Transcript of ‘Judging Freedom,’ 20 August edition

Transcript submitted by a reader

https://www.youtube.com/watch?v=A9pivYDY8gY

Napolitano: 0:34
Hi everyone, Judge Andrew Napolitano here for Judging Freedom. Today is Wednesday, August 20th, 2025. Professor Gilbert Doctorow will be with us in just a moment on what does the Kremlin think of Trump now? But first this.
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2:00
Professor Doctorow, welcome here, my dear friend. Let’s start with Alaska. If President Putin’s goal was to appear presidential on the international stage and to educate in private President Trump on the genesis and the causes of the special military operation in Ukraine, it appears he succeeded. Do you agree?

Gilbert Doctorow, PhD 2:32
Yes and no. I think that President Trump was predisposed to change his position as he did during that meeting, and it was only partially as a result of the tutorial he was given by Putin. I think everyone, absolutely everyone, including myself, have underestimated Team Trump. I stress the word “team” as opposed to– we spoke about the collective Biden; there is a collective Trump. And that is to say he has some very, very clever advisors assisting him. I believe that in this case, just as in the case of the United States security guarantees that we probably could talk about later, Trump’s position is already made up and he is saying what he needs to say to keep his opponents off balance and to prevent their striking too early when he hasn’t yet got his ducks lined up.

3:30
So what do I mean? He didn’t know exactly whether he could do a deal with Putin until he met Putin. And he was persuaded that he could, and therefore he changed positions for the outside world, not for the inside world. I don’t think he needed Mr. Putin to give him the lessons on the root causes. But that is what was convenient for him to allow to happen.

Napolitano:
You’re telling me that all along he knew that his demands for a ceasefire made as recently as during the Air Force One flight from Washington to Alaska was not something he truly expected to happen or not something he wanted and he was just duping people or lying to people or again trying to keep the other side off guard?

Doctorow:
All of the above. That is the latter part. He knew what he wanted. Just as this whole question of the security guarantees, he is stringing the Europeans along. He has no intention of giving US security guarantees for this, because he knows the Russians are dead set against it. But he is saying that to keep them, well, let them play with their toys. And while they’re playing with their toys, the problems will be solved.

4:43
And I believe that the same question comes up, how stupid or smart was it for him to say the next step is a face-to-face between Putin and Zelensky, without–?

Napolitano:
That’s just not going to happen.

Doctorow:
Yeah. Well, I think it could happen. But there’s something that Zelensky can do if he pays attention that would make it happen.

I refer now to Mr. Lavrov’s interview last night on Russian state television, which was very, very interesting. He said that, you know, we Russians, the territorial side of it has not been fundamental. It has been the human side of it, protecting our fellow Russian speakers, our fellow ethnic Russians in that area. And in that regard, we bitterly oppose, and we discussed this with President Trump, we bitterly oppose the language laws and the persecution of Russian speakers.

5:44
That was the very first act of the government installed after the coup d’état and which turned the Donbas region and the Crimea against the new government. That is to say the ban on speaking Russian in schools, the ban on speaking Russian in public, before public authorities, and the prohibition on dissemination of Russian language media.

Napolitano:
Yes, I saw that clip. He made a very interesting point. This is the only country in the world which bans the use of another language.

Doctorow:
Not true. We’ll get to step two. Step two will be Latvia, because they’ve been doing that since 2004, and the Russians have been quiet. I think when the Ukraine situation quiets down, the Russians will come back and revisit what is going on in Latvia. But Mr. Lavrov correctly said that these laws are in violation of the UN guarantees on human rights. Now, if I were in Mr. Zelensky’s shoes, which I really wouldn’t want to be in, I would take note of that. It was a strong hint by Lavrov, hey, you want this negotiation to proceed? Just revoke those laws. It’s a good start, a show of goodwill, and then we can sit down and talk.

Napolitano: 7:06
It’s hard for me to believe that Putin would be in the same room with Zelensky. Zelensky isn’t even the legitimate lawful head of the government.

