President Donald Trump’s shifting rhetoric on Iran’s leaders reveals a fundamental misjudgment of his adversary, according to a new analysis. After calling Iran’s leaders “very rational people” and “nice to deal with” in mid-June, Trump reversed course Wednesday, labeling them “cuckoo,” “evil,” “sick,” “dirty players,” and “scum.” The dramatic shift came as a tenuous ceasefire between the US and Tehran appeared increasingly fragile following Iranian attacks on three ships in the Strait of Hormuz and US retaliatory strikes.
Trump’s changing tone suggests more than just negotiation tactics. The analysis points to a pattern where the president has repeatedly overestimated his leverage and underestimated Iran’s willingness to string him along. Since announcing an initial ceasefire on April 7, Trump has delayed a resolution for three months, bringing the situation perilously close to the 2026 midterm elections. The looming elections make it politically difficult for Trump to return to full-scale war, a conflict that has proven remarkably unpopular at home.
Key indicators of Trump’s misjudgment include his repeated threats of doom for Iran, which were consistently revealed as bluffs. Trump often claimed he was backing off because a deal was near, but that deal never materialized in any lasting form. He also asserted that Iran was “begging for a deal” as far back as March 31, yet Iran’s actions—including violations of ceasefire terms and provocations in the Strait of Hormuz—suggest otherwise.
The administration’s downplaying of Iranian provocations further highlights the misjudgment. In May, when Tehran fired on US ships, the Pentagon argued it didn’t clear the “threshold” for a ceasefire violation. Even after a more substantial ceasefire was agreed to last month with a memorandum of understanding (MOU) that was significantly slanted toward Iran’s demands, Iran continued its provocations. The MOU called on the US to begin removing its blockade, but long-term control of the critical waterway was not specified.
Trump admitted last month that the country might not have the “appetite” for more major military action. With each passing day, the prospect of reigniting a full-scale war looks less and less appetizing. As Trump himself said Wednesday, “They’re saying they want to make a deal, but they don’t… They ask for a timeout, they wanted to do the funeral of Khamenei, and I said give it to them. And they start shooting missiles. I mean, it’s a crazy thing.” Or maybe, the analysis suggests, it’s the same thing that has happened over and over again, and Trump just didn’t want to see it.
