Editor’s Notes: In this episode of Judging Freedom, Judge Andrew Napolitano is joined by Colonel Douglas Macgregor to provide a critical analysis of the escalating conflict with Iran. Macgregor explores why the administration may be seeking a “war-ending offensive” to secure a perceived victory and avoid public humiliation as the campaign fails to meet its original goals. The discussion delves into the dire global economic consequences of the conflict, the depletion of U.S. and Israeli ammunition reserves, and the shifting paradigms of 21st-century warfare. Together, they question the strategic objective of the war and the long-term impact on the American military and financial systems. (March 26, 2026)
TRANSCRIPT:
“Undeclared wars are commonplace. Tragically, 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.”
JUDGE ANDREW NAPOLITANO: What if sometimes to love your country, you had to alter or abolish the government? What if 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, March 26, 2026. Colonel Douglas Macgregor joins us. Colonel, we’ve missed you. Welcome here. Thank you for accommodating my schedule. Why is President Trump so desperate over this war in Iran?
Trump’s Desperation and the Failing Iran Campaign
DOUGLAS MACGREGOR: Judge, I think there are a number of reasons. The first and most important, obviously, is that he faces public humiliation here at home and abroad. Things have not gone as he anticipated or as people predicted they would, that work for him. In other words, this was not a short, decisive campaign designed to decapitate the leadership, crush the government, provoke internal unrest.
Having not succeeded at that, we then began this long, slow process of trying to cause the disintegration of the Iranian state by bombing targets — targets having been picked for all sorts of reasons, most of them military, but not exclusively. And so now he has this terrible mess on his plate, and that’s why he is now taking a five-day break with the goal of putting together a war-ending offensive from the air and with missiles and bombs. And I think that’s what we’re going to see shortly, in the next week.
The Ground Offensive Question
JUDGE ANDREW NAPOLITANO: Is he planning a ground offensive, and what do you think that would look like, Colonel? Something that doesn’t appear as though it was in the original plans.
DOUGLAS MACGREGOR: No, I think there was never any thought given whatsoever to the use of ground forces. And why would you? This is a nation of 93 million people, the size of Western Europe. So it makes no sense to think about something like that unless you want to declare a national emergency, open a draft, and then plan on invading after at least 12 to 18 months of preparation with at least 2 to 3 million people. No, that was never part of it.
And I think what they’re trying to do is first and foremost launch what they hope will be a war-ending offensive. They’ve replenished their stocks, at least on the American side, of the most exotic munitions, missiles and capabilities — JASSM and these other weapons that have been launched from outside of Iranian airspace into the Iranian state. I think they’re going to put those together. And once they feel that they’ve got a comfortable edge that will give them 72 to 96 hours of non-stop attacks, then I think they’ll turn to the ground option, which for them is very limited.
It amounts to the seizure of some islands everyone talks about — Kish Island. Whether or not that actually needs to be seized is another matter, but it’s certainly a target. And there are other islands inside the strait itself, not far from Bandar Abbas, right offshore, that theoretically have Iranian IRGC — Iranian Revolutionary Guard Corps — elements, small boats and so forth, that can exert some influence.
But everybody forgets a couple of things. First of all, what really closed the Strait of Hormuz was not Iran itself, but Lloyd’s of London. Suddenly none of the ships could get insurance. And if you can’t get insurance, you’re not going to take a tanker worth hundreds of millions of dollars through the Strait of Hormuz. So that was number one.
Once it became clear that you couldn’t get insurance, then the Iranians were in a position to say, “Well, if you’re not supporting the war against us, you’re not allied with Israel or the United States in some way, and your destination is China or India — now increasingly Japan — then we’ll be happy to let you through, provided of course that you’ve paid for the oil in yuan.” This is an effort to get at the petrodollar.
So I think what we’ve got now are two levels of warfare. On the one side, there is economic warfare that we’re losing, because the entire world is suffering as a consequence of this war in the Persian Gulf. And then secondly, we have the Iranians who are exercising a new form of warfare.
