Read the full transcript of retired colonel and political commentator Col. Douglas Macgregor’s interview on Judging Freedom Podcast with Judge Napolitano on “What US Security Guarantees!?”, August 18, 2025.
Opening and Introduction
JUDGE NAPOLITANO: Judge Andrew Napolitano here for judging freedom. Today is Monday, August 18, 2025. Colonel Douglas McGregor will be here with us in just a moment. Security guarantees. The United States is going to provide security guarantees for Ukraine. Where did that come from?
Colonel McGregor, welcome here, my dear friend. Before we get into anything particular about what they’re talking about when they say security guarantees for what remains of Ukraine after some mythical peace agreement – maybe I’m being snarky by calling it mythical – what is your big picture take on what happened in Alaska on Friday?
Trump’s Meeting with Putin: A Shift in Relations
COL. DOUGLAS MACGREGOR: I think we saw tangible, concrete evidence for President Trump’s desire to normalize relations with Moscow. I think it’s very clear President Trump treated President Putin with great cordiality in contrast to his predecessor and so many people in Washington that do the opposite.
And I think he recognizes that, quite frankly, we have reason to cooperate on every level – economic, political, military, diplomatic. The problem is we’ve got this rogue state that is now in the last hours, I would say, of its life in Kiev.
And he’s got a problem with the Europeans, particularly in Western Europe, the globalists who see this as a fight against Russia on behalf of globalism. He’s not interested in that fight. He’s happy to support a strong nationalist Russia that rests on the foundation of Orthodox Christianity. He sees nothing wrong with that. He wants to do business with them. He sees them as potential strategic partners.
But he feels constrained regarding how far he can go. That’s why he’s meeting with the West European leaders today, leadership of the EU. We’ll see how it turns out. We know what he would like to do now. We’ll find out what he decides he can do.
Trump’s Remarkable Change of Position
JUDGE NAPOLITANO: Before Friday’s meeting, actually on his way there, he gave an interview to my friend and former colleague Bret Baier at Fox News in which he restated he’d be very angry if there weren’t a ceasefire as a result of his conversations on Friday.
Suddenly and at the end of the conference, he has indicated he’s no longer in favor of a ceasefire. He understands that that’s not realistic. He recognizes that Crimea is, has been and will remain a part of Russia and that NATO should have no place in whatever remains of Ukraine.
But that is a remarkable change, in my view. I attribute it to – he probably heard a lecture from President Putin on the genesis and causes of the special military operation in Ukraine, the likes of which he’d not heard from any of the neocons that he brought to Alaska with him.
Question: General Kellogg gone? Is he thrown under the bus? Are the neocons out of this picture?
The Deep State Resistance
COL. DOUGLAS MACGREGOR: Well, I’m certainly going to keep my eyes on the street and hope, but it doesn’t look that way. And I think President Trump, if he doesn’t understand it, he needs to keep in mind that the CIA, along with MI6 in London and to a lesser extent Mossad, in this case in Ukraine, are arrayed against him.
He’s got to understand that whatever he decides to do, whatever orders he issues, he’s going to have to follow them up very carefully because the Central Intelligence Agency is into this business up to its neck. And they are going to do what they want to do unless he makes it abundantly clear that he will not tolerate disobedience. So I think that’s very important.
The second thing is that I think he knows that this will split NATO. The West European globalists that are running NATO and the EU – people like von der Leyen and Rutte and the rest – they are in favor of perpetual war with Russia because quite frankly, if it stops and the European electorates finally realize they’ve been lied to constantly from the beginning about the Russians, these governments are not going to last very long. They’re afraid of that.
So it’s very important to them. They don’t care about Ukraine. They’re not particularly worried about global peace or anything else. They simply want to stay in power. They can’t stay in power if this ends because people are going to say, “Well, listen, this is remarkably stupid. Why did you drag us into this? Why did you de-industrialize us over this business?”
So I think President Trump knows that. The question is, how far is he willing to go? Because inevitably, I think this will lead to the dissolution of NATO. And everybody’s going to act like, “Oh, my goodness, we can’t live without NATO.” Well, that’s wrong. We can all live without NATO. But that’s going to be the attitude.
