Judging Freedom - COL. Douglas Macgregor : Trump’s Dwindling Options

Episode Date: August 13, 2026

COL. Douglas Macgregor : Trump’s Dwindling OptionsSee 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. Fragically, 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 Thursday, August 13th, 2006, Colonel Douglas McGregor, joins us now. Colonel McGregor, a pleasure as always. Thank you. I do want to talk to you about President Trump's dwindling options to escape from Messy and Benjamin Netanyahu have created in Iran. But before that, I want to talk about military preparedness. When the Pentagon prepares an operation of the magnitude that President Trump apparently ordered, what steps do they take and how long does the preparation take? This is an important question.

It goes to the heart of a serious problem that we have in defense. We have a short war posture that permeates the entire Defense Department. If you go back to 1990, 91, you had this enormous rapid buildup of forces and supplies and ships organized in supply chains. Same thing with aircraft, civil aircraft, military aircraft, and within a remarkably short time from all over the planet came forces. Now, we were lucky we were able to do this without interference from any of the missiles that Saddam Hussein had at his disposal. which had to use them, could have been devastating, but the point is we had on hand on our shelves plans regarding how you would mobilize and move

all kinds of forces, air, space, sea, and also how you would retask satellites and satellite arrays in space to support the communications and operations. So we were prepared because we had spent decades preparing potentially to fight the Soviets in Central Europe. So that was assumed to be a potentially long war. Now, there were different estimates,

but the point was that you had to be able to fight for at least six months, if not longer. And that, of course, would then be accompanied by national mobilization and so forth. We don't have that, Judge. There was no mobilization, per se. We were living on whatever still exists. You've heard people say that we Americans have been living essentially on the industrial capital that was built by our ancestors. In other words, the scientific industrial base that emerges between, say, 1920 and 1960.

And they're right. That's what we've been living on. We haven't gone out to build a new scientific industrial base, per se, as China has in other countries. Well, the same thing is true in the military. We haven't done that because we picked opponents, whether they were in the ball, Balkans, they turned that to be the Serbs, or later on, you know, people like the Libyans, the Iraqis, the Yemenis, any number of different peoples. And the conflicts were short. And it didn't require a great deal of effort or military power to dominate them. And so we became used to this particular setting. This was the problem the British had before World War I. They were used to fighting with

they called opponents inside the empire and for our purposes the middle east africa maybe latin america under certain circumstances but no preparation to fight a powerful continental enemy so what do you get you get what we've got you take what you have you hurl it at iran which was from day one grossly underestimated and misunderstood and you come up short and so we have a navy that was not prepared for long terms at sea, didn't have the depth in the force, didn't have the depth in the personnel. And we're paying a price for it right now. So Benjamin Netanyahu apparently talks President Trump into fighting the war on two occasions around New Year's Eve in Mara Lago and then about two weeks later at the White House.

45 days later, the assault begins. Is that enough time to organize and prepare something of this magnitude? And does the Pentagon consider the economic and cultural responses to war at home? Or is that out of the Pentagon's purview? Well, I think, number one, the 45 days were not enough for what we, set out to do. And this goes back to some misapprehensions. President Trump decided to embrace the Israeli assessment. Remember the initial assessment was, this government may fall apart in four days, at the most two weeks. I mean, we went through this during the Kosovo Air campaign, where the comment was made when the military was asked by President Clinton, what do you think? How long is this going

to last? And the answer was a few days, 10 days, maybe two weeks at the most. Well, it went on for 78 days. And we know that it ended when Strobe Talbot was able to go and bribe Yeltsin to drop Milosevic, at which point in time the Serbs said, well, the game's up. We pull out. We don't have any Russian support. Well, you have something similar right now, except there's nobody you can bribe. Nobody's going to listen to you.

So you're stuck, and your opponent is prepared for the long haul. They've spent 20, 30 years preparing for, what they thought would be an inevitable war against us. So no, 45 days was not enough. Now, as far as the second thing is concerned, when you start asking hard questions about yourself, about what is the social cohesion of the United States? What's the impact on this all-volunteer force,

which in the aftermath of Vietnam, let's be frank, was kind of an expedience that was designed to get us out of a very bad situation with the American public. And again, that force was fine for Iraq and the circumstances and the duration of that campaign, but not much beyond that. And then we made it smaller. So I think the answer to the second question is probably no.

And then you've also misjudged your opponent. It's not just a question of how are we going to react and what do Americans think. I don't think there was any thought given to the possible requirement that you'd have to go out there and convince Americans that this was an existential threat and that our response had to be an existential existential one it's not nobody believes that and subsequently all the efforts by the media which is in the hands of Zionist Jewish forces as well as you know the usual suspects and all the newspapers the television so forth all trying to tell us you know Iran is going to launch nuclear weapons in five years and destroy Los Angeles, if we don't do this. Well, that's nonsense.

