Editor’s Notes: In this episode of Judging Freedom, Judge Andrew Napolitano welcomes Colonel Douglas Macgregor to discuss the critical failures in the Pentagon’s strategic planning regarding the conflict in Iran. Macgregor analyzes how modern shifts in warfare, such as space-based surveillance and pinpoint accuracy, have been underestimated by American military leadership. The conversation also delves into the complex geopolitical influence of Israel on U.S. foreign policy and the severe global economic consequences of the ongoing regional instability. Additionally, the episode marks a significant milestone for the channel as it surpasses 750,000 subscribers during the live broadcast. (April 23, 2026)
TRANSCRIPT:
Introduction
JUDGE ANDREW NAPOLITANO: Hi everyone, Judge Andrew Napolitano here for Judging Freedom. Today is Thursday, April 23rd, 2026. Colonel Douglas Macgregor will be here with us in just a moment. Just how bad, how poor were the Pentagon plans for this war in Iran.
Did America Negotiate for the U.S. or for Israel?
JUDGE ANDREW NAPOLITANO: Colonel Macgregor, thank you, my dear friend. Welcome here, and thank you for accommodating my schedule as you always do. In your view, from your perceptions, did the American negotiators in Islamabad a week and a half ago negotiate on behalf of the United States or on behalf of Israel?
DOUGLAS MACGREGOR: That’s a loaded question, Judge. I think we have to say that there was no negotiation because ultimately we had the Iranians that showed up with a contingent of almost 70 people armed with all sorts of data, information, analyses because they fully expected a negotiation to occur.
Instead, what they got was a team from the United States that presented Mr. Netanyahu’s demands to them, and they can’t accept those demands. And I think that’s been made pretty clear. And while there was some discussion about the enriched uranium, ultimately the outcome was simply, “No, we cannot conform to your expectations, and our expectations are Mr. Netanyahu’s expectations.”
So frankly, I think the answer is pretty clear. We negotiated on behalf of Israel.
Would Netanyahu Wreck a Peace Deal?
JUDGE ANDREW NAPOLITANO: If Donald Trump comes to his senses and enters into some kind of an agreement, say along the lines of the JCPOA, which he condemned as a private citizen and literally ripped up in his first term, would Netanyahu try to wreck or disrupt such a peace plan so as to continue the war? Because without it, he has no political ground on which to stand.
DOUGLAS MACGREGOR: Well, I think Mr. Netanyahu regards this as an all-or-nothing proposition. In his estimation, and I think in the estimation of the people that surround him, this is Israel’s best shot at removing what Israel considers to be its most serious threat, and more important, its most serious obstacle to their domination of the entire region.
Now, why do they feel that way? Because they have essentially unconditional total control of U.S. military power in the region. I think the CENTCOM commander, who’s now Admiral Cooper, his predecessor was Kurilla, these men have fallen all over themselves to ingratiate themselves with Mr. Netanyahu. Understandably, since that’s ultimately the man that is calling the shots in the region.
So I think Mr. Netanyahu’s view is either “I make this work, I realize the greater Israel project, it becomes real as a result of destroying Iran,” or “we in Israel are going to have a tough time surviving in the region.” And I think he’s probably right. Because you can’t call all of your neighbors subhuman or criminals and then expect to get along with them when the war stops.
That’s his position. So yeah, I think he’s in this to the bitter end, and he’s going to do whatever he can to obstruct any sort of arrangement that brings this conflict to a close.
Netanyahu’s Freudian Slip
JUDGE ANDREW NAPOLITANO: Were you struck by the language chosen by Prime Minister Netanyahu at a press conference after that negotiation was over, when he referred to Vice President Pence as reporting to him as other administration officials do daily. Do you think that was just a turn of phrase or revealing something deeper that we should know about?
DOUGLAS MACGREGOR: I think it was more likely a Freudian slip because remember he went on to elaborate and say, “Well, I hear from everyone in the government in Washington on a routine basis, practically every day. They all report.” I think he’s telling you the truth. And when he tells you the truth, you should pay attention because we don’t hear the truth that often from him. So on this particular occasion, I think he very definitely is telling you what’s real.
