Judging Freedom - COL. Douglas Macgregor: Trump Is Sleepwalking Into Another War

Episode Date: January 7, 2026

COL. Douglas Macgregor: Trump Is Sleepwalking Into Another WarSee 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? 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 Wednesday, January 7, 2006. Colonel Douglas McGregor will be with us in just a moment. Is President Trump's sleepwalking or sprinting into the next war?

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Call 800511-4620 or go to Learjudgeonnap.com today. Colonel McGregor, welcome here, my dear friend, and thank you so much for your time this morning. Colonel, are the neocons now triumphant in American foreign policy? I think that's a fair assessment. I think they really are. In fact, I was just receiving notification that the Russians are evacuating the last of their citizens

from Israel. So it's interesting to note what's happening in Israel as well as what's happening in the Atlantic and in Ukraine. All of it is in somewhere, another connected, I guess. I was going to get to Israel at the end, but let me jump there now since you mentioned that the mainstream media, of course, is filled with reports on the kidnapping of President Maduro of Venezuela, overlooking the Israeli slaughter going on in the United States. Lebanon. What is Israel trying to accomplish by killing people in Lebanon? Why isn't the U.S. doing anything to restrain them? Well, I think we've got to go back to the aftermath of June. The Israelis certainly wounded

Hezbollah very, very heavily, but it didn't completely destroy Hispala. His will have been recovering. I think the Israelis want to do two things. They want to go back and try and as much as possible finish off whatever remains of his or at least continue to pound it into submission and also to intimidate the Lebanese government because they expect to it that is the Israelis expect to annex southern Lebanon at some point formally into greater Israel. So I think all of those things are linked. They're preparing to go back against Iran. That's very obvious. They're trying to come to some sort of arrangement that provides instillability for them in syria i don't know how that will work we're trying to broker that as best as we possibly can so israel has a lot of unfinished

business in the region and it wants to finish that business as quickly and as decisively as possible for that they need us why are the uh russians evacuating uh their own citizens from israel are they expecting israel to be in the crosshairs of iran Well, I think that's a foregone conclusion, but I also think that by getting the Russian citizens who are in Israel out, then Russia has some freedom of action. It doesn't have to pull its punches if it should become involved in what happens in the region. I think the Russians have made it pretty clear on more than one occasion that they would like to ensure that Iran survives as an independent state. I think they are still reeling, to some extent, not necessarily in shock, but certainly in a sense of being wounded regarding what happened in Syria several months ago. So I think there's a lot going on.

And remember, a lot of these citizens in Israel, Russian citizens, are actually Jewish and they want to get out. So put it all together, and I think this gives Russia greater freedom of action in the region. Colonel, let's go back to Venezuela. By what authority would the United States be able to claim and control millions of barrels of Venezuelan oil and how efficient a process, by efficient, I mean return on investment, can that be? You know, Judge, you know, this is really beyond my level of competence to judge legality. As I said before, I don't think anyone in Washington is paying any real attention to the issue of legality. I haven't even seen an effort to maintain the facade of legality. I think what's happened in Venezuela is the following.

And this was evident when the press conference was held after, you know, the successful kidnapping. of Maduro and everyone was in the mood to cheer, you know, the great American armed forces. They weren't really sure what they wanted to do. They weren't completely certain of what the impact of the operation was. And that's why you heard President Trump in response to question suddenly say, well, we're going to run Venezuela for a while. Well, how are you going to do that? Who's going to do that? Well, you know, Marco, why don't you come up here and talk about it. I don't think there was ever any plan. No one sat down and carefully structured multiple outcomes and then put together a plan to deal with each possible outcome. I think what they've done now

in haste is try to avoid a direct confrontation militarily on the ground, certainly in anywhere else with Venezuela. They don't want to get into a fight with the Venezuelan population, contrary to what the mainstream media says millions of Venezuelans are not pouring into the streets to cheer the arrival of the American Armed Forces that's love nonsense. So I think he now knows that he's got to come up with some sort of interim solution that won't cost him, his prestige, his influence, his power very much. The easy solution is to essentially say, well, we'll leave the president who's now taken over in power. Well, she's a tough customer. She may say one thing privately to President Trump, but something else publicly.

