Dan’s subhead: These are not very bright people and things got out of hand. My take: when your grand strategy is based on hoping the other side lets you pretend you’ve won, things do indeed easily get out of hand when you confront an adversary who thinks its power depends of being seen as a winner even more than you do. The difference between a decapitation raid in Caracas that was, substantively, a huge victory for the Venezuelan régime and the current state of things in the Persian Gulf:

What was the Trump Administration’s thinking and how did it plan for its war on Iran to end anyway? There was no thinking. There was no plan. There still is no plan. There MAY—repeat: MAY—now be thinking. But probably not. Trump careens among:

• demanding Tehran’s “unconditional surrender”,

• hinting that he might abruptly declare victory—having “mowed the grass” and leave,

• expecting collapse of the Iranian regime,

• expecting the emergence of new leaders who will do a deal on his terms,

• expecting the emergence of new leaders who will concede to fundamental political and strategic demands,

• expecting Iran to pretend it has conceded to Trump’s fundamental political and strategic demands.

Chaos-monkey foreign policy:

CROSSPOST: DAN DREZNER: The Trump Administration’s Incredibly Slow Learning Curve

Dan Drezner

May 29, 2026

<https://danieldrezner.substack.com/p/the-trump-administrations-incredibly> <http://dandrezner.substack.com>

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There’s a scene from All the President’s Men that has become an oft-deployed meme during both terms of the Trump administration. It’s the one where Deep Throat explains an essential truth about the Nixon administration to Bob Woodward — one that maybe, just maybe, applies to the current administration as well.

It’s worth remembering this line when contemplating the administration’s myriad attempts to coerce, browbeat, bomb, and negotiate with Iran in recent months.

For the record, the hard-working staff here at Drezner’s World has been extremely skeptical of all of these efforts from the get go. Here’s a sampling of posts over the past three months:

• “How to Flunk Coercive Diplomacy 101,” February 24, 2026

• “There is No U.S. Plan on Iran,” March 3, 2026

• “‘Nobody Could Have Seen This Coming,’ Says Blindfolded Administration,” March 9, 2026

• “I’m Sick and Tired of All the Winning,” March 12, 2026

• “The Strategic Defeat of the United States,” April 4, 2026

A running theme in these columns? References to Trump officials being “frustrated” that their pressure tactics are not working on Iran. Which is a polite way of saying that the current administration does not understand their current bargaining situation

From the close of that last column:

The longer this war drags on, the greater the costs for the United States. Absent a full-scale ground invasion, Iran can hold out. But Trump can’t simply declare victory and tap out either. Which means he is stuck trying to sell a strategic defeat as a tactical victory. But inconvenient facts mean that not even Republicans are buying that pitch. Trump has lost this war. The only question now is how bigly he loses it…

Nearly two months later, it remains unclear how bigly he will lose it. Sure, U.S. officials occasionally float that a deal is imminent to boost their Polymarket windfall, but the existing cease-fire is incredibly balky and Iran can likely hold out longer than U.S. officials expect.

For example, as the New York Times’ Aaron Boxerman explained earlier this week, Trump’s attempts to pressure the Iranian regime have not worked out well:

Since President Trump announced a cease-fire with Iran in April, he has sought to force Tehran to accept his terms for a peace deal with a mixture of threats and limited military operations. But more than a month later, the contours of a deal emerging this week to end the war reflected how Mr. Trump’s pressure campaign does not appear to have decisively shifted Iran’s stance on its nuclear program.

The impending deal could reopen the Strait of Hormuz, the critical waterway for oil and gas, which Iran has blockaded since the U.S.-Israeli attacks on Iran began the war in late February. But it may delay big decisions on other thorny issues until later. The Strait of Hormuz was already supposed to be open at this point. Free passage had been Mr. Trump’s condition for pausing the war in April….

