, because Trump himself had said the prime purpose of the meeting would be to discuss exchange of territories, meaning Ukraine ceding its loss.

The question, of course, is that if you go into this, the Ukrainians, if they were to cede anything, would be de facto rather than de jure, they would maintain their claims. But the United States, at least with regard to Crimea, already stated openly that it is willing to acknowledge Russian governance of Crimea, de jure. What happens to the rest of the other oblasts will be a subject for negotiation at present or perhaps at a given time in the future.

Napolitano: 16:09
India is thumbing its nose at Trump’s tariffs, which are now up to, I think, 60 percent. Are you surprised?

Doctorow:
There has been some very reasonable analysis of what actually is happening on these tariffs. The most important component of Indian exports to the United States are not commodities, they’re not products. It is IT, it is technology, it is software programming. So I think $38 billion in that. That’s not touched.

Pharmaceuticals are not touched. And we all know that India is a big producer of generic pharmaceuticals, which are in big demand because they cost a fraction of the price of the original owners of the medicines that we’re talking about. These are not touched. What is touched are this: many factory operations were started up in the last two or three years to replace production that otherwise had been going on for American companies in China.

And so this is affected. The products that were being made in India to replace their production in China are under direct threat and become unviable as exports to the United States. That is surprising, but I’m just saying that the Indian commentators do note that it is more complicated than it looks. Nonetheless, Mr. Trump has undone in a matter of a couple of months, what the United States took perhaps 10 years to achieve as a foreign policy objective: to use India as a counterbalance to China and to invite India into its partnerships relating to the Indo-Pacific area.

18:05
That’s all undone. And it’s remarkable. That is the most astonishing reversal, and I say loss of American influence, that Mr. Trump has done since taking office. Mr. Biden pushed Russia into China’s arms, and Mr. Trump is pushing India into Russia’s arms. And also into China’s arms. Mr. Modi is going to China, I think, in the next week or two.

Napolitano;
Right.

Doctorow:
This will be the first visit in seven years.

Napolitano:
Is it fair to say that for all of his bombast and threats and animosity toward BRICS, he’s actually strengthening it, Trump?

Doctorow:
Absolutely. That’s a perfect summary of his achievements from seven months in office.

Napolitano: 18:52
Wow. Last week, the Russians destroyed not- yet-assembled Taurus missiles that had been delivered by Germany to Ukraine. Did Chancellor Merz think that the Russians would allow the Ukrainians to assemble these things and start firing them?

Doctorow:
Well, the Russians did very important damage to the whole missile program in Ukraine, both the deployment of weapons that are received from outside and the construction of weapons using British and other Western technologies. One of the big issues that drove Mr. Trump– if you want to speak, want to find rational decision-making in what he’s been doing for the last 10 days– one of the most important factors was the destruction of the Flex Factory. This was nominally making coffee machines for consumers in Ukraine, 30 kilometres away from the Hungarian border. A company called Flex, I believe, which was the local branch of an American electronics manufacturer. Now, Mr. Trump had to react to that.

20:18
This was, I don’t know, this was a billion dollar or so, so it was a large investment had been made by Americans in this military production, intending to create strike missiles in Ukraine. This was utterly destroyed by a combination of drones and hypersonic missiles. Flattened, destroyed. It took Mr. Trump a day to react.

Of course, he must have been under enormous pressure. “How do they dare?” Just as Mr. Merz must be concerned, “How do the Russians dare?” Well, they dare.

In this sense, there’s acceleration, escalation I should say as well, in what the Russians are doing. Before, they didn’t touch manufacturing facilities owned by foreigners. Now they are. And it was a big signal to the Brits, to the French, to the Germans, don’t even think of setting up military facilities, production facilities in Ukraine, because they will suffer the same fate.

21:17
So in a number of ways, the various threats that Trump and others have made, the various attempts to have a real military presence in Ukraine– such as assisting the construction of latest generation strike missiles there– that has touched a nerve, and the Russians have responded, I’d say, violently.