Doctorow:
The reason why the Russians have been unwilling to, is partly, what you just said, is a major factor. And of course, the West has turned that back on Putin by saying that Putin isn’t legitimate. He’s a wanted man by the International Court of Justice. So that is all a question of a public spat. But I think the issue is that Zelensky has pushed for such a face-to-face because he knew that the Russians didn’t want it, and he expected that to make it possible to say that they don’t want to make a peace, “You see? I told you, they don’t want to come to a meeting and make a peace.”

Napolitano:
Right, right. How was the Russian trip perceived in three categories? By the Kremlin, by Russian elites, by the average Russian folks — in your view from your observations in Europe?

Doctoorow:
You’re speaking now of the … which trip exactly the one going to Alaska, or…?

Napolitano
Yes. Yes. How was Putin’s trip to Alaska with Trump perceived by and how was it perceived today, four days later, by the Kremlin, by Russian elites and by Russian folks?

Doctorow: 8:38
Well, Russian folks, I think, may have been a bit skeptical about it. Russian influencers in the creative classes were probably 100% behind it, Russian intelligentsia has a lot of anglophiles, people who can’t conceive of a summer vacation without being on the Cote d’Azur, and all of those people were very happy about this.

As regards the entourage of Mr. Putin, I think they were strongly in favor of it. Partly as a validation that all attempts to isolate Russia have totally failed. The economic sanctions failed. The military efforts on the battlefield failed. And now the pariah status that the EU and the United States under Biden was assigning to Russia have failed because now here he is meeting not just with Xi of China or Modi of India or the Kazakhstans and the rest of it, he’s meeting with the president of the United States on American soil. He has a red carpet rolled out for him.

9:49
Russian television played this very positively. And I believe that their positivism was backed by the conviction they received from Putin and the people around him that Trump is genuine, is trying very hard, and is likely to succeed because his people around him are very clever.

Napolitano:
What did Trump accomplish from his own perspective?

Doctorow:
I think– I don’t know if he saw this, but he could have or should have. I’m sure that he has people who also are watching Russian television also. What I’m doing is not unique. We have intelligence agencies who have people in Moscow embassy, have people in Washington DC who are doing exactly the same thing. They just don’t share what they see with the general public. But these people would have found what I found, that the Russians, official Russia was very favorably disposed towards Trump.

They believe– my colleague, Ray McGovern, has called out repeatedly the issue of trust. And trust is there. In case anyone had doubts, Mr. Lavrov repeated it yesterday. They trust Donald Trump.

11:07
As I say, the collective Donald Trump. Nobody has any illusions of the, that he is running the show by himself.

Napolitano:
Well, it’s hard to figure out exactly where Trump is. I mean, at the end of the day on Friday, it sounded as though he was pushing the neocons under the bus. General Kellogg wasn’t even there.

The president says he understands the origins of the special military operation. He understands that NATO can’t be involved in the new Ukraine. And he understands that there’s not gonna be any ceasefire. This will end when it ends, either by a grand peace treaty or by Russian triumph in the battlefield. That rejects everything from Victoria Nuland to then Senator Marco Rubio.

11:57
Then on Monday, he makes the unmistakable impression of boots on the ground or boots in the sky over Ukraine working with European troops in order to secure, in order to guarantee some sort of security. That, of course, delighted the neocons. Put aside what the Russians will reject. You and I know, and everybody watching us now know what they’ll reject. [Foreign Affairs] Minister Lavrov has been very clear. Trump is speaking out of both sides of his mouth. Trump is trying to please whoever is in front of him at the moment. Agree or disagree?

Doctorow: 12:35
I disagree. He is trying to please his opponents who are in front of him. Let’s remember what happened in Washington, DC. He didn’t have to, Trump didn’t have to invite them in. In the past, he’s never dealt with them as a group. He’s only dealt with them one to one, and this was remarked upon as meaning that he would try to play them off against one another. This time he allowed the whole lot of them to come and visit him, and he humiliated them all in front of one another.

