Judging Freedom - COL. Douglas Macgregor : The Venezuela Operation Trump Won’t Explain

Episode Date: January 3, 2026

COL. Douglas Macgregor : The Venezuela Operation Trump Won’t ExplainSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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And with Ollie's in-app on-demand health screenings, tap real experts whenever you need peace of mind. Visit ollie.com slash crossover and use code crossover for 60% off your first box. Freedom is a fragile thing, and it's never more than one generation away from extinction. It is not ours by way of inheritance. It must be fought for and defended constantly by each generation, for it comes only once to a people. And those in world history who have known freedom and then lost it, have never known it again. 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. Welcome to this special Saturday afternoon edition of our program, Colonel Douglas McGregor. Thank you very much for giving up your time on a Saturday afternoon to join us in light of the events of the past 24 hours and welcome here. How can President Trump possibly justify the invasion and takeover of the government of Venezuela in American national security terms. Well, Judge, that's a great question, and I think it's irrelevant because he's done it. I think we have to accept the fact that he's now committed the United States Armed Forces

and the wealth and power of the United States to intervention in Venezuela. That's it. I mean, we could sit here and pick apart the allegations about drugs or the presence of Hamas and Hisbalah training camps and all this sort of business doesn't make any difference. He's already acted. And right now, as far as I can tell, the Senate Armed Services Committee has already signed on for the operation, characterizing it as law enforcement. And that is presumably because the DEA was part of the team that went in. with Delta Force to seize President Missouri and his wife. So it's a fate of call plea.

So I guess the neocons have triumph, notwithstanding everything Donald Trump and his accolades said during the campaign. Oh, absolutely. I think what we're learning here is that Washington, led by President Trump, is ready to use whatever means it has at its disposal, including military power,

to stop the diminishment of U.S. national influence and its bid to manage the sort of decline and dissolution of the so-called post-war liberal order. That's what it all seems to be about. Remember, the rules-based order is effectively gone. Rules-based, meaning whatever Washington wants to impose. And President Trump simply stated very categorically, we can do it again. Nobody can stop us. There's nothing with the capability that we have. You know, somebody said, well, Team America is back, if you ever saw that funny puppet show. I think that's where we are right now. And lots of people are saying, fine, this is great. The question is, what happens now? That's, you know, difficult to answer,

but we need to talk about that. Just before we get into what happens now, I can't resist showing you RFK Jr. and President Trump together at the Republican National Convention two summers ago, watch the look of glee on President Trump's face when Bobby, whom you and I both know, says Trump will end the grip of the neocons on the government. Chris, cut number nine. He also told me that he wanted to end the grip of the neocons on U.S. foreign policy. And don't you want a president who's going to get us out of the wars? and who's going to rebuild the middle class in this country? We don't have that.

We have a president who wants to start wars. Well, the question is, who's really in charge? I mean, I know President Trump appears to be, I'm not convinced that's the case. Because remember, during that convention, you had this giant Israeli flag suddenly appear in the middle of the Republican convention. And certainly in my lifetime, perhaps you can remember an example,

but I don't know of a single instance where either the Democratic or Republican parties held a convention and hoisted a giant foreign flag at the convention, talking about, quote, unquote, Israel first. I've never heard of that before. Is there a nexus between this invasion and takeover of the government of Venezuela and the likely coming, you've predicted this many times, Israeli-U.S. invasion of Iran. I think it's pretty hard to, you know, disengage one from the other. I mean, he said what he said about, we can do it again,

nobody can stop us, nobody has the capability we have. People are inferring from that that he's talking about potentially Mexico, doing something of a similar nature, or some other countries in Central America. I think they believe in Washington that they have now frightened everyone in Latin America from the Rio Grande down to the Straits of Magellan. I don't think they have. I think they've infuriated and offended large numbers of people in that strip, but I don't think that we've necessarily frightened them. The other thing is that I think that, you know, one of the first people to congratulate President Trump on this great achievement of arresting them and getting out and back to the United States.

