PDB Situation Report | June 5th, 2026: Trump Faces A New Crisis In Iran & Russia's Massive Kyiv Strike

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**Mike Baker** (1:07)
Welcome to the PDB Situation Report. I'm Mike Baker, your eyes and ears on the world stage. All right, let's get briefed. First up, despite a ceasefire or whatever we're calling it, that remains technically in place, Iran has launched its most damaging attack yet, raising questions about whether the truce is beginning to unravel, and also the question of what do you call a ceasefire where nobody's ceased firing, and what President Trump might do next. We'll be joined by retired Rear Admiral Mark Montgomery to get his insight. Later in the show, after weeks of warnings, Russia unleashes one of its largest attacks on Kyiv.
What's driving Moscow's latest escalation? We'll have more on that with George Barros of the Institute for the Study of War. But first, today's Situation Report Spotlight.
Nearly two months after President Trump announced a ceasefire with Iran, the truce is showing signs of strain. This week, Tehran launched what appears to be its most damaging attack once the ceasefire or again whatever we're calling it began. Striking Kuwait International Airport with a missile and drone barrage that killed at least one person, wounded dozens more and caused significant damage to the airport facilities. The attack raises questions about whether Iran is testing the limits of American restraint while negotiations continue behind closed doors. And here's a pro tip. Yes, Iran is testing the limits of American restraint. Joining us to break it down is retired Rear Admiral Mark Montgomery, Senior Director of the Foundation for the Defense of Democracy's Center on Cyber and Technology Innovation. Sir, thanks very much for joining us again here on the Situation Report.

**Mark Montgomery** (2:46)
Thank you for having me, Mike.

**Mike Baker** (2:47)
Good to be here.
Absolutely. Well, I guess let's start with Iran. I want to get to Ukraine in the second segment, because I know you've just come back from Ukraine. But with the Iran conflict, I've been asking our viewers and listeners the same question, but what do you call a ceasefire when nobody's ceasefire?

**Mark Montgomery** (3:11)
I think what we're in right now is an economic coercion campaign where the United States is trying to squeeze the Iranian economy through the blockade, where we're fairly effectively blocking the 90 percent of exports that went by sea of fossil fuels on what was called the shadow fleet ships.
Conversely, they are providing an economic coercion campaign against both our Arab partners who provide fossil fuel and our Asian and European partners, trade partners like Japan, Korea, Taiwan, Indonesia, Malaysia and the European countries. So people we trade with, eventually that has an impact on our economy as well. So you have two competing economic coercion campaigns going on. And when anyone tries to get a leg up on the other, you end up seeing some weapons being fired.

**Mike Baker** (4:03)
Yeah. And I guess the, I mean, it's straining that the definition of ceasefire. I understand why the White House is reluctant to reignite a full scale military campaign. I get that.
But I mean, at some point, you have to think that in this staring contest, the Iranian regime, which I think is viewing this as if they're in a position of resilience and strength, which could explain sort of the illogical nature of these supposed negotiations. I think they look at it and think that they just outweigh the White House. And I think they're pinning a fair amount of hope on the idea that the White House will at some point make some concessions in order to get the straight open, in order to get gas prices down, in order to get votes during the midterm elections. Am I looking at this wrong?

**Mark Montgomery** (4:59)
You know, I think they're right. You know, the United States is a democracy which has a burden, a burden of public support and a burden of elections, something the IRGC does not have to deal with. And for the IRGC, this is existential, right? I mean, this is, were they to capitulate in a way from which they could not recover, you know, they don't get to come back in, you know, after a bad election. Whereas, this is not existential for Donald Trump yet.