Napolitano:
I’ll tell you what I’m concerned about, Professor Doctorow, and I wonder if you share that concern. And that is the resurgence of the neocon whispering into Donald Trump’s ear. General Kellogg, Senator Graham, Secretary Rubio. The type of threat that Trump made yesterday. Maybe it’s just an idle threat. He often talks off the top of his head. I can’t imagine he’s run this past his advisors first. But I’m worried that that neocon attitude may be resurgent in the behavior of the American president. Do you share that fear?

Doctorow: 22:28
No, I don’t. There are limits on what he’s going to do. And the limits are: if he were to do what he said about giving the Ukrainians these 5,000 missiles and letting them have a go at it, then we’ll have a war. And the last thing he wants is a war. He had just said in the segment that you quoted that he wants an economic war, not a kinetic war. And I believe that is a deep-set feeling.

As to the whisperers, again, this is part of his drama, of his theatre. Not everybody is deceived. There are a few people around who have their wits about them and understand what’s going on, even in Europe. Even in Europe. There were two days ago in a broadsheet publication as a large-format daily newspaper, the “Écho de la bourse”, there was an article interviewing a leading French European security specialist talking about how the European response to Trump and his seeming pivot towards Putin and against themselves explaining that it’s a little bit more nuanced than one would think, that Europeans aren’t complete dolts.

They understand that he could be playing with them, that he could be stringing them along, but they have a choice of two ways to react. One is to turn their back on him and to go against him, to dig in their heels. And the other is to humor him, to play to his vanity and to think that they can bring him around. And the second policy has a little bit more depth to it than it appears. It is that they don’t want to be seen as being that monkey-wrench in the works that Mr. Putin was talking about. They don’t want the failure of Trump’s peace efforts to be their doing. They believe that Mr. Putin will do it and let him take the flak, let him take the opprobrium from Trump for destroying his chances of getting the Nobel Peace Prize and ruining the peace negotiations. And that could be, there’s a logic to that. It makes them look a little bit less stupid than they otherwise seem to be.

Napolitano: 25:01
Right. Before we go, what is the significance, if any, of the arrest in Italy of this Ukrainian intelligence officer? I think I have this right.

Doctorow:
No, you do. I was very glad you brought it up because while very little is said about it in Western news, a lot is said about it in Russian news. And they’re covering it closely. Today’s had a release on the ticker tape news in Russia that you find on their Yandex, that he was the head. The man who was arrested was a Ukrainian officer who was supervising a team of seven saboteurs, of various specialties, who carried out the preparation of destruction of the Nord Stream 1 pipeline. But that doesn’t take away from Sy Hersh’s story that the whole thing, the whole concept was American and that Biden approved the timing and that this was a setup for whenever the American president decided the explosive would be detonated.

26:17
That doesn’t change. But it does tell you that, and as Russians are saying, in fact, the only aspect of this that interests them is this team was Ukrainian and that it could never have been authorized without the personal approval of Zelensky. And they’re saying, and what is Mr. Merz going to do about it?

Napolitano:
And what was this team of Ukrainians doing in Italy? Where in Italy? In Rome?

Doctorow;
No, no, It’s one man who’s captured, as far as I know. And there is an arrest warrant out for six others who were his subordinates in this team that carried out the preparation of the destruction of the pipeline. And I suppose he’s simply enjoying the money that he received for his work.

I think he’s just gotten away from the hardships of Ukraine. I don’t believe that he’s out there in Italy on assignment. Certainly that his team isn’t there, because the job was done.

Napolitano:
Professor Doctorow, thank you very much. Thanks for the broad array of topics. Thanks for the tip on the arrest in Italy. Great chatting with you, my dear friend. We have a holiday coming up here in the US, Labor Day weekend, but it should not interfere with our work next week, and I look forward to it already.

Doctorow:
And I do as well. Thank you.

Napolitano:
Thank you. All the best. And coming up later today, actually beginning shortly at 11 this morning, Professor Jeffrey Sacks; at noon, Aaron Mate; at three this afternoon, Phil Giraldi. Tomorrow, Colonel McGregor and Professor Mearsheimer and Colonel Wilkerson.

28:03
Judge Napolitano for “Judging Freedom”.