June 9, 2026 | The Iran Breakdown

What Does Winning In Iran Look Like?

June 9, 2026 The Iran Breakdown

What Does Winning In Iran Look Like?

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The clock is ticking on the Islamic Republic — but what does finishing the job actually look like? With the regime battered, broken, and the pressure campaign at a critical inflection point, the U.S. faces a defining choice: double down or negotiate from strength? What tools remain in Washington’s arsenal, and how does the Trump administration turn military and economic pressure into lasting political change?

Mark Dubowitz is joined by Marc Thiessen, American Enterprise Institute fellow, former chief speechwriter for President George W. Bush, and Washington Post columnist, to map out the next phase of the U.S. pressure campaign, the strategic choices that will define the endgame, and what it will take to finally free the Iranian people from over four decades of brutal rule by the Islamic Regime.

Link to Mark Thiessen column referenced in the show: https://www.washingtonpost.com/opinio…

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Transcript

DUBOWITZ: Welcome back to The Iran Breakdown. I’m your host, Mark Dubowitz. Today we’re joined by one of Washington’s most influential conservative foreign policy voices, Marc Thiessen. Marc is a columnist for the Washington Post, a Fox News contributor, a fellow at the American Enterprise Institute, and a former chief speechwriter for President George W. Bush. He is someone that President Trump speaks to and listens to. Over the past two decades, he’s been at the center of some of the most consequential national security debates in America, from the war on terror to great power competition to the challenge posed by the Islamic Republic of Iran. In recent months, Marc has been one of the strongest advocates for using America’s unprecedented leverage against Tehran, following devastating US and Israeli military operations against Iran’s nuclear, missile, and military infrastructure. He has argued that this is a historic opportunity, not just to constrain the regime, but to fundamentally reshape the strategic landscape of the Middle East.

So we’ll discuss whether America is winning or Iran is simply buying time, whether President Trump should continue negotiations or return to maximum pressure and kinetic operations, what victory actually looks like in the conflict with the Islamic Republic, whether we’re witnessing the beginning of the regime’s end, and what lessons from Ronald Reagan’s successful strategy against the Soviet Union can be applied to defeat the world’s leading state sponsor of terrorism. So, let’s break it down. Marc, welcome to The Iran Breakdown.

THIESSEN: It’s so good to be with you. I’m a big fan. It’s great to finally be on after listening to so many episodes.

DUBOWITZ: Yeah, I was about to say, I’m a huge fan of yours. I follow your writings in the Washington Post – thank you – which certainly over the past number of years have been, I think, defining and really defining on the way forward. I know you also certainly are not just read by me, but by many more important people than me, including the President of the United States.

THIESSEN: Well, thank you. I appreciate that.

DUBOWITZ: So Marc, let’s begin with that. With respect to the Iran war, your assessment of where we are – and I guess the question to you is, are we winning?

THIESSEN: Yes, I believe we are winning what we haven’t won, if that makes sense. I always start by taking a stock assessment of where we are. So Operation Midnight Hammer buried the Iranian nuclear program under rubble that is so deep that administration officials tell me the Iranians have told them in the negotiations that they can’t get to it – to give it to us, we would actually have to come in and dig it up ourselves. So that’s the state of the Iranian nuclear program. The centrifuges have been probably irreparably damaged. The dust, as Trump likes to call it, is deeply buried. Now, as you’ve pointed out correctly, it’s not just the 60 percent enriched nuclear material – it’s all the material that needs to be deactivated. But that’s a huge accomplishment. And if Trump had stopped at Operation Midnight Hammer, we would all celebrate him as one of the bravest presidents in American history for having done it.

But he knew, after watching the Iranian response to Midnight Hammer, that they were going on a crash course to rebuild their ballistic missile capability, with a goal of having 8,000 ballistic missiles in position by 2027 – with the goal of making it impossible for us to repeat that, because they would be able to so overwhelm Israel’s defenses that they would effectively have the equivalent of a nuclear shield. They would be able to impose such catastrophic losses on Israel that we would never undertake to destroy or disrupt their nuclear program again. So in response to that, he launched Operation Epic Fury – 13,500 US military strikes, another 8,000 Israeli military strikes, 82 percent of Iran’s defense industrial base destroyed, its ballistic missile program either mostly destroyed or deeply buried, because what we would do is, if we couldn’t reach the ballistic missiles where they had been buried, we just buried the entrances so they couldn’t get to them.

The entire Iranian Navy is at the bottom of the Persian Gulf. The Iranian Air Force is grounded to the point that it can carry out no sorties. Admiral Cooper has testified that they have now been limited to what he calls a nuisance capability. They are no longer capable of projecting power like they were at the start of the war. Those are all huge achievements. And so the people who say – well, the Democrats say, look at Donald Trump: he had the Obama nuclear deal, then he went to war, and now he’s going to get the Obama nuclear deal again – no. I’m sorry, I missed the 13,500 strikes that Barack Obama launched on the Iranian military. So we’ve set them back dramatically. Those are all victories – huge victories that have made the world a lot safer. The question for us going forward is: are those irreversible, or are they temporary?

