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Analysis-Three months in, is Trump losing the Iran war?

Published by Global Banking & Finance Review

Posted on May 23, 2026

5 min read

· Last updated: May 23, 2026

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Three Months In: Is Trump Winning or Losing the Iran War?

By Matt Spetalnick

Assessing the Outcome of Trump's Iran Strategy

WASHINGTON, May 23 (Reuters) - 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?

Military Successes vs. Geopolitical Reality

   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.

Expert Opinions on the War's Trajectory

“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.

White House Response

White House spokeswoman Olivia Wales said the U.S. has “met or surpassed all of our military objectives in 'Operation Epic Fury'.”

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

Pressure and Frustration

PRESSURE AND FRUSTRATION

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.

Supporters and Critics

Even so, Trump is not without his defenders.

Alexander Gray, a former senior adviser in Trump’s first term and now chief executive officer of the American Global Strategies consultancy, rejected the notion that the president's Iran campaign was on the ropes.

   He said that the heavy blow to Iranian military capabilities was in itself a "strategic success," that the war had drawn Gulf states closer to the U.S. and away from China, and that the fate of Iran’s nuclear program was still to be determined.

There are signs, however, of Trump's frustration with his inability to control the narrative. He has torn into his critics and accused the news media of “treason.”

The conflict has lasted twice the maximum six-week timeframe that Trump laid out when he joined with Israel in starting the war on February 28. Since then, though his MAGA political base has stood by him on the war, cracks have appeared in his once almost unanimous backing from Republican lawmakers.

At the outset, waves of airstrikes quickly degraded Iran’s ballistic missile stockpile, sank much of its navy and killed many top leaders.

But Tehran responded by blocking the strait, which sent energy prices soaring, and attacking Israel and Gulf neighbors. Trump then ordered a blockade of Iran’s ports but that has also failed to bend Tehran to his will.

   Iran's leaders have matched Trump’s triumphalist claims with their own propaganda depicting his campaign as a “crushing defeat," though it is clear that Iranian officials have overstated their own military prowess.

Shifting Goals Still Unachieved

SHIFTING GOALS STILL UNACHIEVED

Trump had said his objectives in going to war were to close off Iran’s path to a nuclear weapon, end its ability to threaten the region and U.S. interests and make it easier for Iranians to overthrow their rulers.

There is no sign that his often-shifting goals have been achieved, and many analysts say it is unlikely that they will be. 

Expert Analysis on Iran's Resilience

Jonathan Panikoff, a former deputy national intelligence officer for the Middle East, said that while Iran has taken devastating hits, its rulers consider it a success simply to have survived the U.S. a

Key Takeaways

  • US-led Operation Epic Fury inflicted significant damage but failed to break Iran’s hold on key assets like the Strait of Hormuz (media.defense.gov)
  • Despite tactical success, Iran’s government, military leverage and negotiating position remain largely intact (investing.com)
  • Trump faces mounting domestic and political pressure—with few clear off-ramps except a potentially flawed deal or resumption of limited strikes (investing.com)

References

Frequently Asked Questions

What challenges does Trump face after three months of conflict with Iran?
Trump faces doubts about achieving a clear geopolitical win as Iran retains strategic leverage and the US faces regional instability and domestic criticism.
How has Iran maintained its position during the US conflict?
Iran continues to control the Strait of Hormuz, resists nuclear concessions, and retains its theocratic government despite military and economic pressure.
What are potential outcomes if diplomacy fails between the US and Iran?
Analysts suggest Trump could escalate militarily, accept a flawed deal, or try to shift focus to other regions like Cuba if talks break down.
What do Trump's allies say about the US strategy in Iran?
Some allies claim that weakening Iran's military is a strategic success and the war has strengthened US relations with Gulf states, though overall victory remains uncertain.

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