Judging Freedom - COL. Douglas Macgregor : Does Trump Understand Russia?

Episode Date: August 28, 2025

COL. Douglas Macgregor : Does Trump Understand Russia?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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unlimited wireless plan for just 15 bucks a month at mintmobile.com slash john. That's mintmobile.com slash john. Use your own phone with any mint mobile plan and bring your phone number along with all of your existing contacts. Up front payment of $45 required equivalent to $15 a month. Limited time new customer offer for first three months only. Speeds may slow about 35 gigabyte on unlimited plan. Taxes and fees extra. See Mint Mobile for details. Thank you. Hi, everyone. Judge Andrew Napolitano here for judging freedom. Today is Thursday, August 28th, 2025. The summer's almost over. It's almost Labor Day weekend here in the U.S. Colonel Douglas McGregor.

Joins us now. Colonel McGregor, a pleasure, my dear friend. Thank you for joining us. after the MI6 CIA State Department engineered coup against Victor Yanukovych in Ukraine in 2014, the first Trump administration armed the Ukrainians to the teeth. Why did they do that? I think that President Trump was essentially conforming to the status quo. I don't think he had any background or experience with regard to Eastern Europe, certainly didn't understand anything about Ukraine or Russia. I think he judged it a minor conflict that would probably burn itself out.

I don't think he cared. And so he was happy to sign off. And I remember the other thing about President Trump is that he very much likes to be in everybody's good graces. That includes the people that hate him. So, you know, he'll do whatever he can to avoid conflict. with anybody inside Washington. And thus went along with the neocons, who in the second half of his first term

would turn on him and lead the charge for impeachment. Yeah, absolutely. And that was one of the questions that we all had at the time. Why are you cooperating in any way, shape, or form with people that want to destroy you? Not only did he cooperate with him, He appointed them to key positions in his administration.

Witness John Bolton, perfect example. Right, right. Is the CIA and American military in Germany still providing intelligence, surveillance, and reconnaissance for the advantage of the Ukraine military against the Russians? I mean, stated differently, are we still actively involved in trying to kill Russian soldiers? I you know frankly I can't tell you that it has stopped I haven't seen any evidence for a halt in any of that you know this this brings us back to Trump in 2020 who was directing the military to pull out of Syria was interested in getting completely out of Iraq then he discovered before he left that his orders had been completely ignored and disobeyed so I don't see any any reason why the current military leadership and intelligence leadership would be any different now than they were then. So I'm sure they're still providing information to their friends in Keefe.

Is the military leadership the same general, I believe his name is Christopher Donahue, who boasted that the American troops could, with boots on the ground, take Kaliningrad, that part of Russia that's not contiguous to the rest of it? Is he the guy in charge of American troops? Well, he certainly was at that time. I don't know that he's still there. If he's still there, I'm unaware. But he certainly was when he made that statement.

That was made back in June. He was the commander for all intents of purposes of all U.S. Army forces in Europe. So, yeah, he was. But, you know, these kinds of statements are the kinds of things, unfortunately, that President Trump likes. I mean, President Trump has this imaginary picture of a general, and he thinks that every really good serious general is somebody like George Patton. And so when someone speaks in these grandiose terms and scoffs at the potential opponent

or diminishes any potential adversary, he's probably getting an effective pat on the back from President Trump through Higgseth. Hmm. The CIA, if the New York Times is accurate, built between 12 and 20 stations in Ukraine. Well, that's a lot. Ukraine is big, but it's not that big. I think it's about the size of Texas. As far as you know, are they still there? Are American intelligence still on the ground in Ukraine? Well, of course, as far as the stations themselves, I think a number of them have been dismantled and moved, just as many of the biolabs were overrun and captured by the Russians. I mean, this is one of the things that really changed public opinion in Russia and swung it decisively in favor of a serious military action against Ukraine and potentially the West when they discovered that there were biolabs working on genetic engineering design. to develop poisonous weapons to kill Slavs.