And we're not exactly sure how exactly she will behave. We're trying at the same time to induce the various oil corporate heads to go down to Venezuela and meet with her. She was also the minister of oil in Venezuela as the vice president and try to talk to her. We're trying to do a number of things now to at least create the impression that this has been a huge success for us. But the truth is, there's not much to it. The truth is seeping out the way the oil seeps out in Maracaibo. And that is, they're coming out and they're saying, well, you know, we don't really think we're going to see three million barrels of oil a day

for some time. In fact, it may not be for a year or two years or three years. And we're not really sure how that may work out in terms of compensating us to the extent we think we should compensated and then you have of course the problem that's developing right now out in the atlantic with the shadow fleet and essentially taking on the russians now and saying we're not going to allow you to come in here and do anything but the russians and the chinese they managed to get two billion and silver out of venezuela china got about everything it could out of the country before we arrived and china has already compensated for the absence of the little bit of venezuelan oil that they were taking So I think everyone in Washington is now moving in multiple directions, trying to figure out how do we go forward?

If they leave the government that's there in place, Judge, then the question is, why did you bother kidnapping Maduro? Because if Maduro is this drug criminal that we insist he is, he's got an awful lot of support inside the government, and they're not going to go away, and I wouldn't expect their behavior to change very much. So what do you do with the 14, 15, 16,000 troops sitting in Puerto Rico? Where are they going to go? Are you going to put them on the ground? If so, where? What will they do? I don't think any of these things have been sorted out.

And I think it's an increasing predisposition to sort of say, we're making all these wonderful deals. We're all going to profit. Everyone will be happy and hope that in two or three weeks, not too much discussion is underway about Venezuela. To be blunt. Do we still have troops on the ground in Caracas? Oh, I don't think so. I mean, not that I'm aware of. The only troops on the ground are in Puerto Rico.

And that's the huge number that you talked about. Yeah, remember, they were always mentioned in all the conversations I had with people on the inside as a stabilization force. And, of course, the question I asked was stabilizing what? Right. And the adoption was some sort of new government that emerged. as a consequence of a coup. Well, there wasn't really a coup.

There was the removal of Maduro and his wife. And I guess the word on the street is that the intelligence chief was bribed into giving them up. And they did kill the Cuban security detachment. They have killed a few other people on top of that. But otherwise, everything is pretty much as it was when this whole business started. So tell me what you think the thinking is

in the Kremlin now in light of all these events, the kidnapping of President Maduro, the stopping and seizing of a Russian oil tanker in international waters, the likely evidence of CIA involvement in the bombing of President Putin's country home. I think President Putin and his colleagues at the top of the power structure in Russia, and frankly, along with most of the Russian population, as far as I can tell, have largely written President Trump off and us off. They see us as untruthful, deceitful, effectively contradicting, President Trump contradicts himself from one day to the next, and there is no real sense that we have ever recognized Russia's legitimate national security interests

in Ukraine. And there's no sense that we're prepared to recognize any legitimate position for Russian commercial interests in Venezuela or for that matter anywhere else. And I think that's true for the Chinese. They look at what we've done. They conclude the same sort of thing. Now, if that's the case, and I think it is, what can we expect to happen in the near future? Well, I don't think that the Russians are prepared to go to war over a single Venezuelan tanker, which is now flagged from the shadow fleet as a Russian vessel. But I think that they're preparing for a counterstroke. I think most of it will be economic and financial, but we shouldn't underestimate the level of anger and frustration with us in Moscow. It's enormous.

Didn't the Russian military recently attack three manufacturing facilities in Ukraine owned by a company in St. Louis, Missouri? Would that be sending some sort of a message to the Pentagon and the White House? Well, they've done these things before to German-owned companies on the ground in Ukraine as well. I think that has more to do with signaling to us, to the Germans, to others in Ukraine, that they know where we are, what we're doing, and what our interests are, and that they'll take action that they think is appropriate for their own national security. I wouldn't go any further than that. The problem right now is not so much with us, even though we continue to sort of flail about

and vacillate from one position to the next. The big problem for the Russians are these Europeans, not all Europeans, but certain numbers. You know, they had this sort of coalition of the willing meeting where it was discussed what kinds of forces they would introduce into Western Ukraine. Of course, it's sort of a fantasy world that they're entering into. They might as well set sail for the land of Oz. I don't see it happening. But the Russians have to take it seriously.

