Judging Freedom - [EXCLUSIVE] COL. Doug Macgregor : Judgment Day for Trump's War. Does he Know He Lost?

Episode Date: June 26, 2026

[EXCLUSIVE] COL. Doug Macgregor : Judgment Day for Trump's War. Does he Know He Lost?See 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 Friday, June 26, 2006. Colonel Douglas McGregor joins us now. Colonel pleasure, thank you for accommodating my schedule. I've been asking this question all week, and there doesn't seem to be a consensus on the answer. Is the Strait of Ormuz open, or is it only open to those who are approved by the Iranians? I think the latter. I think the Iranians are still controlling it effectively, and it looks like a great deal of their oil, being allowed to leave and head for China. How much of everybody else is, it's hard to tell. But keep in mind, there's something else that continues to plague the Strait of Hormuz,

and that is the insurance companies are not happy with the situation. They don't buy into this notion that the war is over and the problems are being solved. So I think we have to take that into consideration as well. Our friend Larry Johnson has a piece out this morning making a similar argument and concluding that this will keep the price of oil high until the insurance companies are satisfied. I don't know what it's going to take to satisfy them, Colonel. Apparently a non-Iranian ship unapproved that tried to get through was attacked yesterday by the Revolutionary Guard and was forced to turn around.

God only knows if that had insurance. Well, first I think we have to ask who this Revolutionary Guard is that was resurrected from the dead. After all, we said that we sank their Navy and destroyed their Air Force that have defeated them militarily. So how could they do anything? So that's the first question. Second part, obviously, I'm being facetious. But I think we're in for a long haul here. People are saying, oh, well, look, the price of oil is still not rising as fast as we thought.

In fact, it's falling. Things are getting better. I think Wall Street is delusional. And it's going to take another two or three weeks for the impact of this entire mess to really strike home here and around the world. Because let's assume you get a thousand ships through the straight over the next several weeks. They'll take whatever they've got someplace, dump it, and then they've got to come back and refill. How long does this take? How long do you wait?

How many people in the meantime don't have what they need, whether it's fertilizer, nitrogen, and all the various petroleum products. So I think it's a long way from out of the woods. Let's put it that way. Is the U.S. Navy still there? I mean, it was some distance away, sort of going through what some of our guests have characterized as just a performative blockade

because it was so far away. Is it still there? Do we know? Well, I know that the Navy hasn't announced its departure. Have some of the ships left and gone somewhere else to reprovision or change crews or our new vessels on the way, all of that could be possible. But I think the key point is the one that you just made, Judge. And it's the thing that nobody really wants to talk about.

And this is part of the problem we've got with change in military affairs and technology. If you can't get within 100, 200, 300, 400 miles of the coastline as the Navy, then what's your effect on things? You're not going to have the desired impact. So I think that's part of what we've discovered the hard way in fighting Iran. We've been defeated because they have the capability to essentially make themselves invulnerable to us for all intents and purposes. Was there ever, as far as you can determine, Colonel, a serious plan to enter Iran, seize the enriched uranium, decapitate the government and replace it with the Shah's son or whatever? wherever they were going to use.

Well, I think you can argue that the first part, the decapitation attempt was real. We have sadly adopted this Israeli notion that you can assassinate your way to regime, change, or even victory in war. That, of course, is not work. And the attempts to decapitate the Iranian regime have failed miserably.

But that was definitely tried. That was part of the initial plan. Now, as far as the rest of his concern, And remember we had this event down in the vicinity of Isfahan and the supposed pilot rescue that went on and so forth. That was a serious attempt in my judgment from the special operation side to do what you described, to move into an area where we thought there would be uranium that could be recovered. We discovered it's not going to work. Once again, you have air defenses, you have local militia, police, and military.

The country's well defended. Everybody knew what was going on. they showed up in time to stop it. Frankly, we're lucky that we got away with this losing as little as we did. So I think the idea of penetrating Iranian airspace with any kind of substantial special operations force has been pretty much tossed away. Is the United States a ground, a land power?