You can imagine the outcome. And the Russian general who went in and discovered this, along with the efforts to build a dirty bomb in and around Karkoff and other places, he was eventually assassinated by the Ukrainians. But all of that information eventually reached the Russian public, and that stiffened resolve dramatically against Ukraine and the West. So I'm sure that many of those places, have been moved or dismantled, and they're much further west.

Chris, can you put up the truth social that the president published recently? How do you explain this? I won't read the whole thing because I'm not interested in his views of Joe Biden, which are well known. This is President to Trump last week. It's very hard, if not impossible, to win a war without attacking an invaders' country. It's like a great team in sports that has a fantastic defense, but is not allowed to offense, there is no chance of winning. The same week that he published that colonel, he authorized, according to Ritter, these are not yet built. So they're not going to get there for a while

if there's a Ukrainian military to receive them. But he authorized 3,000 ERAMS. I'm not sure what that stands for, but they are missiles that can travel 280 miles. What do you make of this behavior? Well, first of all, let's go back to the statement where he talks about they weren't given what they needed to be victorious. First of all, the most well-equipped army in NATO was the Ukrainian army that was preparing to attack Russia in February 22. They'd had enormous infusions of equipment, enormous personnel. They were in. able to put about 800,000 people into the field. This was the mobilized reserves plus the people that were a part of the regular force. So the notion that they didn't have what they needed

to win is ridiculous. The other thing is that Israeli general, a very brilliant man once told me something that I think President Trump would benefit from, and that is if you focus on winning the long-range fight. In other words, these long-range strikes, you may well lose the close fight. And if you lose the close fight, you lose the war. Well, the truth is that attacking Russian civilians in Beograd or Moscow or St. Petersburg isn't going to help Ukraine win anything. If anything, it'll once again, stiffen Russian resolve, enrage the Russian population, and make it much more likely that the Russians double down and march all the way to the Polish border. So that's a very dumb idea.

The Ukrainians have lost the close fight. They lost it a couple of years ago, and they have not been able to win it back. That's why you have this 1.7 plus million number that's now come out publicly. So the notion that what Trump is saying doesn't make any sense. They've had more than any other army in NATO to fight this war, and it's failed miserably. Now, some of that's our fault because our brilliant luminaries in uniform, stars on their shoulders in the U.S. Army and in the British Army have had a huge impact on their thinking and behavior. That includes Donahue, who encouraged them to execute an amphibious

operation across in the Upper River that got hundreds of people killed and was an immense failure. So naturally, we promoted him. This is the same man that failed miserably in Afghanistan and staged that disaster on the way out of Kabul. We don't seem to hold anybody accountable. That's the biggest problem. But right now, President Trump needs to understand that what he's written doesn't make any real sense. How do you think what he has written and the authorization for the ERAMS is perceived in Moscow? Well, listening not only to the decision to ship potentially over a thousand of these cruise missiles to Ukraine for use against Russia in the so-called deep strikes is just one of several different things, And recently, you know, President Trump was asked about, you know,

peacekeeping forces, guarantees, and someone said that Lavaoff had made it abundantly clear. That was a red line. And President Trump just responded with his favorite eight-letter word. And it wasn't nonsense. I don't think President Trump understands what he's dealing with. I don't think he's got people around him who really understand the gravity of the situation and the Russian thinking and mentality and readiness to fight, but really don't. And I think he is delusional in the sense that, you know, he's living permanently in 1991.

We're the last man standing. No one can resist us. Everyone has to do what we say. You see that in the tariff war. You see the way he approaches the economy. And, of course, there are people in his base that love this. But ultimately, it's driving the world away from us. it's driving de-dollarization.

