Judging Freedom - COL. Douglas Macgregor : Russia to Run Over Kiev

Episode Date: October 14, 2026

COL. Douglas Macgregor : Russia to Run Over KievSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Undeclared wars are commonplace. Pragically, our government engages in preemptive war, otherwise known as aggression with no complaints from the American people. Sadly, we have become accustomed to living with the illegitimate use of force by government. To develop a truly free society, the issue of initiating force must be understood and rejected. What if sometimes to love your country you had to alter or abolish the government? Jefferson was right what if that government is best which governs least what if it is dangerous to be right when the government is wrong what if it is better to perish

fighting for freedom than to live as a slave what if freedom's greatest hour of danger is now hi everyone judge Andrew Napolitano here for judging freedom today is Wednesday October 14th 2026 Colonel Colonel Douglas McGregor joins us now. Colonel, always a pleasure, my dear friend. You recently opined that Russia will soon overrun Kiev. Before we get there, a few other questions. What is the United States Navy doing chasing Chinese ships in the South China Sea? What national security implication is there to the U.S. there? Well, that's a critical question. And I, I asked that when I saw this article about the ship losing power in the midst of chasing a Chinese vessel through the South China Sea.

And I asked a friend in the Navy and said, well, this is an intimidation operation. I said, what are you talking about? I said, well, we're, you know, intimidating the Chinese on the South China Sea to make sure they don't conclude that they ultimately own it. I said, well, that's interesting. Is there any evidence that this is having a beneficial impact on relations? with China. Of course, he laughed and he said, well, nobody cares about that. Wow. He was highly placed. Does the Pentagon, I don't want to blame this on your friend, but does the Pentagon, does the White

House, as far as you understand, still think we're in the unipolar moment where the United States is the only hegemon on the planet? Yeah, well, you know, Judge, I think this is an important point. It's not well understood in the United States. Most Americans, as you know, don't pay too much attention to what happens overseas as it is. And every succeeding administration tries to persuade the American population that we're the contemporary equivalent of Superman, invincible and vulnerable, above all, you know, for truth, justice and the so-called American way, but we know that it's actually quite different.

I think that what Donald Trump has discovered to his disappointment is that we are not what we were in 1991 militarily. and by any stretch of the imagination. And I think his assumption, without really understanding military power and the position of the United States in the world, was from the outset of his administration, that we were the all-powerful force that no one could resist. And that anybody who resisted us would be rapidly beaten into submission. Now, some people say, well, this is Donald Trump's God complex.

I mean, the other day, I guess he spoke and told someone that the hooties, were behaving badly with somebody said, who does this man think he is God? I'm not sure he even knows who the hoodies really are. And I don't think he has much appreciation for what the population in Yemen has been through over the last decade or two, having been either starved or bombed

into submission several times by the Saudis. But at any rate, I think he truly believes that he and the American state is at the center of the universe, and that we are, are still all powerful, which is why I think you're going to see another round of fighting with Iran. He cannot accept the fact that our military supremacy is no longer the case, and neither is our economic supremacy. And for that matter, neither is our financial credibility. We're not even

a AAA creditor in the world anymore. So it's all bound up together, but he seems to be determined that he's going to return us to the unipolar moment. Whether the world wants it or needs it, they're going to get it. And that's why Iran has to be beaten down until it surrenders, frankly, in his mind. I just want to go back to the Navy for a minute. This ship that was chasing a Chinese ship ran out of power, no electricity, no heat, no water, no plumbing. How bad, this is the second time we've heard this, because we heard what happened on the Abraham Lincoln,

which is enormous, had 5,000 sailors and Marines on it. What's with the Navy? Well, you know, I think we have to understand that the Navy is overstretched and has been for a long time. I mean, years ago, this is in the last year of the Bush administration. When I was working for Department of the Navy, one of the things that we examined were the deployments, the disposition of naval forces around the world. We looked at it for the data that we had for 2006 or seven, I think. We compared it to where