It’s the 21st century answer to the American World War II paradigm. Our World War II paradigm is on display — you see it with aircraft carriers and destroyers, offshore submarines, and then at the same time, numerous aircraft flying from various airstrips ashore, and even back in the United States and Diego Garcia. That is being our instrument of war.
It hasn’t worked out as well as we’d hoped, because the new way of war is essentially almost limitless quantities of precision-guided missiles and unmanned systems that can be launched from anywhere inside the border against targets up to almost 1,000 miles from Iran.
And this has been very effective. It’s driven our fleet way offshore. It’s forced us to bring in hundreds of aircraft that have to be refueled on a routine basis over Iraq or Saudi Arabia or other areas.
So it’s a different kind of warfare, but it’s turning out to be very successful. Iran doesn’t need an air force, doesn’t need a navy. It has an army, and it has lots of missiles and drones. And these things are prepared for use almost immediately from various underground enclosures.
So that has to be defeated from the standpoint of President Trump, because if you can’t defeat that and you try to put ground troops on these islands — we have about 10,000 light infantry right now for that purpose — they’re at high risk of being killed once they come ashore. In fact, Iran still has pretty capable air defenses for everything under 15,000 feet of altitude, which means that if you try to fly them in with V-22s and helicopters, they’re going to very much be at risk.
So I don’t know how this is going to work, but I think this is designed to be the war-ending offensive. It is sort of the last throw of the dice, if you will, for President Trump.
Trump’s Claims of Victory
JUDGE ANDREW NAPOLITANO: Here’s the president two days ago saying, “We won,” which I think is absurd, and I’d like you to comment on it. But beyond that, he boasts about things that I’m not sure if they’re truthful, or if they’re truthful, if they’re meaningful. Watch this.
VIDEO CLIP BEGINS:
DONALD TRUMP: “Well, I think we’re going to end it. I can’t tell you for sure. I don’t like to say this — we’ve won this. This war has been won. The only one that likes to keep it going is the fake news. I mean, the New York Times. You read the New York Times, it’s like we’re not winning a war where they have no navy and they have no air force and they have no nothing, and we literally have planes flying over Tehran and other parts of their country. They can’t do a thing about it.”
VIDEO CLIP ENDS:
JUDGE ANDREW NAPOLITANO: Are those statements true? We have total air superiority — putting words in his mouth — and they have no navy. Or if true, are they meaningful?
Assessing the Metrics of War
DOUGLAS MACGREGOR: Well, that’s the real question. Again, he’s using metrics that we saw used in Vietnam. We saw them used during Desert Storm. You’ll recall all the press conferences held by General Schwarzkopf where he would list, “Well, today we destroyed 50 tanks and 150 armored fighting vehicles,” or something. This would go on day after day after day. Now, when we finally got into the place, we discovered that a lot of those losses were absolutely untrue, because they’re based largely on battle damage assessments done by pilots when they come back from their strikes, or from overhead surveillance, which isn’t always perfectly accurate by any means. So that’s the old metric.
And he says, “We destroyed their air force.” Well, frankly, Iran hasn’t had an air force since the Shah left the country, so there was no real air force to destroy. What about this navy thing? Well, they had seven old frigates. We sank one that you’re aware of off the coast of India, that was unarmed and part of a joint naval exercise with the Indian government. And we’ve sunk some boats, I’m sure, but they’ve got large numbers of small boats, fast boats — some are manned, some are unmanned — carrying explosives, firing missiles. You could go against them day and night for weeks.
So he’s using a metric that sounds great if you believe in the World War II paradigm, which is what we’re stuck in and what we’re using. I don’t think it’s very meaningful.
