"Transcript of ‘Judging Freedom,’ 29 May edition"
Gilbert Doctorow (May 29, 2025)
https://www.youtube.com/watch?v=FW9y77Z0TVQ

Transcript submitted by a reader

Napolitano: 0:34
Hi, everyone. Judge Andrew Napolitano here for “Judging Freedom”. Today is Thursday, May 29th, 2025. Professor Gilbert Doctorow joins us in just a moment on just how dire is the situation in Ukraine.

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2:21
Professor Doctorow, welcome here, my dear friend. Congratulations on your new book, “War Diaries …”, which, of course, we will discuss at some point during our interview today. I do want to start with the latest out of Germany. Has the decision of Chancellor Merz to deliver Taurus missiles to Ukraine without geographical limits made Germany a co-belligerent in the war in the eyes of the Kremlin?

Gilbert Doctorow, PhD:
Definitely, yes. I’d say the language has changed a little bit in the last week or two. Now, what Mr. Lavrov said most recently about Merz, is a hair’s breadth away from calling him a Nazi. Lavrov said that like Hitler, Merz is doing this and that. Well, like Hitler, it means that he’s already associating Mr. Merz with the Hitler heritage or legacy.

3:22
And that is a dramatic change in the language coming out of the Kremlin. The Russians have said very plainly that if Merz proceeds with this– and the last news, updated news is that they probably have already shipped the missile to Kiev. When Merz said yesterday that it could be, as soon as a few weeks from now, well, judging by the last three years, we know that when statements like that are made, the shipments have been made weeks before, so that we may assume that this missile is already in the possession of the Ukrainians. For the Russians, that is war.

Napolitano:
What do you expect President Putin to do about it? I mean, Prime Minister, or Foreign Minister Lavrov’s words are strong, but they’re just words. I don’t mean that to demean him, as you know, I’m very fond of him personally and professionally, but what do you think President Putin will do?

Doctorow:
I don’t think that President Putin has any margin for his own opinions in this matter. The latest opinion polls in Russia show that he has gone up to an 82 percent approval rating.

Napolitano:
Wow.

Doctorow:
But let’s not deceive ourselves. The popular mood in Russia has changed, whereas some of my peers and colleagues were saying as long ago as two years ago, that the Russian general staff didn’t like the go slowly approach, softly, softly approach of Mr. Putin and wanted something more dramatic. I didn’t put much credence in what they think or say privately, because the military is wholly under the control of civilian rule in Russia. However, the indications [are]–and this even came up in recent talk show programs from Moscow– that the popular mood has changed, and people are weary of this go-slow approach.

5:10
And they– I don’t believe that Mr. Putin would stay in power if he failed to respond to … attacks by the Ukrainians using the the Taurus missile against against their military or civilian assets.

Napolitano:
I know your field is not military tactics, but how far can these Taurus missiles reach? Can they reach Moscow?

Doctorow:
Not quite, but the objective that Mr. Merz himself made when he first discussed shipping them was to do something dramatic, something that would humiliate Moscow and would put Russia in an impossible position, the regime in an impossible position, namely to destroy the Crimean bridge. And for that purpose, the German missile is much more effective than the shorter range missiles from Britain and from France, the Storm Shadow, that were supplied previously. They are not, those were not in their targeting capabilities and in the power of their punch, they were not capable of delivering a really destructive blow against bridges or fortified underground positions. This missile, the Taurus, has that capability, and the Russians have no experience dealing with the unique features of its targeting and of its path. This is a cruise missile, so it has changeable paths of attack and is difficult to intercept.

7:09
For that reason, the Russians are particularly concerned about its becoming available to Kiev, since it could do what the previous deliveries from Britain and France and the United States with HIMARS were incapable of.

Napolitano:
One of our viewers writes that the range is 300 kilometers. Is that, if that is accurate, and if this is fired from Ukraine territory, can it reach that bridge?

Doctorow:
Well, the, as far as I know, 350 kilometers is the limit on Storm Shadow. The Taurus is 500 kilometers. And that is the significance of Merz saying two days ago that limitations on range no longer hold. He meant precisely the longer-range Taurus.

Napolitano:
Are the Germans prepared for a couple of Oreshniks aimed at their industrial base?

Doctorow: 8:13
I don’t think that Mr. Merz takes seriously the Russian threats. After all, he could say, with entire logic, that the Russians never responded to the American shipment of long-range missiles, the HIMARS, the ATACMS, they never responded to the Storm Shadow. However, that is ignoring the Russian view of Germany as opposed to its former allies. Russia is neuralgic, is hypersensitive to what the Germans do. And the recent celebration of the 80th anniversary of the liberation of Europe on May 9th, we were all reminded about the 26 million Russians who died in that conflict, largely due to German military efforts. And that is unforgivable, unforgettable.

