President 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 United States had in Iran, he had yet to achieve his political objectives.
At 7:44 p.m., 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, Mr. 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 Mr. 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 United States, alongside Israel, launched the war on Feb. 28, Mr. Trump has vacillated between chest-thumping about U.S. 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 Mr. Trump in taking the nation into the war in the first place.
Mr. 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, and that it keeps 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.
The Trump Whisperer
Mr. 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 U.S. Central Command also shares on X. When Mr. 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,” Ms. 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 United States militarily, that is going to be a legacy-making, history-marking moment.”
Mr. Trump gets military advice from two main sources: Defense Secretary Pete Hegseth and Gen. Dan Caine, the chairman of the Joint Chiefs of Staff. Mr. Hegseth is the president’s go-to when it comes to publicly defending military policies, U.S. officials say. But General Caine, a former Air Force F-16 fighter pilot and Pentagon liaison to the C.I.A., is the military’s Trump whisperer — its main interlocutor with the president on operational matters.
Pentagon and White House officials say Mr. 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 Mr. Trump on an array of options, including some that he said could strain U.S. munitions stocks and risk American casualties. General Caine does not advocate one option or another in Situation Room discussions, U.S. 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, Mr. 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 Mr. Trump and other senior advisers.
The disconnect underscores just how much the Iran war is testing Mr. 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 Mr. 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.”
Embracing Military Power
During his first term, Mr. Trump seemed more hesitant to use the force of the U.S. 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, Mr. Trump’s former national security adviser who has supported aggressive military aggression against Iran, including regime change, recalled that Mr. 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 Mr. 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, Mr. 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 Nicolás Maduro of Venezuela; and U.S. 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 U.S. service members have died. Mr. Trump has attended two dignified transfers, and Ms. Leavitt has said that Mr. 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 Mr. Trump’s emotion and “humanity” during a meeting.
At the same time, Mr. Trump insists that he is doing what no other president before him had the courage to do.
“We have unparalleled firepower, unlimited ammunition, and plenty of time — Watch what happens to these deranged scumbags today,” he wrote in a Truth Social post this month. “They’ve been killing innocent people all over the world for 47 years, and now I, as the 47th President of the United States of America, am killing them. What a great honor it is to do so!”
Mr. Trump’s cavalier attitude has shown cracks. When he was pressed about the deadly Tomahawk missile strike on an Iranian elementary school on the opening day of the war, Mr. Trump first blamed Iran and then claimed he did not “know enough about it.”
A preliminary inquiry has determined that the United States was responsible.
The president, who was granted five deferments from being drafted to fight in Vietnam, including for a diagnosis of bone spurs, has often mused that he would be a “good general.” Earlier this month, he posted an old picture of himself in uniform at the New York Military Academy, a notable choice as he launched a war.
As the weeks have gone by, the goals and objectives that Mr. Trump laid out at the start of the war have changed. Last week, as he said he was considering “winding down” military operations in Iran, Mr. Trump no longer mentioned the purpose of supporting regime change through a popular uprising, an objective he had set at the start.
“The war, like everything else that comes out of the White House, is a reflection of Donald Trump’s very unique personality and leadership style,” said Steven M. Gillon, a historian and the author of “Presidents at War: How World War II Shaped a Generation of Presidents.” “It’s focused on him as a great man. It is vague. It’s undisciplined. It’s unfocused.”
Mr. Trump has explained some of his back-and-forth decisions in the war by referring to the lessons he learned before he entered into politics, back when he was a real estate developer in New York.
“You have to understand,” Mr. Trump told an audience in Memphis earlier this week, “my whole life has been a negotiation.”
‘Presidents Don’t Need Permission.’
But Mr. Trump’s allies see his decision to go to war as his duty as commander in chief.
“President Trump is acting like a wartime president should — decisive, unafraid to use his constitutional authority and focused on protecting Americans rather than getting bogged down in the kind of endless and rudderless conflicts we saw under his predecessors,” said Mike Davis, who leads the Article III Project, a conservative advocacy group, and was an early supporter of Mr. Trump’s war.
“Presidents don’t need permission to defend the country, and the media and Democrats will do anything to delegitimize Operation Epic Fury,” he said. “President Trump’s legacy won’t be judged on process or polls, but on whether he succeeds in neutralizing the Iran threat and making Americans safer.”
Still, the conflict is deeply unpopular with a majority of Americans. The president chose to launch the war without first making the case to the American public or Congress, which perhaps contributed to the absence of a “rally around the flag” moment that many wartime presidents see. (He has acknowledged that he has been advised against calling it a “war” because he did not seek congressional approval, so he prefers to call it an “excursion.”)
Aside from the question of congressional approval, Mr. Trump has failed to provide any evidence that Iran posed an “imminent threat” to the United States. And he has repeatedly moved the goal posts for success — even declaring victory while at the same time arguing that the mission was incomplete. He said he would accept nothing less than an end with the “unconditional surrender” of Iran, a condition that his aides have said is up to his discretion.
Mr. Trump is not the first president to put forth a lofty yet elusive goal. President Franklin D. Roosevelt called for the “unconditional surrender” during World War II. It is one of the few similarities between how the two approached war.
“When Roosevelt announced the unconditional surrender goal in World War II, it was not well thought through, and not fully coordinated with his team or his allies,” said Peter Feaver, an adviser to President George W. Bush on national security strategy and now a professor at Duke University who has studied how presidents lead in wartime. “I would not be surprised if President Trump’s announcement of unconditional surrender matched Roosevelt’s in that regard.”
But Roosevelt cultivated something that has eluded Mr. Trump: powerful allies, namely Winston Churchill, with whom he coordinated his aggressive military strategy.
Mr. Trump has instead alienated and threatened his allies for not joining the war effort. He has targeted most of his ire at Prime Minister Keir Starmer of Britain, declaring that Mr. Starmer is “no Winston Churchill.”
“We don’t need people that join Wars after we’ve already won!” Mr. Trump wrote on March 7.
But now, with yet another deadline looming for Iran to fully open the Strait of Hormuz to shipping or face devastating strikes on its power plants, Mr. Trump has a decision to make about the next steps in a war that he estimated, at the outset, would last “four to five weeks.” The war has now been going on for nearly a month.
Mr. Trump is ratcheting up pressure on Iran to accept a U.S. proposal to end the war, even as he sends more troops to the Middle East and warns Iranians that “we’ll just keep blowing them away” if they don’t make a deal.
Iran has publicly rejected the overtures, though it has privately signaled some willingness.
“They’ll tell you, ‘We’re not negotiating,’” Mr. Trump said. “Of course, they’re negotiating. They’ve been obliterated.”
On Friday evening, during remarks at a finance conference in Miami Beach for Saudi Arabia’s sovereign investment fund, Mr. Trump boasted how Iran was “begging to make a deal” and how the United States’ operation was helping ensure that the very “powerful” nation of Saudi Arabia would be safe.
While he was speaking, U.S. officials confirmed that Iran had struck a naval base in Saudi Arabia where U.S. service members were stationed. Twelve Americans were injured in the attack, which amounted to one of the most serious breaches of American air defenses in the course of the war.
Eric Schmitt and David E. Sanger contributed reporting from Washington.
Erica L. Green is a White House correspondent for The Times, covering President Trump and his administration.
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