It is in the Western Hemisphere, but it isn't in the Middle East. It certainly isn't in Europe. You remember back during the Cold War, of the reasons we maintained a force on the ground in Germany of 275,000 troops was that we realized we couldn't bring that many forces into a crisis early. In other words, once the crisis began, you had too many Soviet submarines cruising the Atlantic that would prevent any reinforcement. So you bet heavily that this force in place ahead of time would be helpful. What we've now discovered is that if you put something like that forward today in Germany in the first

hour of any future conflict, the missiles will penetrate whatever air defenses you've got and utterly destroy the force on the ground. So the whole idea of picking up and moving hundreds of thousands of troops to another theater beyond the Western Hemisphere, I think that's a dead issue. It's the same thing with amphibious operations. If you think you're going to mount another Normandy invasion again, you know, whatever you concentrate in England would be identified quickly and then annihilated with missiles. And if you tried to cross the channel, everybody would be hits midstream and you'd lose all the vessels. You know, Eisenhower forecast this in the 1950s. He told people this. It's one of the reasons he said this whole idea of NATO

doesn't make a great deal of sense. And if it's still around in 10 years, we failed. This point was militarily, this is not going to work. He was right. It doesn't. That era is over. That's why the whole idea of going back into the Gulf now is silly. It's been demonstrated. We can't protect any of those bases. So now we should spend billions of dollars rebuilding those bases again that we can't protect and then put more soldiers, sailors, airmen, or Marines risk in them. It doesn't make any sense. That's why this entire negotiation with Iran, I don't know if I'd call it a negotiation. We've lost a strategic initiative. We have been defeated militarily. So just how much can we demand? I don't think we can demand much of anything at all. And yet we continue to act. as though we can. Can the United States disengage from the Middle East? Well, I think the question to that, or the answer to that question is, is really,

if President Trump wants to withdraw us, he can withdraw us. That's not impossible at all. In fact, it makes a lot of sense. For all the reasons that I just outlined, it makes no sense at all to try and get back in there. We need to get the terms with the people that run the strait. I mean, the Turks have just raised the fees for the possible, by 15% they control the Dardanelles.

That's worked. They maintain it. They ensure the waterways are operational. The traffic moves quickly. I think the Iranians and Omanis can do the same thing. Right now are on the hill, the hatred of the Iranians in particular is at all time high because, in addition, they're not liking them for a whole range of reasons that they'll tell you that are all Israeli. They're angry that the Iranians have defeated this militarily. But the point is, there's no point in trying to get back in there and reenact the stupidity that got us into the problem in the first place.

But you've got Israel, and the Israelis are going to do everything in their power to keep us there. Our departure is viewed as an existential threat to Israel. I'm going to ask you in a minute your opinions on whether Prime Minister Netanyahu will engage in a systematic sabotage of the memorandum of understanding. But before I ask, and obviously before you reply, I want to run a clip from Jake Tapper. Now, Jake, whom I've known for years, I believe, to be intellectually honest, is paraphrasing a tape from a transcript that he verifies as a call between President Trump and Prime Minister Netanyahu. It's pretty graphic. Chris, cut number one. Trump told Netanyahu, he was sick of his antics. I've done everything to protect you.

you better fucking go along with this. Everybody's sick of you, B, B, B, Trump said. All the Jews are sick of you. Even the two Jews on this call are sick of you, Trump added, referring to Jared Custer and Steve Whitkoff. You can't back out of this. Trump took through the list of controversial decisions he had made supporting Israel through both of his presidencies.

Now, does that, in your view, manifest a serious effort to make the MOU work or just performative by the president? Well, it's good to know that our Jews are talking to their Jews, and their Jews are talking to our Jews, and the Jews have decided they don't like each other, I suppose. I find the whole thing reprehensible. I don't even want to talk about it. I'm disgusted. I'm tired of listening to people talk about Jews instead of talking about Americans and American diplomats and American governmental officials and an American president. Okay, I got that off my chest. It's really good. All right. Go ahead, please. I'm just sort of sick of that. Now, is this real? Yeah, it probably is real.

But what difference does it make? How much freedom of maneuver does President Trump really have? What have they got on him? Is he under duress? I think he's under duress. This man never wanted to go to war with Iran to begin with, as far as I can tell. That was certainly the case five years ago. So what made him do it to begin with?