we were in 1990. And what a surprise. There was practically no change. In other words, the Cold War ended. We made reductions, some reductions in defense spending. We added more. We added more admirals but we reduce the numbers of ships and we made the mission profile the same as it is always being which means that you're sending fewer people overseas on longer cruises and these cruises are more exasperating you know exhausting than they otherwise would be so the biggest problem the navy has of course is recruiting to fill the ships with qualified people they're they're in bad shape right now. Nobody wants to serve at the surface fleet if they can possibly avoid it. I'm just going to deviate for a minute since we mentioned the Lincoln. Here's the Secretary

of Defense. The Washington Post has begun to call him President Trump's Minister of Manliness. You'll see why. I happen to think this is Pete Hickset. That is worst, but I invite your comments. He's on the deck of the USS Abraham Lincoln. And this is what he's talking about, number 18. This news that came down regarding firing squad, can you tell us about how that came about and what led to that decision process? No-brainer.

Execution by firing squad. Army major betrays his country. Radical Islamist kills a bunch of Americans at Fort Hood. Of course we're going to do it at Fort Hood. We're going to do it on a Thursday. We're going to do it at 1 o'clock, which is when he did it. And it's going to be soldiers with rifles,

executing the firing squad. It hadn't been since World War II since we've done that. Well, I kind of like the mentality we had in World War II, which was win, which was, understand when the enemy attacks you, you need to stand your ground. And so he's going to get a firing squad of soldiers, as it should be. And we'll make sure that people are able to watch it, that it's public, because people need to understand that this is, there's serious consequences for these types of things. Has Major Hassan made any final request, reach out to the president, anything like that to your knowledge, don't care.

Does this inspire confidence among the troops? Well, I think his initial response was accurate when he said no-brainer, because whoever thought this up wasn't thinking. You know, this may come as a surprise to a lot of people, and this is just a note on military history that at the end of World War II, when we arrested people for trial at Nuremberg, there were several that had been officers in the German army. And you had something similar with the importance.

real Japanese Army. When they were found guilty, none of these people were shot. And almost all of them, with very few exceptions, asked for a firing squad, because a firing squad was considered to be honorable. So they were hanged because that was what happened to common criminals. So the first thing I would say is that he's actually doing this man an honor by executing him with a firing squad from a purely military standpoint. Secondly, he wants to do this publicly. Well, we have places in the world like Saudi Arabia and a lot of Muslim countries, Islamic countries in particular with public executions.

I'm not sure we want to follow that model. I certainly would not. Leavenworth has the facilities to hang people have been guilty of criminal acts like this particular individual, who in my judgment is just a criminal. and I don't see any reason why it has to be done publicly. And at Leavenworth, they have rooms where they can execute people and there is no gawking audience. I don't think we need to do it publicly. And I certainly wouldn't shoot him for the reasons I outlined.

I would hang him. But I wouldn't build this as evidence for something good. Anytime you have to resort to this sort of thing, it's depressing and disappointing. It's the last thing that you ought to be interested in doing. But this man has a very strange view of things. He also has a strange view of World War II. He keeps banging on about the Second World War. I think the Second World War was a lot worse than he can even possibly imagine.

I don't think he appreciates what it took to fight that war. He obviously thinks that we had a larger role to play in many cases, particularly in Europe than we did. We were not alone. We had the British Empire as an ally. we had the Soviet Union fighting and the millions and millions and millions of people who died and suffered in that. I don't think that that's necessarily a model for what we want to do today or in the future. But, you know, it's sort of listening to a childlike fantasy based on watching television

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freedom at checkout. That's join delete me.com slash freedom. Code freedom. Segling over to Iran, Colonel, there's been a lot of speculation so much so that the president denied it, which may mean he's going to do it, that he is going to re-attack Iran before election day. And he basically said, no, it's not going to happen before election day, irrespective of when we think this might happen. What is the status of American stock? stockpiles available to him and Secretary Hegseth to wage the type of attack that they probably are considering.

