Billions in frozen assets may be handed back to Iran. Agreements to limit Tehran’s nuclear program may eventually expire. And some of the same hard-line leaders who crushed nationwide protests in January could end up better-resourced than they were before President Donald Trump unleashed crushing airstrikes more than seven weeks ago.
After a decade of fiercely attacking a previous deal with Iran, Trump, pursuing a way out of a war he launched, has authorized U.S. negotiators to consider a bargain that involves many of the same trade-offs one of his predecessors confronted.
Though talks appear paused for now following Trump’s decision on Tuesday to extend the ceasefire indefinitely while Iran comes up with a “unified proposal,” the president will likely face the same challenges no matter when negotiators eventually sit down with each other.
With the conflict on hold, the uneasy truce could solidify. But shipping through the Strait of Hormuz has not returned to normal levels amid a continuing U.S. blockade of Iranian ports and Iran’s assertion of control over the shipping lanes. That has created a drag on global energy markets. Iran retains control over its trove of highly enriched uranium, which Trump has previously said is unacceptable.
The potential terms of a deal have Trump making efforts to shore up his hard-line support as Iran hawks warn that the president should not be too eager to strike a deal.
“‘Pallets of cash’ without the pallets,” Peter Doran, a senior adjunct fellow at the Foundation for the Defense of Democracies, wrote on X, reviving a long-used Republican criticism of President Barack Obama’s Iran deal, the Joint Comprehensive Plan of Action, or JCPOA, to attack the proposals currently under discussion.
Trump and other Republican critics of that 2015 deal have spent the past decade blasting it for handing “pallets of cash” to Iran — a reference to $1.7 billion that the Obama administration agreed to send to Tehran that was the resolution of a decades-old business dispute. Obama administration officials later acknowledged they hoped the money would ensure the Iranians held to their side of the bargain. Trump pulled the United States out of the agreement in 2018.
Now, the Trump administration is floating the possibility of unfreezing $20 billion — in part proceeds from Iranian oil sales that sanctions have locked up in banks around the world. The money would be a bargaining chip to secure Iran’s stockpile of highly enriched uranium. But other elements of the deal are still in question — including points that unsettle some of those who criticized the earlier agreement.
“They’re running into the same fundamental hurdle that shaped the long decade-plus of negotiations that finally led to the JCPOA, which is that the Iranians are completely immovable on the question of enrichment” of nuclear fuel, said Suzanne Maloney, a vice president of the Brookings Institution who is an Iran expert.
Iran has long denied that it seeks a nuclear weapon but argues that it has a right under international law to enrich uranium or other nuclear materials to run a civilian nuclear program.
The Iranians are “prepared to accept certain compromises in terms of timelines and level of enrichment and what happens to the stockpile,” Maloney said. “But they are completely unwilling to simply give up enrichment. And that was one of the core critiques of the 2015 deal.”
Trump publicly insists that his deal won’t share the flaws he had denounced in his predecessor’s agreement.
The 2015 deal “was a guaranteed Road to a Nuclear Weapon, which will not, and cannot, happen with the Deal we’re working on,” Trump wrote on Truth Social on Monday, adding, “The DEAL that we are making with Iran will be FAR BETTER.”
“If a Deal happens under ‘TRUMP,’ it will guarantee Peace, Security, and Safety, not only for Israel and the Middle East, but for Europe, America, and everywhere else. It will be something that the entire World will be proud of,” he wrote.
The political risks, however, are significant, both for Trump and for Vice President JD Vance, who has taken a leading role in the negotiations as he contemplates his desire to win the presidency in 2028.
The vice president, long a proponent of maintaining a restrained approach to U.S. military action around the world, was among the most skeptical of launching a war with Iran in the lead-up to the February attacks by the U.S. and Israel. Now he has been charged with ending it — and potentially owning whatever painful compromises may be necessary.
The White House efforts to seek a deal have put some of its supporters in a tricky place, especially while money is being floated as a bargaining chip.