The Strait of Hormuz: A Failure of Pentagon Planning
JUDGE ANDREW NAPOLITANO: Before the war began, most Americans probably had never heard of the Strait of Hormuz. It was functioning properly and commercially. Now, of course, it is the center of the conflagration here. How could Pentagon planners not have foreseen what would become of the Strait of Hormuz, how Iran would use it as a chokehold to resist American aggression?
DOUGLAS MACGREGOR: Well, Judge, I don’t know that they didn’t realize that. I’ve got to go back 20 years. But if I go back 20 years, I can identify lots of plans connected with potential operations against Iran, and all of those plans were written with an understanding that, first of all, if you were going to try and employ ground troops, you were probably on your way to the loony bin because the various routes of entry and points of invasion and so forth were troubled with mountain passes and lots of choke points, about 300 different points in time and space with bridges and so forth, that you had to give up on the notion of going into the country very far unless your only objective was to occupy Khuzestan, which was ultimately what Saddam Hussein tried to do. Those are the oil fields.
But otherwise, everything revolved around targeting and trying to induce the Iranian government to comply. But most of these plans were developed before there was the full realization of how profoundly warfare had changed.
And I don’t think a lot of people in the Pentagon or the Department of Defense and the planners at the top were completely aware of how lethal the connection would be between space-based surveillance and the persistence surveillance that results and the instantaneous communication of targeting information to hundreds of different strike systems, manned and unmanned, all kinds of missiles, and the pinpoint accuracy with which they would be launched.
I just don’t think people realized that.
They should have figured it out by watching what emerged in Eastern Ukraine when General Surovikin established the initial defense against which our forces, the NATO forces that had been trained by us in Ukraine, tried to attack and failed miserably, but they didn’t do it.
So I think in fairness, that particular item was not fully appreciated. I think they still thought, “Well, we have bases in the region, bases in the Persian Gulf, we’re close enough, we can amass enough firepower that we can enter and leave without too much interference.” I don’t think they understood the implications of the military development inside Iran. So you could say we grossly underestimated them, but I think we missed this paradigm shift in warfare.
Air Power Doctrine and Underestimating the Enemy
JUDGE ANDREW NAPOLITANO: You have often expressed admiration for the professionalism of some IDF officers with whom you interacted. But how could, again, Pentagon planners have brought themselves to accept this Mossad and Netanyahu offered plan that bombs alone and missiles alone would result in regime change. Yesterday we interviewed Joe Kent. You know who he is. He told us everybody in the government, the American government, knows the Israelis exaggerate and are full of themselves.
DOUGLAS MACGREGOR: Well, this is true, and I’m not necessarily saying that about all of the senior officers that I met because large numbers of them were very balanced people. I also happen to know that many of them were removed and replaced by others.
And I think we have to understand that since the ground force option was off the table from the very beginning, at least insofar as invading Iran is concerned, that all of the strategic and operational planning from that point forward was done by the air power community. And by that I mean Air Force officers and Naval officers. Very little attention was paid to the use of ground forces anywhere but potentially within the framework of the Persian Gulf.
So I don’t think it’s entirely surprising because the air power community takes it as an act of faith that if they’re allowed to attack with their aircraft and missiles long enough, they can win any war that you want them to fight. They really truly believe that, and they’ll point to anything, whether it was successful or not, and try to claim credit for having won the war sheerly with the use of air power.
So I don’t think that’s the issue. I think the larger issue is back to what you said. They didn’t really understand what they were up against, that the enemy they thought they were going to fight turned out to be very different.
JUDGE ANDREW NAPOLITANO: Right.
DOUGLAS MACGREGOR: And that’s essentially what happened to us, I would argue, in many places including Vietnam. If you read the intelligence reports and the assessments of the Germans before we landed in Normandy, we depicted the German army as on its last legs. We expected to get much further, much faster than we did. And as a result, when we went to Okinawa, we used far more forces than we did at Normandy because we recognized that we’d underestimated it.
So I wish I could give you a better answer, but I think we just miscalculated and underestimated.
