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Andrew Egger
Donald Trump is dying to get out of this war in Iran, but Iran does not seem to want to let him off the hook. Just days after the president said that we should be moving towards some kind of deal in Iran this weekend Iran issued its biggest ultimatum yet, its largest, most sweeping set of demands. Here is Donald Trump reacting to that in the White house just now.
Reporter
Mr. President, in addition to this big announcement, you've also been posting about Iran today opposing their latest demands. You said this last round of talks was Iran's last chance before decapitating. So what now? What now? You'll find out.
Lieutenant General Mark Hertling
You'll find out.
Reporter
Are you still a massive escalation? Is that still on the table?
Lieutenant General Mark Hertling
Well, we have that certainly in that ability if we want to do that. Yeah, you'll find it.
Andrew Egger
I am Andrew Egger with the Bulwark, joined by our military analyst, Lieutenant General Mark Hertling to talk about the latest what's going on in Iran. General, can you just walk us through what exactly Iran is demanding as of this weekend and why it is an escalation from what we've seen from them before.
Lieutenant General Mark Hertling
Yeah, Andrew, when this came out this weekend, it's, you would have to say from a common sense perspective, it's laughable. They know that the president's not going to live up to it. So a guy named Mohammad Zolgidar, who's the secretary of Iran's supreme National Security Council. So this is a real guy. This is a diplomat. This isn't the irgc, this isn't the Ayatollah. He issued a statement that was then later carried by Iranian state media. So it was the real deal and listed five requirements. And I'll read them for you. The first one was the US Lift its naval blockade and sanctions on Iran. Okay. That's something that you could negotiate. Secondly, withdrawal of US Military from around Iran, which that one isn't really clear because they don't state which military organizations or countries they're talking about. So the United States has, the United States and various allied countries have installations all over Jordan, Syria, Oman, uae, Kuwait especially. So that's saying withdrawal. Is that something that most of the Muslims have asked for in this area? The third one, pay war reparations. And we saw a couple things this afternoon where President Trump and the Ayatollah were going back and forth on what kind of reparations there were. And we can talk about that in a second. Release all frozen Iranian assets. That's quite a bit of money. And then finally, here's the big one, end attacks on Iran's allies in the regions and threats against their country and their proxies. So this is now talking Hamas, Hezbollah, the Houthis, the Iraqi PMF forces that have actually been mobilized to a degree and causing more problems inside of Iraq. So you're talking about anyone who is of a Shia background that's allied with the Iranian resistance, if you will. They said basically the United States can't attack any of them or shouldn't attack any of those. So this is a pretty significant demonstration of what they're looking for. When I first read it, Andrew, I thought, okay, they're poking the bear. They know that the Trump administration doesn't have a whole lot of options, and the options are getting even less and less by the day. So they're basically showing their hand, not only to the United States, but all the other Gulf states that are in the region, that they're taking on a new sense of power.
Andrew Egger
Yeah, this has been the thing that I've been trying to figure out because, correct me if I'm wrong here, my sense of this set of demands is that it is already a pretty significant worsening of the deal relative to the MoU that was agreed to in a very fragile way between the US And Iran a couple of months ago. Now, insofar as all of this, first of all, it's more demands, the business of, I believe, reparations is new, but as well as Iran suggesting they're giving away less because this is all just again, to potentially reopen the Strait of Hormuz and not in a return to the pre war status quo sort of way, but just to reopen the Strait of Hormuz in a way that is now administered and told by Iran and Oman. And any mention of Iran's nuclear program, which was the other sort of leg of the stool for the MoU, is just absent from this. So it seems on the one hand like Iran is asking for. For more here. Is that basically accurate, that this is
Lieutenant General Mark Hertling
a. Yeah, this is a power grab. They're not asking for more, they're asking for a lot more. I mean, some of these things are just unreasonable from any country to say something like this. But they also know they have intelligence in a couple of areas. First of all, this coordination council between Saudi Arabia, Turkey and Pakistan is an interesting dynamic. The negotiations that Iran has been conducting with Oman, off the record, that council, in terms of what can and what can't pass through the straits, even though Iran doesn't agree with what Oman is offering, the potential for the strikes against Multiple targets throughout the region that are affecting other Gulf cooperation states. And the fact that they know that the President is facing an election in just a couple of months, as well as the reports that you know, truthfully are, they're, they're rational and logical of the loss of precision weapon systems, that the United States is decreasingly having the ability to have standoff weapons. So the only option you have left from a military force is either continue to deplete the weapons you have, the long range weapons, or send in the close in troops which are going to result in casualties. I mean, anytime you have a war where there's, as I like to call the term coffee breath close with your enemy, you're going to have casualties. And the President can't afford that because he was the guy that promised no more Middle Eastern wars. So they know that the President and his diplomats, as, as it were, if you could call them that, are in a very difficult position in terms of what they can now negotiate. Especially with the fact that the President just keeps insulting Iran. I mean, that's not diplomacy at all. That's going to turn you a foe off quite a bit.