Well, I'm told that they've improved somewhat over the last several weeks because of the pause. How much have they improved? You know, that's information I don't have. How much is on hand and how long could they sustain an intense air assault? again, this depends on what kinds of munitions you're using. It could reach anywhere from five to ten days of intensive bombardment. My impression is there will be a far greater reliance on the Air Force and particularly on bombers, which is why you saw the bombers that were in Great Britain removed, at least temporarily,

and why we've seen an influx of Air Force personnel into both in Great Britain and German. So I think you're going to see more use of heavy bombers than we've seen in the past, far more use from very high altitude. And then, of course, the fighter pilots will still be there. They'll do what they did before to the best of their ability. But they don't pack nearly the enormous punch that you get from the Air Force and its bomber fleet. Wow. How about it is inflation in the United States today, Colonel? How is what?

What? How bad is inflation today? Well, it depends on who you want to talk to. It's well over 3%, obviously. And that's the target that we continue to hear from the Fed that it has to be driven down below 3%. I've seen estimates of 7% or more. I mean, obviously we have a 7% mortgage now, and we're watching the housing market collapse,

and that's one of the pillars of our economy. You know, it's in some areas it's worse than others. Here's the bad news, Judge. It's not going to get any better. And the reason I say that is that we're sustaining now or experienced now, experiencing now the after effects of many, many policies that we have followed as a consequence, not just of the war, but things that the president has done since he took over and things that he inherited over which he had little or no influence.

So you put those together and it's certainly above 3%, and it's going to get much worse. And the American public is largely suffering. You could even argue that the world is largely suffering because of a decision of two men, Benjamin Netanyahu and Donald Trump, to invade Iran, to attack Iran with utter heedlessness as to the likely and probable consequences. Well, I think the problem now is that Iran has not had, in my judgment, very much incentive to rein itself in. Has nevertheless exercised more restraint than we think. And I'm confident that if we restart this, and I think you'll see something similar to what we saw the last time,

I think the Israelis will lead the attack, and we will be obligated to join them and reinforce them. When we do that, the Iranians will annihilate all that remains of the oil infrastructure on the west side of the Persian Gulf. I think that's a foregone conclusion. The desalination plants, everything. It'll turn it into a desert, literally and figuratively. At the same time, I think you will see ground-based attacks as well. I think Kuwait will be overrun. We'll see what happens in Bahrain.

Could they cross over to the UAE? certainly they may not want to bother, but they could. And that would be in the Iranian mind a true insult to us, because you would think that we would have some ability to protect those countries that we are obligated to protect under a whole range of agreements against ground attack. And I don't think we're going to be able to do that. At the same time, I think there's a lot of evidence that we will try to do something on the ground as well. I don't see that that's going to be much more than a pinprick,

but I think we're going to do something like that. Again, all of this is a search by President Trump for evidence of something that he can present to the American people in the world as a tangible concrete proof of American military supremacy. And that's one of the reasons that Iran is now going to strike with everything it's got against all the potential U.S. and friendly targets all over the Middle East. They don't want that to be restored in any way, shape, or form.

This is the final act, as far as they're concerned, in terms of driving us out of the region. Colonel, moving over to Ukraine, what do you think was behind Trump's calling for Zelensky's removal? I mean, from the Russian perspective, Zelensky is the best thing they could want. He's so erratic, unpopular, and incompetent. You know, I think Donald Trump, and again, this is speculation because I'm not a participant in the inner circle and anything that he may say. I mean, there's a little doubt in my mind that he dislikes the man. That's not the issue. I think he's very frustrated.

On the one hand, I think he'd like to remove him because he sees that as a pathway to some sort of resolution of the conflict. I don't think he's entirely wrong, although I think most of that government's going to have to go away with him. And he's making these statements publicly, but at the same time, he doesn't seem to exert the control over the CIA or MI6, the two principal intelligence agencies that are providing support for Zelensky. They're out there recruiting mercenaries all over the world to fight in Ukraine. There are thousands of mercenaries that are taking the place of Ukrainian soldiers because recruiting Ukrainian soldiers has become a pretty hazardous affair. All you have to do is turn on YouTube and unless YouTube is eliminated the videos, which they do frequently, you'll see lots of evidence for Ukrainians essentially threatening to kill the press gangs that come to collect their men. I think things have really fallen apart inside Ukraine in this sense.