Judging Freedom Reaches 750,000 Subscribers
JUDGE ANDREW NAPOLITANO: Colonel, thanks to you, my dear friend and longtime collaborator Douglas Macgregor. Colonel Douglas Macgregor, PhD. There you have it. Thank you everyone. We just broke 750,000. I could never have imagined this 4 and a half years ago when we started this little program with 93 viewers on day one. But thank you, Colonel. Thanks for being such a significant part of it. I know we are friends as well as professional collaborators. I owe you a nice meal at your favorite Italian restaurant with Mrs. Macgregor.
DOUGLAS MACGREGOR: Well, we’ll do that at some point, no question about it.
Israel’s Nuclear Arsenal and Dual Citizenship
JUDGE ANDREW NAPOLITANO: What would Netanyahu say if a reporter asked him at a press conference, how many nuclear weapons does Israel have?
DOUGLAS MACGREGOR: I think he’d probably say that’s not for discussion, and he might not even acknowledge that they have any. That’s been the policy now for years and years and years, but we know they’ve got at least 300 weapons.
JUDGE ANDREW NAPOLITANO: When I asked Joe Kent yesterday, he laughed and he said everybody in the national security part of the federal government of the United States of America can tell you how many nuclear warheads the Israelis have. But “we’re not allowed to say it in public, Judge.”
DOUGLAS MACGREGOR: Yeah, well, look, this is a unique set of circumstances. We’re dealing with a state that has leverage over everybody in Washington as a result of having systematically invested in control of our government, and they now have large numbers of people all across our government who are absolutely loyal to Israel first. And by the way, they’re by no means all Jewish.
So I can’t be surprised by any of this. You’re familiar with the legal record, and you know that in 1965 there was a Supreme Court case that it founded in favor of dual citizenship.
JUDGE ANDREW NAPOLITANO: Yeah.
DOUGLAS MACGREGOR: And that, I think, was a catastrophe for us. I’ve always been a strong believer that if you are a dual citizen, you should not hold elected office or appointment in any federal position. That’s just my attitude. I think you can only be loyal to one state at a time.
JUDGE ANDREW NAPOLITANO: Well, it makes sense, Colonel, and unfortunately I don’t know who they all are. I think Congressman Randy Fein is probably a dual citizen. John Bolton, the president’s national security advisor, now a defendant in a criminal case, a dual citizen. They’re probably a lot more than we know.
One of the members of the House of Representatives fought for the IDF. The poor guy lost his legs below his knees. He sometimes shows up on the floor of the House with shorts on so you can see the artificial legs that he has. I’m sure he’s a dual citizen. Brian Mast, M-A-S-T, I believe is the congressman’s name.
It’s a terrible, terrible state of affairs. I mean, we talk about nukes and Iran is dangerous and why should they have a nuclear weapon. What about North Korea? He’s a madman. And he has nuclear weapons.
The U.S.-Israel Bond and the Nuclear Question
DOUGLAS MACGREGOR: Well, you’re again, you’re preaching to the choir, and many of us sort of shake our head in disbelief that we’ve gone along with this for as long as we have. Perhaps this event will change things, because right now our president has no easy way out of the position he’s in right now. He’s talked himself into a corner. He’s made bold, rash statements reminiscent of people like Lyndon Johnson during the Vietnam War, that make his retreat from these policy positions virtually impossible.
And so what is he going to do? He can do one of two things, frankly. He can escalate, and I still think that’s his inclination because that’s his nature. You know that. He’s Roy Cohn’s loyal pupil. So I think he’s predisposed to escalate, and I think we’re waiting for additional forces to be in position before we do anything, and I suspect that by Saturday those forces should be on station. So that’s the first thing.
Second thing is he can keep up this blockade, but the blockade is not perfect. Ships have slipped through, I’m told. It also is very expensive. There’s no guarantee that it’ll make any difference. Remember that when we blockaded Cuba, we called it a quarantine to avoid trouble with the legal language, but we used 180 surface vessels. The blockade actually reached all the way out into the North Atlantic, and we did this in effectively our home waters, which meant that we could fly from bases in the United States and we could sustain all the ships at sea very easily. We’re not in that position over in the Indian Ocean or in the Mediterranean anymore. What are we going to stop? Are you going to put ships in the Caspian Sea? I don’t think so. Can you stop rail lines and pipelines Iran has access from operating? It’s tough. It’s not easy. I think at some point someone’s going to wake up and say, we can’t effectively blockade this place.