“You fall into a slippery slope where you forget the money is fungible, and so you know, whether it’s $20 million or $10 billion or $6 billion in the end, if it’s a regime that has not given you a concession on a key illicit activity, like sponsoring terrorism or producing something of a threat, there will always be an argument that ‘Did you free up X amount of money here to pay for this?’” said Richard Goldberg, who worked on Iran issues in the first Trump administration and worked on Trump’s National Energy Dominance Council for part of last year.
“Then you free up that amount of money over there to pay for something else. And so, you know, there will always be an argument that you’re indirectly subsidizing the illicit activities that they have not halted,” he said.
But he said that if Trump can secure the highly enriched uranium and dismantle a deeply buried nuclear facility under construction at an Iranian site known as Pickaxe Mountain, “that’s pretty game-changing. You basically, at least for now and for the next several years, have eliminated the nuclear threat that Iran poses.”
In addition to the nuclear issue, Trump wants a new deal to tackle issues that Obama’s negotiators left aside. The Obama-era deal was always limited in scope to Iran’s nuclear program. It left untouched Iran’s missile program and the regime’s support for regional proxies including Hamas and Hezbollah, which Trump has said he wants a new deal to cover.
The president has also said he hopes to bar Iran from any nuclear enrichment at all. If Iran were to agree to a temporary moratorium, that would be stricter than the 2015 deal, which allowed Iran to maintain its civilian enrichment program for use in its power plants.
“The asks by Iran are going to be greater than they were in 2015, in part because the administration is trying to do so much,” said Wendy Sherman, who was the lead U.S. negotiator with Iran under Obama. “It’s not clear to me what Trump’s bottom lines are. Is it a stockpile? Is it enrichment? Is it missiles? Is it proxies? Is it the Strait of Hormuz?”
“If he gets a suspension of 10, 15, 20 years of enrichment, we did not get a suspension of their enrichment program, so that will be more than we got on that element,” Sherman said. “But how will it be verified? It’s totally unclear to me or anybody, probably to him. And what will Trump have to give in return?”
Complicating matters further, the world has changed in the 11 years since Secretary of State John F. Kerry and Iranian Foreign Minister Mohammad Javad Zarif strode smiling out of a genteel hotel in Vienna having struck a deal. After years of talks, Iran agreed in 2015 to accept strict limits on its nuclear enrichment, in exchange for gradual relief from economic sanctions.
Back then, Iran had no highly enriched uranium. In the years since Trump pulled out of the JCPOA, it built a stockpile of about 970 pounds of uranium enriched to 60 percent — just short of weapons-grade level, according to the International Atomic Energy Agency.
Iran’s current government is also more hard-line than the reformist leaders who made the deal with Obama.
Tehran has been deeply weakened by aggressive military action over the past year: first the 12-day war with Israel in June that was punctuated by Trump’s strikes on nuclear facilities, and now the U.S. war that Trump says has destroyed much of Iran’s military, along with its top ranks of leaders. Its regional proxies Hamas and Hezbollah are far weaker. A major backer, Russia, is distracted by the war in Ukraine.
That could soften the ground for a deal. But Iran, too, has bargaining chips. The Iranian regime has demonstrated its staying power — and it has unleashed a powerful new ability to throttle shipping traffic through the Strait of Hormuz, driving up energy prices around the world, including in the United States. Facing withering U.S. attacks, some hard-liners in Tehran may be more inclined to seek a nuclear weapon, increasing pressure on Washington to address the uranium stockpile.
There are also dynamics that may make Tehran less inclined to strike a deal, said Richard Nephew, a former State Department official who helped craft the sanctions regime against Iran under the Obama administration that built pressure for an agreement.
“In a funny way, the war almost releases some of the pressure on Iran,” said Nephew, who is now a senior research scholar at Columbia University.
“They have demonstrated that they can take a punch and that they can respond accordingly,” rather than fearing what form U.S. pressure on them might take, he said. And the Islamic Revolutionary Guard Corps, the more hard-line part of Iran’s ruling elite, is now firmly at the fore, eliminating the tension with moderates that previously created space for negotiations.
Nephew is a proponent of the 2015 deal. But he said that he was leery of striking a fresh agreement with the new group of Iranian leaders.
“I’m not so sure it’s a fabulously great idea that after the January protests, we should be looking to do major sanctions relief for the Iranian government that killed all those people,” Nephew said.
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