United States was Nate Rothschild or Nat. I don't know if he calls himself Nat or Nate. I couldn't tell, but he was one of the first people to congratulate President Trump. The question you have to ask yourself is, why would he bother what's he got in this game? And I think we have to understand that from the very beginning, we had all these allegations about Hamas and Hisbalah training camps in Venezuela, not that anybody I know in the intelligence business believes that. I don't think anybody in the intelligence business believes the bit about Maduro is a drug kingpin of Trump. We're interested in the most significant exporter of cocaine in the modern history. Well, let's set that aside for a moment and chalk that up to.

one of many justifications for going in and let's keep in mind that what you have in Venezuela is not only the world's largest oil reserves of course this is mostly heavy oil that's difficult to refine and in that sense they're only in the top five but nevertheless you have the oil reserves you've also got natural gas bauxite nickel rare earths and apparently massively endowed with gold in one of the large and also one of the largest iron ore deposits in the western hemisphere so all of those things are wrapped up in this and he's now telling everybody that you know we're we're going to rebuild everything we're going to restore the health of the oil infrastructure it's in ruins and he admits that that's going to

take a long time to happen but that's the sort of thing he's talking about and american corporations are going to march into the country and everybody's going to get rich then as well as population is going to be rich. We're going to get rich. Everyone benefits. And so then the question is, will Washington now provide a lucrative economic package to lift Venezuela out of poverty and chaos? And will all of this happen at our expense? You know, I think it probably will. Remember, Paul Wolfowitz promised that Iraqi oil reserves would pay for the American military intervention in Iraq. How did that work out? You know, the whole thing is a mess, to be frank. I don't see a lot of planning beyond the initial operation, special operations operation, frankly, to go in

and extract Maduro and his wife. They say they've talked to the current vice president, the lady who is the vice president, is supposedly offered cooperation. We'll see what happens. Does she really speak for the rest of the population of Venezuela? And how are they going to react? None of us really knows at this point. All right, I'm back with you. I had some some problem with my computer, but thank you, Colonel, for running the show while I was attempting to solve the problem, which I apparently have, which I apparently have solved. How can Marco Rubio and Pete Hegeseth become the governors of Venezuela? How can the United States government run the government of another country?

Well, I thought that was marvelous when President Trump pointed out that Mrs. Machado frankly, lacks the political strength to govern the country, which is true, by the way. I was glad to hear him say that. That's been a question from the very beginning, remove Mrs. Machado, who steps in and takes over. The question is, who will ultimately be installed in power? Well, nobody knows. And so until that happens, presumably, Secretary of State Marco Rubio will simply govern as an American viceroy. I get that impression.

I don't think Pete Hankseth is going to be diverted into that. because we have the war with Iran looming on the horizon. Operations in Ukraine continue. So what do you do? I think you turn to Marco Rubio and effectively make him an American viceroy. And if you ask me, well, on whose authority and under what sort of rule international law is that possible, I don't think it matters. I mean, again, we've seen demonstrated repeatedly that who cares what international law says? who cares what the United Nations Security Council says.

This president doesn't care, and neither does Congress. So if that's what they're going to do, then that's what will happen now. Is that going to work out well? I don't know. What is your view of the reaction or the likely reaction in the Kremlin? I think that President Putin, who is a very cautious person, remember he's actually trained as a lawyer, he's very legality oriented in much of his thinking believe it or not i think he'll be somewhat

surprised but i think he's going to take the position that if the americans want to go in there if they want to sink their national treasury into venezuela which is what's going to happen i think then we should allow them to do so because his priority is to end the war in ukraine i think he's going to accelerate that process so from from his standpoint, this is not a bad thing, particularly since Russia is now actually preparing to fight the Europeans. Now, you and I have talked about that. I don't think the Europeans want to fight him, but the people in power in Berlin, Warsaw, Paris, and London all seem to be interested in pushing war with Russia. So he's preparing for it. And if he has to do that, I think he would

prefer to see the U.S. Armed Forces mired in the Southern Caribbean. Was the CIA involved in the attempted assassination or destruction of one of Putin's residences last Sunday? Well, apparently the CIA, or a spokesman for them, has suggested that they had a role in it, which shocks me. You know, otherwise, I think it was on the whole a British-run operation on behalf of Zelensky and his friends at Kiev. But did we have something to do with? Apparently, we did. I was shocked today when I listened to the chairman of the Joint Chiefs describe in great detail how this operation was conducted. I don't know why we do that.