And then the third consideration, I think this is more relevant now than ever, Judge. About 50% of the fertilizer in the world that is utilized by the Global South comes out of the Persian Gulf. And right now in India, for instance, the cost of fertilizer has more than doubled.
Now, there are two things that keep our civilization operating. One is cheap energy. We’re losing that very, very rapidly. Our prices here at home are going to rise. They’re rising all over the world. It’s really catastrophic in places like Europe. It’s very hard on our friends in Japan and Korea, all of Southeast Asia, Thailand, Vietnam, Malaysia. So cheap energy is no longer cheap, and that’s disastrous for us.
The second thing you get with cheap energy is cheap credit. That is drying up. And when you look at the world today and the countries that are in a position to provide cheap credit, there’s only one, and that’s China. And China is very rapidly becoming the safe haven for cash from all over the world. Not the United States, not anymore.
And we also forget that when we freeze billions of dollars that belong to the Russians, billions that belong to Iran, billions that belong to anybody, we send a terrible signal to the rest of the world that if you put your money within our reach, if you use our system, our SWIFT system and so forth, we can do with your cash, with your assets, anything we want whenever we want to do it. Right? China is not going to do that. It’s made it very clear.
So what we’ve done with this crisis thus far is not simply made China that much more attractive as a reliable business partner for the world. We’ve also made BRICS an extremely attractive organization to join and get out from under us.
So logic dictates dump the blockade, release the funds, and announce to the world that on humanitarian grounds you, President Donald Trump, are ending this conflict because it’s hurting the world, and you know that, and you don’t want to hurt the world. You want complete freedom of navigation for everyone. And so we’re ending this blockade and we are disengaging, and we will find other ways to resolve our dispute with Iran. But Judge, we have a party that’s involved. Israel. Israel. And Israel is not going to allow that.
The U.S.-Israel Relationship: A Philosophical Question
JUDGE ANDREW NAPOLITANO: Let me ask you a philosophical question. You do, of course, hold a doctorate of philosophy.
DOUGLAS MACGREGOR: No, no, no, no, no, international relations. Don’t make me into a philosopher, Judge.
JUDGE ANDREW NAPOLITANO: All right, all right, it’s called a PhD, but it’s certainly in international relations. But this is imbued with international relations. How odd is the bonding between the United States and Israel. Israel is a messianic, eschatological — interested in the end of times — apartheid nation. The United States is the opposite. It is secular. It believes in the value of every human being, and it embraces the Enlightenment. How did we get to this bond?
DOUGLAS MACGREGOR: Well, I think you’ve got to go all the way back to World War II and Harry Truman. You know, a close friend of mine that I went to school with for years, and he happens to be Jewish, and he would tell me routinely, “The death of 6 million Jews in World War II was the down payment on the state of Israel.” And to a large extent, I think he’s right. And I think that Truman saw it that way. Many people did at the time, that as a result of this long history of being tossed out of virtually every country in Europe and many other countries in the Middle East and around the world, Jews deserved a safe haven.
I don’t think anybody at the time, including Harry Truman, thought that the safe haven would be turned into a platform for the projection of military power against all of its neighbors. And so people like me and a lot of other Americans thought that whatever we could do to help Israel defend itself and preserve the State of Israel was virtuous. I don’t think we thought in terms of Israel expanding at the expense of its neighbors, conquering its neighbors, dominating the Middle East, or anything else. But that’s where we’ve ended up.
The Nuclear Codes Question
JUDGE ANDREW NAPOLITANO: How inappropriate is it — I mean, I don’t know if these reports are true or not, they come from credible sources — that President Trump asked General Cain to explain how the nuclear codes work? How inappropriate and dangerous — if this is true — would that have been for the President of the United States to contemplate the use of nuclear weapons against this country at this time?
DOUGLAS MACGREGOR: Well, the only source for any of this that I’m aware of is Larry Johnson, and he has some pretty good access.
JUDGE ANDREW NAPOLITANO: Yes.