And that’s what’s before us right now – the challenge we’re facing. There are two ways to make them irreversible. You get a deal with Iran similar to the Libya deal in 2004, where the US military comes in, we land, we dig up all the nuclear material, all the centrifuges, and everything, take it to Oak Ridge, Tennessee – where Trump can greet it and have a nice ceremony celebrating that – and we blow up all their ballistic missiles and they completely surrender their program. I find that to be very highly unlikely that the Iranians will ever agree to that. Or you finish the job, which, according to Admiral Cooper, he was 10 to 14 days away from completing the target list he had when President Trump announced the ceasefire. Now the ceasefire will go down in history either as a stroke of genius or a massive strategic mistake, depending on what happens.

It could be a stroke of genius in that it allowed us to impose the blockade. We were able to send ships through the Strait of Hormuz that were critical in imposing the blockade, and we were also able to use the period of time when we weren’t firing missiles to rearm. Jack Keane says that we have about double the combat power in the region that we had at the start of Operation Epic Fury. If we use that combat power to finish the job and go from 82 percent of the defense industrial base to say 99 percent destroyed, that’s a huge victory as well – but we’re not there yet. Trump is still trying to get the deal. I’m sorry, I’m filibustering here, but I used to work in the Senate.

Last point, and then I’ll turn it back to you: even if we got what Trump would arguably call a great deal – they allow us to come in and take everything, the Arab states join the Abraham Accords, all huge successes – Iran’s going to want something in exchange for that. What do they want? They want their frozen assets. They want sanctions relief. They want a reconstruction fund. I’ve been hearing stories in the news, which I’m told are exaggerations, of a $300 billion fund to rebuild Iran. That is not worth the deal. That would be a huge strategic blunder, because Iran would just wait out Donald Trump for two and a half more years and use that money – when there’s a weak American president – to rebuild everything that he destroyed. So Trump should not give Iran the money to reverse all the massive accomplishments he’s had with Midnight Hammer and Epic Fury.

DUBOWITZ: Okay, Marc. Great summary. Now I’m going to be in an unusual position for me, because I agree with everything you said, but I’m going to raise arguments that our critics are raising against us and against this policy.

THIESSEN: Happy to take them on.

DUBOWITZ: Even though I don’t agree with the criticisms, I think they’re important criticisms to at least refute. The first is on the nuclear side. The criticism is we were in a JCPOA – in a nuclear deal that had, as Jake Sullivan said, put Iran’s nuclear program in a box. We had these tight restrictions and these inspections that would have prevented Iran from developing nuclear weapons. And Iran had gotten some sanctions relief, but certainly companies were still concerned about doing business with Iran, given the fact that it was engaged in terrorism and missile proliferation and other malign activities. We knew it was a good deal but not a perfect deal. So at year 13 of the deal, when all of the restrictions were going to start to sunset, we were going to renegotiate that agreement and extend the sunsets. Iran would have gotten some more money, but that money would have actually helped potentially moderate the regime. And so we would have had a more moderate regime with extended restrictions and Iran’s nuclear program in a box, instead of having to go to war with all of these unforeseen consequences.

THIESSEN: So you’ve faithfully presented their case, and it sounds a lot like what people were saying about the Munich Accords. We had a great deal and we didn’t need to rearm because we had peace in our time. I mean, first of all – the Trump sanctions when he reimposed them – first of all, Obama sent pallets of cash to the Iranian regime, and Trump says that, and it’s literally true, because they couldn’t get banks to take it to wire the money, so they literally sent planeloads of cash. And you saw an immediate uptick in Iraqi support for terror proxies around the world. Trump imposed massive sanctions on the Iranian regime – the crippling sanctions during his first term. I’m sorry, Biden lifted them when he came into office, and you saw the result on October 7th, because the cash started flowing again. So the idea that there are moderate Iranians in the regime – it’s like saying, ‘Oh, you took out Hitler and now the really bad Nazis are in charge.’ There are no moderate Nazis, and there are no moderate Iranian radicals.

The people that Trump says are much more moderate – we’re working with them. So we’re working with the SS instead of the Gestapo. It’s a distinction without a difference. The Iranian regime is ideologically determined to get a nuclear weapon. They have been since the beginning, and it’s a unique danger in that they want it for a different reason than other countries have pursued nuclear weapons. If you look at North Korea – and by the way, you could have made all the same arguments that you just made for the Clinton North Korea nuclear deal. And all they did was cheat on it and break out and become a nuclear power. The North Koreans want the bomb because they want to be left alone. They’re a hermit kingdom. They want to have their dictatorship, oppress their people, and have the world leave them alone. The Iranians want a nuclear weapon because they want to use it, because they’re subscribers to a radical sect of Shia Islam that wants to bring back the 12th Mahdi, which will usher in the apocalypse and the end of times.

And so they want this because they’re religious radicals who see it as a tool in fulfilling their religious destiny of bringing about the end of the world. And you don’t have to take my word for it – they say this. And so if you look at history, what is the biggest mistake that Western leaders have made throughout history? It is not taking the words of our enemies seriously. I mean, go back to Lenin and ‘What Is to Be Done,’ where he laid out his plans to overthrow the Czars and build a worldwide communist revolution, and no one paid much attention to it. He came in, established the Soviet Empire, 100 million people died as a result of that, and communism spread around the world. Then you look at Hitler. Hitler wrote Mein Kampf, and he laid out his plan to build a thousand-year Reich and eradicate the Jews and wage war on Europe and restore Germany’s greatness after World War I.