And then once he got into it and he figured out this was a catastrophe. the Israelis and their agents in the United States wanted him to continue to bomb and bomb and bomb. You know, bomb your way to success, kill your way to success, just keep bombing. You know, the old Air Force argument, argument, well, drop some more bombs eventually it'll work. He rejected that to his credit. That's a good thing. He went along with this MOU, although he hates it because he knows he's effectively admitting that, you know, we lost militarily. But, you know, I think it's probably real.

But again, what difference does it make? The only way out of this is a military solution, and that military solution is not to attack. It's to disengage, which is why I wrote the piece I did on the substack, Judge. Right. You're a substack piece, which I commend to everyone. Judgment Day for Trump's war is a profound act of military understanding, personal courage, and intellectual honesty. But back to what you don't want to talk about. Will Netanyahu do his best to sabotage the MOU?

Because he can't stay in power and probably can't even stay a free man if he doesn't have a war to fight. Oh, I'm sure that's true. But I also don't see any evidence that he or the people around him are prepared to stop any of it. I think they're clinging to the notion that if they can keep this going long enough, they will somehow another be victorious. And I don't think that's going to change.

So the answer to your question is President or Mr. Netanyahu will do everything in his power to sabotage any agreement whatsoever with Iran. And unfortunately, I think that President Trump

is being duplicitous because on the one hand, it's clear that he does want to disengage and he would like to find a way out of this, but at the same time he's got the CIA, MI6, and Mossade working out to drag Syria's head chopping brigade into the war against Hezbollah in Lebanon.

And he's actually given the green light to the sale for $700 million of jet engines to the Turks that they're going to put in their new jet fighter of the Khan. So it looks like we're trying to bribe the Turks to turn their gaze away from Lebanon and allow us access to the Arabs they control in, Syria, the headchoppers, and move them over to fight Hisbalah. This doesn't sound like a man who's trying to disengage and restore stability, does it? I mean, here's another clip from another friend of mine, Tray Yinks, at Fox, who had a phone conversation with President Trump and then went on air to characterize

what the president told him on the phone. I mean, involving Syria in this mess? Is Syria really going to side with the Israelis against Hezbollah? But before you respond here is Trey Yankst on this yesterday, his phone call with the president, Sutner, a cut number two, Chris. The president told me he is disappointed. Israel can't put Hezbollah away. He went on to say they can't do anything without knocking buildings down and that he is

close to giving it to Syria. And he is talking about empowering. Syrian president, Dachma al-Sharah, to actually go into southern Lebanon and fight Hezbollah, because the president believes that he would do a more precise job in terms of the way he would deal with Hezbollah, not knocking down buildings, but fighting them on the ground. If this is accurate, does the president know what he's talking about? The president is essentially presenting to you a very old Israeli strategic axiom, which is try and create conditions conducive to wars and conflicts between the various Arab, Muslim, Turkish, Iranian elements in the region.

In other, whatever they can do to persuade the people in the countries that surround them to kill each other, they view as an inherently positive thing. Remember that the people that are currently in charge in Syria ultimately report back to Mr. Erdogan. Mr. Erdogan is running the show inside of Syria. They are there to do two things, to oppose the Kurds and oppose the Israelis to the south, to keep them from advancing any further into Syria, which Mr. Erdogan considers his province. Now Mr. Trump wants to repurpose these Islamist terrorists and killers, the head shopping brigade, as are referred to in the region, and move them to kill Shiite Muslims that are in Hezbollah.

Well, I think Mr. Erdogan needs to think that one through very carefully because right now, this is not going to help him personally in the region. It's not going to help him in his relations with Iran. And thus far, the Iranians and the Turks have cooperated with intelligence and even firepower against Kurdish problems. I don't know how this is going to work out. But I do see the green light for the jet engines that we're going to sell for $700 million to Mr. Erdogan as a bribe, if you will. to get him to look the other way. This, of course, won't solve anything. Iran will be dragged back into this in one way or the other to support, obviously, their co-religionists. Perhaps the Israelis are hopeful that by pushing President Trump to do this, that this will create a war between the Turks

and the Iranians. I mean, that certainly seems a prudent Israeli strategy, if that's the way you look at the world. I don't know that President Trump understands just how hopelessly manipulated he really is by his Israeli friends. He's still backed in a corner. I wonder if the White House even grasps the economic damage and political destruction the war has caused. I mean, do they think they can reverse this by flipping a switch? No, but I think President Trump told us the truth when he was in Broussai.