And I'm sure that President Trump probably has some grasp of this. I don't think he believes the nonsense that he's being fed up to this point about horrendous Russian losses and Russian weakness. I think he's smart enough to know that's nonsense. So perhaps this is an act of frustration on his part just to go public and say, this man Zelensky needs to go in so many words. But the truth is, if he were really in charge of his government, he could make that happen within 24 hours, Judge. It's not happening.

The operative language is if he were really in charge of his government. Colonel, if he orders the CIA to stop cooperating with MI6, and leave Ukraine, will they do so? Right now under Radcliffe, I would say absolutely not. And the question is, who does Radcliffe work for? Is he simply there to represent Israeli interests, effectively working directly for Netanyahu because the Israel lobby and their Zionist donors have put him where he is.

They got him elected to Congress and they have backed him ferociously to get into this job. of CIA director. I don't know. I mean, I'm not on the inside, but I have serious doubts about the man. I don't think he's qualified for the job, but that doesn't really make any difference. What he's there to do is follow orders. The question is, whose orders? Whose orders? Colonel, can Kyiv survive this, the capital of Ukraine, survive this winter? You know, it's hard to tell. If you have, if you feel nothing but contempt for your own people. And there's a lot of evidence that that Zelensky in his regime.

Then I suppose it doesn't make any difference to you. How many people die as a consequence of no heat, no food, no water, and so forth. I don't see much evidence that Zelensky cares. I think he's more concerned about himself, the preservation of his regime and the people that support him, including the forces around him. So in that sense, he'll persist. And this is the frustration in Moscow. I don't know why it's taking them this long, but I think they figured that out. But right now, I think they're going to wait. They're going to wait in the hope that the winter does its work. They're also waiting to see us increasingly disengage from the place. But as a good example of what we were discussing earlier, Zelensky still enjoys the intelligence

surveillance surveillance, reconnaissance data and information. that comes to him that is critical for the various remaining missile launches and unmanned system launches that he engages in. That doesn't, that hasn't stopped. Again, we're back to if President Trump were really in charge and President Trump really wanted an end of the war, and President Trump were really concerned about the fact that 50% of everything we've sent to Ukraine has either ended up in the pockets of Zelensky and his friends in bank accounts all over the world.

or has ended up on the black market being resold all the way to Mexico and the drug cartels, if he were really concerned about those things, he would stop it all. So what's the answer? He's the one that talks about bad behavior with the hoodies as though he was the father of the world. But then he can't seem to exert any real influence over the conduct of operations by his own intelligence departments. Well, tell me if this makes sense. Two weeks ago, he signed into law legislation named after the late Senator Lindsey Graham, absolutely prohibiting U.S. sale of or U.S. purchase of any oil-based product from Russia and sanctioning any country that does so. And then he signed an order based on a phone call with President Putin providing for just, that? Who got the better of those two deals, Trump or Putin? Well, I don't think that the amount of diesel involved is particularly large. I mean, it's

fractional. It's not going to make much different. Somebody said, if you took all the diesel that's being promised, that would fuel the world for, you know, at least Europe and the United States and a few other places for, what, 24 hours? So I don't think it amounts to much. I think this is another desperate search by President Trump to find some evidence for some. something good happening. Look, I spoke to President Putin and President Putin did what I asked, and President Putin is going to do X, Y, and Z because I negotiated this. He's not in control of his own government. He's not in control of Congress. What's he in control of? This is the problem that he had in his first administration. We all sat around and kept saying, you know, certainly

this man must know something about how Washington operates. But based on his behavior, he He never seemed to figure it out. Colonel, I'm going to play a clip of the commanding officer of NATO. I'd like you to watch it for a minute, and I'm going to ask you, why is he saying this? Chris number 17. No one should mistake our defensive nature for weakness or lack of resolve. Through our collective strength, we aim to deter and keep the peace. But if someone is foolish enough to attack us, we will fight.