No one paid attention. We had the Munich deal. Hitler rose and did exactly what he said. 25 million people perished, including six million in the camps. Then you can go to Osama bin Laden. Bin Laden issued a fatwa in 1996 in which he declared war on the West and declared his intention to attack us, and we didn’t pay attention, and the result was 9/11. In 2022, Vladimir Putin published a 4,000-word essay on a presidential website – it’s still there if you want to go read it. I read it, and he lays out his plans to restore the unity of Ukraine and Russia, that they’re the same people going back to the history of, I can’t remember, Oleg the Great or Vladislav the Magnificent, whatever these rulers were in the 900s. And no one took him seriously. He wouldn’t possibly invade Ukraine. And look what’s happened there.

And so now you’ve got that, and you look at it in that context. You look at the Iranians and they say death to America and they say death to Israel, and they’re enriching uranium to 60 percent, which no one needs for civilian nuclear use. And you look at that and you say, baby, they’re going to do what they say. And Donald Trump is the first Western leader in centuries to look at the words of the enemy, take them seriously, and do something about it. And that’s what he did – first with Midnight Hammer and Epic Fury. And it was courageous, because it’s very hard to take action based on the words of the enemy without them having acted. It’s easy to get into World War II after Hitler invaded Poland – and even then it took us some time. We usually wait until the enemy has acted on his words to justify the action.

What Donald Trump did was take action before the enemy acted on their words. He took their words seriously. They intend to build a nuclear weapon. They intend to destroy Israel and the United States, and he acted before they were able to do it and set them back. And for that, he will go down in history as one of the most prescient foreign policy leaders, certainly in the history of our country and certainly in the history of the West. The question is, does he finish the job? And that’s what we’re all hoping that he does.

DUBOWITZ: Right, right. And obviously the criticism of the JCPOA is not just that it flooded this theocratic jihadist regime with billions of dollars of cash, which they’ve used to obviously spread chaos and bloodshed through the region, including October 7th, but also that those restrictions were going to expire and Iran was going to take patient pathways to nuclear weapons. As you’ve said, quite rightly, they built up this massive missile arsenal that they could use as a shield to deter America and Israel from using military force to strike at the very nuclear weapons capabilities they were building. So I would also say, Marc, it was really interesting – I was very involved in that 2015 debate over the JCPOA, out there publicly testifying and taking on the likes of Jake Sullivan and others who negotiated and defended it. And I would say they never actually ever made the case in 2015 that they had any intention of extending the deal.

They said it was a great deal and it had permanently closed Iran’s pathways to nuclear weapons. So I never heard that argument in 2015. I did hear that argument in the Biden administration, when they came in and acknowledged that the deal was less than perfect, and at the time they were going to negotiate a longer, stronger, and broader agreement, as they quite eloquently put it, but then proceeded, as you say, to stop enforcing sanctions and looking for every way – this was Rob Malley’s obsession – providing massive sanctions relief to the Iranians. And I’ll just end with this point: most of Iran’s nuclear expansion occurred not when President Trump withdrew from the agreement, but actually occurred when Joe Biden was elected. In fact, very little expansion occurred under Trump’s watch in the first term, and a massive amount – including Iran going to 20 percent, 60 percent, and 84 percent uranium metal, and advanced centrifuges, and all the rest – occurred because the Islamic Republic didn’t fear that Joe Biden would use military force, and that’s why most of that expansion occurred on his watch.

Okay. So we get to the first Trump administration’s maximum pressure. We vault over that when Biden relieves that pressure. We get to the second Trump administration. And as you say, Trump understands that if he doesn’t deal with Iran’s expanding nuclear weapons program and missile arsenal, no one will, and certainly not his successor. All right, he launches Midnight Hammer. I think many people acknowledge that as a success. I think the criticism of Epic Fury, from reasonable people – meaning not like hyper-partisans, but reasonable people – is that it did significant damage to Iran’s missile and defense capabilities, but was it worth the cost given what’s happened on Hormuz? So let’s address the Hormuz issue and, Marc, give us your assessment of where we’re at and where you expect the president to go.

THIESSEN: So here’s the thing – and this is sort of my frustration on this – Iran cannot keep the Strait of Hormuz closed if we choose to open it. They’re simply incapable of doing it. Admiral Cooper has a plan to open the Strait of Hormuz and to do it safely. He was starting to execute it. And the only reason we stopped that mission is because our Arab allies objected and pushed us into stopping it. And that’s problematic because we have given them a weapon they didn’t have before, which is control of the Strait of Hormuz. And they need to be disarmed of that weapon, because if they think they can take the global economy hostage anytime they choose, then they don’t need a nuclear weapon as a deterrent. They want it for offensive purposes, but they don’t need it because they can just take the economy hostage.

So the way I would want to see this go: we need 10 to 14 days of military operations to finish off the target list. And in fact, if we launched them now, we would be even more effective than we would have been before the ceasefire, because the Iranians dug up a lot of their ballistic missiles so that they could use them. And so we now have new targets. They are deeply exposed. We could take out much of the remaining ballistic missile capability and their offensive capability, which would in turn leave them even less capable of threatening traffic in the Strait of Hormuz. So Trump should do that – 10 to 14 days – and then open the strait and implement Admiral Cooper’s plan to open the strait. You tell the Iranians that if they threaten Gulf oil infrastructure, we will destroy Kharg Island, without which their economy no longer exists, because it’s so central. I think 96 percent of their oil goes through that infrastructure. We’ve hit Kharg Island, but we haven’t hit the oil infrastructure. And if they test that, you just take out one oil facility on Kharg Island and say, we can destroy the rest, and that provides a deterrent. And then you open up the strait and hand that mission over to an international force that can take it over, so we’re not doing that indefinitely.

