Perhaps the most bizarre moment in the monthslong Iran war occurred in mid-April, when President Donald Trump insisted that Tehran had just “agreed to everything” he had demanded.
That didn’t pan out, of course. And there’s no reason to believe the agreements existed — even tentatively — anywhere except in Trump’s own head. Pretty much everything else continues to suggest, even weeks later, that the two sides remain far apart.
Trump acted like he could will an agreement into existence. Instead, he made it abundantly clear to everyone, including Iran, that he was desperate for a deal.
It wasn’t the first time, or the last.
Over and over again, Trump has appeared remarkably hesitant in recent weeks to resume fighting if Iran doesn’t give him what he wants. He and his administration have tied themselves in knots to explain why they keep giving Iran latitude and time.
But while this approach might occasionally calm the markets, Iranian leaders seem to be taking it as a signal that they can just wait out a US president who doesn’t want to go back to full-scale war.
Returning to open military hostilities, after all, risks prolonging the economic pain of high gas prices, potentially risking American lives and depleting dwindling US weapons stockpiles.
None of it means Trump won’t ultimately strike Iran again. He declared Monday from the Oval Office that the monthlong ceasefire was “on massive life support.” He could ultimately decide Tehran has been stringing him along and that such attacks are necessary. But he’s clearly given it a remarkable amount of leeway.
The most frequent indicator of this dynamic is Trump’s repeated setting of deadlines for Iran to agree to a deal or else, and then his pulling back even when Iran didn’t agree to said deal. It happened on no fewer than five occasions in one month, between March 21 and April 21.
Most times, Trump said the deadline was being relaxed because a deal could be imminent. But by the fifth time, he didn’t even bother to claim that — and he explicitly said there was no deadline that time.
Even the very beginning of the ceasefire announced on April 7 revealed some anxiousness to end military strikes on Trump’s part. The two sides couldn’t even agree on some of the main aspects of the ceasefire, like whether it included Israeli attacks in Lebanon. But as Iran threatened to pull out, Trump and his administration rushed to work out some of those issues. It all suggested that the agreement was rather haphazardly and hastily assembled to avoid making good on Trump’s apocalyptic threats.
By April 19, Trump signaled the United States would send another delegation to Pakistan to negotiate. But Iran hadn’t publicly agreed to the peace talks. By April 21, the US delegation was called off.
That same day, Trump still extended the ceasefire, which was due to expire after two weeks — despite previously labeling that outcome “highly unlikely.”
Then came last week.
On Tuesday, the Defense Department said several bouts of Iranian aggression — including Tehran firing on US ships guiding vessels through the Strait of Hormuz and attacking the United Arab Emirates — didn’t clear the “threshold” for violating the ceasefire.
Defense Secretary Pete Hegseth also suggested the episodes weren’t even part of the war. He depicted efforts to guide ships through the strait, which Trump had dubbed Project Freedom, as a separate operation. He urged Iran “to be prudent” in its actions during the ceasefire.
It was a striking moment. Top US defense officials seemed to be saying some Iranian attacks on the United States were fair game and straining to pitch the ceasefire as intact.
Later that day, Trump ended Project Freedom despite Hegseth, Secretary of State Marco Rubio and Joint Chiefs of Staff Chaiman Gen. Dan Caine having spent the day espousing its value.
Thursday saw a similar series of events. Despite another exchange of fire with Iran, in which the US struck military facilities it said were responsible for the attacks in the strait, Trump called it “just a love tap” and said: “The ceasefire is going. It’s in effect.”
But more than a month after the ceasefire began, there is little evidence it’s producing an environment for a deal. It mostly seems to have given two sides that would prefer not to fight right now an excuse not to fight.
That’s more helpful to Iran, though, which has telegraphed its willingness to dig in for a prolonged conflict. For Trump administration officials, that risks looking like they’re being willingly strung along while they try to figure out a face-saving exit from a potential quagmire.
Trump on Sunday responded to Iran’s latest proposal by calling it “TOTALLY UNACCEPTABLE.”
That missive got a ton of attention Sunday, but another post might reveal more about where Trump’s head is at. Earlier Sunday afternoon, he wrote a whole social media post about how Iran had spent 47 years “‘tapping’ us along, keeping us waiting.”
It sounded like he might now believe that Iran isn’t so interested in cutting a deal — at least on terms that would be acceptable to Trump. Maybe the guy who has spent two months assuring Iran is desperate for a deal realizes it’s actually not.
But recognizing that and figuring out what to do about it are two different things.
And it appears Trump isn’t done giving Iran time and space.
On Monday, moments before he said the ceasefire was “on massive life support” and compared it to a patient with a 1% change of surviving, Trump signaled to Fox News that he was still focused on a diplomatic solution.
“They’re going to fold,” Trump said, adding: “I will deal with them until they make a deal.”