9:09
So anything that Germany does, is a special case for Russia. And as I said, whatever the personal preferences of Mr. Putin, he cannot go against the popular will. He wouldn’t want to. The popular will in Russia is to differentiate between German missiles and the others, in a way that means the Russians will have to respond in a dramatic way.

Now, taking out military production facilities, I’m not sure that that would be the first thing that happens, because that particular facility making the Taurus has been idle for more than a year. They have not been producing it, so it wouldn’t accomplish much to bomb it out. That means that they will probably have to find another target for Orashniks. The Russian talk shows spoke vaguely about Berlin. What exactly is meant, we don’t know.

Napolitano:
Wow. Here’s Chancellor Merz two days ago on this very topic. Chris, cut number seven.

Merz:
There are no longer any range restrictions on weapons delivered to Ukraine neither from the British nor the French nor from us nor from the Americans. This means that Ukraine can now also defend itself, including, for example, by taking actions such as attacking military positions located within Russia, or by targeting other strategic sites as necessary. Until recently it was not able to do that. Until recently, with very few exceptions, it also did not do that. Now it can.

In jargon, we call this long-range fire, meaning equipping Ukraine with weapons that can attack military targets in the rear. And this is the decisive, this is the crucial qualitative difference in Ukraine’s conduct of the war. Russia attacks civilian targets completely ruthlessly, bombing cities, kindergartens, hospitals and nursing homes. Ukraine does not do that and we place great importance on ensuring that it stays that way. But a country that can only confront an aggressor on its own territory is not defending itself adequately. So, and this defense of Ukraine is now also taking place against military infrastructure on Russian territory.

Napolitano: 11:24
Before I ask you to analyze that, that was an AI translation from German to English using his voice, amazing what can be done today. What is he trying to accomplish?

Doctorow:
He is preparing a justification in advance for the deployment of these missiles, for their use in striking against Russian targets, and he is lying through his teeth. Everything that he said about the Russian conduct of the war is an outrageous lie scripted in Kiev.

12:02
It is precisely the Ukrainians that have been using terror techniques and deploying their drones and what missiles they have, primarily against civilian targets. That’s been the nature of the warfare going back to 2014. They were destroying civilian residential neighborhoods and playgrounds and hospitals and the rest. And that’s continued to this date.

They have used, the Ukrainians have made some attacks on militarily important facilities. But that is the number of such attacks versus their overall activity, like 2,000 drones were sent into the Russian Federation in the last two weeks by the Ukrainians. They knocked out, or they hit at least, one facility producing chips or something or other for military use. Otherwise it is all ambulances, buses and the rest of it.

13:07
So Mr. Merz is turning everything on its head. The reality is just the opposite. And the Russians have demonstrated this on air, what exactly they targeted and with what effect, because they have drones that inspect, that follow, monitor the destruction.

Napolitano:
Is it too early in his chancellorship for me to ask you fairly, in fairness to you, whether you agree with the Scott Ritter analysis that Merz is the most dangerous German Chancellor since Hitler?

Doctorow: 13:43
Well, I agree completely with that. He is utterly irresponsible, and he is courting disaster for his country. If he believes, and there’s another factor here, that he may well think, first, that the Russians won’t dare strike against Germany. There is dead wrong. They’ve said it openly. They will.

And second, that if they were to do so, then the United States and the other allies in the North Atlantic Treaty Organization would respond and come to Germany’s aid. Nonsense, maybe other European countries singly will do that, but the United States, I believe, will abstain. And that will condemn completely the notion of the united defense to save Germany from itself. Therefore, Germany will likely suffer uniquely Russian revenge.

Napolitano:
Wow. Let’s transition a little bit. In one of your recent pieces, you wrote about the things Ukrainian soldiers returning from the front are saying about their Russian counterparts. What are they saying?

Doctorow:
Well, I want to point out that this came from an article that was posted by a non-staff person from the “Financial Times” on the front page of their newspaper online, perhaps two days ago. And it was quite astonishing, because of the openness, transparency of the reporting. Much of the information was coming in fact from Russian television. Though the reporter, the writer, author of this piece did not refer to Russian television. Nonetheless, he also interviewed on the battlefield, on the front, Ukrainian soldiers who were saying openly that the Russians are using very effective new tactics. For example, they are instead of coming in on tanks, which are quite vulnerable to destruction by Ukrainian drones as well as others, they are coming in on scooters. They’re coming in on motorcycles in small groups.

16:05
And they’re surprising the Ukrainian defenders of various hamlets on the front line and taking over territory. But the Russians are being very inventive while also they are supporting their forward movement by heavy artillery, by glide bombs, and other serious military equipment. So the Ukrainians are acknowledging the Russian advantage technically in the drone warfare where Russians started out at a big disadvantage three years ago.