And when you look at Russian preparations right now on the ground in Ukraine and nationally, for that matter. It's very obvious that they're not going to take any chances, and they're going to position forces large enough and strong enough to take on anyone from Europe that tries to interfere in Western Ukraine. So hopefully this little coalition of the willing will just die away, but it's there, and at least for the moment, the Russians are treating it seriously. Well, the coalition of the willing, minus Hungary, yesterday in Paris, offered military troops in Ukraine post-war as a security guarantee. Trump's two real estate agents who purport to negotiate for the United States,

as business partner and his son-in-law, were there and didn't agree or didn't disagree. They just stood in silence and smiled when these announcements were made. Are these people out of their minds? Do they think there's any circumstances? under which the Kremlin would accept this? I don't believe that they do, no. I think this is more of a show for the European electorates than anything else.

Now, as far as Whitkoff, Kushner, BlackRock, and all of their friends are concerned, they're cashing in wherever they possibly can. And we've already seen that happen down in Venezuela with various billionaires. You know, the Koch brothers were one, singers another. sort of stepping in and purchasing and buying up Venezuelan property here in the United States.

Now, the Koch brothers are already in oil and gas anyhow, so it's not really surprising. But the point is that I think they're there to see what happens, and they're also present to ensure that if anything should happen, if there is any kind of agreement that results in a Ukraine that is truly independent, which I think is unlikely at this point. that they can profit from this, that they can gain control of acreage, of agricultural resources, or whatever else Ukraine has. It's sort of like moving in to preside over what's left of the corpse after, you know, the decision is being made to hold a funeral. It's depressing. It's disgusting.

But that's the way it is in Washington right now. Everything is transactional. How do you see the special military operation ending, Colonel? I think it will end potentially with an all-out war to finish off any opposition in Ukraine, period. I think that's where the Russians are headed. Now, what does that mean beyond destruction of any remaining Ukrainian administration and military power? That's unclear. But I think they're going to make it very clear to everyone.

By crossing the river, taking Odessa, I would. not be surprised if they don't also move into Kiev, sort of finish things off and make it clear that they can come and go from Kiev at will without any interference and no one can stand against them. I would not be surprised if they did that. Next question is what happens in Europe? Does anybody who's sober-minded, who cares at all about the future of Europe, as well as the future of the people that live in Western Ukraine, steps forward and says, enough's enough. We need to talk directly to the Russians and find a way to end this. I think that has been Mr. Orban's message from day one. And everything that Mr. Orban has said over and over

and over again has come true. He's told everyone, look, the Russians are going to win this. The Russians are going to determine what actually happens. And if we want any influence over what the final outlook is or what the final appearance of the map is, we Europeans need to talk to the Russians. I think that will probably happen, but it's still too early. They're not convinced yet. And I think Putin knows that. And so the larger, more powerful Russian force that is currently developing will have to be used further beyond the Yemper River. Is there any reason for hope in these conversations that Whitkoff and Kushner have been having, with President Putin.

I mean, let me take a step back. Why would he meet with them in the current circumstances? Why would he waste this time with them? A lot of Russians are asking that question right now. I don't think there's any hope for that team to achieve anything that is good for the United States, for Europe or Ukraine. I just don't see it.

I think they've had their shot. They failed. Now, President Trump will stand there and talk about how wonderful they were and how great they are and how their influence is so vital, that's fine. But the truth is, it's been a complete bust. And changing Kellogg out for the Secretary of the Army hasn't made any difference.

I think we just have to come to terms with reality that the United States policy, if there is one at all, has been a failure. And the Europeans, I think, sense that. The Europeans don't sense leadership from President Trump. They just sort of regard him now as this unpredictable individual who lives at the end of the hallway in the hospital. They call him patient one. What's he going to do next?

I don't know, but let's find a way to contain him in the left wing of the hospital so that he doesn't come out and destroy everything. I think that's the European view of President Trump. At home, his supporters obviously think this is wonderful. And I think President Trump, on the whole, is actually more happy with things right now. now that people realize because he likes this idea of bullying others into submission. What I don't think he realizes is that he's about to reach the limits of his bullying. What will Europe's reaction be if American troops show up in the middle of the night in Greenland? I think they'll talk, but I don't think they'll do anything.

I don't think that the Danish Navy will intervene and that will be in a fight with them. I certainly hope not. Now, I've been told that privately, in discussion, ostensibly with a journalist, that Mr. Rubio, the Secretary of State, said, we really don't want to go to war over Greenland. We just want to buy it.