People are trying to shed our dollars and get out from under us. That's what Bricks is all about. So I don't have a good answer, but that's the best I can come on. Oh, no, no. It's a fascinating, fascinating analysis. I think what you're saying is known by and understood by the Russians. President Trump is questioned on some of this. And in this clip that we're now going to play,

he uses his favorite eight-letter word. Chris, cut number 11. This past weekend, Sergei Lavrov was saying that Putin will not sign a peace deal with Zelensky because Russia views him as illegitimate. I'm just wondering if the Russians had been relaying this to your team, if they've used Zelensky, you know, as a leader worth signing a peace deal with, if they will go to him. It doesn't matter what they say. Steve can answer it to it.

It doesn't matter what they say. everybody's posturing. It's all bullshit, okay? Everybody's posturing. Steve, do you have a different answer? I agree with you, sir. What do you expect Whitcroft to say? It's the cabinet meeting, and they're on national television. I think Trump should take seriously what Lavrov says. What do you think? Yeah, well, I also noticed that Ludwig was also nodding his head in laughing as well. Who was? Looknick, who is Whitkoff's partner in crime and probably the closest, if you want to call him an advisor, certainly one of the people closest to President Trump. That's the Secretary of Commerce, right.

Yeah, I think, you know, look, if you look at this tariff thing, it's insane. It's been very destructive. It's not helping us. It's harmed us. And it's going to get worse before it gets better. So he's a co-architect of that disaster. you're dealing with people that don't understand the world beyond the borders of the United States. I'm sure that in real estate business, people posture. People say things that are

utterly ridiculous, that they hurl abuse at each other and all walk out of the room after signing a deal. This is not real estate. This is Russia, the Russian state. The things that Lavrov and Putin say, are not said for effect. They are speaking very directly and very seriously to us. And I think they now realize that they've reached the point with us where President Trump is capable of saying or doing almost anything from day to day, that there is no stability in any relationship with the United States. It's not that Trump is unpredictable, which is my greatest strength. You know, that's the kind of stupidity you here in Washington. Be unpredictable. That's a good thing. No, unpredictability is not an aid in this operation.

It's very dangerous. I think they've just written him off. I think they don't pay any attention to anything he says. And that's very dangerous because you never know when the man is serious and what he isn't. Colonel, did the United States gain anything by the conference between President's Putin and Trump and Anchorage, Alaska three weeks ago? Well, I thought that potentially we could because there was a willingness to talk about issues other than just Ukraine because I felt that President Trump had discovered that there wasn't much latitude for change in the Russian position vis-a-vis Ukraine. But the Russians have a keen interest in restoring better relations with us. I thought President Trump shared that interest.

I guess I was wrong. So I guess the only thing that came out of this was the – optics. In other words, Trump got what he wanted. He got wonderful pictures of himself on the world stage, strutting in front of the F-22s and looking at a flyover and standing with the president of Russia at a press conference. And he looked very presidential. He looked strong and powerful. I think that was his main goal. And as far as the United States is concerned, I think he achieved that with the American public. It's something, though, that is purely optical, so it has no lasting or enduring effect.

And then two days later, that image was projected again. In fact, it may have even been enhanced when the G7 appeared in the Oval Office, like schoolchildren, being summoned by the principal or the headmaster because they were caught doing something they shouldn't have been doing. And they dutifully sat there like school children. And when he said, would you please leave so I can call my friend Vladivus. him here. They stood. He didn't even give them a place to sit. They stood outside the Oval office for 45 minutes and came back in. Yeah, it was humiliating, I think, for Europeans. I'm

surprised that any of them took it. I can't imagine Charles de Gaulle or Helmut Schmidt or Helmut Cole or any of the larger than FDR treating Winston Churchill like that. Oh, actually, Wednesday, you know, FDR was very hard on Winston Churchill. You know, he never even discussed with him the unconditional surrender. And when Churchill heard that in Casablanca in January 1943, almost fell out of his chair, because there had been no discussion of it under any circumstances. He just blurted that out. And, of course, Churchill was horrified and tried to say, look, this could lengthen the war. We don't want this.

