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Three months in, is Trump losing the war against Iran?

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23.05.2026

WASHINGTON (Reuters) — US 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?

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 US 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 US 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.

Analysts say 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 then-US President Barack Obama’s 2015 nuclear deal with Iran, which Trump scrapped in his first term.

White House spokeswoman Olivia Wales said the US has “met or surpassed all of our military objectives in ‘Operation Epic Fury,’” the US name for the bombing campaign it launched with Israel in Iran on February 28.

“President Trump holds all the cards and wisely keeps all options on the table,” Wales added.

Pressure and frustration

Trump campaigned for a second term promising no unnecessary military interventions, but has brought the US into an entanglement that could do lasting damage to his foreign policy record and credibility abroad.

The........

© The Times of Israel