Two weeks ago, President Donald Trump launched a war of choice to topple Iran's regime expecting a quick, clean win. What he's gotten is a regime that's proving far more capable of enduring and fighting back than he anticipated. Seven American troops are dead, 140 wounded. The Strait of Hormuz has been shut for almost ten days, creating the largest oil supply shock in history. Iranian missiles and drones keep striking targets across the Gulf and Israel. And in a show of defiance, Tehran replaced the assassinated Supreme Leader with his hardline son.
Trump wants out. But contrary to his claim that he can end the war any time he wants, he has no easy exit.
This is shaping up to be the biggest foreign policy blunder of either of Trump's presidencies. Compare it to Venezuela, which went almost exactly according to plan – militarily, diplomatically, economically, and strategically. Iran has been the opposite on every front, with far greater consequences. And the reason comes down to a fundamental misreading of where Iran sits on the FAFO-TACO spectrum.
Trump believed Iran was nearly as FAFO as Nicolas Maduro’s Venezuela: extremely weak and incapable of resisting the United States. And for good reason. The last few times Washington hit them – Qasem Soleimani's assassination, the Twelve-Day War with Israel – Tehran barely punched back. Then came his Venezuela win: swift, surgical, and with minimal blowback. With Iran looking weaker than ever – economy in shambles, proxies degraded, mass protests brutally crushed in January – Trump saw what he thought was a historic opportunity with no real downside.
But as I’ve gotten tired of writing, Iran isn’t Venezuela. And those earlier strikes the US got away with weren't existential threats to the Islamic Republic; they were met with limited reactions because they were limited strikes. This time, the US and Israel (initially) framed the operation as a maximalist regime change campaign – “I will rescue the Iranian people, go and take your government” – whose opening move was the assassination of Ayatollah Ali Khamenei and most of Iran's top brass, with the expectation that the rest would fold.
As it turns out, when the stakes are existential, Tehran is considerably more TACO than Trump expected.
That’s not to downplay the damage inflicted on Iran thus far. The US and Israel have killed Iran's leadership and destroyed huge chunks of their military capabilities. The Iranian Navy is sunk. Missile sites are rubble. The Axis of Resistance is a shell. By conventional military standards, the US has mostly won. But that's not how the White House framed the goals at the start, and it's certainly not how Iran measures defeat. The regime knew from the beginning they can't match the US and Israel militarily. Their bar for success is lower: survive, and make Trump hurt more than he's willing to tolerate. So far: mission accomplished.
Like China leveraged critical minerals during last year’s tariff wars, Iran has its own chokepoint it is deftly (and predictably) weaponizing: the Strait of Hormuz. They still have tens of thousands of drones and can make more quickly. Most will get intercepted, but it only takes the occasional hit on a tanker, pipeline, or refinery – really, just the threat of it – to keep Hormuz effectively closed and oil and gas prices elevated. Iran’s also laying mines in the Strait, and while the US said it destroyed 16 Iranian mine-laying vessels, thousands of small craft remain. Even with the military escorts and insurance guarantees from the Americans, the French, and other Europeans, shippers still won't send their vessels through until the threat is gone. Sure, most ships would get through, but some won't. You can insure ships and cargo, but no one’s prepared to risk human lives. The Strait, which had never been closed before this, stays blocked until Iran decides otherwise.
That asymmetry is the whole ballgame. Militarily, this fight is wildly lopsided in America's favor. Strategically, it tilts toward Tehran. Yes, the US and Israel keep destroying Iranian capabilities every day, but with diminishing returns. The longer it goes, the more the balance shifts as Iran imposes mounting costs on the world economy and Trump's political standing.
Which is why Trump is now scrambling for an offramp. Over the past 48 hours, he's gone as far as to push Israel to wrap up operations in Lebanon, which surprised the Israelis. Whether they’ll listen is unclear, but the signal is obvious: he wants to declare victory and move on. Narrowing the war aims to what’s already been achieved, as Secretary of State Marco Rubio did earlier this week, makes that easier: destroying Iran's Navy and degrading the missile threat, check and check. But the outcome would be a hollow victory at best, possibly an outright strategic failure.
First, you’re leaving in place the regime you set out to remove, whose new leader you called “unacceptable” just days ago, whose previous leader you assassinated along with its military command – but which remains very much intact and just as stubborn on nuclear enrichment and ballistic missiles. Venezuela, this is clearly not.