No, I think FDR treated the British ban. But having said that, I think you're right about these Europeans. but at the same time, they know that Trump can be taken. They know that with the right amount of coddling and stroking, that Trump can be enticed into whatever direction they want him to go. So I think they're willing to put up with a lot of nonsense. How much longer that will last, I don't know. But if you look at what he's been saying about Russia,

very incautious remarks, very stupid things, It's now this business with the cruise missiles. The Europeans are probably saying, see, we got what we wanted because they're the globalists that want this war to continue in perpetuity. There's that picture taken from over President Trump's shoulder, and you can see them there standing in the back or Rubio and Heggseth and a few other advisors. Does the United States still lead the world?

The United States for the moment still wields tremendous power and influence because the financial system has not yet collapsed. It's getting there. Yeah, it also wields influence because the U.S. military has not been challenged directly by anybody with any real capability and defeated. Now, those things could change very quickly. but right now I think on the basis of those two things he does now if you go back to that picture there is one person in there who is signaling unambiguously just how utterly appalled disgusted and disappointed she is I bet I know it's George Maloney you go back and look at her she's got her arms folded and she's scowling of course she has to sit next to Funderlion

and I'm surprised that she hasn't vomited all over Funderline she is all the way on the left as we're viewing it in the pink jacket is vonder lion to vonder lion's right and our left is the prime minister of italy who's not happy with this mertz doesn't look very happy either but he always slouches and of course the other thing about this is so fascinating is that the people that have the most to lose or gain from any decision in ukraine are not present. Where is the new president of Poland? Where is the leadership of Slovakia? Where is the leadership of Hungary? Where is the leadership of Romania? Well, you just named the only European leaders with enough sense to recognize that Russia's not the enemy. Russia wants the trade with everybody,

and Russia has legitimate security concerns just like everybody else. They're the only ones. Well, yeah, except that I would say that the Romanian president is effectively picked by the CIA. They had the legitimate winner of the presidential election who was denied appointment, and we got another NATO puppet into the job. We're doing the same thing right now, by the way, in Moldava. We're trying to keep everyone in the anti-Russian camp. And this goes back to your other question. Does Trump understand what's happening? Does he really understand what the CIA,

MI6, and Mossad are up to on any given day, both in Europe and in the Middle East? I don't think he does. You know, he recently fired a number of senior CIA officials, including a female whose name has not been made known with 29 years' experience who was about to head the station in Moscow. I don't think that makes a difference in terms of what the CIA still does and gets away with it, whether he knows it, wants it, or not. Do you agree?

Well, of course, if you look at Radcliffe, how much more neocon could you have in anybody who runs the CIA than Radcliffe? This is someone who was a creature from the very beginning of the Israel lobby, and he's inhaled all of the neocon nonsense about Russia and Iran and everything else. So, you know, I don't think it changes anything in the short run. Hey, Colonel, while as we speak, I'm getting a message that the United States has just launched 68 airstrikes in Somalia, surpassing the annual record set by Joe Biden of 63 in a year. Why, in God's name, are we bombing Somalia? Do most Americans even know where it is?

Well, these are ISIS-like elements, I'm told. Does this make any difference? Does this help us? Does this improve our national security? I don't think so. But we're in Africa right now trying to compete with the Russians and the Chinese for influence, and we're losing badly. Not just in Central Africa, I would argue also in North Africa. We don't know what we're doing.

And, you know, we turn almost immediately to the use of military power. And if you question it, then somebody tries to tell you, well, this person was involved in 9-11 or this person killed this or that or someone else in Syria or whatever. It's a hopeless endeavor. The institutions are running amok. They're robed. They're not under any strategic leadership per se. If that strategic leadership exists, it sure is not the president. Just to change topics to another area of mutual interest between you and me, and I know a lot of our viewers, next week, the President of Brazil and the President of Iran will be meeting with the President of China, with the Prime Minister, Premier of China, and with President Putin.