Napolitano:16:42
What are the numerical differences of which you’re aware and which you find credible … between Russian enlistments and Ukrainian conscriptions.

Doctorow:
Again, this was also repeated in the article I’m making reference to. And the importance of citing this article is that, editorially, the “Financial Times” is viciously anti-Russian. Some of their journalists slip in some interesting and useful information, considering it is a business newspaper, after all, regarding the state of the Russian economy. Even yesterday, they had an article citing the prosperity and the good feelings of the Russian consumers and general population.

But the newspaper is anti-Russian, and yet they are putting up this material that I just described as a kind of forewarning, I think, to their business subscribers to expect a Ukrainian defeat, something which would not have been acknowledged in any way going back a few months ago.

Napolitano:
Let’s talk for a moment, if we could, about the attempted— this has gotten very, very little play in the West— the attempted assassination of President Putin using drones while he was in a helicopter. Isn’t it reasonable to believe that the information about his presence in that helicopter and the location of the helicopter was supplied to the Ukrainians by either MI6, CIA or Mossad?

Doctorow: 18:25
It is possible, but not necessary. One of the points that bears mentioning and the way that military intelligence has changed in the course of the war, thanks to drones.

The Russian targeting of Ukrainian Western- supplied equipment is largely coming from constant reconnaissance drones. It’s not coming from satellites. And so it is entirely possible that the Ukrainians themselves could have detected a special movement. After all, Putin was coming close to the border. He was visiting Kursk, and that is a bordering oblast. So it is possible the Ukrainians could have learned this through their own reconnaissance, that is, technical means, or they could have learned it from espionage, from leaks.

19:25
Let’s face it, it recently came out, that the reason why the Ukrainian incursion, later invasion of Kursk succeeded so well, was because of widespread corruption in the oblast of Kursk. And this has come out in the last several days. Severe attack on a local administration, which had stolen the money that had been appropriated for defense of the border. It is possible that there are Russians within Kursk who are working for Ukraine.

Napolitano:
But the concept of assassinating President Putin, is it rational that that plan would have been hatched without the Americans knowing about it?

Doctorow:
I think we have to acknowledge that the Ukrainian government, regime, what you want to call it, is desperate. Now, this leads us to the question, is a collapse of the army imminent? I don’t think so. But they are desperate. They are fearing, perhaps, that they will be overthrown because of the military reverses. And they are ready for anything, meaning primarily terrorism.

20:44
Let me alert you to something that isn’t talked about. Turkish airlines have warned passengers on their flights to Russia now that they may be grounded if Turkey believes that its flights from Istanbul could be subject to Ukrainian drones. So that the Ukrainians would even think of attacking Turkish airlines shows you how desperate and totally violent and irresponsible ,and terrorist in nature, the Ukrainian government has become.

Napolitano:
Do you think that mainstream media here in the West is beginning to recognize all this ,or is the “Financial Times” not a barometer of mainstream media?

Doctorow:
No, I think it is a barometer, but that doesn’t mean that they are totally current in and bringing up to date all aspects of Ukrainian activities. As recently as a day ago, nobody was talking in the “Financial Times”, just as they weren’t talking in other Western mainstream, about the massive increase in Ukrainian drone attacks on Russia that preceded the Russian counterattack, which is the only thing that has been covered, in which the Russians have done massive bombing of Kiev and other cities.

22:11
That got everybody’s attention, but what provoked it has been ignored by the “Financial Times”, as well as the rest of mainstream.

Napolitano: 22:21
Here’s President Trump expressing disappointment with the current state of affairs. Chris, cut number 13.

——–

Reporter:
Do you believe the Russians are being disrespectful when they say that your criticisms of Putin are simply an emotional response, and do you still believe that Putin actually wants to end the war?

Trump:
I can’t tell you that, but I’ll let you know in about two weeks, within two weeks. We’re going to find out very soon. We’re going to find out whether or not he’s tapping us along or not. And if he is, we’ll respond a little bit differently. But it’ll take about a week and a half, two weeks.

We have, Mr. Witkoff is here, who’s doing a phenomenal job, is dealing with them very strongly right now. They seem to want to do something, but until the document is signed, I can’t tell you. Nobody can. I can say this, I can say this, that I’m very disappointed at what happened a couple of nights now where people were killed in the middle of what you would call a negotiation.

I’m very disappointed by that. Very, very disappointed. Yeah, please.

——–

Napolitano: 23:30
What do the Russians think of him when he makes comments like that?