When he told them to leave the room during his meeting with them in the White House, to go to the Oval Office and wait because he had to make a call to Putin, because that was very important; then he spent 40 minutes on the phone with Putin, letting them wring their hands in the next room and understand that they had been treated like second-class people, which is what they are.

Now, I do not believe that he has any intention of providing security guarantees in the sense that the Europeans expect it and that he was just stringing them along, just as he was stringing them along on whether there would be an immediate ceasefire. If they don’t see it, then they are very stupid.

Napolitano: 13:56
Well, I don’t think your view and my view are very far apart on that, but I’m looking for President Macron. Here is President Macron the day after, which I guess would be yesterday before he left Washington. Chris, cut number 12.

Questioner:
As it relates to security guarantees, does that mean European troops, and does that mean U.S. Troops?

Macron:
Look, I think for me it’s a very important progress of the past few days that your president expressed a clear commitment of the US to be part of the security guardantees. It’s brand new. And last February, when I took the responsibility to gather a series of European leaders with President Zelensky in Paris, and we followed up in London, and we created this coalition of the willing.

And it was a reaction to the feeling we had that we could see a temptation to go to a rapid peace, but without any guarantee for Ukraine. And we know what it means. It was Georgia 2008, but it was as well Crimea 2014. And there is full certainty that if you make any peace deal without security guarantee, Russia will never respect its words, will never comply with its own commitments.

15:23
So it’s for us totally critical. And this is an essential part of any deal for Ukraine and for the Europeans. This is for our own security. So this is a very important progress of the past few days that the US now is willing to be part of this.

Napolitano:
“The US is now willing to be part of this.” He left that impression unmistakably with them. And it’s an untrue impression, because he must know that the Russians would never go along with it. What difference does it make if American boots are on the ground or if they’re on jets overhead?

Doctorow: 16:00
Well, let’s revisit this. I spoke categorically and I think I should correct myself. It is possible that Trump will participate in security guarantees, but not in the way that any of the Europeans expect or want. I was interviewed this morning by WION, the main, almost the largest Indian global broadcaster in English. And they are pretty close to the Indian government. And the, I was asked, or I was told rather, that the, there is talk that the Chinese are going to be invited in to take part in the peacekeeping mission.

Well, there you have it, Judge. It’s entirely possible they will. And in that case, the Americans can go ahead and provide air cover. But what’s the difference here? The difference is that a strictly European peacekeeping force, which would not be monitors in fact, they would be armed, they’d be ready to go into action. They would be a trip wire for direct European and American intervention in the war and then start or restart a war. They could provoke a new war.

Napolitano:
Right,

Doctoorow:
What was going on before the Russians moved in in February of 2022? The OSCE monitors who were along various parts of the border were reporting finally– because mostly they kept their mouths shut since they were being given instructions by Europeans– about [how] the firing of artillery and missiles against the rebelling provinces had stepped up enormously. And this sent messages to Moscow that yes, the anticipated “final solution” of the Ukrainian rebellion was about to start. And that the, because of 150,000 Ukrainian soldiers amassed next to the border ready to pounce on Donbass. And that that triggered the war.

Now this– what was going on was firing, massive firing of weapons against the East. If these Europeans were there as the so-called peacekeepers, who’s to say that they wouldn’t start firing artillery and missiles? And there you have it. They could end the Russian– yeah.

Napolitano:
What is a security guarantee? I mean, what is being guaranteed? Ukraine’s neutrality, or that the Russians won’t use military force against Ukraine? What’s the guarantee?

Doctorow: 18:50
Well, the Europeans and Zelensky are presenting it in the latter case. That the Russians are aggressive, they’re going to restart the war at the first opportunity, they want to take Poland, the Baltics and France at the first opportunity and so forth. This is, of course, rubbishy propaganda, but that’s what they’re saying, and that’s what the BBC is repeating. So that is their official position, and of course, it’s completely false.

