JONAH GOLDBERG: Trump stuck between two realities that don’t serve Americans

The miscalculation that started it all was killing Iran’s Supreme Leader.

Published Jun 05, 2026  •  Last updated 25 minutes ago  •  4 minute read

U.S. President Donald Trump. Photo by Samuel Corum /Getty Images

Normally, I worry that events may overtake a column. But not so with the Iran war. I don’t worry about running afoul of a headline or Truth Social post from U.S. President Donald Trump because what is said about the situation is no longer very relevant to reality.

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On April 8, Nick Catoggio, my Dispatch colleague, dubbed an earlier stoppage with Iran “Schrodinger’s ceasefire.” This was a reference to the famous thought experiment by the physicist Erwin Schrodinger, who was trying to explain the weirdness of “superpositionality” in quantum physics. A cat in a box is both dead and alive at the same time until you open the box. Schrodinger meant to illustrate the absurdity of the idea that particles aren’t any one thing, but a “cloud of probabilities.”

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The Trump administration is stuck in a word cloud of probabilities of his own making. The war is over. The war is on. The war isn’t a war. We have a deal, but we don’t have a deal, but we’re about to have a deal. We destroyed Iran’s military. No, we left it intact. We want regime change. No, we don’t. We already accomplished it. We “obliterated” Iran’s nuclear program a year ago. We had to go to war in February to prevent nuclear war. The Strait of Hormuz is open, closed, or something in between. No deal without “unconditional surrender.” Let’s make a deal!

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This everything-all-at-once vibe can be disorienting, particularly since most Americans didn’t have a war with Iran on their bingo cards until the shooting had already started. Trump didn’t prepare the country or consult with Congress beforehand because he thought it would all be a smashing success in a matter of weeks.

The miscalculation that started it all was killing Iran’s Supreme Leader, Ayatollah Ali Khamenei, and much of Iran’s senior leadership, on the first day of the war. To “the great proud people of Iran, I say tonight that the hour of your freedom is at hand,” Trump announced on Feb. 28. “When we are finished, take over your government. It will be yours to take. This will probably be your only chance for generations.”

I support regime change in Iran and shed no tears for Khamenei or his goons. But when you start a war by killing the regime’s top leaders, it’s not unreasonable for the remaining ones to conclude that you really intend regime change. Khamenei was a murderous fanatic, but he was a fairly cautious one. He liked to threaten closing the Strait of Hormuz or attacking our regional allies, but he was reluctant to do it, fearing it would invite a regime change war. The mullahs and IRGC goons believed, not unreasonably, that if they lost their grip on power, they would be lynched by the Iranian people they have brutalized for decades.

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By starting with a regime change war, Trump removed any reason for the regime not to go for broke. When you have nothing to lose — particularly when you are a millenarian religious fanatic — a Persian Alamo strategy makes a lot of sense. So, Iran closed the Strait of Hormuz and attacked its neighbours. But it turns out this wasn’t the Alamo.

In the contest of wills, Trump blinked. The Iranian regime’s tolerance for punishment proved — so far — to be greater than Trump’s and that of our Gulf allies. Militarily, we could finish the job, but that would require ground troops and much greater economic turmoil. In a conflict Trump launched unilaterally without the prior support of Congress, NATO or the American people, Trump doesn’t have the political capital for that. But that’s only half the problem.

Trump wants the war over, but he doesn’t want to pay — militarily, economically, politically — what that would cost. So, he wants to make a deal that ends it. But there is no deal available that wouldn’t come at an equally undesirable cost. Any deal that looks like what President Barack Obama struck with the Iranians would be too embarrassing to bear. But the Iranians are convinced that they can get just such a deal and they’re willing to drag things out as long as it takes. The result: Trump’s in a box of his own making. He thinks he can talk his way out by simply asserting a reality that doesn’t exist. When the financial markets get nervous, he announces a breakthrough that is, at best, a possibility. When the Iranians agree to a deal that looks like one Obama might negotiate, Trump goes back to his threats. It can’t go on forever. But I’m sure it’ll last until long after this column is forgotten.

Jonah Goldberg is editor-in-chief of The Dispatch and host of The Remnant podcast 

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