You declare victory in the sense that you’ve eliminated their military capability. You draw a circle of death around their nuclear sites and say that any Iranian who enters that circle of death will die, and you demonstrate your ability to do that. And then you tell the Iranians that if you fire on a single protester, we’ll take out the base of the besieging force that did that. And then we do what we did during the Cold War: we arm the Iranians to overthrow their regime, because ultimately none of this is permanent if the regime survives.

And Trump famously said last year, ‘What’s wrong with regime change?’ And I agree with that. There’s nothing wrong with regime change. We know that the United States has tried two methods of regime change in the last half century. One was the Iraq model, where we sent 350,000 troops to occupy a capital, take out the regime, and install a new government. And we don’t want to do that again. But there’s another model, which is the Cold War model: we armed the Contras, we armed the UNITA rebels in Angola, we armed the Mujahideen, we provided support to Solidarity – non-military, but very important support to Solidarity – and for the forces in Prague and the Velvet Revolution. And we supported freedom movements around the world, and those people liberated their own countries without a single American troop. We liberated 400 million people in the fall of communism without any American boots on the ground.

And so we have this muscle memory. The CIA has this muscle memory. There’s a wonderful book that recently came out called ‘The CIA Book Club,’ which just documents a whole history of us breaking the information blockade in Poland by sending information into Poland – printing presses and all the rest of it. We know how to do this. We did it in Iran in the 1950s. The CIA helped the Iranian people overthrow Mossadegh. So we’ve literally helped the Iranian people once overthrow a government. There’s no reason we can’t do it again. We’ve got the muscle memory. There are people still alive who were participants in that process and who could give a new generation tips on how to do it and help the Iranian people overthrow their government. We don’t worry about the French nuclear program. We don’t worry about the British nuclear program, because they have governments that would never point those missiles at us. We don’t have to worry about Iran – a free Iran will hand over its nuclear program tomorrow if they come into power.

So the only way that what Donald Trump achieves is not permanent – and he’s raised this concern, which I think is correct – he says the reason he acted is because he doesn’t think there’s another American president in the future who would do it, and he doesn’t want to hand this problem over to a successor, even a good successor, because it’s a mess. He wants to take care of the problem himself. So that’s the way you take care of the problem.

A deal with Hitler isn’t worth the paper it’s written on, and a deal with Khamenei or any of these Iranian thugs also isn’t worth the paper it’s written on. We have to end up changing the regime, and they’re down. They’re in bad shape. I mean, people seem to think just because they survived this so far that they’re strong, that they’ve emerged stronger. No, they haven’t. They’ve lost the top two or three layers of leadership. They’re down to their minor leaguers who are running the country right now, and they’re weakened – economically weakened. The blockade, as Miad Maleki from your fantastic organization has been documenting, is absolutely devastating them. They are weak. Don’t let them up off the mat. One lesson we’ve learned in dealing with terrorists and Islamic radicals is you never take your boot off their necks, and you certainly don’t give them your hand and help flip them up.

So we should keep our boot on their necks and help the Iranian people replace them with a government that doesn’t wake up every morning thinking first thing – it doesn’t have to be a perfect democracy, but it has to be a government that wakes up in the morning and doesn’t think, with its morning coffee, ‘death to America.’

DUBOWITZ: Marc, I of course agree with all of that, except I would say we’ve had the great Iran historian Ray Takeyh on the show, who talked about the myth of Mossadegh and the myth of ’53. Ray’s argument is we didn’t play that important a role in the overthrow of Mossadegh, but your point is well taken, which is we have –

THIESSEN: – the ability to do it. We can do a better job this time.

DUBOWITZ: And this time we can actually – right. We can bring down Mojtaba Khamenei and the IRGC. But I 100 percent agree with you. But here’s what critics say, and that is that President Trump wants a deal. He’s a deal maker. He thinks he can get a deal. In fact, this whole ceasefire has been opening up space to negotiate with Iranians. Phase one is kind of a Hormuz-for-Hormuz deal: we lift the blockade on Iranian ports and they stop interfering with international shipping. And President Trump gets the win there because ships now can transfer oil through the straits and stabilize oil markets and get the price of Brent and WTI down and the price of gasoline down heading into the midterms. And President Trump is really concerned – as are Republicans – about Democrats winning the House and Senate. And then he’s going to move to a phase two, negotiating with the Iranians over the dismantlement of their nuclear weapons program.

So President Trump wants a deal and seems to be doing everything to advance a deal. And you’re saying there’s no deal to be had with this regime – they’re not likely to meet President Trump’s minimum concessions on the nuclear side. And even if we do a Hormuz deal with them, they will retain the ability to blackmail us, and then we’ll move from nuclear extortion to Hormuz extortion, and at any time the Iranians decide it’s in their interest, they will go back and threaten those oil tankers. So why is President Trump spending so much time and energy and diplomatic capital while our military is sitting there waiting, and weeks are going by and the Iranians are reconstituting? Why is he doing all of that and trying to get a deal?

THIESSEN: Because he’s a deal junkie. He loves deals. That’s what he does. He cuts deals. He uses military pressure to get people to negotiate. That’s his approach to the world. Look, I think a couple of things. One, I think that criticism is legitimate. I have similar concerns. I think that to some extent he’ll end up in the same place. I would have never done the ceasefire to begin with. I would have finished the military operation. He wanted to give diplomacy a try, and that’s fine. I think that in a sense, sometimes our enemies are our best allies, because he’s not going to accept a bad deal, I don’t think. I don’t think that he’s going to accept a deal short of his red lines in terms of the nuclear program. He wants the dust. He wants that to be irreversibly denuclearized. And so I don’t think the Iranians are going to go where he wants to go, and therefore he’ll end up back where I would say he should have been – with military action.