Well, that may be true. And that may yet be possible, despite what the Prime Minister of Denmark says. I don't know. But I don't think that we want to push to the point of violence and i don't think that we will i still haven't i haven't completely understood judge why we think we have to own greenland i mean i understand all the implications for the arctic the extraction of resources uh the opening of waterways and all these

kinds of things that provide for more rapid transit between asia and the west but i don't understand why it has to be militarized. I don't understand why we can't lead a conference and convince everybody that we should all sign a treaty that allocates these resources in some fashion, even if it takes us a year or two years to negotiate it, and why we think we have to occupy any portion of it. I mean, we already have bases in the Arctic, as you and I both know, in alaska and greenland and we have access as needed in northern canada i i don't i don't understand except this is in the line with the thinking of this president that if he's standing over you with a baseball bat he's happy and he thinks that standing over everyone with a baseball

bat called u.s armed forces is a good way to do business at some point there'll be reactions to this i don't know i don't know what the reaction is going to be but you alluded to it earlier At some point, enough will be enough. Well, this bit about running Venezuela, CNN caught the otherwise loquacious Stephen Miller at a loss for words when he was asked, what are your day-to-day responsibilities going to be running Venezuela? Watch this. Number 15. Stephen, you were a part of that group, the select group that the president said, is his staff that is running Venezuela.

What exactly are your day-to-day responsibilities? The President of the United States has asked Secretary Rubio, who also happens to be his National Security Advisor, to directly, of course, under the President's close guidance and direction, to be the lead on this process. But obviously, there's many other elements involved. You have energy policy, treasury policy, financial policy, military policy. So it's a big team and group of people. everybody's working great and closely together.

But what are you specifically doing? What are you specifically doing? I make a habit for not to talk too much about myself. I'm just happy to serve on this incredible team on behalf of President Trump. It's the dark prince of the neocons who gets to whisper into the president's ear every day. Well, I thought it was interesting

that he doesn't like to talk so much about himself. Everybody in Washington spends most of their time talking about themselves and he's no exception. I think he's probably taking Spain. Spanish lessons along with the rest of the team. You know, this sounds like somebody's trying to put a team together similar to what we sent into Iraq, a group of people that wrote the Constitution that turned Iraq, which at the time was secular under Saddam Hussein into an Islamic State by saying that Islam was the

core element of the Constitution. I don't know what's going on. And again, we're back to where we were before. the president makes decisions he just decides to do things people play catch up they're trying to catch up and provide details and backfilling for whatever it is that he says or does at this point i would not assume anything because when when you begin to look at the size of venezuel in that population and the difficulties of dealing with the complexities of the administration the economy and remember that the military is still largely

intact and you've got an awful lot of weapons that have been distributed to the population. If you try to go in there, I think it'll be one giant ambush. In other words, you're just walking into a giant ambush, thinking that you're going to be able to sort out Venezuela's present and future. I think people will come to the conclusion. I mean, President Trump is not dumb. He is an intelligent man. When he looks at this, if this is laid out for him comprehensively. And I think that Secretary of State Rubio is somebody that could do it. If it's laid out, as I've just described this, it's a nightmare. And he's going to recognize that it will absorb enormous time and resources from his government that he doesn't want

to invest. So he's going to look for ways to circumvent that responsibility. He doesn't want to run Venezuela. He wants Venezuela to cooperate with him. He wants the government. to do what he says that's very different he's going to look for ways to persuade the government to cooperate without directly governing it and directing it i think that's what he will ultimately decide to do now will that happen that's a big if uh i don't know perhaps they can find other ways to compensate key members of the government right now you have this new president who's telling everybody that she's going to find all of the people responsible for effectively selling out Maduro and his wife

and try them for treason and potentially execute them. So it's quite a dilemma right now. Well, Colonel, thank you very much. Thanks for your time. Thanks for letting me go all across the board on these topics as usual. Much appreciated. It'll be later to happy New Year to you, such as it is.

All the best, we'll look forward to seeing you next week. We'll all stay tuned. Yes, thank you, Colonel. Thank you. I'm coming up later today at 1 o'clock this afternoon, Professor Glenn Deeson at 3 o'clock this afternoon, Phil Giraldi, Judge the Paletano for Judging Freedom. You're going to be.