And he looked up after he signed this MOU, and somebody said something you really want to sign this and he said we've got to open this straight he said that's very clear if we don't we're going to we're facing a global depression that's what he said judge so that's clear unambiguous evidence that president trump understands the consequences what he doesn't seem to be able to do is tie all the rest of this together back to israel you know fomenting this kind of conflict between sunni islamist and hisbila which sounds very appealing to an Israeli that's not going to restore any measure of stability that's not going to improve the situation the Iranians have made it very clear they are not going to abandon his

law they're not going to abandon the people in in Gaza they've said that you still have the hootis down south they can easily re-engage very very quickly in this contest so if this if if if president trump understands the bigger picture this could lead to a global depression and I I agree with him. He needs to pour some cold water over his face and understand that these little tactics that he thinks or somehow or another may help him in his discussions with Iran are catastrophic. They'll make everything infinitely worse. And we're back to the original question. How does he get out? He says, Mr. Dandiniahu, we've done all we're going to do. Thank you very much. We're out. You're on your own. He hasn't been able to do that.

He's under duress. But unless he does that, Netanyahu and the IDF will continue their invasion, occupation, and killing in southern Lebanon. And that will provoke the Iranians to either withdraw from, violate, claim they don't have to comply with, whatever you want to call it, the MOU, and the fighting will start again. Yes. And the Iranians will say, everybody can use the strait freely without interruption. But if you're an American flagship or you're carrying something to the United States or you're an Israeli flagship or you're carrying something to Israel, you can't use the straight. That's what they'll try to do. But again, the problem is the insurers in London and around the world, they're not going to play that game because they're say, how do we know that one of these ships that we've insured for millions of dollars won't accidentally be caught up in the violence?

So again, it's an either-or proposition. Either we get out and disengage, period, or we risk this continuing to the point where finally you will get the regional war that everyone is warned about. Because once the Turks enter this, that then becomes a truly regional war. And if the Turks become involved in any way, it's not going to take very long before the Russians and the Chinese become involved, especially the Chinese. And what side would the Russians and the Chinese beyond, not the Israeli side?

No, they will both come in against Israel, period. And I'm sure that Moscow, along with Beijing, will prevail upon Mr. Erdogan to reconsider the wisdom of entering the fray in any way that could help Israel's position. So bottom line is, how do we use President Trump's favorite analogy? President Trump is going to the table, and he may have some cards in his hands, but they're worthless. And he needs to understand that. He's the one who's being played right now by Israel. This is a delegate subject, Colonel, but are you hearing serious questions about the president's mental fitness for office? No, no, I'm not.

In fact, I've heard the opposite recently. And people are telling me that the man is as sharp as he ever. was his hearing may not be the best that's that people have said that may well be the case but no i haven't heard anything about his cognitive capabilities or health at all so where do you think this goes he either tells mrs adelson okay i accepted your 250 million but i can't go alone with what you want uh now uh or this large regional war will commence judge if i find me I knew that I'd be a multi-billionaire. I could place my bets and win, but I don't know the answer.

I think right now it's 50-50, because I'm sure President Trump knows what he wants to do. The question is, is he willing to risk everything he's got to do what he knows to be right? And I think from his standpoint, that's where he sees it. Remember, the same people that put him into the White House have the ability to turn around and withdraw their support. They can turn around and bankroll all the people. on the hill that hate him who want to impeach him, who want to destroy him and drive him out of office. You're dealing with very ruthless people in this Israel lobby and the warmongers and neocons that are part of that. They play for keeps. He knows that. So the idea that he can simply say, I've made the choice,

this is what I'm going to do, that sounds great in theory, but in practice that's very hazardous for him. And he knows it. You think that the lobby, which has steadfastly supported him until now, may turn on him. I mean, Mrs. Adelson's newspaper that she owns in Israel, it's a Hebrew language newspaper, but translated into English, called the MOU a betrayal of Israel, and used the harshest language against the president personally that we have. that we have seen. I don't know how he deals with this. Judge, with these people, you are with them or against them.