And what the Iranians are using are two levers. They’re using the lever of their control of the strait, and they’re using the lever of the midterm elections. And to some extent, the president has boxed himself into a corner, because if he had done a two-week ceasefire instead of – I guess we’re in week nine, week ten of the ceasefire now – if he had done a two-week ceasefire, maybe three, given them a chance, saw that they weren’t acting, then hit them again and said, ‘Okay, now do you want to negotiate?’ That might have made more sense. But because he stretched it out so long, we’re now close to the midterms. And the concern is – and I think it’s a legitimate concern – that if Iran were to hit the Gulf oil infrastructure, I don’t know why he doesn’t have confidence in our military to protect the Gulf oil infrastructure, because we were able to help Israel protect itself. So I don’t know why we can’t protect Saudi Arabia and Qatar and the UAE’s infrastructure.

But let’s say they were to hit some of that and they take 40 percent of the world’s oil off the market. We could have $8 gas going into the midterm elections, which probably wouldn’t be good for the Republican Party. And add to that, if they get hit hard in their oil infrastructure, then the capital going into global markets from the Gulf would dry up, and that could cause a global recession or a global depression. And so these are concerns that are deterring us from resuming combat operations. Okay, fine. Trump has the advantage of strategic patience. He’s not in a hurry. So that lever runs out the first week of November. And then what happens? I think it’s entirely possible that Trump will drag this out and resume combat operations after the midterms. That is a possibility if he doesn’t get the deal he wants.

But then you’ve hit on something which I think is a broader flaw in the Trump doctrine. So big picture here for a sec. Donald Trump came into office facing a very similar situation to Ronald Reagan when he came into office in 1980, which is that we faced a world full of threats, but Americans had soured on sending American troops around the world to fight them. After Vietnam, nobody wanted to put boots on the ground to push back on communist expansionism. So Reagan had to come up with a new doctrine for how to push back on communist expansion, Soviet expansionism, and especially since he set the goal of actually overthrowing the regime, pushing back, rolling back, and ending communism. And so he came up with the Reagan Doctrine, which was: we would arm and train freedom fighters around the world, we’d have the Strategic Defense Initiative, we would have a strategy to bankrupt the Soviet Union and expose all of its weaknesses, and we would accomplish our goals in a different way without American troops on the ground.

Trump inherited a similar situation after Afghanistan and Iraq, which is that there’s no appetite for sending American boots to the ground. So there are two options. You can retreat into isolationism, which I think unfortunately some on the right would love to do, or you can find a new way to flex American military muscle on the world stage – and that is to use a combination of diplomatic, economic, and military pressure on our adversaries to bend to our will. And so he did that with the Houthis. He did that with Midnight Hammer. He did that with Boko Haram in Nigeria. He did that in Venezuela by overthrowing the Maduro regime. He uses a combination of diplomacy. With Midnight Hammer, he gave the Iranians 60 days, and on day 61 he unleashed Israel to go ahead and carry out military operations. And then he came in with the coup de grâce with our B-2 bombers taking out their enriched uranium. And then he said, okay, now do you want to negotiate? And they said no. And so he did it again.

The problem – the weakness in the strategy – I think all of that’s great, because to some extent Trump is saving conservative internationalism in doing that. He’s decided: no, the response is not to retreat from the world; we have to flex military muscle and we have to find a new way to do it that doesn’t involve ground troops. I’m 100 percent for that. The weakness or the flaw in that is that all the gains are temporary if we don’t change the regimes.

So if you look at Venezuela, which is an unmitigated success – capturing Maduro, Delcy Rodriguez is now doing what Trump tells her to do, right? Well, is she going to do what Gavin Newsom tells her? Is she going to do what AOC tells her? If we have a new weak president like Biden, that success dissipates entirely the second we have a president they are not afraid of anymore. The only way you consolidate the success in Venezuela is if we push them into having free and fair elections and we have a new government there that will actually be an ally of the United States and want to do this not because they’re being forced to and they’re afraid of us, but because they actually want to build a relationship with us. And the same is true in Iran. All the successes he’s had with his military strikes are eventually reversible.

It depends on how long – it could be decades, it could be years – it depends on how decimated the Iranian military is. But unless we have a government there that wants to work with us and doesn’t wake up saying death to America and death to Israel, eventually it’s reversible. And so Trump’s doctrine is right in finding a new way to flex America’s power on the world stage without ground troops, but it’s missing a piece. It’s almost like you have to marry the Trump doctrine and the Reagan doctrine to have the success. And I think that final piece is what’s missing. The deal is not the end of the story. The change of the regime is the way to lock in all the gains. And sometimes part of being a great deal maker is recognizing when your adversary doesn’t want to make a deal and can’t be trusted to make a deal. And you have to just say, okay, we have to do it another way. And I think that’s not where Trump is yet. I think he thinks that he can make deals and have sustained success, and I’m skeptical of that.