Andrew Egger
Yeah. This is the thing that has been psychologically interesting and maybe even a little confusing to me as I have been watching these sort of statements of bravado and counter bravado from Iran and the US the last few days is you can kind of make a psychological argument, I guess, that Iran knows that Donald Trump is willing to give a lot of concessions to get out of this war. He has shown this since the days of the mou. And I guess you could construct, construct an argument that it might be useful for Iran to leave him with a bit of a fig leaf here, to leave him with one or two things that he could then take to his people and strut and strut and crow and trumpet. Look, I got, I got this great deal. I got this great deal. And instead it seems like Iran is almost leaving him without a single diplomatic leg to stand on in terms of some of these demands. And it really does make you think like they are really betting that, that, that no matter what they say and do, Donald Trump will not have the appetite for going hot with this war again. And I just wonder, is that maybe too optimistic on Iran's part? I mean, it doesn't seem like, like maybe, maybe at this point Trump, Trump is in fact just spent and just done with this bombardment campaign. And maybe as, as you suggest, he in fact under no circumstances would escalate to ground troops. But it does seem like kind of a gamble on Iran's part, or am I wrong?
Episode: Trump Is Running Out of Missiles—and Options—In Iran
Date: August 10, 2026
Host: Andrew Egger
Guest: Lt. General Mark Hertling (Military Analyst)
This episode of The Bulwark analyzes the escalating standoff between the U.S. and Iran, focusing on the Trump administration’s dwindling leverage and the latest, sweeping set of demands issued by Iran. The discussion explores how Iran’s bold posture and maximalist demands expose the administration’s strategic vulnerabilities, especially as President Trump seeks a face-saving exit from an increasingly untenable war.
Context: Iran has just dramatically increased its demands for ending hostilities, going far beyond previous agreements.
The Demands:
Lt. Gen. Hertling lists Iran's five key demands (00:57–03:14):
"When this came out this weekend... you'd have to say from a commonsense perspective, it's laughable. They know that the president's not going to live up to it."
— Lt. Gen. Hertling (00:57)
Analysis: Hertling sees the demands as a deliberate overreach — a way for Iran to exert psychological pressure and signal power not just to the U.S. but to other Gulf states.
Worsening Terms:
Andrew Egger points out that these new demands are much tougher than the terms of the prior MoU — particularly the introduction of reparations and the exclusion of any language about Iran’s nuclear program.
“It is already a pretty significant worsening of the deal relative to the MoU that was agreed to... the business of, I believe, reparations is new... Any mention of Iran’s nuclear program... is just absent from this.”
— Andrew Egger (03:30)
Result: Iran is not just asking for more—it's asking for "a lot more," as Hertling confirms.
Iran’s Confidence:
Hertling describes Iran’s posture as a “power grab” capitalizing on several U.S. weaknesses:
"The options are getting even less and less by the day. So they're basically showing their hand, not only to the United States, but all the other Gulf states."
— Lt. Gen. Hertling (03:14)
"The President can't afford that because he was the guy that promised no more Middle Eastern wars."
— Lt. Gen. Hertling (06:07)
Diplomatic Strain:
Iranian leaders also perceive that the Trump administration’s insults and lack of diplomatic finesse hinder any real negotiation.
“Especially with the fact that the President just keeps insulting Iran. I mean, that’s not diplomacy at all. That’s going to turn your foe off quite a bit.”
— Lt. Gen. Hertling (06:30)
Psychological Dynamics:
Egger questions whether Iran’s maximalist stance gambles too heavily on Trump’s desire for an exit, possibly underestimating his willingness to escalate.
“You could construct an argument that it might be useful for Iran to leave him with a bit of a fig leaf... And instead it seems like Iran is almost leaving him without a single diplomatic leg to stand on.”
— Andrew Egger (06:44)
Strategic Risk:
The discussion closes on the question of whether Iran's move is risky: Are they right that Trump will not escalate, or are they inadvertently pushing him into a corner?
The conversation is analytical but direct, with Lt. Gen. Hertling often punctuating military analysis with frank, plain-spoken assessments. Andrew Egger provides clarifying questions and frames issues for a non-expert audience, pushing the conversation towards the psychological and political implications of the standoff.
The episode delivers a sobering analysis: Iran’s sweeping new demands are less about realistic negotiation and more about capitalizing on U.S. strategic fatigue. As Trump faces dwindling military options and domestic political pressure, Iran is pressing its advantage, betting that Washington now has no appetite for escalation — leaving the administration trapped between humiliation and costly escalation.