And everybody knows it's nonsense. So it hasn't worked. Do the people that really bear the burden in this war, take, for example, the 5,000 sailors and Marines, I guess it's both genders, male and female, I don't know if they have male and female on the USS Abraham Lincoln. But do people like that understand that they're not fighting a war for the United States of America? I think if they did not understand it when we left to go fight, I think large numbers of them now believe that. Yes. I think they know this is not an existential threat to the United States and that we're fighting for some other purpose. And I'm not sure they're clear on that purpose. Someone has told them we have to destroy Iraq. Iran, we have to open the straight. And they'll listen to that to a certain point, but no one has bothered to explain that this entire war is a product of the Greater Israel Project, the decision after the 7 October

attacks to sort of repurpose the response to the Hamas attacks, which we now think in retrospect were allowed to happen, but to repurpose those attacks in a way that would justify a regional war for Israeli Jewish supremacy tied up with interests here in the United States. So I think people have said, wait a minute, where's the Imperial Japanese Navy? It's not out there. We're not fighting it. Where's the Soviet Navy? It's not out there.

We're not fighting it. Then what are we doing? And I don't think most people are very happy with the outcome. Where's the Vermeck that's not there? That's right. Right, right, right. How do we know? Well, let me backtrack a little bit.

Benjamin Netanyahu not only talked Trump into this absurd war, he talked him into participating in an assassination of the Ayatollah. The Ayatollah was assassinated within the first 48 hours. His son, the Ayatollah that was killed was anti-nuk and moderate. The son, we don't know where he is on nuclear weapons. but he's certainly not a moderate from the hardliners he has assembled in the government around him. Is that an understanding with which you concur? Oh, no, you're right.

And I know that Max Blumen Thaw has talked about that. There's also Artimawaini, who's a true expert on Iran and the region. And let's understand what's really happened. Sure, you've killed off the leadership that was there at the outset of the war. Surprise, surprise, the people have risen up have turned out to be tougher, more aggressive, and fundamentally less likely to cooperate with you. That's something that the Germans discovered when they fought the Soviets. You know, Stalin had murdered an estimated, what, 50 to 60,000 Soviet army officers. And people inside the German general staff, many of them were convinced, well, this is going to have a terrible impact.

on the conduct of operations they've weakened the soviet armed forces but there's always another side to this when you remove certain people that are older who have been in those jobs for some period of time you suddenly remove them and replace them with younger people new people with new sets of eyes new ideas things actually get tougher for you you end up fighting people that were better than the ones you disappeared at the beginning now the difference this time around and this is hard for people to get. This is very important. When I was at the Dayton Accords, when General West Clark there was advising Ambassador Holbrook, I would sit and listen to Europeans and members of the Clinton administration, and they would talk about how all of these people in the Balkans

are really the same, and all of these people would come together and understand each other. And trying to explain to people that these individuals, whatever they were before the Civil War in Yugoslavia began, is now different, for what they are today. Too much blood has been spilled. Too many families killed. Too many friends and sons and fathers have died. Too many women have been violated and raped, all these things.

I said, what do you expect these people do to embrace each other and say, oh, well, let's all bygones, be bygones, love each other and get along? Nonsense. That's what's happening in Iran today. For them, this is an existential war. that you're seeing the emergence of a new population, and I would argue, and Art of O'Oenie argues, a new state, a new Islamic Republic that is going to be much tougher, much stronger, much more cohesive and determined than anything we countered or encountered in the past, much more so. What you've just articulated, was it not known and perceived by American intelligence, but rejected by the Israelis whom Trump, Trump chose to believe. Is this war a fundamental, a result of a fundamental character flaw in the

President of the United States? Well, character flow may not be the right word. The right word might be lack of understanding, lack of confidence in his own people, because he does seem to have deferred to the Israelis along the way, Judge. I don't see any evidence that he's ever really said, no, thank you, don't agree with you, go back and reexamine your assumptions, which is normally what you say to somebody when they present you with an assessment as Phil Giraldi or Larry Johnson can tell you, you look at this thing and say, well, listen, I've read this, I've also read your assumptions. I don't think they're right. That doesn't seem to have happened. It seems to have just been taken on

uncritically by the president. And that's the fold of the six or seven people that surround him. They allowed him to do that. It was up to them to intervene and say, no, wait a minute, boss, before you buy into this 100%. Let's go back and reexamine these other reports where the assumptions are different. That doesn't seem to have happened.

