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regular-article-logo Saturday, 28 March 2026

Iran conflict: Freestyle Trump diplomacy tested with diverse emissaries including a friend, family, dove and hawk

As the war stretches longer than Trump seems to have anticipated, he appears to be casting about for a diplomatic offramp even as he threatens to escalate the conflict

Michael Crowley Published 28.03.26, 07:39 AM
Trump’s Iran war tests limits of unorthodox diplomacy as he seeks offramp

Donald Trump. (Reuters)

US President Donald Trump’s war with Iran is testing the limits of his unorthodox diplomatic style as he grasps for a deal to end the conflict shaking the West Asia and the global economy.

As the war stretches longer than Trump seems to have anticipated, he appears to be casting about for a diplomatic offramp even as he threatens to escalate the conflict.

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In a social media post on Thursday, Trump seemed confounded by the challenge, calling Iranian officials “very different and ‘strange’” and claiming that they were “begging” for a deal while insisting that they “better get serious soon”.

It is unclear who in the Trump administration may be in charge of talking with a battered Tehran’s surviving leadership. On Tuesday, Trump said that Vice-President J.D. Vance and secretary of state Marco Rubio would join his special envoy Steve Witkoff and his son-in-law Jared Kushner in any negotiations. “They’re doing it, along with Marco, J.D., we have a number of people doing it,” Trump said.

Vance is a past opponent of US intervention in West Asia generally and Iran in particular. Rubio, by contrast, is an Iran hawk who has publicly defended Trump’s decision to attack the country.

That jumble of emissaries — a friend, a family member, a dove and a hawk — reflects Trump’s improvisational approach to foreign dealings and his disdain for career diplomats and their often cumbersome protocols. The picture is further muddied by Trump’s stream-of-consciousness commentary on social media and before the television cameras during which he declares, revises and sometimes reverses his threats and demands.

The situation is testing the bravado many Trump officials expressed about their early foreign policy initiatives. “Turns out a lot of diplomacy boils down to a simple skill: don’t be an idiot,” Vance posted on social media last March, in praise of Witkoff.

Daniel Kurtzer, a former US ambassador to Israel under President George W. Bush, rated Trump’s Iran diplomacy a failure, in part because the President seems unsure of his own goals. “Trump says he wants to de-escalate, but does he even know what that means?” Kurtzer added that the 15 demands Trump has submitted to Tehran “are non-starters, because they would require Iran essentially to give up on everything”.

Kurtzer also blamed Trump for sidelining career diplomats, cutting key policymaking jobs and largely placing his West Asia diplomacy into the hands of Witkoff and Kushner, who have backgrounds in real estate. That has left Trump without skilled teams of experts to help guide him out of the current crisis, Kurtzer said.

“If you’ve hollowed out the state department and substantially reduced the size of the National Security Council and fired some of your top generals, and if so much of what you’re doing is about political loyalty, then maybe there isn’t that reservoir of expertise to draw on,” he said.

Many foreign diplomats share the concern that America’s diplomatic machine is malfunctioning. “America has lost control of its own foreign policy,” the foreign minister of Oman, Badr Albusaidi, wrote in The Economist magazine last week.

Albusaidi suggested that Trump could not solve the problem on his own. “The question for friends of America is simple,” he said. “What can we do to extricate the superpower from this unwanted entanglement?”

Albusaidi is one of many who have been questioning whether Trump missed an opportunity to avoid war when he sent Witkoff and Kushner for last-ditch negotiations with Iran over its nuclear and missile programmes. Critics charge that Witkoff and Kushner were out of their depth and too quick to conclude that Tehran was not open to a deal.

A particular quirk of Trump’s diplomatic approach is the minimalist role of his state department and its leader, Rubio.

During past West Asia crises, US secretaries of state have typically raced across the region to build personal trust and glean insights in ways that veteran diplomats say requires in-person interaction.

The war with Iran reveals the risk in what Aaron David Miller, who served as a West Asia negotiator under several Presidents of both parties, calls Trump’s “huge break with convention and common sense”.

“That the secretary of state is playing a subordinate role and not managing the administration’s most serious foreign policy crisis attests to how dysfunctional the decision-making process is,” he added. “Because there’s no structure, it also allows Iran to try to pick and choose which US officials they want to talk to.”

Gulf crackdown

In the UAE and Qatar, the authorities have arrested hundreds of people since the war began, accusing some of spreading rumours and others of merely sharing videos and imagery of Iranian attacks, according to statements published by their official news agencies.

New York Times News Service

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