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Home » COL. Douglas Macgregor: Iran Stronger Now; Putin Takes Off the Gloves (Transcript)

COL. Douglas Macgregor: Iran Stronger Now; Putin Takes Off the Gloves (Transcript)

Editor’s Note: In this episode of Judging Freedom, host Judge Andrew Napolitano welcomes back retired Colonel Douglas Macgregor to dissect escalating global conflicts and critical shifts in geopolitical power. The discussion dives deep into Russia’s hardening stance in Ukraine following recent drone strikes, as well as the collapsing diplomatic options and massive economic threats surrounding the conflict with Iran. Together, they analyze the domestic political pressures influencing President Trump’s foreign policy and the growing risk of a wider regional war in the Middle East. (May 28, 2026) 

TRANSCRIPT:

Introduction

JUDGE ANDREW NAPOLITANO: Hi everyone, Judge Andrew Napolitano here for Judging Freedom. Today is Thursday, May 28th, 2026. Colonel Douglas Macgregor will be with us in just a moment. Is Iran stronger now than it was in February when the war started? And is Vladimir Putin ready to take the gloves off?

Colonel Macgregor, welcome here, my dear friend. Thank you for, as always, accommodating our schedule. Let’s start with Ukraine. How morally wrong and militarily disastrous was the Ukrainian drone attack on the female dormitory in a Russian college that killed 25 schoolgirls?

The Ukrainian Drone Attack on Russian Civilians

DOUGLAS MACGREGOR: It was despicable and unforgivable and unnecessary, but it’s certainly not the first time. And what we’ve learned over the last several years is that whatever Kiev accuses Moscow of doing that is immoral is usually evidence that they’ve done something and not the other way around. We can go all the way back to Bucha, as I’m sure you’ll remember, when the atrocity there was blamed on the Russians. Russians had nothing to do with it. It was a Ukrainian atrocity. So I think this is nothing new, but it’s depressing, and its impact on Russia has been quite profound.

JUDGE ANDREW NAPOLITANO: And what do you suspect that Foreign Minister Lavrov said to Secretary of State Rubio when he insisted on speaking with him, even though Secretary Rubio at the time was in India. This was 3 days after this attack.

DOUGLAS MACGREGOR: I think that both President Putin and Secretary Lavrov individually talking to President Trump about Iran and then subsequently with Lavrov to Rubio about what happened in Ukraine are trying to make the same point. “You have not taken us seriously. You listen to us, but you don’t hear what we say. And what we’re telling you now is that we are not going to take this lying down. We’re going to respond decisively, and we reserve the right to respond as we see fit against what we think are the sources of the real problem.”

And the sources for these long-range drone strikes are components that are produced in the West and then shipped into Ukraine, assembled in Ukraine. So I think that’s the essence of it. And I think the Russians are trying to emphasize that they’re ready to act to end this war in Ukraine on their terms.

Western Co-Belligerence and Russian Restraint

JUDGE ANDREW NAPOLITANO: Colonel, are those facilities in the West, Great Britain and Germany, fair, moral, lawful targets for the Russian military?

DOUGLAS MACGREGOR: Well, under international law, not that anybody in the United States pays much attention to it, it would certainly suggest that if you are providing critical components to a belligerent in a war, then you are a co-belligerent. So I suppose on that basis, they definitely could inflict pain on Western states.

Now, the Russians obviously are not interested in widening the war. They have exercised a lot of restraint over the years. Remember, everything that happens involving these long-range drone strikes actually involves us. We’ve actually sent Rivet Joint and other surveillance aircraft to systematically map out every potential air and missile defense battery, every potential radar site, every potential ammunition storage site, refineries, all the targets of interest to the Ukrainians. And we’ve provided that information to the Ukrainians. This in spite of the fact that President Trump has insisted he wants an end to the war and is trying to largely disengage from it.

It hasn’t happened, which once again reinforces something that President Putin has said repeatedly. He’s met many, many American presidents over the years, and he’s discovered that while many of them have good intentions, nothing they ever say or do finds a way to be translated into action. That the so-called deep state or the federal bureaucracy or the Congress continue to operate as they will. So I think that’s also what’s going on right now in Russia. They’ve said, “We’ve listened to this before, we’re not going to put up with it anymore.”

JUDGE ANDREW NAPOLITANO: Can the Russians justify attacking MI6 and CIA facilities in Ukraine?

DOUGLAS MACGREGOR: Oh, absolutely. In Ukraine, without a doubt, and they have. Let there be no mistake about it. They have actually attacked those places in Ukraine. So that’s already happened. They’re concerned more right now at this stage about the components Ukrainians cannot build themselves that are critical to these long-range unmanned system strikes.

The Oreshnik Missile and Russia’s Next Move

JUDGE ANDREW NAPOLITANO: So I think it was last weekend the Russians fired off an Oreshnik, maybe for the second or third time. My count may be wrong, and it was aimed at factories on the outskirts of Kyiv. What happens if they unleash Oreshniks on the government buildings in Kyiv?

DOUGLAS MACGREGOR: Well, I’m sure they’ll level them. And I think that’s coming. I think they’ve put everyone on fair notice. They’ve announced that any foreign diplomats that are operating in the area should plan to leave as soon as possible. I think that’s a pretty clear indication, but I think that’s the beginning of something much larger. I think we’re finally going to see Russian forces on the ground move more decisively than we’ve seen in the last couple of years.

Germany: Merz, the AfD, and the Future of NATO

JUDGE ANDREW NAPOLITANO: I remember about a month or so ago you saying to me in one of our many communications, you were critical of Chancellor Merz.