DOUGLAS MACGREGOR: So I don’t doubt Larry. The only thing that I would say is as follows: that presidents do have every right to involve themselves in the whole nuclear business. In fact, one of the complaints that several chairmen of the Joint Chiefs of Staff have made over many, many years is the lack of interest that too many presidents have shown in the whole business.
Now, I don’t know precisely what President Trump said. I don’t know what his words were. I sincerely hope that he was not contemplating the use of a nuclear weapon in this particular setting, or for that matter, in my judgment, in any setting.
But having said that, we need to keep a couple of things in mind. The Chairman of the Joint Chiefs is the senior military advisor to the President of the United States. He commands nothing. Nothing. He has no command authority. The man with all the command authority is Pete Hegseth, the Secretary of War. And once you move beyond Pete Hegseth and you go out to the combatant commanders and the functional commanders, that’s where you have command authority. So you have people out in the field or around the world and inside the United States who do have command authority. They report directly to the Secretary of Defense or the President. The Chairman of the Joint Chiefs has none of that.
The Chairman, however, is obligated to advise the President. And that means that if he thinks this is a dumb idea or a bad idea, he’s obligated to say that. And we don’t know what the content of the conversation was. It may well be that the chairman told the president, “Mr. President, we’ve come as far as we can go with what we have. We can probably do more damage, but that damage may not produce the result that you want.” And then perhaps President Trump made some flippant remark about nuclear weapons. You know Donald Trump makes flippant remarks. We don’t know, and I’m quite sure that the chairman responded and said that has no relevance, no bearing here, we shouldn’t even consider it, which is what I would say. So I’m hoping that that’s what occurred.
Civilian Control and Military Accountability
But you know, there’s something else that people need to get through their heads. I listen every day to somebody who’s saying, “Well, look at the Secretary of War, he’s fired somebody else, and the president wants to get rid of this person.” We fired — really, relieved is the correct terminology — dozens and dozens and dozens of general officers and admirals during both World War I and World War II. Not so many admirals in the first war, but certainly during the second. You relieve more senior officers in wartime than at any other point in their careers, and it makes sense.
And sometimes the relief is not because they’re incompetent. It’s because they haven’t been successful. And sometimes they’re not successful for reasons that they don’t have much control over. But as George Marshall used to say, “I don’t have time to do that. I’ve got to win. This man’s been unlucky. We’re going to put somebody else in there and find out if he can do better.” In other words, it wasn’t necessarily personal. And sometimes the people that you remove are exhausted. They can’t keep up.
I just want to make that point clear because there seems to be this attempt in Washington, in partisan politics, to demonize anyone in the chain of command — the president, Secretary of Defense, or anyone else, senior officers — who relieve people. That’s their job. It’s called supervisory authority over the military, civilian control of the military. That’s what’s supposed to happen. Now, you could quibble over the reasons. I haven’t heard President Trump express the view that he wants to relieve the Chairman of the Joint Chiefs. He seems to talk to the man and the man talks to him. That’s a good thing. Let’s hope it was what I described and not something worse.
Closing Remarks
JUDGE ANDREW NAPOLITANO: Well, Colonel, thank you very much. Your analysis on the economic implications of all of this and the safety in China as opposed to the U.S., empirically observable from everyday events, was right on the mark, and I’m deeply grateful for it. I’m also very happy that it was you on air that pushed us over 750,000, and I promised that Italian dinner. Thank you, or any dinner you want. Thank you, Colonel. What a pleasure.
DOUGLAS MACGREGOR: I wouldn’t be eating anything else with you but Italian food.
JUDGE ANDREW NAPOLITANO: Oh, God love you. Have a great weekend, and we’ll see you next week, Colonel. All the best.
DOUGLAS MACGREGOR: Okay, same to you. Thanks.
JUDGE ANDREW NAPOLITANO: Thank you. Coming up tomorrow, Friday, at the end of the day at 3:30 in the afternoon Eastern, the end of the week, the Intelligence Community Roundtable with Larry Johnson and Ray McGovern, and maybe a surprise addition. Thank you for watching. Just Napolitano for Judging Freedom.
Related Posts