CIA and Deep State Entrenchment
JUDGE NAPOLITANO: You mentioned a few minutes ago that the President is going to meet resistance from the heads of state in Western Europe. He’s also going to meet tremendous resistance from the deep state, is he not? You’ve indicated how invested the CIA is. How about 20 CIA stations built in the first Trump administration and the Biden administration throughout Ukraine? How about MI6 directing Ukraine military to target Russians? These people are going to just roll over and act like what they’ve been doing for the past 10 years is suddenly going to end?
COL. DOUGLAS MACGREGOR: No, that’s my point. And I don’t think this man Radcliffe, who is currently running the CIA, is going to be much value added to President Trump. He’s a prisoner of the intelligence community as well as, of course, the various lobbies – the Israel lobby, the Defense lobby, and so forth.
He’s also got a problem with all these luminaries in uniform called generals that have helped the Ukrainians to kill more than a million of their soldiers in pointless operations that never made any sense.
People like Donahue and Cavoli and others – got to remember that we didn’t just send arms and equipment, we established headquarters. We tried to help direct operations. We planned things and urged these people to charge into the teeth of Russian ISR strike capabilities. In other words, put millions of people in harm’s way, and for what? Nothing.
He’s going to have to come to the conclusion that simply sending out an order, simply directing people to do something is not going to change anything. You can remember from the first time he was in office, towards the end, he wanted to get out of Syria. And then people told him, “Okay, we’ll get out and we’ll do this and this.” And then he found out nobody left Syria, nobody left anything.
And Jeffrey, I think, was the ambassador at the time. And he actually took a bow on Capitol Hill for lying to the President and ignoring his orders. You got a lot of people like that right now.
Just because he walks out and says, “I’ve done all I can do,” which I hope he will do, “And I am suspending all further aid to this Ukrainian state, except for humanitarian aid. And I am urging my European colleagues to meet with President Putin” – if he does that, then I think he has a chance for success, because I don’t think he is in a position to, quote unquote, “deliver NATO,” which, of course, is something that President Putin hopes he will do. I’m just not sure he can do it because of the forces arrayed against him.
The Mysterious “Land Swaps” Proposal
JUDGE NAPOLITANO: One of the strange phrases that came out of Mr. Witkoff’s last meeting with President Trump, so strange that Alistair Crooke this morning opined that it must have been a misunderstanding or a mistranslation, was this phrase “land swaps,” and the president picked up on it as well.
I mean, isn’t it inconceivable and probably illegal under Russian law that the Russians would give away some land to the Ukrainians in return for Crimea and the four oblasts that they’ve succeeded in dominating militarily? What could possibly been meant by this phrase “land swaps”?
COL. DOUGLAS MACGREGOR: Well, my impression is that there was some flexibility on the Russian side about territory in Kherson and Zaporizhzhia, territory that could be conceded or, quote unquote, “ceded” to the Ukrainians as part of any sort of arrangement. Now, I don’t know how far that goes, and I don’t know the exact parameters. I was a little surprised to read that, frankly.
But they did – President Putin did apparently say that, you know, obviously, the oblasts that are now part of Luhansk, Donetsk, and so forth, and Crimea, those are part of Russia. That’s not going to change. They’re officially recognized constitutionally by the Russians. So that’s not open for discussion.
But there was some flexibility on Kherson and Zaporizhzhia. Now, the problem is you’re dealing with a Ukrainian president who says, “Nothing will be given up. We will cede nothing.” Okay, fine. That gives President Trump an opportunity to walk away from this nonsense and say, “Well, then you’re on your own. I’ve done all that I can. I’m not going to do anymore. We have more important issues now to face.”
The Russians are not being unreasonable. The Russians are not wedded to no change whatsoever. So if you’re not going to talk to them with your European colleagues that support you, then you’re on your own. I’m not going to go along with it. That’s the real question. Will he stand his ground on that point?
So I think the Russians were more flexible than I think anybody thought they would be, but that, you know, that’s the sort of thing that needs to be understood. And I think when he said “land swap,” he may have been overstating it, but that’s the genesis of it.
