Negotiators are pessimistic Iran will bend to meet President Trump's demand to reopen the Strait of Hormuz before his Tuesday-night deadline, paving the way for the U.S. to target Iranian bridges and power plants in a fresh escalation of the war.
Twice in his second term, Trump set a deadline for a deal with Iran, said he would bomb the country if its leaders didn't comply, then followed through with military operations.
Now, as everyone from Vice President JD Vance to top Middle Eastern spy chiefs push for a last-ditch cease-fire, Iranian officials are telling mediators they expect the same pattern to play out again, U.S. officials and mediators said. Trump also could extend the deadline, something he has also done multiple times already.
Some U.S. officials say there is too large a gap to narrow between the U.S. and Iranian positions before Trump's 8 p.m. Tuesday deadline. Meanwhile, Iranian officials have told mediators that they expect the U.S. will continue to attack targets in their war-torn country and Israel to keep conducting airstrikes to take out senior Iranian officials -- even if negotiations with the U.S. move forward, Arab officials familiar with the matter said.
Iran was "negotiating, we think, in good faith," Trump told reporters Monday at the White House, but if not the U.S. would be "blowing everything up."
Some U.S. officials said Trump has privately been less hopeful that Iran will make a deal, expecting to issue final orders for strikes Tuesday evening -- though they note his assessment could change based on how talks play out overnight.
"Only President Trump knows what he will do, and the entire world will find out tomorrow night if bridges and electric plants are annihilated," said White House spokeswoman Anna Kelly.
Hopes for a deal soured Monday morning after Iran rejected a U.S. cease-fire proposal, claiming Washington sought maximalist concessions, including on its nuclear work. Trump later told reporters Tehran's counter wasn't enough to secure an agreement.
Both countries were once again in the familiar position of staring down a deal, deadline extension -- or more war.
Last June, Trump cut off talks with Iran over its nuclear work and struck three of its nuclear sites. Then in February, after a month that saw an extensive U.S. military buildup, he again accused Tehran of stalling for time in nuclear talks and launched the current war.
The episodes have made Iranian officials skeptical that Trump is serious about negotiations in this round. They also point to how the U.S. hasn't stopped Israel from continuing to attack Hamas targets in Gaza even after reaching a cease-fire last year. Tehran still expects Israel to target senior Iranian leaders even if serious negotiations proceed.
U.S. officials counter that if Iran showed a serious desire to end its nuclear program, it wouldn't have triggered the war in the first place. The officials said the U.S. would face significant hurdles in getting Tehran to agree to a cease-fire, because the Iranian regime sees its survival is at stake and thinks it retains leverage over the U.S. through the global economic pressure of blocking maritime and energy trade through the Strait of Hormuz.
Escalating the war carries significant risks for the U.S., including hardening the Iranian regime's resolve against negotiations, prolonging the shutdown of the strait and expending more of its diminishing stockpile of high-end munitions in global demand.
Trump is itching to end the war, U.S. officials have said. The president realizes the American public has a limited appetite for more military operations, telling reporters Monday he would prefer to keep Iran's oil but knows there is widespread opposition for a long-term deployment in Iran. In addition, Republicans are quietly telling Trump they fear rising gas prices amid a prolonged Middle East conflict -- which cuts against the president's campaign promises -- could sink their chances in November's midterm elections.
The Iranian regime, meanwhile, faces its own risks in defying Trump's demands, U.S. officials said. Iran would endure a devastating new wave of U.S. and Israeli strikes on civilian infrastructure that could further thin the ranks of its leadership and crush an economy already on the brink after decades of corruption and global sanctions.
Trump has said the ultimatum could end the war or prolong it. "It depends what they do. This is a critical period," he said Monday at the White House. Iran could lose all of its bridges by 12 a.m. Wednesday, Trump said, if it doesn't make a deal.
Law-of-war experts and human-rights groups say striking civilian infrastructure with no clear military need amounts to war crimes. Trump said the Iranian people support the actions, claiming they would be upset if U.S. strikes stopped. "They want to hear bombs because they want to be free," he said.
Vance, along with special U.S. envoys Steve Witkoff and Jared Kushner, are involved in the day-to-day talks from the U.S. side as Trump ratchets up pressure on Iran to reopen the strait and agree to a cease-fire to pave the way for longer-term peace talks.
Egypt, Turkey and Pakistan are helping deliver U.S. messages to and from Iran through both formal diplomatic channels and their intelligence services, officials said. A complicating factor is that mediators from those countries have overlapping channels to the Iranian regime. Another is that waves of airstrikes took out numerous senior Iranian officials and government-communication infrastructure, making it difficult for the U.S. to determine which Iranians to negotiate with and how to reach them.
Trump openly acknowledged the problem from Iran's side on Monday. "The biggest problem we have in our negotiation is that they can't communicate," he said.
Still, the U.S. and Middle Eastern mediators say they have a good sense of how decisions in Iran are being made and that is informing their efforts to reopen the strait and broker a cease-fire.
Decisions on any negotiations are being run through Iran's Supreme National Security Council and Ahmed Vahidi, the new head of the Islamic Revolutionary Guard Corps, a U.S. official and other Middle Eastern officials said.
Spy chiefs in Egypt and Turkey, as well as Pakistan's army chief are focusing their mediation outreach on Vahidi and other senior IRGC intelligence officials.
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