There is no in between. And if you do not support them unconditionally 100%, you are the enemy. And everybody who's dealt with them understands that. That's true for Thomas Massey. That was true for Marjorie Taylor Green. Everybody on the Hill has seen all of that as an object lesson. So I think President Trump understands that as well. He will have very powerful enemies arrayed against him if he does not go along.

And of course, he may believe that his power of personality and personal charm and brilliance will be enough to avert a larger regional war. I'm not convinced of that at all. Colonel McGregor, thank you very much, my dear friend. Thank you for all of this. Actually, before we go, if I could, for just a minute. What is the state of affairs in Ukraine? Are the Russians coming close to a military resolution of the special military operation?

On the one side, you have President Putin who is watching with great interest what's happening in Western Europe, particularly in London, Paris, and Berlin. He knows that the nationalist elements in these countries aren't. not pro-war. They are anti-war. They want nothing to do with the war in Ukraine. And he knows that increasingly the polling data reflects that attitude in the public. The problem is that even though the majority of the populations are opposed to war in Ukraine, they have not yet been able to organize themselves and take over the governments. So on the one hand, he says, I know these people don't want a war. On the other hand, they can't get control of the government. So that's one

factor in this sort of analysis that he has to take into consideration. Secondly, thus far, all of the attacks that the Ukrainians have launched against Russia, I would characterize the most as pinpricks or irritants. In other words, they don't pose existential threats to Russian power, Russian industrial might, Russian military might. They really are done more than anything else for a Western audience to try and convince someone like President Trump. give us another $90 billion and we'll win the war.

I mean, we've heard this so many times, Judge. We just give us 500 more tanks and 700 more artillery pieces and ammunition, and let us go and we'll win the war. How many times will we listen to this? It's ridiculous. It's sort of like President Trump saying we're two or three days from a peace agreement and an end of the war. We're nowhere's near any peace agreement.

But the Ukrainians use the same thing. And they're saying that and arguing, look what we were able to do. We hit this factory, we hit this crossroads, we hit this train or whatever. And then finally, you have the Russians, the Russian population, and this is not contrary to popular belief, the pure authoritarian dictatorship that everybody says it is. Russian popular opinion wants an end of this war. The Russian National Security Council that reports to President Putin is arguing for an end of the war. And the argument is very simple. They say, look, you've got all the forces that you need.

You have all the capabilities. Let's crush these people once and for all. The Russian people are behind you. They will support you. We know this is going to cost some Russian lives. We're all prepared to accept that. Go and crush these people once and for all. So those are the three things.

And you're Putin and your president. And the last thing you want, and from your vantage point, the most important consideration is you don't want a war with NATO. Now, people like me who served in NATO and worked over there for years and know these Europeans, we know that these European military powers are weak. They have no means whatsoever of conquering Russia. They'd be hard pressed to defend against the Russians if the Russians launched any sort of serious attack,

which, of course, the Russians don't want to do. But President Putin looks at that final factor and says, I don't want a war. So what does this produce? I don't have an easy answer. I think the sort of majority opinion in Russia is let's go get this over with and end it. But I think President Putin is looking at all of those factors and he will eventually reach a decision. But he's got to reach one pretty quick because in Russia by mid-September, the ground is in terrible condition. And you can't really move large forces very far.

So if he's going to do something, he better do it pretty quickly. Colonel McGregor, thank you very much. Thanks for your analysis all across the board. As you always generously give us, have a great weekend. We'll look forward to seeing you next week. Same to you, Judge. I'll look for you on newsbacks. Thank you, my friend.

All the best. Coming up later today, at 3 this afternoon, Anya Parampil, what just happened in Venezuela and what happened earlier this week in Colombia? She's our eyes and ears on Latin America. And of course, at 4 o'clock this afternoon, the end of the day, the end of the week, our Intelligence Community Roundtable with Larry Johnson and Ray McGovern. Justin Palatano for Judging Freedom.