When President Donald Trump launched his war of aggression on Iran earlier this year, he suggested it could end in as little as “two or three days.” The toppling of Iran’s government, he predicted, might take a little longer: within “four to five weeks.” 

As of Friday, the U.S. has been at war against Iran for six months. And there is no end in sight. The White House says it’s not even on speaking terms with Iran after an always-shaky ceasefire collapsed last month. 

The president figured that much like in his handling of domestic policy and politics, he could power through any obstacles.

Trump’s quagmire in Iran is one of the most shameful acts of his presidency. He has failed at what he haughtily presumed would be an easy victory — and left Iran strategically stronger and the world worse off than when he started. And what makes it doubly tragic is how much of this catastrophe was foreseeable. At the heart of his failure was a total incuriosity about the plausibility and the likely consequences of the “little excursion” he decided to embark upon.

Trump initially framed the war as a way to force regime change, using bombardment to disable Iran’s military capacity and encourage the Iranian people to rise up and overthrow their government. But as Robert Pape, a professor of political science at the University of Chicago, pointed out, that objective was doomed from the start. “President Trump was up against the weight of history,” Pape told me in March. “I’ve studied every air campaign since World War I, and in all that time, over 100 years, air power alone — without ground forces — has never toppled a regime.” Among other reasons, bombardments hurt the local population and turn them against the country carrying out the bombings, even when they oppose their own government.

Unsurprisingly, Trump did not achieve a historic first. Iran’s national security apparatus proved resilient; its population did not rebel against the government en masse. Some sectors of the Iranian public that initially favored the U.S. bombardment reportedly shifted against the war once they experienced its brutality and the absence of any intelligible plan from the U.S. And Iran’s government is now more hard line than it was before the war. 

Tehran’s geostrategic advantages — using its control of the Strait of Hormuz to suppress maritime traffic, elevate oil prices and damage the global economy — was commonly understood among experts who observed the region. Trump disregarded that concern, even when he was presented with it by his own officials. Instead, the president figured that much like in his handling of domestic policy and politics, he could power through any obstacles. He was wrong. Iran is now well positioned to increase its control over, and potentially profit off of, this crucial swath of global maritime traffic. And its new power over the waterway gives it an extremely strong negotiating position in any talks to end the war. 

Trump has leaned into foreign policy adventurism in his second term in part because, compared to the harder work of legislating, it’s easier for him to take big policy swings with fewer institutional obstacles.

Trump’s refusal to think through how Iran’s government and people might respond to the war is what got him into this mess. And now his inability to empathize with the American public is helping keep him mired in it — and pushing him toward political disaster.

In May, Trump confessed to a reporter that when negotiating with Iran, “I don’t think about Americans’ financial situation. I don’t think about anybody.” The public has felt that blithe indifference — and it helps explain why he’s hitting the lowest approval ratings of his presidency, driven in part by anger over cost-of-living concerns. Trump has also infuriated the part of his base that believed him when he pledged to start “no new wars,” causing a sector of the MAGA movement led by pundit Tucker Carlson to rebuke the GOP and even agitate for a third party. And Democrats are using the failed war in Iran as a cudgel against vulnerable Republicans as the midterms approach.

Trump has leaned into foreign policy adventurism in his second term in part because, compared to the harder work of legislating, it’s easier for him to take big policy swings with fewer institutional obstacles. For that exact reason, he also has a lot more freedom to harm the world, and create messes that he can’t climb out of.

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