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Home » COL. Douglas Macgregor: The Pentagon’s Terrible War Planning (Transcript)

COL. Douglas Macgregor: The Pentagon’s Terrible War Planning (Transcript)

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.

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I just don’t think people realized that.