DUBOWITZ: So Marc, it’s interesting. In the podcast you’ll see in the background the logo of the organization, FDD – Foundation for Defense of Democracies – obviously established in the wake of 9/11 to really defend the United States and our democracy, but also defend beleaguered democracies under attack: Israel, Ukraine, Taiwan probably being the most beleaguered democracies, but clearly democratic allies in the Indo-Pacific that are threatened by China, democratic allies in Europe threatened by Russia. I want to ask you, just sort of zooming out a bit, because you’ve been a longtime player and observer of conservative politics. What is going on inside the Trump administration and inside the Republican Party with respect to the issue of Ukraine? I worry that the Republicans are not willing to defend Ukraine against Russia. I worry that Democrats have abandoned Israel against Iran and against jihadism. And by the way, if I were in Taipei, I’d be deeply concerned that neither party has my back.

Do you think that Midnight Hammer and Epic Fury are a message to the Taiwanese, the Chinese, the Europeans, the Russians that America is back and we do have the backs of our allies, and a message to our adversaries that we are serious about using coercive power – at least during the Trump administration, if not post-2029? What’s your overall assessment of our strategic position with respect to being no better friend, no worse enemy out there in the world?

THIESSEN: So let’s go out even further and just take it away from Trump for a second and just look at the MAGA movement. If you look at the Reagan Institute polls – and I’ve done columns on this now for the last couple of years, every time the Reagan Institute poll comes out I dig into the crosstabs to find out what MAGA Republicans think versus Americans generally and establishment Republicans – what you find is that on every issue, from Russia and Ukraine to Venezuela, Iran, Israel, and Taiwan, MAGA Republicans are the most hawkish Americans out there. There’s an isolationist right, but it has no public support. It has leaders. It has a voice in Washington. It has people in Congress, but it doesn’t have any support in the grassroots of the country. And it’s not just a reflexive ‘let’s do whatever Donald Trump says because MAGA is what Trump says it is.’ And so therefore, if Trump says we bomb Venezuela, okay, we’re for that, but we wouldn’t have been otherwise. Because look at the numbers on Taiwan – and I don’t have them in front of me, but maybe we can link to my column in the show notes – the MAGA Republicans are overwhelmingly in favor of defending Taiwan, of deploying US forces to do it, of arming the Taiwanese, and of helping them. And Trump has actually been quite ambiguous about that. He seems to see Taiwan to some extent as an irritant in his ability to forge a relationship with China. So that’s not something where the MAGA base is just blindly following what Trump says. They’re leading on it, and they think we need to defend Taiwan.

So, the Republican Party is still a – I don’t think we’d call it internationalism anymore, or they would like that label, but they’re certainly hawkish Jacksonian. They think we need to have a strong military. We need to flex American military muscle on the world stage. That’s where the movement is. That’s where the grassroots is. Now, what about Trump? Trump is clearly not an isolationist. I mean, just look at the last 16, 17 months: bomb the Houthis, bombed Iran, bombed Nigeria, bombed Venezuela, blockade of Venezuela, then bombing Iran again. These are not the actions of an isolationist. This is not the actions of a leader of a party that wants to retreat behind fortress America. Now look at Ukraine.

I mean, Trump has been a better friend of Ukraine than either Obama or Biden were. When Russia invaded in 2014, the Ukrainians begged us for offensive weapons, and all we gave them were MREs and blankets under the Obama administration. It didn’t help at all. It was Trump who came in and gave them Javelins, which they ended up using to defend themselves when Russia invaded in the full-scale invasion in 2022. What did Biden do? Biden slow-rolled weapons for three years. I could go through every category of weapon – when the Ukrainians requested it and when it finally arrived. He wouldn’t allow them to use US weapons to fire into Russia. When he finally gave them HIMARS, he wouldn’t give them the longer-range missiles to use them that could reach Russian territory, because that would be destabilizing – but he said lots of nice things. He said, ‘We’ll be with you forever. We’ll be with you as long as it takes,’ and all the rest of it. But he didn’t have a strategy for victory; he just had a strategy for Russia not having a victory.

Trump comes in and what has Trump done? Well, he smartly changed our weapons provision from aid to sales, which is what we’re doing with Israel right now, actually – Bibi now, who just approved that. I think generally speaking, if you want to have a long-term defense relationship with a country, it’s got to be on the basis of military sales, not military aid. So, he’s selling the weapons, the Europeans are paying for them, but we’re giving more and better weapons than Biden ever did. We’re giving them targeting intelligence to fire inside Russia, which Biden refused to do. Trump imposed oil and gas sanctions on Russia, which Biden refused to do. He seized Russian shadow fleet tankers in the North Atlantic, which Biden refused to do. He’s also trying to end the war, because he sees it as a stalemate and he doesn’t want people to continue dying. And so you can disagree with some of the negotiating tactics – I don’t think the Ukrainians under any circumstances should give up Donbas and the fortress belt in Donbas, which they were being pressured to do – but he’s trying to end the war while arming the Ukrainians, and he’s committed to the sovereignty and independence of a free Ukraine.

His first act as president was to forge a minerals deal with them. You don’t forge a minerals deal with a country that you don’t think will exist in a few months. That was a literal investment – not figurative, literally investing the United States in the sovereignty and independence of a free Ukraine. So, I think he wants Ukraine to survive, but he wants the war to end, and I think that’s the right approach. But he’s done more. I would categorically say that Donald Trump has done more to help Ukraine survive than Biden did during his entire presidency.

