There is a particular kind of hubris that afflicts powerful states on the eve of a war they expect to win quickly. It is the conviction that the enemy will behave according to the planner’s model rather than its own military and defence strategies. The Trump administration carried that conviction into Iran on 28 February 2026, and it has spent every week since discovering, expensively, how wrong it was.
The plan was never made fully public, but its outline was legible. Trump was still high on the opiate of Venezuela, where he decapitated the leadership without opposition and took control of the country’s oil. He would seek to do the same in Iran, then shatter the nuclear and missile programmes, trigger a popular uprising, and emerge with a compliant regime, a reordered oil market, and a useful new lever over China, Iran’s largest crude buyer. An Israeli plan, apparently devised by Mossad chief David Barnea and adopted by Netanyahu, anticipated that several days of strikes and assassinations would galvanise the Iranian opposition into a mass uprising that would topple the government. Overwhelming force, the theory ran, would do the rest.
It has not worked out. More than three months on, the United States is not winning this war in any sense its own architects would recognise. A harder reading is that it has already lost the war it intended to fight, and is now stuck inside a different, uglier one it never planned for, one that can only be mitigated by humiliating retreat.
The mirage of regime change
Start with the central conceit: regime change. The strikes did kill Iran’s leadership. They killed Supreme Leader Ayatollah Ali Khamenei, whom Trump called “one of the most evil people in history,” along with senior figures including Ali Larijani and Basij commander Gholamreza Soleimani. Trump initially leaned into the project with characteristic bluster. “We want to go in and clean out everything,” he told NBC News in March of this year. “We don’t want someone who would rebuild over a 10-year period.”
Iran’s response was to demonstrate, quickly and pointedly, that a regime is not a roster of names. Tehran announced that Mojtaba Khamenei, the dead leader’s son (who was injured, but survived), would take over as supreme leader – an unmistakable signal that it had no intention of backing away from the theocratic system at all. A Politifact article from March describes foreign-policy and military experts who were near-unanimous: regime change is about changing governing institutions, not just changing (or killing) personnel, and Iran’s government structure has shown no sign of loosening its grip or shifting its ideology.
Faced with this, the administration did what administrations do when the original goal becomes unreachable: it changed the goal. Officials began deflecting questions about regime change towards narrower military objectives; Trump backed away from his earlier demand for unconditional surrender, saying that it did not matter whether Tehran actually surrendered, provided that the US held a position of dominance. Then, when negotiations stalled, he reversed again. By April he was insisting both that he had never sought regime change and that he had achieved it: “We never said regime change, but regime change has occurred because of all of their original leaders’ death – they’re all dead.”
A war aim that mutates this freely is not a strategy. It is the absence of one.
Another problem is that the war revealed the United States to be fighting on the wrong side of the cost curve. Iran could not match American airpower. It did not try. Instead, it reached for the weapon that has rewritten the rules of every recent conflict: the cheap, mass-produced, one-way attack drone, which should have been evident from the prosecution of the Ukraine–Russia war.
Iran relied heavily on low-cost systems, especially the Shahed-136, deployed in large numbers against the US and its allies across the region, including Israel. Each Shahed costs only tens of thousands of dollars. The defending side does not enjoy comparable economics. Gulf states that had poured fortunes into conventional militaries found themselves firing $4 million missiles to bring down drones costing $50,000 to build. No air-defence budget on earth survives that exchange rate indefinitely. Analysts now describe this as the era of “precise mass” – the high-volume use of low-cost, increasingly autonomous systems with high-accuracy guidance. As one assessment put it, Iran’s one-way attack drones demonstrated that even a heavily degraded force can maintain offensive capability and shift the balance through persistent, low-cost attrition.
And then there was the most consequential action of all – the Strait of Hormuz, where Iranian harassment choked one of the world’s critical oil arteries and sent fuel prices climbing across three continents: the precise opposite of the oil-market windfall the planners had imagined. There were many analysts and military professionals who predicted this, but no one was listening. Why?
Purging expertise
It was because all of this unfolded inside a Pentagon that the administration had spent a year systematically hollowing out. Long before the first strike, Defence Secretary Pete Hegseth (a hopeless military amateur by any standards) had fired or forcibly retired 24 generals and senior commanders, with no performance-related reason given: a purge framed explicitly as the removal of a culture he denounced as “woke”. At Quantico in September 2025, he told assembled commanders to resign if they did not support his agenda.
When the war began, the purge intensified rather than paused. Hegseth removed the Army’s top general and two other senior officers in a wartime shake-up as the Iran conflict escalated. The danger here is not abstract. Removing senior officers during active operations badly compromises escalation management: the disciplined business of pursuing objectives while avoiding the red lines that trigger catastrophic responses. A war fought against an asymmetric adversary, with no fixed objective, is precisely the war in which experienced professional judgement matters most. It had been shown the door.
The American public, for its part, never bought the premise. A Pew survey found 59 per cent saying the US made the wrong decision in using force; a Reuters/Ipsos poll put disapproval at 61 per cent. Quinnipiac found 74 per cent opposed to sending ground troops, with more than three-quarters expecting the action to provoke a terrorist attack on US soil. By April, even support among non-MAGA Republicans was sliding, and Americans watching their petrol prices climb were markedly more likely to oppose the war.
One could scratch deeper still: the shock of Iranian ordnance falling on US bases and those of its allies in the Middle East, the loss of US aircraft and death of personnel, the absence of an organised pro-US Iranian civilian swarm, the fact of ally Spain closing its airspace to the US military. And irony of ironies, a confidential IAEA report saying that nuclear development in Iran is less verifiable than it was before the war; a complete monitoring blackout.
What happened, in the end, is the oldest story in the catalogue of military disaster. A powerful state mistook firepower for strategy, assumed its enemy would collapse on schedule, assumed geopolitics would remain predictable for the duration of the war, and then gutted the very professionals who might have warned otherwise. The attack on Iran was supposed to be easier than this.
Notwithstanding Trump’s multiple proclamations that a deal is imminent, as I write, the rockets have started and stopped and started again in the region, with no end in sight. Peace seems as far away as ever. And the US cannot really look the other way – they built it and own it.
The word quagmire comes to mind, so memorably used in the Vietnam War. There seems to be no way out for Trump except to turn tail, skulk home humiliated, and try to declare victory anyway to his gullible but shrinking base.
Steven Boykey Sidley is a professor of practice at JBS, University of Johannesburg and a partner at Bridge Capital and a columnist-at-large at Daily Maverick, Daily Friend and Currency News. His new book “It’s Mine: How the Crypto Industry is Redefining Ownership” is published by Maverick451 in SA and Legend Times Group in UK/EU, available now.
[Image: Pedro Farto for Unsplash]
The views of the writer are not necessarily the views of the Daily Friend or the IRR.
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