I'm shocked that we would admit that under any circumstances, but that's where we are. Here's his boss crowing about his in a moment of glory about how America is back. I wonder how seasoned veteran military, people like you take Secretary Hegseth. Chris, cut number five.

Ellis Maduro had his chance just like Iran had their chance until they didn't and until he didn't. He hefted around and he found out. President Trump is deadly serious about stopping the flow

of gangs and violence to our country. Deadly serious about stopping the flow of drugs and poison to our people. deadly serious about getting back the oil that was stolen from us and deadly serious about reestablishing American deterrence and dominance in the Western Hemisphere. This is about the safety, security, freedom, and prosperity

of the American people. This is America First. This is peace through strength. And the United States War Department is proud to help deliver it. Welcome to 2026, and under President Trump, America is back. General Kane should be ashamed to stand there, listen to that nonsense. What does this have to do with safety, security, freedom, and prosperity of the United States? Not much.

In fact, I think it probably will weaken our national security. It's going to make it harder for us in the Western Hemisphere. Frankly, Judge, we already dominate the Western Hemisphere. We have for decades, probably at least 200 years. I don't know why anybody questions that. Who is going to challenge us in the Western Hemisphere? It's impossible. So I don't think we had to demonstrate that.

But this is a useful distraction in many ways. Long-term consequences for this, I think, are going to be severe. Our position at home has not improved. Our economy is fragile. the financial system is in bad shape. There are all sorts of things happening behind the scenes in Basel and New York City and Washington about what are we going to do about this enormous debt load that we're carrying

and our inability to preserve it, to keep it, to sustain it. We just can't. So I think we're going to see the bond market go up in flames over the next few weeks. It may happen sooner rather than later. I think we're going to watch the Chinese and others essentially dump all the debt that they own that belongs to us. I think a lot of bad things are going to happen economically.

Our standard of living is not rising. You know, we're not, everything is not becoming cheap and affordable overnight. So all those problems at home and our national social cohesion isn't an all-time low. All you had to do is look at this mayor of New York's inauguration. and the one thing that struck me is very, very telling was the absence anywhere of a single American flag. So we've got large numbers of people in this country who are not terribly American. And I'm not just talking about the foreigners that are here legally or illegally. I'm talking about people that even were born here don't seem to care about the country.

I don't see how any of this helps us. But I think in the minds of President Trump and others, this is a short-term win. This is convenient distraction from our failures to achieve any kind of peaceful outcome in Ukraine. It's a distraction from our failure to achieve this supposed ceasefire in peace in Gaza. On the contrary, we all know that that's a facade, that's a fraud. And now we know we're on the road once again to war with Iran. So this is a distraction more than anything else. I don't think in two weeks or three weeks there'll be a lot of people talking about it.

But we'll see. What are you, what are your thoughts about Beijing's reaction to this and its former, I guess it doesn't exist anymore, relationship to the government of Venezuela? Beijing and Moscow both understand something. There really is a strategic advantage when you take on the enemy in your home court. In other words, they're not going to challenge us in the Caribbean. They're not going to challenge us in the Western Hemisphere. So the idea that the Chinese or the Russians and their military influence or power would be squandered in some way in the defense of Venezuela is absurd. They're not stupid.

They're not going to repeat the mistake that we have made by investing heavily in Ukraine in a war against Russia that there was no chance of ever winning. So that's not going to happen. I think the Chinese will be mildly, mildly offended, but they'll turn around and say, well, there's oil elsewhere. They'll get it from other sources. I think that'll be the sum total of it. And I think the Chinese will then increasingly make life harder for us by shedding the debt, by selling off the U.S. Treasuries. And we're already, you know, in a vulnerable position in that connection, I think that's only going to get worse.

It's going to get worse because the government will have to offer higher interest rates, and then the government will be borrowing, again, borrowing money in order to pay interest on borrowed money. If anything's a recipe for economic collapse, it's that. You commented a few minutes ago about your surprise at General Kane giving the details that he gave. I'd like to dive into this for a little bit. The chair of the joint chiefs of staff is not a command position, is it? No. He's just an advisor.

