Trump asked questions of Iran when he did not know the answers. Now he must pay the price
The president started a war in the Middle East without considering foreseeable risks. The US memorandum of understanding with Iran leaves many of the repercussions of that miscalculation unaddressed.
There is a maxim every trial lawyer learns early in their career: ‘Never ask a question you don’t already know the answer to’. In Operation Epic Fury, US President Donald Trump violated this fundamental principle.
Trump is not the first US president to misjudge an endeavour in the Middle East. From George H. W. Bush to George W. Bush, to the Biden era view that the ‘region is quieter today than it has been in two decades’, successive US administrations have all searched for peace in the Middle East through war, sanctions, economic leverage and diplomacy – and all failed to secure a lasting, favourable outcome.
On 28 February 2026, Trump thought the main question was: ‘Will the Iranian regime be compelled into compliance with US demands through the use of overwhelming military force?’ He hoped – but did not know – that the answer was ‘yes’: that the US and Israel could wage a quick military operation lasting four to six weeks, grounded in a set of objectives that included destroying Iran’s missile industry and navy, neutralizing Iran’s regional proxy network, and ensuring Iran could not obtain a nuclear weapon.
Also at the heart of Trump’s ambition was an ideological attachment to seeing regime change in Iran. The president believed the operation would put in motion the first domino in a chain that would lead to the collapse of Iran’s Islamic Republic.
Launching the war, he asked an explicit question of Iran’s citizens – another which he did not know the answer to. Were they capable of seizing the opportunity the US was providing and overthrowing the Iranian regime? ‘So let’s see how you respond,’ he said.
Negotiations over the last year have made clear that the US and Iran are rarely on the same page or even reading from the same book.
But the conflict and its outcome were never for Iranian civilians to decide. As Iran’s leadership structure faced early decapitation and personnel losses, it reconstituted itself and adopted a ‘nothing to lose’ approach.
Iran exported the conflict across the region using ballistic missiles and drones and disrupted global markets through a de facto closure of the Strait of Hormuz. This strategy of horizontal escalation re-established leverage for Iran. For Trump it meant digesting tactical success but strategic failure.
Now the US and Iran have agreed to a Memorandum of Understanding (MoU) to extend the April ceasefire 60 days and ‘reopen’ the Strait of Hormuz, while providing a framework for additional negotiations between the parties.
Negotiations over the last year have made clear that the US and Iran are rarely on the same page or even reading from the same book. Yet Americans, regional players and the market are meant to believe that after successive failures and false starts, negotiations have turned the corner.
The MoU rests on very little common understanding and is already raising scepticism among the US intelligence community and in Israel. What comes next will be more telling than what has already been achieved.
Re-establishing a timely, safe and open passage through the Strait of Hormuz represents the most pressing test. But the US and Iran have a host of open items to address in the coming months – including all the questions left unanswered by the war: What is to be done with Iran’s stockpile of enriched uranium (the ‘nuclear dust’)? What is the future of Iran’s nuclear programme, sanctions relief and frozen assets? Will Iran be persuaded to halt its support for its regional proxies? And what are the prospects for genuine peace in the Israel–Hezbollah theatre?
With trust between the conflicting parties so weak, the door remains open to a range of scenarios. Negotiations may fall apart during the 60-day ceasefire extension – perhaps over fighting in Lebanon. The ceasefire may be extended again to allow for more meaningful progress on negotiations. Or a peace deal may be reached with deeply compromised terms that fail to resolve the outstanding issues.
For Trump, the MoU announcement comes as a relief. It has been clear for weeks that the conflict in Iran has been testing the president’s patience, as he seeks to focus on other items on his agenda.
Can the deal between US and Iran become a lasting settlement?
Atop the list is America’s 250th birthday in just a few weeks, and November’s US mid-term elections. American support for Operation Epic Fury peaked at around 40 per cent and has been waning over the last month.
Polling indicates that voters have consistently been more concerned with the state of the US economy than the state of the Middle East. Any easing the MoU brings to prices at the gas pump and on inflation will play favourably at home. On the international stage, Greenland remains of interest to Trump, as does Cuba.
In the coming weeks, analysts will draw comparisons between the MoU (and any follow-on negotiations) and the Obama-era Joint Comprehensive Plan of Action (JCPOA).
Trump has repeatedly referred to the JCPOA as ‘the worst and most one-sided transaction the United States has ever entered into’. The truth of how any new arrangements stack up to the JCPOA will be complex and complicated, but for now remains unmmeasurable.
Dr Lindsay Newman is a geopolitical risk expert, thought leader and an Associate Fellow, US and North America Programme, Chatham House, London. This article was first published by Chathamhouse.org on 17 June 2026.