The Global Economic Crisis
Now, let’s stop and consider something. What else is really happening in the world? Well, the strait is functionally closed to anybody that supports us and Israel against Iran. But we’ve already had a tremendous disruption in the supply chain for oil and petroleum and liquefied natural gas. The world is facing a crisis of food, fuel, fertilizer, and feedstock. Think about that — the whole world is struggling with this right now.
In two weeks, Great Britain will no longer have any oil reserves. None. India is in trouble. India now has hundreds of thousands, probably millions of people lining up to buy gas. It can’t keep up with the demand. It’s shutting down industries — plastic industries in particular, which depend upon petroleum, are shutting down. You have a similar situation in Japan.
Now, China is actually prepared for this disaster. They have a much larger strategic fuel reserve that has more months in it. But the bottom line is the whole world looks at this as a catastrophe for themselves, for their security, for their businesses. And I think the Iranians know that. And I think the Iranians have planned on tremendous pressure being exerted by the rest of the world on us to stop the war. And I think that’s beginning to build, and I think it’s going to be very powerful in the weeks ahead.
We haven’t talked about what’s happening here and the impact of inflation, the fragility of our financial system. And the question is coming up more and more — how do you pay for all of this? It’s no longer a $1 trillion defense budget. It’s now a $1.5 trillion defense budget to pay for everything you can conceive of. And how are we going to do it? And people are asking that question, and Bessent says, “Oh, it’s a ridiculous question. We just print money. We just buy up our own debt because nobody will come in and buy it.” We’re headed to a catastrophe, financially and economically as well. It’s just going to take longer to happen here than it’s happening today in Europe.
Hegseth’s $200 Billion Request
JUDGE ANDREW NAPOLITANO: Secretary Hegseth has asked for another $200 billion, using one of his snarky phrases: “It takes a lot of money to kill bad guys.” Well, the $200 billion, even if authorized tomorrow, wouldn’t be used to kill bad guys. It would be used to enrich the manufacturers of ammunition that we’re depleting.
DOUGLAS MACGREGOR: I think he, along with our 15-point proposal to the Iranians, is disconnected from reality. We’re not really interested in negotiating with Iran. We want to destroy Iran. That has always really been the goal. Whatever is left over, we plan to divide up. We and the Israelis plan to control the oil, obviously, and the gas, whatever else is there.
But this is effectively another version of the strategy that we embraced against Russia, that has ultimately failed in the Ukraine war. Ukraine has lost 1.5 to 1.8 million men fighting. The Russians are in control of the critical terrain that they went in to liberate to begin with. They don’t really want this war to go on. They’d like to bring it to an end, but no one is willing to cooperate with them. But this is not costing them anything. And as we all know, they’re doing a land-office business in oil right now, because they’re supplying oil to everybody that can possibly afford to buy it, and they’re doing it at very, very lucrative prices. So you can say we’ve done wonders for Russia, and whatever sanctions we’ve imposed have turned out to be completely irrelevant.
The point is, though, now we have what — 10,000 light infantrymen — and we’re trying to figure out what we can do with this. Is it going to make any difference to who controls the Strait of Hormuz? I think that’s a very tall order. I think it’s going to be very difficult and extremely dangerous.
U.S. Ammunition Supplies
JUDGE ANDREW NAPOLITANO: Colonel, how depleted are U.S. ammunition supplies as we speak, late March of 2026?
The Reality of Ground Invasion and Iran’s Defensive Capabilities
DOUGLAS MACGREGOR: Well, I found an article from RUSI, the Royal United Services Institute. I think I forwarded it to you. It has a table in there showing how many days left of various kinds of munitions we and the Israelis have. Now, of the two, the Israelis obviously are in very serious trouble right now. Eight out of every 10 missiles that are launched at Israel penetrate the Israeli air and missile defenses. So Israel is taking one hell of a beating. There’d be no question about that.
What about us? Well, we have some concerns about theater, high altitude air defense missiles. That’s the high end. If there’s anything out there that we could possibly succeed in using against hypersonic missiles, that’s what they are. But we too are running very low. We’re running very low on PAC3.