He doesn't direct troops, does he? Yeah, federal law, Title X, U.S. Code, says that he is the senior military advisor to the president of the United States. Now, that's all he is. But he probably, as some of his predecessors have, exercises greater influence than simply advice to the president. but I think he's also a prop for the administration. If you go back to the Vietnam War, you remember that every time LBJ wanted to announce something or say something, all the military leaders were hauled out in uniform. Right.

In order to confer legitimacy on whatever it was that President Johnson was saying or doing, I think that was also true in Mar-a-Lago. Now, that doesn't mean he's saying something that isn't true. I think he's saying what is true. And he may have actually discussed it with the president, says the president may have said, tell them everything. Let them all know. Let them know. This is good.

This will frighten the hell out of our potential opponents and competitors. Well, I disagree with that. I would not have stood up there and provided any details on the operation. I would simply say this was a very successful operation. He's now in custody. He's going to be tried in a court of law. The Department of Defense, the Department of War, the Department of War has executed its mission. per the guidance of the president.

That's it. That's all I would have said. But he's part of the team, just as Westmoreland was part of the LBJ's team. I think this is always a bad thing. You know, Marshall and the people immediately after the war, when they testified, in most cases, they actually did it in civilian clothes. Very few Americans understand that. His chief of staff crossed the river, and he wore a suit. And that was for the expressed reason that people at the time did not want to be intimidated by the military.

And the military leadership did not want to be cast in the role as intimidating political figures, political elected officials. And finally, people like Marshall did not want to be seen as creatures of FDR. Well, right now, that's all gone. Everybody that you appoint to any high rank in the armed forces today is encouraged to do the opposite. and they are, in fact, creatures of the administration they serve. Here's the president boasting that what happened yesterday was the greatest assemblage of American military power. I can't say this of a straight face.

It's World War II, Colonel, your thoughts on this, a crisp cut number two. The United States Armed Forces conducted an extraordinary military operation in the capital of Venezuela. Overwhelming American military power, air, land, and sea was used to launch a spectacular assault. And it was an assault like people have not seen since World War II. Does that make any sense to you, Colonel?

Well, well, it makes sense in terms of President Trump's approach to everything. remember whatever discussion he has with anybody is terrific whatever he thinks of whatever he advocates whatever he sets out to do whatever program he embraces is spectacular and unlike anything in human history so that's all very predictable in truth we took a very large jackhammer and killed a flea uh that's those are the facts uh the forces that we assembled were probably disproportionately large for what we set out to do, at least to this point. And Venezuela was never in a position militarily to stop us. I mean, again, the old adage applies here. It's very easy to get into a place like Venezuela, just it was very easy for us to get into Vietnam. But it always

turns out to be hell to get out. And I'm not really worried about, you know, what we've done thus far. I'm worried about the fact that we're going to double down, we're going to occupy, We're going to involve our forces on the ground to provide, quote, unquote, stability and protection for whatever we do. And that inevitably becomes a nightmare. And it costs a lot of money. And it inevitably costs some lives. So that's what's at stake here. But, you know, otherwise, no, what we did, we could do almost anywhere in much of the developing world.

It's not a great military achievement. But I wouldn't try it against the Chinese, the Russians. the North Koreans. I would be careful about trying it against the Iranians. Here's the president responding. I think this is a terrifying answer, Colonel, but you, of course, have a military lens through which you can examine what he said, boots on the ground. Chris, cut number seven. Does the U.S. running the country mean that U.S. troops will be on the ground? How will that work? Well, you know, they always say boots on the ground, oh, so we're not afraid of boots on the ground if we have to have. We had boots on the ground last night at a very high level, actually.

We're not afraid of it. We don't mind saying it, but we're going to make sure that that country has run properly. We're not doing this in vain. This is a very dangerous attack. This is an attack that could have gone very, very badly. Could have gotten very badly. We could have lost a lot of people last night. We could have lost a lot of dignity.