Donald Trump has economically attacked Bricks in his own mind. Hasn't he, in reality, strengthened Bricks? Oh, yes, absolutely. The Bricks movement has benefited enormously from his tariff war. It's benefited enormously from all of his economic and financial activity. Again, President Trump is a true believer in bullying. And the age of bullying, of course, was the age of imperialism. That's when you would sail your gunboat in and threaten the Sultan of Zanzibar

that if he didn't open his harbor to your access and didn't allow you to come in and control his markets that you would destroy him. I think Trump is locked into that paradigm. That's over. The age of imperialism is completely unalterably dead. the countries that are joining bricks who are rushing into the arms of bricks are people that have had lots of experience with colonialism

and they don't want to have any more. So he's the best advertisement, I think, that we probably have ever seen for bricks. And he continues to finance genocide and starvation in Gaza. Well, he does. does and i think that that's just something we have to understand that there are a lot of people in the united states because i run into them on a pretty frequent basis who just tell me flat out

they could care less how many people die in gaza and when you ask them why well these are muslim arabs you know they're terrible people uh i think that the decades of systematic propaganda pumped into us through the mainstream media to defame, destroy, degrade, Arabs in general has been very effective. And so at this point, I'm not surprised that he still has enormous support inside the United States, at least inside his base, for his support of mass murder and expulsion of people in Gaza. Now, how much longer will this go on? I don't know, but how often do you see film footage, pictures, and listen to eyewitness testimony from people in the mainstream media and what's happening in Gaza. I don't think very much. And Americans still rely on mainstream

media. The other thing is that my generation of boomers could care less. They just do a very negative picture. And look, I'm not here to defend Islam. I'm not by any means saying I think the world should all embrace Islam. I'm simply saying that I oppose this sort of thing everywhere that it happens. I would oppose the mass murder of Chinese by Japanese in Shanghai. I would oppose the mass murder of any people anywhere and then the systematic removal of them from their homes where they have lived for thousands of years. This is just outrageous and unacceptable. But that's not being driven home here in the country, despite the good work of Aaron Mote and Max Blumenthal, as you know. Yes, I'm sorry to say

that I agree with you. Neither you nor I nor many people watching us are fans of the British government, particularly the current British government, but this is a very articulate condemnation of the Israelis in the presence

of their monomaniacal UN ambassador by the UK ambassador. This is yesterday in New York City. Chris, cut number seven. The IPC's confirmation of famine in Gaza City marks the first officially recorded famine in modern history in the Middle East.

It is entirely man-made and, as my Foreign Secretary has said, it is a moral outrage. Over 100 children in Gaza have died of malnutrition while food is sitting at Gaza's borders. I have two clear messages for Israel. immediately lift restrictions and allow food, medical supplies and fuel to reach those in desperate need in line with international humanitarian law. Israel's attack on NASA Hospital this weekend killing civilians, health workers and journalists, is appalling.

A ceasefire remains the best way to secure the release of all the remaining hostages. The Israeli government's plan to expand military operations in Gaza will only put them in further danger. We condemn this decision and urge Israel to change course. Israel's decision to approve plans for settlement construction in the E1 area in the West Bank, if implemented, would be a flagrant breach of international law, and it will take us further away from peace.

Nicely and articulately said, but nobody will do anything about it. Well, when we say nobody, we need to understand that it all is contingent on what we do. Right. And as long as Israel has the unconditional support of the American government, specifically President Trump and Congress, then I suspect the dying will continue, the killing will continue without interruption. And we're heavily invested in all of this because we're part of a larger strategy in the region to balkanize and destroy Iran to essentially turn Iran into some version of Syria to ultimately get control of the oil and gas regions as a means we think of breaking up bricks, destroying the one-belt, one road project that runs from Iran up into Central Asia and Russia. I mean, all of this is bound up together.

none of this should be seen in isolation it is nice to see the british government finally come around i wish more would in europe but the interesting part is that this british government's not likely to last very long right and you have a similar situation in germany right now the german government is is following the british example trying to suppress free speech and erase the existence in the political arena of the alternative for germany to his credit uh vice president vance has spoken on this subject and being very critical of what the British and the Germans and others are doing. That's a very good thing. Will it make any difference? I don't know. Hasn't Trump just fallen totally in line with the policies of Joe Biden with respect to Gaza?

