The latest threat, the latest deal. When it comes to Iran, the problem isn’t just Donald Trump

"They just make me angry. They just make me angry.” Donald Trump said this to journalists last week, referring to Iranian leaders, and there is more analytical truth in that repetition than in any government briefing. It is an unwitting admission of a failure that has spanned Democratic and Republican administrations for forty-six years, and which Trump has brought to its most visible expression.

Every US president since the 1979 Islamic Revolution has attempted to decipher Tehran. Jimmy Carter believed he had secured a deal for the hostages, as documented in his private notes: Ruhollah Khomeini scuppered it without warning his own negotiators, who were just as stunned as the Americans. Ronald Reagan sought out the supposed Iranian moderates through the secret sale of arms. There were no such moderates, and the operation ended in the Iran-Contra scandal. Bill Clinton went so far as to publicly defend the CIA-backed coup of 1953: Ali Khamenei replied that no dialogue was possible with Washington. Barack Obama secured the JCPOA (the 2015 nuclear deal) after twenty months of negotiations – a genuine exception rather than a replicable model.

Trump scrapped the deal in 2018, thereby providing Tehran with definitive proof that agreements with Washington are not worth the paper they are written on.

Kenneth Pollack, a former analyst with the CIA and the National Security Council, has studied Iran for decades. His assessment of Trump is clear-cut: no president has understood the Iranian leadership less. Trump, says Pollack, embodies in an extreme form the contradiction that has paralysed Washington for half a century: he has used more force than any predecessor in pursuit of victory and has been more eager than any predecessor to reach a deal, without achieving either victory or a deal. Dennis Ross, a veteran of Middle Eastern diplomacy who has served under presidents from both parties, sums up the argument: the Iranians understand the Americans better than the Americans understand the Iranians, and they have done so consistently, ever since before Trump entered the White House.

On 28 February, a US air strike killed Ali Khamenei, who had been the Supreme Leader of the Islamic Republic for almost forty years. Trump called on the Iranian people to ‘take control’ of their own government, announcing that he would choose the next leader himself. In March, Iran appointed Mojtaba Khamenei, the son of the late Supreme Leader, as the new Supreme Leader. US officials regard him as more hardline than his father and more determined to equip Iran with a nuclear weapon. Tehran had ignored Trump’s statement that such a choice would be “unacceptable”, and the new Khamenei did not even respond to the offer of a face-to-face meeting.

This is where the second problem arises, one more serious than the first. The strategy that led to Operation Epic Fury (the military campaign launched in February) was based on a specific doctrine, known in strategic circles as the ‘octopus doctrine’: cut off the head, and the tentacles will die. Strike Tehran, the command centre of the Axis of Resistance (the network of armed organisations funded and led by Tehran, from Hezbollah in Lebanon to the Houthis in Yemen and the Shia militias in Iraq), and the groups that make up the Axis will disintegrate. Two decades ago, this logic made sense, when weapons, technology and know-how were channelled through Tehran via a structure that has since transformed into something radically different.

Salisbury, Paes and Thompson argue, on an empirical basis, in one of the most significant papers to have appeared on this conflict, that the Axis of Resistance has ceased to function as a hierarchical system with identifiable points of failure. It has transformed into a self-replicating network, in which knowledge, resources and operational decisions are distributed simultaneously across different locations, so that when a leader is eliminated or a production site is bombed, the network adapts, replaces the killed leader and re-establishes supply chains via alternative routes. Since 2015, Hezbollah has begun to train other groups, including Hamas, the Houthis and Iraqi militias.

In 2026, according to a forthcoming report by Century International, the Houthis are teaching al-Qaeda’s Somali affiliate how to fly drones. The components needed to build the Ababil-T drone can be purchased on Alibaba for around $1,500. For the FPV (First Person View) drones that Hezbollah has been using against the Israel Defence Forces since early 2026, all that is needed is a credit card and access to YouTube, with the difference being that the key bottlenecks for halting this proliferation lie within Chinese supply chains, beyond the reach of US sanctions.

John Bolton, writing in the Washington Post, argues that the correct response is to step up military pressure: to topple the regime in Tehran whilst simultaneously holding the line in Ukraine and increasing deterrence against Taiwan. It is a position that is internally consistent, but it does not explain why five months of intensive bombing have not brought about the expected collapse, nor why Hezbollah is putting up more tenacious resistance than anticipated in southern Lebanon, nor why the Houthis, a year after a truce that Washington had interpreted as a surrender, have resumed attacks in the Red Sea. The ‘octopus’ doctrine worked when the axis was a structured entity. Today, that structure has evolved into a distributed ecosystem that air strikes cannot degrade any faster than it regenerates.

Meanwhile, Iran is playing the card it has always handled better than the Americans: time. For the Iranians, time is on their side. The Americans always seem to be lagging behind their own schedule. Suzanne Maloney, vice-president of the Brookings Institution, put it succinctly: American policymakers have underestimated the ideological commitment and the institutionalised power structure in Tehran, and the war has strengthened the grip of the religious and military leadership by eliminating any credible alternative. What appears to be a dysfunction is in fact the Iranian system functioning exactly as its founders intended.

In this context, the US political calendar becomes a variable that Tehran knows how to interpret and exploit: Trump’s approval rating stands at between 32 and 34 per cent, the lowest of his second term; inflation is running at 3.5 per cent; and the Strategic Petroleum Reserve (SPR) is at its lowest level since February 1983. Tehran has no incentive to negotiate before November, because every poll showing a competitive Democratic candidate in Texas or Alaska puts further pressure on Trump, and the more anxious the president is to reach a deal, the more costly the conditions imposed by Tehran become.

I don’t think the problem is Trump. The mistake predates him by half a century: it has swung between ‘criminal madmen’ and ‘highly intelligent’, and ‘cold-blooded bastards’ and ‘reasonable’, as if the labels changed the nature of the other party, but Carter, Reagan and Clinton had already projected onto Iran what they wanted to see, each with their own version of the same illusion. America looks at Iran and sees a mirror: a country that could reach an agreement if it wanted to, which has its own rational logic that can be corrected with sufficient incentives and pressure, and which has an oppressed people ready to overthrow the regime at the first sign of outside intervention. None of this corresponds to the reality of the Islamic Republic. A political system built on hatred of the United States as its founding principle does not produce moderates waiting to shake hands with Washington. It has produced Mojtaba Khamenei.