We could have lost a lot of equipment. Equipment is less important, but we could have lost a lot, and we're going to make sure that this is proper. We're there now. We're ready to go again if we have to. We're going to run the country right. It's going to run very judiciously, very fairly. You know, they stole our oil. We built that whole industry there, and they just took it over like we were nothing.

And we had a president that decided not to do anything about it. So we did something about it. We're late, but we did something about it. Yeah, please. Does he say buying us or himself another Vietnam? Well, he's dismissing out of hand the possibility that once you put ground forces into an area like that, you are committing the United States to potentially a long-term strategic investment. And he's simply saying that's the way it is.

We're not worried about it. we're comfortable, we think we can make this work. Well, we'll see. I think it's a mistake. We have a long record. We don't need to go over it of failure in Latin America, where interventions with Marines or soldiers have produced outcomes that were not favorable to the United States. Certainly weren't favorable to the people where we intervened. So I think this is a mistake, but he's taking this position. What other position could he take? Right. It's very clear that if he turned now and simply said, well, this is victory.

We've just spent billions and billions of dollars. We've captured two people, Maduro and his wife. They're going to be tried. We're happy with that. We're leaving. Well, that changes nothing. He knows that. So if you're going to change something, if you're there to extract the resources and, quote, unquote, eliminate the drug trade, even though we all know that's modest, if at all, then you've got to put forward.

forces on the ground. That's why they assembled all those forces up in Puerto Rico. In previous discussions, I told you that it was my impression, based on what I was hearing, that the 15,000 troops up there would be used as stability forces. In other words, in Caracas, at airfields, on oil rigs and so forth. In other words, they're trying to preserve the new order which we've now committed ourselves to create. Now, how is that going to work? What What is the flow of resources back to the United States look like? What's the flow of money from the United States in Venezuela look like? What is the end state that we're trying to achieve?

I mean, leading cheers for freedom, democracy, human rights. How many times have we heard that? Ask all the people that are dead right now in places like Iraq or Libya, Libya, how much they enjoyed, you know, freedom, democracy, and human rights for Vietnam. Forget it. So, you know, we're going to hear all this stuff. It's all meaningless. At this point, he's committed to the United States because he knows he has to.

If you're going to go into this place, you cannot be a little bit pregnant. Either you go in and get it done or you don't. My point from the very beginning and many others who've looked at this is very simple. You're not going to get out anything out of this. Right. It's not going to work. A lot of my legal colleagues have been. been defending this as nothing more than an effort to capture a fugitive from justice and bring him

before the court in front of which he was indicted. And it may have seemed that way last night. Now we know it's an invasion and the takeover of a government, all without lawful authority and all without any consent to the Congress. Was there a great debate in the Congress? over the weekend that i missed something no no absolutely not and you know when we talk about washington dc we refer to it now as washington uh donor controlled it's not the district of columbia it's just donor controlled washington the donors are behind this the people that own your congress that own your government are behind this they're they're quite content with it they see themselves as benefiting from it i think you've had larry johnson on talk about

underway tracing millions and millions of dollars meant for Ukraine that end up somehow or another magically finding their way back into the accounts of people like Lindsey Graham or Chuck Schumer. This is a bipartisan operation. These people are going along because they expect to profit from this, because their donors expect to profit from it. The notion that this could be another Titanic failure, like Iraq, like Afghanistan, cost us hundreds of billions, trillions of dollars from which we extract no strategic benefit whatsoever, that is simply not understood. It's not even seriously considered.

Colonel, right now, you have drawn one of the largest live audiences we've ever had. It's a holiday weekend. It's a Saturday afternoon. I thank you very much for your time and your analysis. I hope we can discuss this again in a few days during the week. We probably will know more about it than we do right now. but thank you very much, Colonel. Well, the important thing now, Judge, is for you and for me to stay alive through all of this

because we're not taking a very popular position right now. No, no, we're not. When my computer came back a minute ago, I was wondering if it was the Gremlins. I think it was just one of those, the bad Gremlins. I think it was just one of those things. But thank you, Colonel. Okay, thank you, Judge. I'll be a new year to you.

One more show for you this Saturday afternoon. cold, snowy, windy here in northwest New Jersey. At 3 o'clock, Scott Ritter. Judge Napolitano for Judging Freedom. I'm going to be.