DUBOWITZ: Yeah. And certainly, I think very few people would say that President Trump hasn’t done a huge amount to support Israel – and supporters of Israel would acknowledge that, and critics of Israel would acknowledge that and say that that was a mistake. But let me get to Israel. It’s Monday, June 8th when we’re recording this podcast. We just saw over the weekend an exchange where the Iranians fired ballistic missiles at Israel. Israel struck back and destroyed more Iranian air defenses and took out key petrochemical facilities that were being used by the IRGC to help rebuild the missile program, because certain components from those petrochemical factories are used for their missiles. And yet there were some tense moments, Marc. I recalled President Trump at some point said, ‘Well, they’ve had their fun,’ meaning the exchange between Iran and Hezbollah and Israel, and now let’s stop. It reminded me of when Biden said, ‘Take the win,’ back in April of 2024 when Iran had attacked Israel with ballistic missiles – the Israelis had taken out air defenses and then Biden called them to stand down.

Critics of the administration – at least those on the pro-Israel side or the Iran-hawk side – say that President Trump is making a mistake in allowing the Iranians to link together these two theaters, the Iran theater and the Lebanon theater. And in doing so, giving Iran a veto right over Israel’s ability to hit back against Hezbollah, which, as you know, has been launching thousands of missiles and drones and rockets at Israel for years, including recently these fiber-optic drones that have inflicted significant casualties on Israeli soldiers and civilians. Are you worried that President Trump, in his zeal for a deal, is restraining our Israeli ally?

THIESSEN: Yes, to be quick about it. From the start of the ceasefire, the Iranians have been trying to link a Lebanon ceasefire to the ceasefire between us from Operation Epic Fury, and we’ve resisted that, but they’ve slowly been able to sort of indirectly link them. Now, Trump apparently gave a green light to Israel to carry out the retaliatory strikes, and Israel did. And how could Bibi Netanyahu not? I mean, he’s about to face an election. If you let Iran strike your country – even if they don’t succeed in getting the missiles through – without retaliation, you’re not going to be the leader of the country much longer. If the cartels were firing missiles into Texas, I don’t think there’s any circumstance under which we wouldn’t retaliate against them. So that’s what Israel’s facing, both from Iran and from Hezbollah. And so I think it ought to be a wake-up call to the president and to his team that if Iran really wanted a deal like they say they did, they probably wouldn’t be striking Israel and they probably wouldn’t be helping Hezbollah strike Israel.

So this is not the behavior of a regime that wants peace or that feels it doesn’t have any leverage. And so this is why I’m fairly confident that this deal’s not going to happen, at least not in a form that would be acceptable. But again, the president is an incredibly patient negotiator, and so he doesn’t want anything to disrupt the negotiations, and that’ll hold for a period. But in the end, the Iranians will do the work of the critics for them, because they’re going to overstep in a way. Now what I do worry about is when the president says – when they fire at our Arab allies or they fire at US bases and US ships – ‘Well, they haven’t killed any Americans yet. If they killed Americans, that would be different.’ That sort of reminds me a little bit of Biden saying, ‘Well, minor incursion.’

Our troops should not be target practice for the IRGC, and we shouldn’t have to wait until they’ve actually killed somebody. If they fire at us, we should bomb the hell out of them and take out whatever capability they have to do that. And so I hesitate to say that Trump is projecting weakness, because he’s not. What he’s done with Epic Fury and with Midnight Hammer and the blockade and all the rest of it – but he’s showing patience that would normally get you sainthood, and you don’t get sainthood for having patience with terrorists.

DUBOWITZ: So I’ve long said that the only place Iranians beat Americans is at the negotiating table. And if you look back on Iranian-US negotiating history, it’s much in evidence, most obviously and most profoundly during the Obama administration and the Biden administration. But I worry that as you look at these negotiations today, the Iranians have successfully negotiated missiles off the table, their support for terrorism off the table. I worry that they’re now negotiating the Lebanon/Hezbollah/Israel issue off the table. And they’ve gone from what was supposed to be a much broader deal dealing with all of Iran’s malign activities to a strictly nuclear deal. And then I worry that that nuclear deal could very quickly diminish from the full dismantlement of Iran’s nuclear program – zero enrichment permanently, zero plutonium reprocessing permanently, and the shutdown of all of Iran’s nuclear facilities, including the deeply buried Pickaxe Mountain, which will very soon be an Iranian nuclear and centrifuge facility.

Are you worried about the trajectory of negotiations and seeing these issues being successfully negotiated away by the regime?

THIESSEN: I agree with everything you just said. I’m very worried about it as well. I think that Trump is uniquely focused on the nuclear program. My idea of what an acceptable deal is: no ballistic missiles, no support for terrorist proxies, no nuclear weapons, and no firing on Iranians ever again. Those are the four elements of a deal. I think that three of those are either off the table or in a weakened state, and the only one left is the nuclear. And I think though that Trump is fairly determined that if he gets a deal, he doesn’t want to be painted as having gotten a weak deal. And so I don’t think he’ll agree to anything that can be credibly presented as a weak deal on the nuclear issue. But again, for me, my concern is less that he’s going to weaken on the nuclear issue than what he would give in exchange – the financial incentives to the Iranian regime – because yeah, they might let us take the centrifuges out and all the rest of it, but if they’ve got money, they can find a new way to do it and they’ll be back at it as soon as there’s another president who won’t do anything about it. So I don’t want to give this regime a lease on life even for a good nuclear deal. That’s my bigger concern.

