Photo: The White House
U.S. President Donald Trump may have won just about every battle against Iran, but three months after attacking the Islamic Republic he now faces a bigger question: Is he losing the war? – Reuters puts a question.
With Iran’s grip on the Strait of Hormuz, its resistance to nuclear concessions and its theocratic government largely intact, doubts are growing that Trump can translate the U.S. military’s tactical successes into an outcome he can frame convincingly as a geopolitical win.
His repeated claims of complete victory ring hollow, some analysts say, as the two sides teeter between uncertain diplomacy and his on-again-off-again threats to resume strikes, which would be sure to draw Iranian retaliation across the region.
Trump is now at risk of seeing the U.S. and its Gulf Arab allies emerge from the conflict worse off while Iran, though battered militarily and economically, could end up with greater leverage, having shown it can throttle one-fifth of the world’s oil and gas supplies.
The crisis is not yet over, and some experts leave open the possibility Trump might still find a face-saving way out if negotiations break in his favor.
But others predict a grim post-war outlook for Trump.
“We’re three months in, and it’s looking like a war that was designed to be a short-term romp for Trump is turning into a long-term strategic failure,” said Aaron David Miller, a former Middle East negotiator for Republican and Democratic administrations.
For Trump, that matters, especially given his famous sensitivity to being perceived as a loser, an insult he has often lobbed at opponents. In the Iran crisis, he finds himself commander-in-chief of the world’s mightiest military pitted against a second-tier power seemingly convinced it has the upper hand.
And this predicament could make Trump, who has yet to define a clear endgame, more likely to resist any compromise that looks like a retreat from his maximalist positions or a repetition of the 2015 Obama-era nuclear deal with Iran that he scrapped in his first term, analysts say.
Trump campaigned for a second term promising no unnecessary military interventions but has brought the U.S. into an entanglement that could do lasting damage to his foreign policy record and credibility abroad.
The continuing standoff comes as he faces domestic pressure over high U.S. gasoline prices and low approval ratings after he embarked on the unpopular war ahead of November’s midterm elections. His Republican Party is struggling to maintain control of Congress.
As a result, more than six weeks into a ceasefire, some analysts believe Trump faces a stark choice: to accept a potentially flawed deal as an off-ramp or escalate militarily and risk an even longer crisis. Among his options if diplomacy collapses, they say, would be to launch a round of sharp but limited strikes, frame it as a final victory and move on.
Another possibility, analysts say, is that Trump could attempt to shift focus to Cuba, as he has suggested, in hopes of changing the subject and trying to score a potentially easier win.
If so, he might end up misjudging the challenges posed by Havana, much as some Trump aides privately acknowledge that he mistakenly thought the Iran operation would resemble the January 3 raid that captured Venezuela's president and led to his replacement.
Adding to Trump’s challenges, he is now dealing with new Iranian leaders considered even more hardline than their slain predecessors. Post-war, they are widely expected still to have enough remaining missiles and drones to pose a continued danger to their neighbors.
He is also facing fallout with further erosion of relations with traditional European allies, which have mostly refused his calls for assistance in a war they were not consulted about.
China and Russia, meanwhile, have drawn lessons about the U.S. military’s shortcomings against asymmetric Iranian tactics and how some of its weapons supplies have become depleted, analysts said.
Robert Kagan, a senior fellow at the Brookings Institution think tank, has argued that the outcome will be even more of a decisive setback to U.S. standing than its humiliating withdrawals from much longer, bloodier conflicts in Vietnam and Afghanistan because those countries “were far from the main theaters of global competition.”
“There will be no return to the status quo ante, no ultimate American triumph that will undo or overcome the harm done,” he wrote in a recent commentary entitled “Checkmate in Iran” on the Atlantic magazine’s website.
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11:23 25.05.2026 •















