For five years in office, President Trump has operated with intuition, impulse and improvisation.
The Iran war, now entering Week 3, is the first time Trump's style has made it impossible for him to easily talk or improvise his way out.
Why it matters: Trump could wind up trapped between his caprice and the realities of war. He expects a quick, clear victory. But unlike tariffs that can be swiftly imposed and rescinded, the war's outcome is beyond unilateral control and quick fixes. And Iran gets a say.
Trump is working to help break the Persian Gulf oil jam. But in doing so, he risks getting caught in an "escalation trap," where a stronger force is incentivized to keep attacking to demonstrate dominance amid diminishing returns.
A senior Trump administration official practically admitted as much, telling Axios' Marc Caputo: "The Iranians f*cking around with the Strait makes [Trump] more dug in."
State of play: Israel wants regime change in Iran and more dramatic military destruction as it weighs an invasion of Lebanon. Bibi Netanyahu has shown several times that when it comes to Iran, he has the ability to convince Trump to take his side.
Iran wants survival — and to prove it can impose pain, militarily and economically, to scare off future attacks.
And other nations want the free flow of oil and commerce through the Middle East's waters and air.
What we're watching: Averaging out the timelines mentioned by Trump and his aides, it's fair to assume the administration expected an intense military operation lasting about 4-6 weeks. That makes April 1 (Day 33 of the war) a real gut-check moment.
But in Washington and in capitals around the world, officials are preparing for a much longer crisis. Axios' Barak Ravid tells us he's heard from three different people in the administration and in allied countries who believe the instability in the Middle East and U.S. involvement could continue until September, even if the war shifts to a low-intensity conflict.
Israel told journalists it plans at least three more weeks of attacks on thousands of additional targets in Iran.
The president said Sunday in a phone call with the Financial Times' Ed Luce: "We've essentially decimated Iran ... They have no navy, no anti-aircraft, no air force, everything is gone. The only thing they can do is make a little trouble by putting a mine in the water — a nuisance, but the nuisance can cause problems."
Anna Kelly, the White House's principal deputy press secretary, emphasized to us that Operation Epic Fury is the result of "months and months of meticulous planning," with "ample options" provided to the president, who took all of his top officials' views into account as he made the final decision.
Trump could pull out tomorrow. But the Iranians could keep the Strait of Hormuz closed and push oil prices so high that America would have to re-engage.
The Iranians have made it clear in private and in public that even if Trump decides to end the war, they could continue shooting missiles and rockets until they get guarantees that this is the end of the war, not just a temporary ceasefire.
Behind the scenes: Trump has grown accustomed to doing what he wants and then quickly improvising if things go south. But this time, some in his inner circle have what one official called "buyer's remorse" — growing fears that attacking Iran was a mistake.
A source close to the administration said some key officials around Trump were reluctant or wanted more time. "He ended up saying, 'I just want to do it,'" the source said. "He grossly overestimated his ability to topple the regime short of sending in ground troops."
The source said Trump was "high on his own supply" after last summer's quick strikes in Iran and January's abduction of Venezuelan President Nicolás Maduro: "He saw multiple decisive quick victories with extraordinary military competence."
Reality check: Trump's war of choice certainly looks like a military success so far. Iran's missile and drone launches have greatly decreased, indicating it's running out of weapons or the ability to fire them.
The U.S. and Israeli air forces have overhead supremacy to bomb at will.
Much of the Iranian navy is underwater.
The ayatollah and senior leaders have been killed.
The U.S. military death toll (at least 13) could have been greater for this breadth of action.
What's next: Trump now may have to make a tough decision on a significant military escalation — new territory for him as president.
Some officials close to him had hoped he'd be able to show some quick gains and declare victory. Now, it's not apparent how he'd do that convincingly.
As Barak reported, the U.S. doesn't have clear enough lines of communication with the Iranian regime to make a deal that's sure to stick. Trump said on Truth Social on Friday night that Iran "is totally defeated and wants a deal - But not a deal that I would accept!"
The bottom line: To claim victory, the Iranian regime just needs to stay alive.