DUBOWITZ: Yeah. So maybe as a final question, Marc, let me ask you this. You’ve mentioned Ronald Reagan, you’ve mentioned the Cold War, you mentioned Reagan’s strategy. I mean, I think we’ve been reading you for many years and listening to you and taking your advice and insights, and we’ve really turned it into what we kind of look at as a three-pillar Iran strategy doctrine, which is maximum pressure on the regime, maximum support for Iranian opposition, and maximum fracturing of the support base of the regime. Reagan was very successful in all three, right? Massive pressure on the Soviet Union, massive support for anti-Soviet dissidents behind the Iron Curtain, as you mentioned, and the ability to actually fracture the Soviet elite to the point where they ended up getting a Gorbachev who negotiated the end of his own empire. You’re persuaded – I think I am too – that President Trump understands the importance of pressure.

Are you persuaded that he understands the other two pillars of the Reagan doctrine, which is providing maximum support for anti-Iranian dissidents and really understanding this regime – and that he’s not going to get a Delcy Rodriguez in Iran? There is no Delcy Rodriguez in Iran. They are all, as you said, hardline jihadist theocrats who would rather die than surrender. Are you worried that those other two key pillars of the Reagan doctrine are not something that President Trump believes in? And if you’re not worried, please give us some sort of evidence of the positive signs you’re seeing that President Trump gets that.

THIESSEN: Yeah. So I think he knows that there’s no Delcy Rodriguez in Iran, that he’s going to have to coerce somebody. Nobody’s going to be willingly going along. There’s no Gorbachev in Iran. I think Ronald Reagan wouldn’t have been able to persuade any of the Iranian leaders to sort of play that role in the demise of their system, because I think in the end there were people in the Soviet Union who were fanatical communists, but they weren’t religious fanatics who thought that the end of the world was the goal. Ultimately, the Soviets wanted to survive. I don’t know that the Iranian regime cares about survival. They care about the survival of the regime, but they don’t care about the survival of the world. So it’s a different animal. I share your concern.

I mean, even in Venezuela, where there is a Delcy Rodriguez, there’s only a Delcy Rodriguez as long as Donald Trump is president. Again, I don’t think that Delcy Rodriguez stays the second Trump leaves the Oval Office, if he’s not replaced by somebody who is just as tough and just as determined as him. They go back to doing what they were doing before under Maduro and Chavez. They are narco-capitalists. They are completely flexible in doing what they need to do to survive, but they’ll just revert back to form. None of the progress Donald Trump has made anywhere in the world works if the Venezuelan regime or the Iranian regime survives his presidency. I have told him, and I’ve said publicly, that my goal for the end of the Trump presidency is for Donald Trump to visit a free Caracas, a free Havana, and a free Tehran. And if he can do those things, that would be a huge, huge success and would lock in everything that he’s achieved. If he can’t set foot in those three countries, then he hasn’t fully met the moment. He’s made the world safer, but he hasn’t made the world safe.

DUBOWITZ: Yeah. I mean, it’s exactly right. I think you mentioned our unwillingness to put boots on the ground given the Iraq-Afghanistan experience, which certainly makes sense, but there are millions of Iranian boots on the ground. 85 percent of that population despises the regime. They’ve been out protesting since 1999, 2009, 2017, ’18, ’19, 2022, 2023, 2025. So I mean, what we’ve seen is –

THIESSEN: – and now we’re seeing student protests happening. As soon as the internet came back on and they were able to communicate, all of a sudden they’re back out in the streets right now. I mean, look, Ronald Reagan’s great insight was that we don’t have to put boots on the ground everywhere to fight for freedom, because there are people who want to fight for their own freedom and they just need our help – they need weapons, they need intelligence, they need diplomatic support, and they need training. And those are things that we can do at very little cost. And we’ve liberated 400 million people doing that. We can liberate the Iranian people, we can liberate the Venezuelan people, and that’s the way you eliminate threats in the long run: when the radical followers of radical ideologies no longer are in power and able to carry them out.

I’m very hopeful. We’ve got two and a half more years of the Trump presidency. Ultimately, I think Trump will see, as his presidency comes to a close – first of all, I think he’s going to be the first lame-duck president who’s not a lame duck, because Donald Trump is not going to stop flexing American military might on the world stage just because he’s in his final term. He’s going to be planning to lock in his achievements. And I think over time he will see that the way to lock in the achievements in Venezuela and Iran is to have governments in those countries that want to work with us, not because they’re afraid of Donald Trump, but because they love America.

DUBOWITZ: So final closing question, Marc: you talk to the president, and so if you had five minutes alone with President Trump before he makes his next major Iran decision, what would you tell him?

THIESSEN: Finish them. Doesn’t even take five minutes. Finish them. We stopped Operation Epic Fury with 10 to 14 days to go. In 10 to 14 days, take out all the targets on your list and military operations are done. Open the strait – four moves – hand it over to an international force to handle it. And then arm and train the Iranians and help them overthrow their regime.

DUBOWITZ: Great advice. President’s listening. Marc, thank you so much. Grateful to have you on the show, and I look forward to having you back as we hopefully get back to – or get to – a Reagan moment where we can visit a free Tehran with President Trump.

THIESSEN: It will be a Trump moment. He successfully adapted the Monroe Doctrine and turned it into the Donroe Doctrine. I want him to do the same with the Reagan doctrine and make it his own. And thank you for all you guys are doing at FDD. I follow everything you do, as do all freedom-loving Americans, and I’m very honored to be on the pod with you.

DUBOWITZ: Great. Thanks, Marc.

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