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

Aug. 28, 2025 - Judging Freedom - Judge Andrew Napolitano

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COL. Douglas Macgregor : Does Trump Understand Russia?

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	Hi, everyone.
	Judge Andrew Napolitano here for Judging Freedom.
	Today is Thursday, August 28, 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 on it.
	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 them, 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 Ukrainian 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, Then he discovered before he left that his orders had been completely ignored and disobeyed.
	So I don't see 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 Kiev.
	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, and that was made back in June.
	He was the commander, for all intents and 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 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 Hegseth.
	The CIA, if the New York Times is accurate, built between 12 and 20 stations in Ukraine.
	Well, that's a lot.
	Ukraineine 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 serious military action against Ukraine and potentially the West when they discovered that there were biolabs working on genetic engineering designed 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 Kharkov 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 invader's country.
	It's like a great team in sports that has a fantastic defense, but is not allowed to play 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 E-RAM.s.
	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, you know, 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 2022.
	They'd had enormous infusions of equipment, enormous personnel.
	They were able to put about 800,000 people into the field.
	This was the mobilized reserves plus the people that were 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, And if you lose the close fight, you lose the war.
	Well, the truth is that attacking Russian civilians in Belgrade 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.
	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 with stars on their shoulders in the U.S. Army and in the British Army have had a huge impact on their thinking and behavior.
	And that includes Donahue, who encouraged them to execute an amphibious operation across the Niagara 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.
	I mean, recently, you know, President Trump was asked about, you know, peacekeeping forces guarantees and someone said that Lavrov 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.
	I 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 BRICS is all about.
	I don't have a good answer, but that's the best I can come up with.
	No, no, no.
	It's a fascinating, fascinating analysis.
	think what you're saying is known by and understood by the Russians.
	President Trump is And in this clip that we're now going to play, he uses his favorite eight-letter word.
	Chris, cut number eleven.
	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 view Zelensky as a leader worth signing a peace deal with, if they will.
	It doesn't matter what they say.
	Steve can answer, but I can answer too.
	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 whitcoff to say it's the cabinet meeting and they're on uh national television well i think trump should take seriously what lavros says what do you think yeah well i also noticed that uh lutwick was also nodding his head and laughing as well who was Lutnick,
	who is Whitcoff'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 hear 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 when he isn't.
	Colonel, did the United States gain anything by the conference between Presidents Putin and Trump in 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...
	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 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 school children 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 Vladimir?
	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 Kohl or any of the larger than FDR treating Winston Churchill like that.
	Oh, actually, FDR was very hard on Winston Churchill.
	He never even discussed with him the unconditional surrender.
	And when Churchill heard that in Casablanca in January 1943, he 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 badly.
	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.
	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 are Rubio and Heg Seth and a few other advisors.
	Does the United States still lead the world 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.
	Her name is Georgia 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 von der Leyen and I'm surprised that she hasn't vomited all over von der Leyen.
	She is all the way on the left as we're viewing it.
	And the pink jacket is von der Leyen to von der Leyen's right and our left is the Prime Minister of Italy.
	uh 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 to 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 Moldova.
	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 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 amuk.
	They're rogued.
	They're not under any strategic leadership per se.
	And 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.
	of the Prime Minister, Premier of China, and with President Putin.
	Donald Trump has economically attacked BRICS in his own mind.
	Hasn't he in reality strengthened BRICS?
	Oh yes, absolutely.
	The BRICS 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 BRICS, who are rushing into the arms of BRICS, 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 BRICS.
	And he continues.
	to finance genocide and starvation in Gaza?
	Well, he 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.
	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 on 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 have 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 Mate and Max Bluenthal, as you know.
	Yes, I'm 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 Nasser 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 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 that 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 round.
	I wish more would in Europe.
	But the interesting part is that this British government is not likely to last very long.
	Right.
	And you have a similar situation in Germany right now.
	The German government 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, Vice President Vance has spoken on this subject and been 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.
	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.
	It's, 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 Colombia, 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 on Saturday, the 5th of October.
	4th.
	4th of October, sorry, along with Augar Rabasi and Natalie Brunell.
	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.
	Yours is very elegant.
	Mine's rather animated, but there we are.
	Sandwiched.
	Sandwiched to beautiful and brilliant women.
	Yeah, well, 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 Rivazi asks us.
	But then we're going to interact with the audience.
	We want to know what the audience thinks because one of the reasons 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..
	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 it.
	Thank 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.

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