President Donald Trump was fresh off the golf course, and his fury was building.
It was March 21, and as he settled back into his Mar-a-Lago estate for the evening, he was reading another news account about how, for all the military success the US had in Iran, he had yet to achieve his political objectives.
At 7.44pm, the President made his frustration known with an extraordinary ultimatum: If Iran did not reopen the Strait of Hormuz within 48 hours and allow much of the world’s oil and gas to flow through, he would bomb Iran’s civilian electric power plants. It was the kind of attack that could constitute a war crime under the Geneva Conventions.
But just hours before the Monday deadline expired, Trump delayed his threat by five days, easing fears of an imminent escalation with profound military, diplomatic and economic implications.
Still, he warned that “we’ll just keep bombing our little hearts out” if Iran would not make a deal, and as the week progressed, he made new threats that left allies off balance and spooked the markets. So on Thursday afternoon, after stocks on Wall Street suffered their largest daily decline since the start of the war, he added another 10 days to the clock, again seeking to ease the fears ignited by his own hard-line positions.
It is too soon to know whether the extra time will result in productive diplomacy. But it is already clear that Trump’s wild swings — from optimism to frustration and anger, from de-escalation to escalation — have combined to give his management of the war an erratic, make-it-up-as-it goes feel.
Ever since the US, alongside Israel, launched the war on February 28, Trump has vacillated between chest-thumping about US military superiority and deep frustration that the tactical achievements on the battlefield did not seem to be producing the strategic outcome he predicted.
Although the Supreme Leader and many top military and intelligence leaders have been killed, the regime in Tehran remains in control. Iran’s leaders have all but sealed off the Strait of Hormuz, sending gas prices skyrocketing and rattling investors. And Iran retains control of the material it would need to produce a nuclear weapon, the main threat cited by Trump in taking the nation into the war in the first place.
Trump has said he understands there will be short-term pain from the war, which he accepts as a necessary price to ensure that Iran cannot have a nuclear weapon. And the President’s allies have always said that his unpredictability is his superpower, keeping his enemies guessing.
But it also suggests an inconsistency of purpose that has led the President to keep shifting his goals, even as the risks of the war grow bigger by the day.
Advisers
Trump spends his days immersed in the war, receiving several briefings a day either in the Oval Office or the Situation Room. Some of the briefings include a short montage video of less than a minute, White House officials say, primarily raw footage of military strikes that the US Central Command also shares on X. When Trump is deliberating a decision, he goes around the room and asks his advisers what they think.
Karoline Leavitt, the White House press secretary, said the President makes every decision with the same goal: victory.
“He understands that these sorts of things throughout history are ultimately judged by the outcome,” Leavitt said, “and the President knows that at the end of this, when we are able to declare that the Iranian terrorist regime no longer poses a threat to the US militarily, that is going to be a legacy-making, history-marking moment.”
Trump gets military advice from two main sources: defence secretary Pete Hegseth and Gen. Dan Caine, the chairman of the Joint Chiefs of Staff. Hegseth is the President’s go-to when it comes to publicly defending military policies, US officials say. But General Caine, a former Air Force F-16 fighter pilot and Pentagon liaison to the CIA, is the military’s Trump whisperer — its main interlocutor with the President on operational matters.
Pentagon and White House officials say Trump has developed a good rapport and strong personal trust with the low-key General Caine, whom he plucked from retirement to be chairman after Gen. Charles Q. Brown Jr. was fired in early 2025.
Before the war started, General Caine briefed Trump on an array of options, including some that he said could strain US munitions stocks and risk American casualties. General Caine does not advocate one option or another in Situation Room discussions, US officials say. Instead, he lays out the risks, benefits and consequences.
That occasionally puts General Caine in a difficult position.
Late last month, in the run-up to the war, Trump said General Caine believed that any eventual military action ordered against Iran would be “something easily won”. But that is not what General Caine had told Trump and other senior advisers.
The disconnect underscores just how much the Iran war is testing Trump’s usual strategy for dealing with crises: imposing his own reality and disregarding inconvenient truths.
“He thinks everything is transactional; he can deal with the deal one step at a time and see how things unfold, but war is fast, uncontrollable, unpredictable and deadly,” said Julian E. Zelizer, a Princeton history professor and the editor of a book of essays about Trump’s first term.
“He’s doing the same techniques he always does — threatening people, insulting people, seizing attention to what he wants to say — he’s learning that it doesn’t always work,” he added. “He’s doing the art of the deal in a way that’s just creating chaos.”
Military might
During his first term, Trump seemed more hesitant to use the force of the US military. In 2019, he approved military strikes against Iran only to call the operation off with minutes to spare, citing the possibility of Iranian casualties.
John Bolton, Trump’s former national security adviser who has supported aggressive military aggression against Iran, including regime change, recalled that Trump had seemed uncomfortable in his first term with the idea of striking Syria, which was using chemical weapons on its own people.
“He wanted it to look like it was a strong response, but not really be that strong,” said Bolton, who has become one of the President’s most vocal critics.
Now, after campaigning on a promise to keep America out of foreign entanglements, Trump is embracing American military might. And with the war in Iran at least, he has been far more matter-of-fact about the possibility that there could be American casualties.
He dispatched B-2 bombers to strike Iran’s nuclear facilities in June; he launched a raid in January that resulted in the capture of President Nicolas Maduro of Venezuela; and US forces have blown dozens of boats out of the water in the Caribbean, killing more than 160 people, in what the Trump administration says is an operation to combat drug smuggling.
His operation in Iran is far more complex, less popular and deadlier for American forces than those operations. So far, 13 US service members have died. Trump has attended two dignified transfers, and Leavitt has said that Trump considers it the most important, yet the hardest part of his job as commander in chief. The father of one fallen soldier recently recounted the “pleasant surprise” of Trump’s emotion and “humanity” during a meeting.
At the same time, Trump insists that he is doing what no other President before him dared to do.
New York Times News Service