The security guarantees that Trump might take part in would otherwise be called monitors. And they will be consistent– if it happens at all, there will be global-south countries participating. That would be probably acceptable to the Russians because it’s not a first step towards a pseudo-NATO Ukraine.

Napolitano:
What’s wrong with the Austrian model of true neutrality, no military activity, economic prosperity, personal liberty. It may have been you who pointed out to me that when the Austrian Treaty of Neutrality was agreed to with the old Soviet Union and everybody else, the Soviets actually had an official on the Austrian National Security Council and it worked out fine.

Doctorow: 20:12
That’s fine, if the West European countries can be brought around to it. In fact, one country seems to, in a most paradoxical way, the president of Finland, Alexander Stup, when he was in Washington, I’d say rather stupidly, commented that, you know, the end of the war in Ukraine could be similar to what happened with us in 1944 when we concluded a peace with the Soviet Union and gave up territory. And after that, we all lived happily together and prospered.

Napolitano:
Yeah, until they joined NATO.

Doctorow:
Until they joined NATO. And he undid– and he violated– Mr. Lavrov spoke about this yesterday in Russian television and reminded us what that treaty was in ’44. It was a treaty of permanent neutrality in which Finland was obliged never to join an alliance directed against Russia. And that’s what they’ve just done.

Napolitano:
Wow. … Well, I’m of the view that the war in Ukraine is not going to end by any kind of an agreement. It’s going to end when the Ukrainian military collapses. What do you think?

Doctorow:
It’s entirely possible. No one cab say. I don’t pretend to have superior vision on this. It really is, you cross your fingers and it’ll go one way or the other. But the one thing that is outstanding and certain is the Russians are going to win. The Russians will get what they want, the basic things that they want. And here, of course, there’s a lot of confusion about what do they want, but you’ve touched upon them.

They want neutrality, They want the size, they want the nature of the Ukrainian armed forces to be described and certain categories of weapons not to be delivered to them. And they want progress on the well-being of their ethnic co-nationals, you could say, who remain under Ukrainian control to end the persecution of these people, which is ongoing.

Napolitano:
You know, as we speak, this was not mentioned in any of the commentary and that’s American intelligence. If you’re going to have American planes in the sky, Mr. President, that means you’re going to have American intelligence on the ground.

Right now, There are still 20 CIA stations in Ukraine. American intelligence is still helping Ukrainian soldiers aim American equipment at Russian soldiers, and MI6 is doing the same. That’s not likely to stop, is it?

Doctorow: 22:52
Well, it depends on their agreeing on definition of armed forces. The CIA people that you’re describing are for all practical purposes an army, but as you yourself have discussed, they are an army, although they are outside, formally speaking, the US Armed Forces.

That goes counter to the Russian demand that there be no foreign military forces or installations on Ukrainian soil. So, all of this, but this, this, they have gone through all of this with the Ukrainians in March of 2022. And this was more or less accepted by the Ukrainians. So I don’t see something horrible, impossible to achieve now. It all depends on whether Mr. Zalensky can be persuaded to avoid 20, 30, 40,000 more unnecessary deaths of his soldiers. And will sign on to give up the Donbass now, rather than waiting until the Russians to conquer it.

Napolitano:
Professor Doctorow, a fascinating conversation. You always present a very unique viewpoint, and it’s deeply appreciated here and around the world for all the people that watch us. Thank you very much. We’ll look forward to seeing you next week.

Doctorow:
And I look forward to it as well.

Napolitano:
Thank you. Coming up later today at 11 this morning, Max Blumenthal; at one this afternoon, Ian Proud; at two this afternoon– I’m not sure where he is, but he’ll be here with us–
Pepe Escobar; at three this afternoon, Phil Giraldi.

24:27
Judge Napolitano for Judging Freedom.