Well, this happened as recently as last week with the Air Force One. Mossad said, we have been told that the Iranians are going to bomb, are going to attack the plane with a missile. You better get the president out. CIA said, no, it was very low confidence in there, very low confidence in the Iranian threat. Trump chose to believe Mossad, leave his senior staff and cabinet members on the plane as a decoy

and go hide in another plane, because Netanyahu's people wanted to scare him. Well, I saw some pictures of the president and in one of these trucks carrying supplies for the aircraft. And several people told me he looked really good with the vegetables. Listen, I can't explain all of that. I mean, obviously, he wasn't terribly worried about having to replace the people on the other plane. That may tell you something.

But beyond that, it just doesn't make a lot of sense. And if you're going to be the commander-in-chief of the U.S. Armed Forces in war, time. You have to listen to people that are concerned about your safety, but at some point, you can't say, I'm going to sneak out of here. I'm worried about my safety, especially when you have people in the Gulf, people at sea, people on the land, whose lives are at risk all the time. At some point, as president, you say, look, okay, thanks. I'm going out on Air Force One. If I don't go out on Air Force One, people will genuinely think there's something wrong. There isn't. And I don't want to be viewed negatively by the men, women that I command in the armed forces. But that did not occur to him.

Colonel to Ukraine, did the United States Army and the Ukrainian army recently engage in war games in Germany? Well, this appears to have occurred in May, June time frame. Maybe it started an April. I think I sent you the blurb about it. We conduct these kinds of exercises on a routine basis. But it's important to pay attention to this because there were apparently people quite surprised that the Ukrainians, who of course been at war now for four years, came in, and they employed tactics that had been employed against them, and some of the tactics they've employed against the Russians. And it turned out we were completely unprepared for it, and we were annihilated. Now, why is this important? Does this say our army is terrible or our Navy isn't

right or anything else? No, that's not the point. The point is that a lot of years have gone past. Things have changed dramatically. If you were going to point to an analog for the battlefield that we face today, in other words, what you have on the ground in Ukraine, and to a lesser extent, what we're seeing today with Iran, looks a lot like World War I, Judge. In other words, People went into World War I prepared for a war of maneuver and they lost hundreds of thousands of dead, hundreds of thousands killed, and were then forced into static positions of defense. And then suddenly became very clear to everyone. The defense was superior to the offense. We spent the next four plus years trying to break out of this defense posture really never did. The war ended because of a state of exhaustion. And I would argue on all sides, not just the defense.

German. So the point right now I think we need to take from this is that this is a very different warfare state right now. When I say state, I mean condition. It's a lot like World War I. You're not going to be able to do the things you did in the past, behave as you did in the past. You're going to have to prepare it for a very lethal environment. It's different. And we're going to have to live with this environment in which the defense is superior to the offense. And And I hope somebody is looking at it for that statement. It goes also back to the other comment. It's time to start preparing to fight a long war because any war you get involved with as

a result of the changes in technology is likely to be long, not short anymore. That assumes that you're going to travel anywhere to fight anybody. That's another question. So I think it's a good thing this information has gotten out. I hope the senior military leadership of the Army and the Marines, everybody's looking at. at this because we've got to come to terms with it. If we fight in the future, you've got to expect to confront this kind of lethality and threat. We've got to plan for it. We've got to find a way to counter it.

To me, it's almost inconceivable that the Ukrainians beat the Americans and that the Ukrainians had time to engage in war games when they're fighting an existential battle against the military five times their size. Well, we've paid for that. We brought them out, we set them up, and they were enabled to do this. I think whoever did it deserves credit was a smart thing to do. And you know, you know my view on this whole thing. The war, for all intents and purposes on the ground is lost. Ukraine is not going to win anything.

There is not going to be any comeback. The question is, will there even be a Ukrainian state in the future? But we can learn from this. So I'm glad that they brought out these veterans. And we did this in the 1970s. If you go back to 1977, 78, 79, there were still German generals alive who had fought on the eastern as well as the Western fronts, fought against us, the Soviets and the British. And they did something similar with NATO. And then they were brought in to reorganize the way NATO should fight if it has to fight the Soviets.

And when they were put in charge and they were allowed to make those changes, they defeated the Soviets. we had lost over and over and over again. That's one of the reasons they brought them in. I do think they had an impact, and you see changes in the U.S. Army in particular in the 1980s that reflect that influence. So this is a good thing, and we should not misinterpret it. It's not a bad thing.

What would have been bad is to run another rigged exercise, and we certainly have done a lot of those, Judge. What is the U.S. doing in Ukraine now? The United States continues to provide valuable intelligence at every level to those few forces that are left, especially those that have the capacity to launch long-range drones and missiles. And this data is very detailed. I mean, you have U.S. Army and Air Force surveillance aircraft that fly along the periphery of Russia and Ukraine. You have our overhead satellite pictures. All of this is provided

on a real-time basis. You recall the attacks that the Ukrainians launched on Mr. Putin's residence in northern Russia. Fortunately, he was not there. Well, how did they know that that was his residence? How did they know that he was or was not there? How did they plot the attack on the map? How How did they know where to fly? What air and missile defense batteries to avoid? All of that was because of us. So that helps to create the illusion that there is still a viable force in Ukraine that is going to pick itself up off the floor and suddenly become rocky and defeat the Soviets.

