Trump's Gut Is Running a War. Iran Isn't Blinking.

When asked when the war with Iran would end, the President of the United States said he'd know it "in his bones."

That answer — offered to Fox News Radio thirteen days into an active military campaign — might be the single most revealing thing Donald Trump has said since US and Israeli warplanes began bombing Iran on February 28. Not because it's wrong, exactly. But because it tells you everything about how this war was started, and why it isn't going the way anyone in Washington expected.

What Happened — and What Didn't

The opening strike was, by any military measure, dramatic. The first wave of airstrikes killed Ayatollah Ali Khamenei, Iran's Supreme Leader, along with his closest advisors. Trump and Netanyahu followed the bombs with a direct challenge to the Iranian people: rise up, topple the regime, finish the job.

A month later, the regime hasn't fallen. The protests haven't materialized. Iran is now on its third Supreme Leader, and the government is functioning. According to HRANA, a US-based human rights monitoring group, 1,464 Iranian civilians have been killed so far. The regime's response to any potential unrest was swift and unambiguous — in January, government forces killed thousands of protesters, and official broadcasts have since warned that anyone taking to the streets will be treated as an enemy of the state.

Instead of collapsing inward, Iran expanded outward. It struck Gulf Arab neighbors, targeted American military bases on their soil, and hit Israel. Then it played what may be its most consequential card: the Strait of Hormuz.

The Choke Point Nobody Planned For (Or Did They?)

The Strait of Hormuz is 33 kilometers wide at its narrowest point. Roughly 20% of the world's oil supply passes through it. Iran has effectively closed it using cheap drones launched from mountainous terrain hundreds of kilometers inland — assets that are nearly impossible to neutralize without a ground invasion of Iranian territory.

Global financial markets have lurched. Energy prices have spiked. And former NATO Deputy Supreme Commander General Sir Richard Shirreff made a point on the BBC that cuts to the heart of the matter: any war game simulating an attack on Iran would have concluded that the Islamic Revolutionary Guard Corps would close the Strait of Hormuz. It wasn't a surprise. It was a predictable consequence that appears not to have been planned for.

This is where the old strategic wisdom becomes uncomfortably relevant. The Prussian military theorist Helmuth von Moltke the Elder wrote in 1871 that "no plan survives first contact with the enemy." Mike Tyson put it more bluntly: "everyone has a plan until they get hit." But it was Dwight D. Eisenhower — the man who commanded D-Day, the largest amphibious operation in history — who offered the most useful formulation: "plans are worthless, but planning is everything."

Eisenhower's point wasn't that plans don't matter. It's that the process of planning — of understanding the problem deeply enough to adapt when the unexpected happens — is what separates effective military leadership from improvisation. Without that process, when the unexpected arrives, you're starting from zero.

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Trump's inner circle, by most accounts, is structured to execute the president's instincts, not to challenge them. That's a deliberate choice. But it's a choice with consequences when the enemy doesn't cooperate with the script.

The Venezuela Miscalculation

To understand how Washington got here, it helps to understand what came just before. In January, the US executed a swift, stunning operation: Nicolás Maduro, Venezuela's president, was seized along with his wife Cilia Flores. They're now in a New York prison awaiting trial. Maduro's deputy stepped in and, by all accounts, is taking direction from Washington. It was fast, clean, and effective.

The problem is that Iran is not Venezuela. The Islamic Republic was born in the 1979 revolution that overthrew the Shah, then hardened by eight years of brutal war with Iraq. It is built on institutions, not individuals — reinforced by religious ideology and a culture of martyrdom that treats the deaths of its own people, whether at the hands of the regime or foreign bombs, as an acceptable price of survival. Killing the Supreme Leader is disruptive. It is not, as events have shown, a death sentence for the system.

Assuming otherwise wasn't just optimistic. It was a fundamental misreading of what Iran is.

Netanyahu's 40-Year War vs. Trump's Open-Ended One

The contrast with Benjamin Netanyahu is instructive. On the first full day of the war, Netanyahu stood on the roof of Israel's military headquarters in Tel Aviv and recorded a video statement with unmistakable clarity: "This coalition of forces allows us to do what I have yearned to do for 40 years: smite the terror regime hip and thigh."

For Netanyahu, this war has a defined purpose rooted in decades of strategic thinking. Iran has been, in his view, Israel's existential threat — the architect of Hezbollah, the backer of Hamas, the patron of the network of proxies that has menaced Israel for a generation. His critics note, with some bitterness, that this fixation on Iran may have contributed to the intelligence failure that allowed the Hamas attacks of October 7, 2023 to succeed. But Netanyahu's war aims, whatever one thinks of them, are coherent.

Trump's are less clear. And that ambiguity matters, because the US and Israel — while aligned — are not fighting the same war for the same reasons. A regional power's calculus is different from a global superpower's. The US has bases across the Gulf, treaty obligations, trade relationships, and a global economy to consider. Israel has a neighborhood.

The Escalation Ladder Nobody Wants to Climb

On Friday, the Houthis in Yemen fired a barrage of missiles at Israel — their first attack since the Iran campaign began. If they resume targeting shipping in the Red Sea, Saudi Arabia's western oil export route to Asia gets cut. If they extend attacks further south through the Bab al-Mandab strait, the Suez Canal route connecting Asia to Europe closes too.

That would be two simultaneous choke points on global trade. The economic consequences would be severe and immediate — not just for the Middle East, but for Europe, Asia, and anyone who buys goods that travel by sea.

Trump now faces a choice that no amount of instinct makes easy. If a deal with Iran cannot be reached, the options are: declare some version of victory that convinces no one, or escalate further into a conflict with no clear endpoint. Neither is a good option. Both were foreseeable.