We will stop the attack and deny them the ability to achieve their objectives, whatever those may be. So it's important that allies continue to consult, think about how we might respond and make sure that we message clearly and concisely to the Russians where our red lines are. He poking the bear. Well, look, I listened to this and then I went back and looked at some of the material he was using. If you went back to the file cabinet in the office of the Supreme Commander Europe, the SACU as we called him, I think you could find a lot of the material that he's using on file. It sounded like something that people would have said in the late 70s, early 1990s or mid-1990s, that we're strong and we can face you down and you have no chance and so forth to the Soviet Union.

Well, the truth is that by the time you get to the mid-80s, any chance of the Soviet Union, Soviet's launching a major offensive against us were largely gone. We can talk about that. But once Poland was destabilized in 1981, there was no possibility of a conventional, high-end conventional Soviet offensive. Today, there is absolutely no interest whatsoever, nor is there the capability, frankly, right now, for the Russians to launch a major offensive against the West. They don't have any interest in that.

They want to end this war, too. And they're just interested in ensuring that this thing called Ukraine that we've weaponized against them is not going to present a problem in the future. They want some sort of solution that addresses their security interests. We've refused to listen to that. The other thing is stressing this, well, we're a defensive alliance. Well, if we're a defensive alliance, why are we expanding to the east? If we're a defensive alliance, why are we recruiting members in the caucuses? Why do we try to drag in Georgia?

Why are we trying to drag Ukraine into the alliance? We don't need these alliance members. Judge, we have too many alliance members as it is. We've got 32 members. That's like herding cats. These people are never going to move in the same direction at the same time. All this business is nonsense. You know, in 1980, 1985, even in the early 1990s, you had a German army on the ground of 420,000 men.

brilliantly equipped, trained, organized, and led very, very efficiently that was part of a force that included almost a quarter of a million troops from the United States Army, along with another hundred plus thousand French and British troops. Now, what have we got on the ground now? Who is this man kidding? We don't have the means to wage a high-end conventional war against the Russians. The good news is the Russians aren't interested in attacking us. So why is he saying these things to create the illusion of a threat? And how long have we been working on this? We've got to go all the way back to Senator Lugar in 1992, who said either NATO is out of area.

In other words, a vassal state supporting our expeditionary operations around the world, or it's out of business. We have to give it a fight. We have to give it an enemy. We have to justify it. We have to rationalize it. do you do that now? Well, you try to make the argument that Putin woke up one morning and for no reason whatsoever decided, well, I think I'll invade Ukraine. We all know that's nonsense because when

Ukraine was invaded, it became pretty clear very quickly to the Russians that they were up a much more, up against a much more ferocious opponent in NATO than they thought. It wasn't just Ukraine. This was a NATO army that sat in front of them. They said, gee, we don't have enough troops. So eventually, they go over to the defense and they build up their forces. And we keep arguing the Russians are coming. The Russians are coming. The Russians are coming. Well, they haven't wanted to come. And they're still sitting largely where they were a couple of years ago with a few exceptions. But they are capable of moving now. There's no question about it. And they're becoming irritated to the point where they feel they may not have any choice of the matter. And that's why I say we may see

them cross that river in the next few months in order to root out this neo-Nazi regime once and for all and to secure the remaining objectives in this thing we call Novel Russia, which essentially is Odessa linked to most of what today we call eastern Ukraine, which was historically Russian. Now, will that happen? It's possible. It is not 100% certain, but with each passing day that we utterly refuse to even acknowledge legitimate Russian national security interests, it becomes more likely. And the sad part is that with each passing day, Europe is in greater turmoil.

All you have to do is turn on your YouTube or turn on television or cable, whatever it is, and look at the situation in France. Look what's happening across Europe. France is a bellwether. It's only started in France. We've got serious problems in Great Britain and Ireland. We're going to see similar things in Germany.

Everyone, it looks at this seriously like Professor Betts from King's College at London. He's done a whole study on this. We're in trouble in the West. We're in no shape to find anybody. It's absurd. Colonel, you mentioned that Russia may soon achieve its military objectives in Ukraine. will it be achieving those objectives minus some very senior generals whose confinement is a matter of fact but not generally known in the West? What's the story behind this?