Now, as far as the offensive munitions and missiles, we’ve got several weeks left. I’m told the Israelis may only have a couple of weeks left. And then when you run out of the exotic material, that’s when you turn to the, quote, unquote, “dumb bombs.” You know, B52 that flies over Tehran. I don’t know if they’ve done that yet, but I have a feeling they probably have because I see a lot of evidence for carpet bombing. Each B52 carries 9,500 pound bombs. This is the sort of thing that was developed during the Second World War for Japanese and German cities. They just fall on the population and on the city and inflict what everybody hopes will be unrecoverable damage.
But I think we also need to understand that after all it was said and done and all these air offensives, the air offensives did not win the war. And that’s what people seem to fail to understand. And we’re not going to defeat Iran without some other approach. And the only other approach that anybody can come up with is a massive ground invasion.
But in addition to Iran not presenting any threat to us, which has always been true, what’s the strategic payoff for us to spend a trillion dollars to invade the country and essentially occupy it? A hostile place that’s going to hate us in perpetuity. Note that Iraq, the place that we occupied, is in the forefront of declaring war on us, trying to drive us out of their country and supporting Iran. So what are we trying to do? What is the real objective? And I think at this point it is to create the illusion of victory so that Donald Trump can escape humiliation.
What Would a Ground Invasion Actually Require?
JUDGE ANDREW NAPOLITANO: You used an interesting word to describe the size of the boots on the ground troops that would be necessary. “Massive.” What did you mean by that in terms of numbers?
DOUGLAS MACGREGOR: I’ve heard several people say, “Oh, we could do it with 200,000. We could do it with 500,000.” And my question is always, what are you on? A punitive exercise? You want to cross the Zagros Mountains, which are like the Rockies, move down into the low country where Tehran, Tabriz, Isfahan are, march in there, devastate the cities, and then eventually march out. Is that what you want to do?
I mean, I don’t know what the answer is, but I think first of all, we have to understand the two ways of war. What the Iranians are doing is that they have built enormous quantities of standoff attack weapons, primarily ballistic missiles and unmanned systems. We call them drones, in huge quantities, most of them underground. They can be launched at will. And we keep saying, “Well, we’ve eliminated all their launchers.” Well, I have a lot of difficulty understanding that. I don’t think we’ve eliminated all their launchers. I think there are more launchers out there than we care to admit. I don’t know how many decoys we’ve struck. We hit a lot of decoys in Kosovo back in 1999. I think we’re hitting lots of decoys inside Iran.
But the point is, they built all these systems. They have what we call persistent surveillance. Sometimes people call it a surveillance stare, as in staring at something at all sorts of levels. Now, if they come down to lower levels like the MQ9, the Israeli Hermes, the Iranians have been shooting those things down. But at higher levels, they haven’t been able to do that. And unless you can jam the satellites that the Chinese and Russians are utilizing on behalf of the Iranians, I don’t think we can disrupt them in some dramatic way.
That means that wherever we go within a thousand plus miles of Iran, we are being watched. Whatever we do is being identified. In other words, from where do you move if you’re going to attack inside the strait? Are you going to fly off of carriers that are, what, 700, 800 miles away from the strait? Are you going to fly ashore somewhere into Saudi Arabia? Are you going to fly into Jordan? Are you going to fly into Kuwait? Anywhere you go, you’re going to be identified. They’re going to find you. They will discover you. Then the only question is how long do they wait until they concentrate their tactical ballistic or theater ballistic military power against you, along with untold numbers of drones?
It’s going to be very difficult to protect against that, especially since we haven’t found that our air and missile defenses are nearly as effective as is claimed. I mean, we hear, “Oh, we have 90% effectiveness.” That’s not true. I’m getting reports from people in the fleet to suggest it’s infinitely lower than that. So how are you going to guarantee that they could even get in? And how do you protect them once they are in? How do you get them out? This is another exercise in, “Well, we’re going to be successful, so don’t worry about that.” What if you’re not successful? How do you extract your troops? How do you evacuate the wounded? How do you keep these people alive? Where do they get water?