It's not going to happen. But in the meantime, we've helped them do damage that is both irritating but also galvanizing. And I think that's what you're seeing happening in in, in Russia. Russia, I'm sure you and others saw President Putin's most recent speech in response to an attempt to stop one of Russia's freighters. I think it was moving to the Baltic or the North Sea. And he put everyone on notice. We're not going to take this anymore.

We will respond, and we will respond wherever we care to, globally. So these attacks are not going to change the outcome of the war, but they could make life miserable for everybody in Europe. And General Karin Kavich was having. actually pointing to the deficiency in air and missile defense. Even if we had everything in Europe now that we had just a year or two ago, we'd be lucky to cover five to 10 percent of the critical targets in NATO. So he's saying it's worse now than ever. Yes. Well, here's President Putin. I don't know if this is the speech to which you refer. This is just two days ago. He's in uniform.

He's addressing troops. And it sounds. me like he's going to attack NATO facilities. Well, you tell me what you think. Chris number 12. NATO is gradually seeping into the area and new military political blocks are being formed right before our eyes. New weapons systems are currently being deployed and are also planned for deployment here, which pose serious threats to our country as well. Tensions are also been significantly ramped up in the neighboring Arctic zone, which we have already mentioned, specifically regarding the ongoing use of the Northern Sea route. Although Russia has always, and I truly mean always,

consistently educated for and now confirms its full and complete readiness for broad international cooperation and utilizing the many strategic advantages of the Northern Sea Roe for the mutual benefit of everyone in Poland. And those states that are genuinely interested in working with us are now showing a significant level of interest, primarily from our close friends such as China, India, and other nations. They are currently engaged in active discussions with us regarding these issues, and we will certainly welcome and encourage joint cooperation, both with our friends and with all

countries there. It was gradually seeping into the area and posing serious threats to our country. Is he going to attack NATO facilities in Ukraine, which would mean killing a contract, or officers from Germany, Britain, Poland, the U.S.? Well, in Ukraine without question, he's already done that. Not necessarily deliberately, but you had a group of NATO officers at a school in the vicinity of Poltava in eastern Ukraine. In fact, several Swedish officers, they were all killed

in a tactical ballistic missile strike. What he's saying now is I think not simply Ukraine, but I think it could expand. I think we're reaching the point where we risk a confrontation with Russia at a point in time when we're not equipped for it. And again, read the subtext on Grinkevich. He's trying to send a signal.

If the Russians decide to move decisively with theater range ballistic missiles, cruise missiles, or unmanned systems against specific targets in Romania, Poland, Germany, Latvia, Lithuania, wherever, there's nothing he can do about it. That's not a good position to be in, but that's what he's saying. And I think Putin is saying that. Now, there's something else, and this goes back to a question you asked earlier.

Robert Burns wrote a poem years ago in which he said, grant me the gift of being able to see myself the way others see me. You were asking that about the Pentagon, about the Department of Defense. Right. Do we see others in a realistic light? The answer is no. We've never understood the Russians. We've never tried. You know, this rules-based liberal international order nonsense throws international law out of the window. Under international law, the existing body, Russia is a sovereign state. You cannot arbitrarily violate Russia's sovereignty.

We decided it doesn't matter. Democratic states, liberal democratic states, are those that fancy themselves as being liberal democratic, we can debate that, as you know, seem to think that they can do whatever the hell they want. They can challenge anybody, anytime, anywhere. They can decide what is morally right or what is morally wrong. And that's the problem. All of this is wrapped up together in this sort of insane liberal internationalism that's dragged us through the Balkans, dragged us into Africa, dragged us into the Middle East, and ultimately it's being part of the justification for war in Iran. It's crazy. It needs to stop. And the Russians are prepared to stop it. And I think we ought to take them very seriously. Colonel McGregor, thank you very much, my dear friend.

Thanks, as always, for letting me go across the board from the Pentagon to war games in Germany to Iran. Thank you, Colonel. All the best, my dear friend. We look forward to seeing you next week. Thanks very much, Judge. Sure. Coming up tomorrow Friday, at 8 in the morning from Tehran, Professor Muhammad Miranda, from outside of Paris, if we can find him. Sometime during the day, we'll let you know, Pepe Escobar, and at 4 in the afternoon,

the Roundtable, the Intelligence Community Roundtable, with Larry Johnson and Joe Kent. Judge Napolitano for judging freedom.