Iran experts say the country’s leadership has emerged emboldened from the war, believing that the country had weathered an attempt to topple the Islamic Republic. The leadership views time as on its side, analysts say, in part given their ability to rattle global energy prices…

Over the past week, however, more stories have come out demonstrating that the Trump administration is slowly, painfully, fitfully approaching the same conclusion that the hard-working staff here at Drezner’s World — not to mention other analysts — knew going into the conflict.

As the administration pushed towards some kind of negotiated arrangement with Iran this week, Hawks like Mike Pompeo and Lindsey Graham started chirping about the crappy terms of the deal. In response, Washington Examiner columnist Byron York — probably the most articulate Trump apologist out there — relayed comments from a senior administration official background briefing to explain why the Trump White House was reluctant to escalate in Iran.

It’s an extraordinary read:

“We have to ask ourselves at any time we take an action, what does it accomplish for the American people?” the official answered. “And I think where the president’s view is right now is that you would need a substantial escalation in order to meaningfully change things that are on the ground.” That appeared to be a frank assessment — the official emphasized the word “substantial” — of the amount of U.S. force that would be needed to “finish the job,” as some of the president’s critics define it. Which leads to the question: Would that be worth it?

“You could, of course, exert more pain, which is more pressure, which means more leverage,” the official said. “Maybe that allows you to have a better deal. But I hear some people saying we need to do this, or you can’t stop until the regime tips over. And my question on that is, well, what do you actually mean by that? Because the president of the United States has taken a lot of action.”…. So why doesn’t Trump just finish the job in Iran? The short version of this conversation was that it would take a substantial escalation of military force to change the current situation, and the president does not think it is worth it. The official did not detail just what a “substantial escalation” would involve, but the U.S. has already applied a lot of military force in Iran, so it would be a lot of force on top of force. It’s no surprise the president is reluctant to do it if there are other options available…

The Atlantic’s Jonathan Lemire and Nancy A. Youssef report something similar about Trump’s current thinking: “Despite his frequent threats, Trump is reluctant to resume hostilities; aides told us he is mindful of depleted U.S. munitions supplies and fears that Iran would retaliate against the energy infrastructure of its Gulf neighbors, worsening the world’s fuel crisis.”

Oh wow, so it only took three months for Trump and his policy principals to realize that all of the assumptions it had made going into the conflict were wrong.¹

Meanwhile, there is still no guarantee that the U.S. can even negotiate a cease-fire. Lemire and Youssef also report that, “Trump has grown deeply frustrated with his inability to get Iran to fully capitulate, aides told us, and angry at the commentators who have said the persistent stalemate has left him looking weak.”

For the record, the hard-working staff here at Drezner’s World does not think the stalemate leaves Trump looking weak. Rather, it actually leaves him weak.

And, as the New York Times’ Michael Crowley and Eric Schmitt report, Trump keeps screwing things up at the negotiation table:

Three months after President Trump launched war on Iran, his seemingly haphazard approach to the conflict is bewildering allies at home and abroad as he veers between diplomatic dealing, military strikes and increasingly far-fetched ideas.… At the Defense Department, military officials expressed bewilderment over the stop-start nature of the conflict. A senior defense official said that the more than 50,000 U.S. troops assigned to Iran who are scattered throughout the Middle East, Europe and the United States were “in limbo” as Mr. Trump swings from option to option.

For centuries, statesmen from Otto von Bismarck to Henry Kissinger have argued that diplomacy with adversaries is most effective when backed by force, real or threatened. “Negotiations are a euphemism for capitulation if the shadow of power is not cast across the bargaining table,” Secretary of State George P. Shultz said in a 1986 speech. But Mr. Trump’s pendulum swings on Iran have often seemed driven by mood and moment rather than any discernible strategy…

At the start of this year I told Politico that one of the obligations of being a foreign policy commentator is acknowledging that, “there comes a point where you just want to say this is a fucking stupid idea.”

On Iran, I know we reached that point even before the war began. And if you’ve read this far, it means that you likely know that we have reached that point. Unfortunately, it seems clear that it will take Trump a much longer time horizon before he internalizes that point.

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