And remember, Iran has already said if we’re going to destroy their power plants, they’re going to destroy everything in the Gulf and 90% of the electric plants. In other words, the power plants in the Persian Gulf on the eastern or the west side are all along the coast. They’re all identified. They’re easily struck and put out of business. What about the desalinization plants? We hit those, they’re going to hit them. And the people in the Arabian Peninsula are then in very serious trouble. Not just our troops.
I don’t think this is a good idea. But we’re back to the war ending offensive. “Develop a war ending offensive for me so I can walk out of the Oval Office and say, ‘Victory at last. The Iranians are surrendering.'” Good luck, Colonel.
Video Clip: Lindsay Graham on Marines and Peace
JUDGE ANDREW NAPOLITANO: I apologize for the heartburn, but here’s the guy that whispers into Trump’s ear in the golf cart a couple times a week. Chris, cut number five.
VIDEO CLIP BEGINS:
LINDSEY GRAHAM: We got two Marine Expeditionary Units sailing to this island. We did Iwo Jima. We can do this. The Marines. My money is always on the Marines. I don’t know if you take the island or you blockade the island, but I know this. The day we control that island, this regime, this terrorist regime has been weakened. It will die on a vine. And here’s what I want to do. I want to get with Chris. I want to sprint to peace. As the war winds down, I want peace to ramp up.
The reason we don’t have Saudi Arabia and Israel making peace is October 7, 2023. Iran, through Hamas, attacked Israel, stopping normalization. I want to take up and complete what Biden started. As soon as we get Iran defanged so they can never do another October 7th, I want to start up peace talks between Saudi and Israel this year. I want a peace deal between Saudi and Israel normalizing, ending the Arab-Israeli conflict. It’s been going on for 2000 years this year, and you can’t do it with a lethal Iran. So we’re weeks away from this Iranian regime not having the capability to stop people’s peace.
VIDEO CLIP ENDS:
The Lies of “The Road to Jerusalem”
JUDGE ANDREW NAPOLITANO: Does he know what he’s talking about?
DOUGLAS MACGREGOR: Well, Judge, don’t you remember that Saddam Hussein was responsible for 9/11, right? We had to go and get him. I also remember Paul Wolfowitz telling everybody, “The road to Jerusalem begins in Baghdad.” Going to Baghdad, then we have the road to Jerusalem. We’ll have peace break out all over. This is all crap. It’s all nonsense. It’s lies. And that’s the only thing that you can say.
And when he starts talking about Marines, 19,000 Marines were killed in the Pacific during the Second World War. And in retrospect, many, many studies out there have demonstrated that at least two or three of the islands on which these men died in great numbers probably didn’t need to be attacked. And then nobody ever talks about Okinawa, which was the last big operation of the war. And strictly speaking, when you look at our losses, the casualties we took and the ferocity of the Japanese defense, most people don’t regard Okinawa as a great victory. In fact, Okinawa played a major role in the decision to use the atom bomb because we said, “If this is the quality of resistance we will face, we’ll forget invading Japan. That’s an impossibility.”
What I’m trying to say is throwing around these World War II analogies and statements that may evoke one or two positive images, but the reality is ugly. The war was ugly. We are not involved in a life or death struggle against an enemy in Iran. We are there because of Israel. That’s it. And the Israelis, agents inside the United States who have a great deal of money and influence. These are the people that brought us into this war.
I don’t know how Americans feel right now. Most Americans in uniform will always do what they’re asked to do. But I’m sure there are more than a few out there beginning to wonder, does this really make any sense?
And we have always talked about this too, Judge, on the show. Let’s assume I’m wrong. Let’s assume that this war ending offensive works and we utterly destroy Iran to the point where the state and the society disintegrate. Then what happens? The answer is clear. Chaos. And that chaos is going to spill over into other countries in the region, into Turkey, into Syria, into the Arabian Peninsula, and ultimately into Europe.
