President Donald Trump has considered himself an effective dealmaker above all else, but he appears to have hit a wall with Iran as his tough talk, threats and even military action have not moved Tehran from its long-established positions.

With shifting goals that make it difficult to judge the status of the US effort, Trump and his top aides have insisted the United States has already won the war and that Iran is ready to reach an agreement in the wake of escalating US threats during a tenuous ceasefire.

But Trump once again backed down, saying Monday that he had put plans for an imminent resumption of attacks on hold at the request of Gulf Arab states because “serious negotiations are now taking place, and that, in their opinion, as Great Leaders and Allies, a Deal will be made, which will be very acceptable to the United States of America, as well as all Countries in the Middle East, and beyond”.

Although he said he had called off strikes planned for Tuesday, Trump kept up the bravado, saying he told military leaders “to be prepared to go forward with a full, large scale assault of Iran, on a moment's notice, in the event that an acceptable deal is not reached”. Trump has repeatedly set deadlines for Tehran and then backed off.

Despite growing internal unrest, a crippled economy and the deaths of many of its leaders, there is no evidence Iran is set to meet Trump's demands — many of which it has long rejected. In fact, it has dug in.

That has left Trump's stated top objectives unrealised: Iran has yet to agree to abandon its nuclear programme or its ballistic missile development, or cease support for its proxies in the region, including those in Gaza, Iraq, Lebanon and Yemen.

The White House on Monday defended the president's approach, saying, “Trump's preference is always peace and diplomacy” but he will only accept a deal that puts America first.

“President Trump holds all the cards and wisely keeps all options on the table to ensure that Iran can never have a nuclear weapon,” spokesperson Olivia Wales said in a statement to The Associated Press.

Crucially, Iran still has a chokehold on the Strait of Hormuz, the vital shipping lane for global oil supplies, even as the US military has enforced its own blockade on Iranian ports.

The wild shifts in the global energy market that followed have raised gasoline prices, hurting US consumers and causing potential problems for Trump's Republican Party ahead of congressional midterm elections in November.

Trump's playbook of turning up the pressure — economically and militarily — to bend foreign governments to his will is not playing out in Iran as it has in Venezuela, Cuba and elsewhere.

Oil blockades have squeezed those two countries and the Trump administration quickly ousted Venezuelan leader Nicolas Maduro, but they do not hold a bargaining chip as effective as Iran's control over the Strait of Hormuz.

With the Iran war driving up costs for Americans, Trump's approval rating on the economy has slumped, according to an AP-NORC poll conducted last month, with even Republicans showing less faith in his leadership.

For all of Trump's rhetoric, Iran has been unwilling to accept limitations on any of its policies that amount to more than what it conceded during the negotiations for a nuclear deal with world powers during the Obama administration.

Trump called it the “worst ever” agreement negotiated by the US and pulled out of it in his first term in 2018.

Since a fragile truce in the war went into effect last month, Trump has lashed out over the slow pace of negotiations to reach a permanent deal.

“For Iran, the Clock is Ticking, and they better get moving, FAST, or there won't be anything left of them,” Trump posted on social media Sunday shortly after a call with Israeli Prime Minister Benjamin Netanyahu.

The Iranian response was quick. “Our armed forces' fingers are on the trigger, while diplomacy is also continuing,” Mohsen Rezaei, a military adviser to Iran's supreme leader, said on state television.

Ali Vaez, Iran director at the International Crisis Group who has watched years of fruitless diplomacy between Washington and Tehran, said the longtime adversaries do not see themselves as being defeated by the latest conflict.

“Since the ceasefire took effect, both Washington and Tehran seem to be working on the assumption that time acts in their favour: Each believes that the blockade and counter-blockade in the Strait of Hormuz raises the costs for the other side, while giving a reprieve to prepare for a potential resumption of hostilities,” Vaez said.

Despite the impact of America's economic pressure campaign, Iranian officials have not reached the pain threshold “to the point of accepting what it perceives as capitulatory demands,” he said.

David Schenker, a former assistant secretary of state for the Middle East in Trump's first administration who is currently at The Washington Institute for Near East Policy, described the current situation as “a stalemate".

He said Trump likely has “misgivings” about returning to full-on military conflict, especially because of Gulf Arab anxieties about Iranian retaliation and the volatility in the energy markets, with its political implications in the US.

Rich Goldberg, an Iran hawk and former National Security Council official in both of Trump's administrations who is now with the Foundation for Defence of Democracies think tank, insisted that Trump is still operating from a position of strength, including with the Strait of Hormuz.

Goldberg, who has a special interest in American energy dominance, said that while reopening the strait would ease the “pain at the pump” felt by many Americans, it was not critical.

“The short-term pain at the pump is distracting people from US overall energy dominance,” he said. “This is not a permanent crisis.”

Published on May 19, 2026