Yes, I think so. And that's what we witnessed in his first term. But over time, he came in with a very fresh perspective, fresh ideas, determined to do something. thing. The Russia gate hoax, obviously, hamstrung him at the time. But ultimately, he leaves office not accomplishing any of the things that he thought were really important. I think we're seeing that again. Now, in fairness, he has tried very hard on the border with regard to illegal immigration and the drug trafficking. He now seems to be committed or at least interested in potentially another front in the war down in Venezuela. I don't think that's the right solution for what we don't like about Venezuela, but that seems to be where he's headed. Again, there is no long-term,

coherent strategic framework to explain anything. I think what we're dealing with is this predisposition to say, well, I don't like this, I'm going to do this, and everybody around Trump just reinforces it. Sure, go down to Venezuela boss. let's make them an object lesson that'll get everybody on board in the region with what we want i don't think it will i think it'll have the opposite effect it could bring down columbia which is very fragile i think it'll stiffen resistance to us in mexico i don't think it'll hurt the drug cartels in the least so you got to go after the drug cartels you don't necessarily have to remove the head of state in a country to do that especially since that head of state may not have

much to do with any of it it looks like the generals of the venezuelan army are the ones cashing in on the drug trade and shipping the drugs that come out of Colombia up to the United States from Venezuela. You know, all of this is more complex and difficult than President Trump imagines. Remember when he was running for office, he said a lot of things, but probably the most ridiculous was, I can end this war between Russia and Ukraine in 24 hours. but I think it encapsulates a very childish, uninformed, infantile view of the world. And unfortunately, that's what we're stuck with.

And there are a lot of people, obviously, that love this and applaud it, think everything's just great, but it's not. Things are bad, and they're going to get a lot worse the way we're headed. Colonel, you and I will be discussing all of this before a live audience in Dallas, Texas, Saturday, the 5th of October. Fourth of October, sorry, along with Agar Rabasi and Natalie Brunel, and we'll be questioning each other, and the audience will be questioning us, and it'll be a great opportunity for people who are in the Dallas area to get to meet you and to interact with us, and there it is.

I don't know where they found the picture of me pointing. is very elegant. Mine's rather animated, but there we are. Sandwich the two beautiful and brilliant women. It looks like you just sentenced someone to a long-term prison. And so anyhow, it's an experiment, and we need people to understand.

We're interested in not sitting up there and lecturing the public. We'll make our comments and our statements in response to the questions that Dr. Olga Rabazi asks us. But then we're going to interact with the audience. audience. We want to know what the audience thinks because we want to do this every sort of 120 days or so, every 90 to 120 days, is we want to go around the country to different cities. We want to hear what Americans think. Okay. For those of us who are watching and want to learn more about it, scan the QR code and you'll get all the information you need, particularly if you are in Texas or are going to be in the Dallas area on the weekend of October 4th, which is kind of. coming up very soon. Colonel, thank you very much. Thanks for your time today.

Thanks for letting me go across the board on all these topics. Have a great holiday weekend. We'll look forward to seeing you next week, my dear friend. Yeah, thanks, Judge. Appreciate you. And coming up a great conversation with a great man, not because he's my friend, but because he just knows so much

and has such strength of character to articulate it so beautifully. Coming up later today at 1 this afternoon, Pepe Escobar at two this afternoon, Colonel Lawrence Wilkerson, at three this afternoon, Professor John Mearsheimer. Judge Napolitano for Judging Freedom. Thank you. Thank you.