As we’ve seen before, I don’t think the Russians or the Chinese are going to sit still for that. They’re not going to sit still for the permanent closure of the Straits of Hormuz, which is damn near what would probably result, because it would be the end of the Gulf Cooperation Council, the end of the Emirates. They will vanish and there will be nothing there. And it will take us a decade or more to recover from this.
Video Clip: Jim Webb on Honor and Mercenary Wars
JUDGE ANDREW NAPOLITANO: Colonel, one last clip for you. A young Marine named Jim Webb, whose grandfather was Ronald Reagan’s Secretary of the Navy, and also a Marine, the grandfather, and also a United States Senator from Virginia, being interviewed by our friend Tucker Carlson. It’s very telling what he says. Chris, number 22 as of right now.
VIDEO CLIP BEGINS:
JIM WEBB: I hate to say this, I love this country. I am not as proud of anything as I am of my service in the Marine Corps. But I will not let my kids join because of the way that we went to war with Iran. Because if you look at it philosophically, we have gone to war on behalf of another country to further their interest. Those are not my words. The administration has said as much. The Speaker of the House has said as much. And when that’s the case, you have reduced our military to effectively a mercenary force. And there’s no honor in that. This is an offensive war of choice.
VIDEO CLIP ENDS:
JUDGE ANDREW NAPOLITANO: Sounds right on the mark to me. I wonder if a lot of young people in uniform share that view.
DOUGLAS MACGREGOR: Well, I don’t know. You’d have to ask. My experience with most Americans in uniform is they will always do their duty, even when it’s distasteful to them. This is a little different because the blowback financially and economically on us is going to be severe.
But this brings to mind a conversation I had many years ago, about 2000, with a member of Congress. This person was a key figure on the House Armed Services Committee. And the issue of the draft came up and he said, “Well, thank God we got rid of that draft. That would have inhibited us, prevented us from doing all the things we’re doing. Thank God we have a volunteer military because we can do pretty much what we want.”
I think going to the volunteer military had many, many positive features, but ultimately it was a lot like going off the gold standard. Once you no longer had a gold standard and you had currency that was not anchored to anything tangible except the supposed faith and confidence in the US Government, what you had was the ability to print money to cover the costs of anything you wanted to do, and that meant wars. And that’s what we’ve done.
At the same time, you have a similar situation with the military. Well, there’s no draft. Less than 1% of adult Americans is affected in any way by what we do militarily. So who cares? What difference does it make?
Ronald Reagan never felt that way, which is why he reacted as he did to the loss of those Marines in Beirut back in 1982, 83. But since then, I’ve detected a greater willingness to sort of expend us without a great deal of concern. I think the last person that cared deeply about the whole business was President George Herbert Walker Bush.
Since then, I don’t think it’s meant very much. Remember George W. Bush telling everybody, “Go shop, just go shop. Don’t worry about what we’re doing in Iraq, just go shop. Shop long enough.”
Closing Remarks
JUDGE ANDREW NAPOLITANO: Colonel, thank you very much. A great, great analysis, my dear friend. Deeply appreciate it as always.
DOUGLAS MACGREGOR: Be well.
JUDGE ANDREW NAPOLITANO: We’ll look forward to seeing you next week.
DOUGLAS MACGREGOR: Okay, Judge, thanks.
JUDGE ANDREW NAPOLITANO: Thank you.
DOUGLAS MACGREGOR: Wow.
JUDGE ANDREW NAPOLITANO: A great man who does not hesitate to speak his mind and whose ability to analogize history with present day facts is second to none. Coming up tomorrow, Friday, the end of the day, the end of the week, almost the end of the month, our Intelligence Community Roundtable, Larry Johnson, Ray Govern, 4 o’clock in the afternoon. Thank you for watching Judging Freedom.
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