Doctorow:
Let’s divide this between what they think and what they say. What they say is very diplomatic. You know what Pieskov said, precisely that the Americans are reacting emotionally, that it’s very tense and therefore it could be explained away. However that’s not what Moscow thinks. That’s what Moscow feels obliged to say, not to tip its hands to the to Donald Trump’s enemies and opponents.

They would– what Moscow thinks is that Mr. Trump is basically well disposed, is looking for detente, and they applaud his efforts, but they are very open to acknowledging the level of opposition that he faces, which was most recent. It was called out also on Russian news yesterday that is Lindsey Graham’s 80 Senate signatures on the bill that he has advanced to call for drastic sanctions to be imposed on Russia. This is a bill that will be veto-proof and this may condition what Mr. Trump was saying yesterday. You’ll see in two weeks what our response will be.

24:48
I think that if this motion by Lindsey Graham and that’s 80 he signed up, proceeds and they force Trump’s hand on this issue, that he will respond by indeed walking away from the negotiations, saying “We’ve done our best” and leaving with a fair-handed equal treatment. That is, the Russians will get more sanctions and the Ukrainians will get no more financial, military aid or reconnaissance aid from the United States. And that will look very good.

Napolitano:
Wow.

Doctorow:
He’s prepared. But I do say that he is not ignorant. The man who delivered that speech in Saudi Arabia, which you, I, and so many others consider to be a brilliant and the most astonishing denunciation of the whole ideology of neocons in the presence of the Saudi leaders, saying that “You’ve done it yourself, you’ve gotten democracy, you’ve gotten prosperity, no thanks to us, because we’ve only brought death and destruction wherever we tried to do nation building.”

The man who delivered that, he didn’t write it, it’s not important, he delivered it, and he knew what he was delivering. That man cannot be described as a buffoon. I am certain, Judge, that he knows as much and probably a lot more than you or I or anyone else around, about what the situation is on the ground in Russia today. And it’s not thanks to the National Security Council, which he has been busy depopulating.

Napolitano:
Right, right.

Doctorow:
Because it was packed by Biden.

Napolitano:
I have to note that standing next to him, I don’t know if you could just put up an image, Chris, of what we just saw from Cut 13 where President Trump was speaking just for a second. Just put up the beginning of number 13. Chris? All right, maybe we can’t get it out.

——–

Reporter:
Do you believe the Russians are being disrespectful when they say that your criticisms of Putin are simply an emotional response, and do you still believe that Putin actually wants to end the war?

Trump:
I can’t tell you that, but I’ll let you know in about two weeks, within two weeks. We’re going to find out very soon. We’re going to find out whether or not he’s tapping us along or not. And if he is, we’ll respond a little bit differently. But it’ll take about a week and a half, two weeks.

We have, Mr. Witkoff is here, who’s doing a phenomenal job, is dealing with them very strongly right now. They they seem to want to do something, but until the document is signed, I can’t tell you. Nobody can. I can say this.

——–

Napolitano: 27:34
Right. I had to comment about the woman standing next to him. That is Janine Pirro, the interim US attorney for Washington DC, my former colleague at Fox News, whom I’ve known for 20 years. That is the longest she’s ever been in front of a camera without saying a word. Tell us about your new book, “War Diaries”, Professor.

Doctorow:
Well, this is a book– I’ve noticed when I went to Amazon that somebody in Ukrainian has published “War Diary” in singular, about a year ago, telling the story from the perspective of the Ukrainians. I’m telling the story as in how it looked, how the development of the war looked on the ground in Russia from my visits there, from my close following their press and so forth.

28:24
It is not intended to be a comprehensive history of the war; it’s intended to be a personal account of what has changed in Russia, how society has changed, the thinking of the man on the street, the thinking of the intelligentsia, the rise in patriotism. All of these are features that I tracked over the course of the war, as you know, in essays that I wrote day by day, week by week.

Napolitano:
Right.

Doctorow:
And I have culled that to produce this very large book, which in some respects will be a reference book. But I think that readers will find that there are good chunks of it which speak to them directly and interest them, particularly my travels in Russia, which were four times a year before I curtailed them as travel became more difficult. Nonetheless, this was a unique reportage because Western journalists all left the country at the start of the special military operation. I think it’s ultimately a valuable contribution.

There will be a volume two. I’m hoping that I can produce it by the end of this year, because the war will be over by then. But of course, nobody knows.

Napolitano:
Nobody knows. Well, we all know how much we appreciate you. Thank you for sending the essays, however long or short they may be. I have the benefit of your thinking all the time and almost instantaneously. I can’t wait to get my copy of the book. And thank you very much for your time today and I’ve already heard from Janine Pirro who apparently is watching this. She loved the wisecrack that I made. All the best. Thank you for joining us, Professor.

30:09 Well, thank you.