Yeah, a few weeks ago, excuse me, it was not public knowledge, but it was, I would say, inadvertently leaked by the current Ministry of Defense in an interview. that they had several Russian generals under suspicion of effectively two things. One, corruption. And it's the sort of corruption that you would expect from a contractor in Afghanistan or Iraq, who says, give me $50 million to build this installation. He does $10 million worth of work stops. The rest of the money is pocketed and nothing changes. We've had those kinds of experiences with contractors.

This sort of thing is what many of the generals engaged in, but then they discovered evidence for treason, that general officers, particularly with children in school or in business in the West, they had been approached by the Ukrainian security services, and they had accepted additional monies in return for information about Russian plans and operations, particularly logistical, strong points and so forth. Right now, we're hearing that 20 of these generals have been arrested. How many will be tried for treason as well as corruption?

I don't know. But it looks like it's a substantial number. And more important, very recently, the news, Minister of Defense spoke to members of the Dumas. And in his remarks, he said a couple of things of interest. The executive officer that was previously working for Mr. Shogu, or General Shoygu, who who's the former minister of defense, was arrested and is now in custody in prison. She seems to have had significant knowledge about the corruption inside the Russian military,

and this corruption seems to have touched Shoygu because he is now under house arrest. This is very serious material because you're talking about a man who is the equivalent of our Secretary of Defense, who is under house arrest for alleged involvement, certainly is a minimum in corruption. Could this also involve treason? I have no idea. But the fact that he's under house arrest and is eventually going to be, I think, questioned based upon what his former executive officer is saying suggests that this is a very embarrassing event for Mr. Putin because this man, Shogu was a personal friend of Mr. Putin. So it's not only a question of betraying his office and potentially betraying Russia.

He is betraying a friendship. Now, this is not a good thing, but it's also interesting that it happens right now because there has been an enormous discontent inside the Russian military with many, many people for a long time concerning the conduct of the war against Ukraine. What I'm talking about are people, everyone from Germany, pilots to brigade, brigade commanders, to senior generals who have said, listen, this needs to stop. We need to get on with this war and end it. We need to take the gloves off and crush these people.

And Putin has routinely exercised control over this to keep this in bounds because he didn't want a war with NATO. Everybody knows that. But I think the frustration has built to a very serious point. And you have to go all the way back to the Progossian incident. And Progosion, who eventually ends up dying at a plane accident, gosh, I'm shocked. He was pushing very, very hard for a more vigorous and aggressive offensive posture on the ground in Ukraine. And one of the general officers who was identified as sympathizing with that approach, of course, was General Suroviken.

Seroviken was kept on board but sent to Africa where he did Yom and work for the Russians in Africa. He's now back and apparently is being put to work in some capacity in the theater of war. But I think this development suggests that we're going to see turnover in the senior leadership that we really haven't seen since the beginning of the war. And I would not be surprised to see Seroviken at the top in some fashion, at which point in time I would expect the pace of offensive operations to pick up substantially. And would you be surprised if general, former defense minister, good friend of President Putin Shoygu turns up in prison? No, but he could also experience an untimely death.

The rest of the generals undoubtedly will go to prison and those who are guilty of treason will suffer. to be executed. But again, stop and think this war has now lasted longer than World War II did for Russia. And you've had practically no change whatsoever at the senior levels. You still have Garasimov as chief of the general staff who was widely disliked and also reportedly an advocate for slowness and excessive caution and so forth. I think we're going to see turnover. If nothing else, this is an alarm going off in the Kremlin saying, you've got a big problem. This war has lasted too long. It's too static, and we have the wrong people in charge.

Mr. President, what are you going to do? Carter McGregor, terrific, terrific, over-the-top analysis on all of these topics from toilets and ship in the South China, to a major disruption in the Russian defense leadership. Thank you, Colonel. All the best, my dear friend. Okay, thank you, Judge. Sure. See you again soon. On all of these topics, if you're watching this live in 22 minutes at 3 o'clock,

the great Phil Giraldi, Judge Napolitano for judging freedom.