Ukrainian Leadership and Nationalist Control
JUDGE NAPOLITANO: We – you and Scott Ritter and Larry Johnson and Ray McGovern and many of the regular guests on the show who are military veterans – have opined that President Zelensky is not free to make his own decisions, that in fact, he is subject to and controlled by a cabal of arch nationalists. Our friend Pepe Escobar calls them Nazis. They don’t want us to use that word. But arch nationalists who are driven by ideology and not reality. Do you think that that group of folks recognizes the precarious state of the Ukrainian military?
COL. DOUGLAS MACGREGOR: I’m not sure that they believe that if they stand their ground – in other words, they refuse under any and all circumstances to negotiate with the Russians and give anything up – I think they may believe that they can survive that because they don’t think the Russians will cross that river, come into Kiev and eliminate the regime. I happen to think they’re wrong, but that is part of the problem.
Some of your viewers may remember – maybe not – at the end of the Gulf War in 1991, when it became clear that we were willing to call a ceasefire and not advance any further, despite the fact that we had allowed most of the Republican Guard to escape. And I watched that grim chapter in our history – in my judgment. But nevertheless, that happened.
And as soon as Saddam asked the question, “Are they crossing the Euphrates River?” And the answer came back “no,” he got up and danced around the table and started celebrating. I think that’s what you’re dealing with in Kiev. These people figure if we sit here and refuse to negotiate, refuse to cooperate, insist on fighting to the bitter end, the Russians won’t cross that river. We’ll get away with it, and then people will have to support us. I think that’s the problem.
Kellogg Still in the Picture
JUDGE NAPOLITANO: I don’t want to give you heartburn, but apparently General Kellogg has not been thrown under the bus. There he is. You can see him next to Secretary of the Treasury Bessent, who’s next to Defense Secretary Hegseth. That’s just about 45 minutes ago in the Oval Office. He doesn’t look very happy, but he’s there. If he’s there, he must be whispering his NATO generated nonsense into the President’s ear when he gets a chance.
COL. DOUGLAS MACGREGOR: We have to understand that he is part of the Washington community that wants perpetual war everywhere, not just against the Russians in Ukraine, but also in the Middle East and probably out there beating drums for stupidity over Taiwan against China. So I’m not surprised.
The other thing is that President Trump – people need to understand this – he’s a very nice person. You know that from having dealt with him, too. He is a nice person. He is sentimental and he likes Kellogg. He does. And I think it pains him to turn to Kellogg and say, “Thank you very much for your interest in national defense. You’ve got to go.” I don’t see that happening. I think he wants harmony and he wants to be liked. If anything, that’s one of his weak points.
The Security Guarantees Question
JUDGE NAPOLITANO: All right, here’s what I’ve been waiting to ask you all weekend, since I first heard this phrase. What security guarantee? What are they talking about? “Oh, a security guarantee, but not NATO. Oh, it’ll include the United States, France, Great Britain, Germany, and the coup from Brussels. But not Brussels, but not NATO.” Who are they trying to kid?
Security Guarantees and NATO’s Future
COL. DOUGLAS MACGREGOR: Well, a lot of people. And let’s hope that President Trump isn’t one of them. First of all, the president of the United States should not be prepared to guarantee anything over which we have no actual control and influence.
And I think we’re going to find out, if things happen, as I think they will, that we really don’t have control or influence over Zelensky and what he does or doesn’t do. And therefore, how can you guarantee any arrangement that is reached that involves him and his current government? So I hope that. I hope President Trump reels back in shock from that one.
I did hear more intelligent and balanced remarks from Secretary Rubio, who was somewhat more nuanced, and he understands what security guarantees mean. I don’t think Witkoff does what’s really important, and this is something that President Trump has to sit down and work out.
NATO is dead man walking, has been for a long time. That’s an empty facade. Pull our military establishment out of the equation and NATO collapses like a house of cards. It’s irrelevant. That’s one of the reasons they’re going to do everything they can to keep us engaged in Ukraine, where we should get out. Ukraine has never figured prominently in any strategy we have for NATO. It needs to be abandoned 100%.
Regional Solutions for Ukraine
However, the people that border Ukraine, Lithuania, Poland, Slovakia, Hungary, Moldova, Romania, those states have an interest in peace. In Ukraine, they have an interest in a new relationship with Moscow. They need to sit down and work that out with Moscow directly. We should be prepared to support that and assist it in other words, we should encourage it.
