A 60-day deadline for Iran to make a nuclear deal with the threat of US military force looms as President Donald Trump says he hopes for a deal even with Iran’s leadership remaining defiant and Israel pushing for military action.
Sound familiar? While déjà vu is technically an illusion of the mind, the above has happened once before. It is both where the Middle East is today, and where it was in April 2025, in the weeks before the first Israeli strikes on Iran last year, and the US attack on its nuclear facilities. The past year may resemble a circle in US-Iranian relations back to the same place, but the trajectory has spiraled downwards, for the US and the region as a whole.
To recap: Trump wrote to then-Supreme Leader Ayatollah Ali Khamanei, in March 2025, suggesting a two-month deadline to make a nuclear deal, or force could follow.
His envoy, Steve Witkoff, flew to Oman in April 2025 to foment diplomacy. The entire project fell apart when Israel’s “Operation Rising Lion” imposed force as the path ahead on June 13. A 12-day war followed, in which Israel took out a large part of Iran’s security apparatus and claimed to have damaged its missile capabilities. The US then struck – and claimed to have “obliterated” – Iran’s nuclear program.
After thousands of lives lost in the past three months – over 3,000 in Iran, about half of them civilian, according to monitoring groups, and over 3,600 in Lebanon, many of them civilians too, according to its health ministry – attempting a Xerox moment of June last year seems brutally, if not foolishly, repetitious.
But Trump has literally tried the same thing twice. And on both occasions he has been bounced into military action by Israeli Prime Minister Benjamin Netanyahu. Trump has emerged from both military campaigns claiming success, and extensive damage to Iran that some of his own intelligence community disputes. Yet the nature of the latest 60-day deadline – an apparent part of the memorandum of understanding – suggests the cycle may repeat itself again.
Two key questions remain for this White House: What has been gained from the past year of violence in the Middle East, and has each cycle of violence made an Iranian nuclear weapon more, or less, likely?
The true test of Trump’s Iran agreement will come only if the fighting stops
The second is easier to answer. Iran surely would – after the assassination of its supreme leader and much of its top security cabinet, together with the onslaught against its conventional arsenal – want a nuclear weapon more than ever. But it is likely further out of reach than in April 2025, when Iran’s enrichment was at a peak, facilities unscathed, and scientific expertise mostly alive. Any bomb now would have to be rushed together under intense US and Israeli scrutiny, with enriched material or equipment retrieved from under the rubble. It is important to remember Iran’s capabilities were underestimated ahead of the US and Israeli attacks of February 28. But building a bomb is a whole new level of sophistication, and Tehran managing to do so in its current moment of crisis and strain would be unlikely, albeit not impossible.
The wider, first question is more nuanced, but its answer provides little comfort for this White House.
Trump now confronts the surviving heirs, or successors, of his dead enemies, and must hope that violence and grief has made them more open to a deal. Supreme Leader Mojtaba Khamenei – whose injury in the strike that killed his father, wife and son, is often derisorily referred to by Trump – would seem an unlikely candidate for quick reconciliation. The United States faced the same issue in Afghanistan, where endless night raids against Taliban leaders left angry, vengeful sons calling the shots, and fewer comparatively moderate elders around when it was time to negotiate.
The lesson of decapitation strikes was not heeded in the February and March attacks: Israel and the United States either did not know who would replace the leaders they killed, did not care or actively preferred to eliminate relative moderates. The succession process has arguably left Iran with more hardliners in power – or at least able to exert influence in the chaos and anxiety of the security measures Iran’s leadership relies on just to stay alive. The humiliating start-stop announcements of a partial deal is evidence to this effect. Trump has had to admit the Iranian chain of command is messy, and that has made the dealmaker’s deal-about-a-deal the subject of about 40 declarations of how close it is.
Iran has been damaged, make no mistake. Its leaders must be on edge, laden with grief, sleeping poorly and battered by sanctions and airstrikes. But the United States has been damaged too, in four key ways.
First, the US military deterrent seems less impactful than four months ago. More than 13,000 targets have been hit, Centcom has said. But still Iran’s ability to cause chaos from drones, mines and missiles is something the United States and its allies palpably fear: less because of material damage than the economic damage of high hydrocarbon prices and a global energy recession. America’s limited appetite for pain has been exposed: it really cannot take more months of high gas prices. Iran’s hardliners are, on the other hand, willing to toy with renewed aerial bombardment, and their possible targeting by precision munitions.
Secondly, the United States’ relationship with a key regional ally, Israel, has been heavily impacted. Netanyahu began in February, it seems, talking Trump into the idea of a swift assault. He ends, according to reporting from Axios, in June on the receiving end of expletives-laden calls, in which the Trump says the Israeli leader would be in prison without his help. The United States, widely criticised under President Biden for not reining in brutal Israeli excesses in Gaza, is now trying to curtail Israeli action in tackling the more existential security challenge to its north with Hezbollah. That is a stunning twist, in and of itself.
Third, Iran has now extended its security umbrella to its proxy Hezbollah in Lebanon, after it struck back at Israel, on June 7, following an Israeli strike on Beirut’s southern suburb of Dahieh, a Hezbollah area. It was the first time, analyst have noted, Iran has hit Israel for attacking another country. The concept of Iran being a protector may, to many Lebanese, seem laughable, given Lebanon was dragged into conflict by the rash actions of the proxy militia when it joined Iran’s war against Israel in March. But the June 7 Iranian attack showed peak strategic confidence in Tehran – when really it should be in a trough.
Fourth is the damage to Trump’s personal reputation. He has begun a war of his own choice that has hacked away at support from his MAGA political base, hit US pocketbooks hard ahead of midterm elections, removed his ability to claim to be the Nobel-aspiring peacemaker, and left him looking a little desperate to get the Iranians to consent again to diplomacy that he’s twice interrupted with bombing.
There is no dispute that US retains the might. The question – as we enter into perhaps the same cycle of 60 days of talks ahead of military action – is whether their wash-and-repeat policy is right, or whether it has left the Middle East, Israel and the United States less secure, and requires a radical reboot.
