The definition of stupid.....

How Trump has misjudged Iran

Analysis by Aaron Blake

On June 16, President Donald Trump called Iran’s leaders “very rational people” who were “nice to deal with.” He even assured they were “not radicalized.”

On Wednesday, Trump offered a nearly polar-opposite take. He called Iran’s leaders “cuckoo,” “evil” and “sick,” “dirty players” and “scum.”

“They violate the agreement every day,” Trump said at a NATO summit in Turkey. “They lie. They cheat.”

The president offered his sharply revised review of Iran’s leaders as the tenuous ceasefire between the US and Tehran looks to be more endangered than ever after Iran targeted three ships in the Strait of Hormuz and the US launched strikes in response. Trump on Wednesday even declared the ceasefire to be “over,” though he has at other times suggested he holds out hope for a peace deal.

One way to look at Trump’s rosy words in mid-June was that he was just flattering people with whom he was engaged in high-stakes negotiations. That’s not unheard of.

But Trump’s track record on the Iran war suggests another explanation entirely: He has badly misjudged his adversary’s intentions and his own leverage, and has repeatedly allowed Tehran to string him along.

That posture has delayed a resolution for three months (since Trump announced the initial ceasefire on April 7) and brought the situation perilously close to the 2026 midterms for the GOP. And the looming elections make it politically difficult for Trump to crack down on Iran and return to full-scale war.

That’s not to say that Trump believed Iran’s leaders had truly moderated. Asked on Wednesday, for example, what had changed in his assessment of Iran’s leaders, he said, “I got to know them.”

But he seems to have repeatedly wagered that Iran was close enough to a deal that he could push their leaders over the finish line with some modest rhetorical concessions and just a little more time — only to be proven wrong over and over again.

There are countless signs of Trump’s misjudgment at this point.

Perhaps most strikingly, he repeatedly threatened Iran with doom if it didn’t comply with his demands. But just about every time, those threats were revealed to be a bluff. Trump often claimed he was backing off because a deal was near, but that deal still hasn’t materialized in any lasting form.

It’s not difficult to see how Iran might have concluded that Trump simply didn’t have the nerve to make good on his threats — and that it could just wait him out.

Trump has also repeatedly claimed not only that a deal was near — which could perhaps be dismissed as unfounded optimism — but also that Iran was desperate for a deal. Trump said Tehran was “begging for a deal” as far back as March 31, more than three months ago.

But if Iran has been desperate for a deal, it sure has a funny way of showing it.

Almost immediately after the initial ceasefire was announced, disputes broke out over what precisely had been agreed to, and Iran seemed to repeatedly violate the terms, as Trump had described them.

In announcing the ceasefire in April, Trump said it was “subject to … the COMPLETE, IMMEDIATE, and SAFE OPENING of the Strait of Hormuz.” But even though that never happened, Trump pressed forward in trying to keep the truce going.

Iran threw on top of that a series of provocations seemingly intended to test the Trump administration’s resolve. Repeatedly, the administration downplayed the provocations and strained to argue how they didn’t technically violate the ceasefire.

That included in May when Tehran fired on US ships that were attempting to guide vessels through the Strait of Hormuz, which the Pentagon said didn’t clear the “threshold” for a ceasefire violation. Defense Secretary Pete Hegseth even gamely suggested the attacks weren’t part of the war because US actions in the strait were a separate operation.

Fast forward to today, and the provocations have continued even after a more substantial ceasefire was agreed to last month — this time, with text laid out in a memorandum of understanding.

Perhaps most strikingly, the MOU was already significantly slanted toward Iran’s demands — so much so that many Republicans criticized it and the Trump administration tried to downplay its written terms as not reflective of the full series of agreements. (There have also been disputes about what the language in the MOU actually means.)

And yet, Iran seems more interested in controlling the Strait of Hormuz than accepting what appears to be a pretty favorable temporary agreement. (The MOU called on the US to begin removing its blockade but long-term control of the critical waterway wasn’t specified.)

None of this means the ceasefires over the past three months have been completely for naught, from a US perspective. CNN’s David Goldman noted Tuesday how the sharp decline in oil prices in recent weeks gives Trump some leverage, considering how large that loomed over the domestic political picture. And CNN global affairs analyst Brett M. McGurk, who served in senior national security positions under presidents of both parties, argued last week that the US buying time can apply pressure on Iran in a number of ways.

But at this point, the Trump administration is on the clock, too. The stitched-together ceasefires have brought the conflict three months closer to the November elections, which have looked like a potential Democratic rout of Trump’s party, at least in the House.

The president has repeatedly made it abundantly clear that he doesn’t want to return to full-scale war, and the administration has even privately acknowledged it just wants the war to be over with. The president last month admitted the country might not have the “appetite” for more major military action.

And with each day, the prospect of reigniting a full-scale war that has proven remarkably unpopular at home has to look less and less appetizing.

Trump said repeatedly a month ago that he feared Iran was “tapping us along.” And he signaled again Wednesday that might be the case.

“They’re saying they want to make a deal, but they don’t — you know, they ask for a timeout, they wanted to do the funeral of Khamenei, and I said give it to them,” he said at the NATO summit. “And they start shooting missiles. I mean, it’s a crazy thing.”

Or maybe it’s the same thing that’s happened over and over again, and he just didn’t want to see it.