Second, that regime now has every incentive not only to reconstitute its military capabilities (including the ballistic program) but to eventually dash for a nuclear weapon, the one thing that would have prevented Khamenei’s assassination in the first place. There's no threat to Kim Jong-un for a reason. The Israelis and Gulf states know this, which is why they're pushing Washington not to stop until the job is finished. But destroying Iran's 440kg stockpile of enriched uranium would require a risky commando raid on the hardened facility at Isfahan. Trump has been reluctant. The fact that the nuclear program hasn't come up in recent days suggests it may be off the table.
Third, while Iran’s ballistic missile stocks are down significantly – they've shifted increasingly to launching drones over the past week – they don't need many to cause massive disruption. And the country’s homegrown drone capabilities, which pose a persistent threat to the Gulf and the Strait, can't be eliminated without a near-permanent bombing campaign and/or boots on the ground, if at all.
Yet as bad as this narrow-aims exit may be, Trump seems eager to take it. But can he?
The Israelis get a vote, and they don’t look ready to stop yet. They have more tolerance for escalation and chaos than Trump does. They're the ones who did the decapitation strikes. They hit the oil facilities outside Tehran over the weekend, which angered the White House so much that the administration asked Israel not to strike Iranian energy infrastructure again. With Hezbollah reeling and the Lebanese government calling for arrests, they think they're making real progress in Lebanon. So getting them to stand down now isn't trivial. The Americans have leverage, like we saw with the Gaza phase one deal. But Trump doesn't have veto power over Israeli operations, or at least he hasn't used it.
More importantly, the Iranians get a vote too. And while they’re getting pummeled militarily, they're unlikely to agree to a ceasefire until they’re satisfied they have imposed enough costs on their adversaries to make them think twice about attacking them next time. Even if Trump declared the war over unilaterally without demanding any concessions, Iran’s leaders would want to have the “final word” – maybe symbolic salvos at Israel or Gulf states to end on their terms, claim victory, and create some deterrence. Which means Trump has to make the first move to de-escalate and not retaliate to Iran's parting shots. Not exactly his style.
Markets seem to think this is essentially over, pricing Brent in the upper $80s to low $90s – far below what a 13-15 million-barrel-per-day supply disruption would justify. They’re betting on normal traffic resuming soon with no lasting damage, on Saudi and UAE pipelines to the Red Sea picking up slack, on convoys and insurance coming online quickly, on meaningful relief from SPR and IEA emergency releases. Trump is doing his best to feed that narrative, saying Tuesday that the war will end “very soon.” Never mind that he contradicted himself in the same speech, or that Secretary of Defense Pete Hegseth said Tuesday's bombings would be the “most intense” yet. Or that Iranian drones hit an Abu Dhabi refinery hours later and three ships on Wednesday. Or that Gulf producers keep cutting output. Or that it could take months for production and prices to normalize even after the shooting stops and tanker traffic resumes. Even the largest coordinated SPR releases in history can't fill a physical supply gap this size. And none of this matters as long as Iran keeps Hormuz blocked – which it will, until Tehran is ready to reopen it. I don’t know if markets are wishcasting, complacent, or just pricing in the end state, but by acting as if this is already over, they may be reducing pressure on Trump to end it.
When this does end – however it ends – things are likely to be worse than if the war had never started. Iran's Navy is destroyed, its missile program degraded, its leadership dead. But the same regime remains in power, now led by a much younger, less experienced, likely less competent, and even more hardline Khamenei who will be just as determined (if less able) to rebuild and resist. Not to mention, Iran still possesses its enriched uranium and nuclear know-how, and Mojtaba may well reconsider his father’s stance against weaponization as the only way to avoid suffering the same fate. The regime will likely emerge weakened but hardened, more isolated but intent on reconstituting. The Iranian people will certainly be worse off.
The lesson is straightforward: you can't apply the same playbook to different situations if you don’t understand why it worked the first time – and when it may not.
Trump had other options to exploit Iran’s weakness. He could have repeated the Twelve-Day War’s devastating but contained strikes: hit nuclear facilities, missile sites, and drone capabilities hard, maybe sent commandos to destroy the enriched uranium at Isfahan, then reopened negotiations from a position of overwhelming strength. Instead, he went for maximalist ends with insufficient means to achieve them, based on flawed assumptions about Iran’s reaction function. He thought he was dealing with an extremely FAFO country. Turns out he was wrong.
Now that he’s ready for a healthy helping of TACO, it’s Iran that decides when he gets it – and at what price. Paraphrasing Leo Tolstoy, Trump may be done with the war, but the war isn't done with him.