But we can’t guarantee anything from 6,000 or 7,000 miles away that happens in Ukraine. We can support it by saying that we will contribute whatever we can in terms of resources, such as humanitarian assistance. And through our discussions with Moscow, which I think are very good right now.
And I think it’s very clear that just as President Trump wants a new and positive relationship with Moscow, that’s exactly what President Putin and his team want with him. So hopefully we’ll have a more nuanced perspective on this thing called security guarantee, because we can’t do much about it.
The Austrian Model
Now, you’ve heard Jeffrey Sachs say this as well as me. I’ve been saying it for years. I think it’s come up with John Mearsheimer. We talk about the Austrian state treaty from 1955. What a lot of people don’t know is that the negotiating that went on in Austria and Vienna with the Russians was conducted by the Austrians. And the Austrians were the ones that helped draft that treaty.
And the Russians then were very comfortable with it because they were sitting across from a former opponent that wanted peace, wanted to get along, wanted to restore prosperity, and was willing to work with them to the point where the Russians maintained for at least two decades a Russian representative on what was effectively the Austrian state’s National Security Council.
And that’s going to have to happen in Kiev, regardless of how this turns out. And he was there to ensure that the provisions of the treaty were implemented properly. And they were. Our view was our role was essentially Eisenhower who said, yes, by all means, let’s neutralize Austria. Eisenhower wanted to neutralize Poland, the Czech Republic, Hungary. He would have neutralized everything because he said we can’t possibly defend it.
Well, if we couldn’t defend it in 1955, judge who thinks we can defend anything now out in Ukraine?
Trump’s Comments on American Troops
JUDGE NAPOLITANO: When the president was asked just about a half an hour ago, it’s now Monday afternoon around 2:20, seated next to President Zelensky if he would rule out American troops on the ground. He declined to rule them out.
COL. DOUGLAS MACGREGOR: Well, I don’t know.
JUDGE NAPOLITANO: I saw General Kellogg make the sign of the cross. No, I’m kidding. I didn’t see Kellogg make the sign of the cross. I don’t know if he’s Catholic. I don’t know how he express his glee. I’m being a little sarcastic, but my jaw dropped when he, as I was watching as he declined to rule out troops. Troops on the ground shouldn’t even be in any American troops shouldn’t even be in anyone’s mind, I would get all.
COL. DOUGLAS MACGREGOR: Of the US Troops that are currently sitting in Poland and Lithuania and Romania completely out of the picture. We need to get out of those places. We may. We need to make it very clear we’re not underwriting any future wars with Russia, because all of this was provoked not by Russia, but by us and London.
JUDGE NAPOLITANO: Yes.
COL. DOUGLAS MACGREGOR: And supported by these other West Europeans. And as you pointed out, it seems as though the president has finally figured that out. Well, talking about the use of US Troops is just ludicrous nonsense.
The other thing is that, remember, he’s got these people that voted for him and they voted really for an end to these endless conflicts and crises provoked overseas. Putting more US Troops on the ground over there is an invitation to trouble. So I hope he reconsiders that. Sometimes President Trump says things and then subsequently revises his opinion. I hope that will happen here.
Putin’s Position on Security Guarantees
JUDGE NAPOLITANO: Well, we know he has done that. You know that from having been one of his senior advisors. I know that from having talked to him about the Supreme Court till I’m blue in the face. Hopefully, he’ll do that here. But why would Vladimir Putin accept security guarantees with anybody’s troops on the ground in Ukraine when he wants a neutral Austrian like Ukraine?
COL. DOUGLAS MACGREGOR: Well, he won’t. That’s obvious. And President Trump should understand that. If we’re talking about guarantees, what could President Trump guarantee? He can guarantee that we will not push any forces any further east under any circumstances. He could set up a line beyond which no future European and American joint exercises will be held.
I mean, there are all sorts of things you can agree to, what you will or will not do in the Baltic, what you will or will not do in the Black Sea. I mean, after all, that’s the way we regard the Caribbean. Correct. So there are ways to do this. Those things make sense.
But if you’re trying to guarantee the independence of this nascent Ukrainian state, that emerges from the ruins of this war, and that is somehow or another going to develop along lines that Russia will accept. You’ve lost your mind. Because the Russians are not going to refight this war. That’s in the back of their minds. Why would we ever want to come back here and refight this? We don’t want to do it. We want an arrangement that ends the hostilities, period. We don’t want to return.
So you can’t get that if you start guaranteeing things with U.S. forces east of the Polish border.
The Neocon Challenge
JUDGE NAPOLITANO: How I wish Trump and his people would listen to you. But I fear that a stake has not been driven through the hearts of the neocons and they will rise up again, just like having General Kellogg there. Nothing against him personally. And the president’s comments that he wouldn’t rule out troops on the ground, well, we’ll see where it goes. But the concept of security guarantee has to be a non starter for the Russians.
COL. DOUGLAS MACGREGOR: Oh, absolutely. And I think, again, I think President Trump knows this. But you’ve got to watch out for Senator Tom Cotton, Senator Lindsey Graham and others on the Hill. They’re not the only ones by any means. And then of course, you’ve got people surrounding Trump as it is.
And I’m sure he’s got to sit there and think, well, look what we’ve got committed in the Middle East. How much can we afford to bite off? You know, the good news is that if you proceed to normalization of relations with Moscow, that may be enormously helpful to us in the Middle east bringing that terrible, terrible situation to an end. And I’m sure President Trump has probably voiced that and would like to do it.
But again, he has just as much opposition to ending the atrocities in Gaza and future conflict in Syria with Iran. It’s a tough thing. You’ve got to be a very strong individual right now to be president of the United States.
The Voice of the People
But here’s the good news, Judge, and there is good news. If he decides to fly tomorrow morning and meet with people on the outskirts of Kansas City, Missouri, or up to Missoula, Montana, or Boise, Idaho, what’s he going to find out? Sir, we support you. Get out. Stop this. We have to work at home. We have problems here. Everybody’s going to say that.
And everybody that voted for him is going to say, get out of those places. End that. In other words, stop listening to the voices of derision in Washington and listen to the people that voted for you.
Upcoming Dallas Event
JUDGE NAPOLITANO: Nicely put, General.
COL. DOUGLAS MACGREGOR: Colonel.
JUDGE NAPOLITANO: Sorry. Nicely put, Colonel. Beautifully put. You and I had a happy experience on Saturday morning when we were together on a Judging Freedom panel at the Ron Paul Institute. It was very widely watched both here and on the Gray Zone website because Max Blumenthal and Anya Parampil were also on the panel. Jeff Sachs was on the panel, but you and I are doing one together in Dallas. There we are in Dallas, Texas. I’m trying to see the date.
COL. DOUGLAS MACGREGOR: Where is the for October.
JUDGE NAPOLITANO: There you go.
COL. DOUGLAS MACGREGOR: It begins at 5pm and then at 6pm we, you and I and Natalie Brunel, more and more people are recognizing what a talented and intelligent woman she is. In addition to being attractive. The three of us will constitute a panel and we’ll talk for two hours back and forth with a selected audience. We want to interact with the audience. We’re not just holding it in Dallas because we decided we like local beefsteak or something.
We’re there because we want to know what people think as well as talk to them about all these issues. And then we’ll have Dr. Olga Ravazzi. She’ll monitor the panel. Very lovely, intelligent woman. And I think as a result, people will enjoy this. But this is what we hope will be a new national conversation. You know, we talk a lot about, well, let’s have a conversation about this or the other. Judge. I never hear it.
JUDGE NAPOLITANO: Right. Right. Well, I’m looking forward to a colonel and we’ll be promoting it in the next month or so. Thank you very much for your time here. As always, thank you for your insight. We’ll look forward to seeing you again next week, Colonel.
COL. DOUGLAS MACGREGOR: Thanks, Judge. See you soon.
JUDGE NAPOLITANO: Sure. All the best to you. Coming up at three o’ clock today. Aaron, mate. Aaron just finished a fascinating conversation with a former official of the French Defense Ministry. And you won’t believe what he said about the genesis and the origin of the special military operation in Ukraine. It’s the guy that used to work for President Macron. Also, we’ll be talking to Aaron about what’s been happening in Israel while the world has been focused on Alaska. Judge Napolitano for judging freedom.
Related Posts
