Politics
May 30, 2026
Donald Trump, despite his self-proclaimed dealmaking expertise, is struggling to negotiate an end t…
The Failed Dealmaker: Trump's Iran Dilemma
For weeks, Donald Trump has tried to find a way to end the war he started with Iran – a deal that would allow him to declare victory and move past the conflict before it causes severe damage to the global economy and sinks Republican chances in the US midterm elections. But the self-proclaimed master dealmaker can't seem to stop sabotaging his own negotiations or to acknowledge that Iran is now in a better position to demand concessions than it was before the war.
Strategic Missteps: From Military Action to Negotiation Deadlock
Over the Memorial Day holiday, Trump skipped his eldest son's wedding in the Bahamas and canceled plans to spend the weekend at his New Jersey golf club. The last-minute changes heightened speculation that Trump was ready to unveil a deal to end the war. Trump then announced that he would hold a cabinet meeting at Camp David, the presidential compound in Maryland that has been the site of historic diplomatic summits. But that meeting was moved back to the White House, as it became clear that Trump had not been able to close a deal he could announce with great fanfare.
The Art of the Deal: Trump's Negotiation Paradox
Why has an agreement eluded the business titan who wrote the bestselling 1987 book The Art of the Deal? Trump admires strongman leaders and is loth to project any sign of weakness – and he's afraid of reaching a deal with Iran that makes him look weak. The president is also sensitive to criticism that any agreement he negotiates will be worse for the US than the 2015 nuclear deal between Iran and six world powers, which was brokered by Barack Obama's administration.
Leverage Reversed: How Iran Gained the Upper Hand
Trump's main problem is that Iran has more leverage than he does – and Iranian leaders are well aware of that advantage. On 28 February, Trump launched a joint US-Israeli war against Iran, killing the supreme leader, Ayatollah Ali Khamenei, and other top military and political officials. But Iran retaliated with missile and drone strikes against US military bases across the Middle East, and it targeted the energy infrastructure of its Gulf neighbors. Iran also deployed its most effective economic weapon: it closed the strait of Hormuz, through which more than a fifth of the world's oil supply passed each day.
Economic Fallout: Global Disruption and Rising Oil Prices
The closure of the Strait of Hormuz – along with Iranian attacks on pipelines and gas fields in Kuwait, Saudi Arabia, Qatar and the United Arab Emirates – disrupted the global economy and increased oil prices. In the US, average gas prices have jumped by 50%, up to nearly $4.50 per gallon, since Trump launched the war. Trump and his ally, the Israeli prime minister, Benjamin Netanyahu, could not topple the Islamic regime that rose to power after Iran's 1979 revolution. Instead, they ended up strengthening it – by allowing Tehran to deploy its geographic control of the strait of Hormuz into a weapon that could instigate a global energy crisis and a worldwide recession.
The Emerging Deal: Limited Concessions and Unresolved Issues
The emerging deal is focused on solving a problem that didn't exist before Trump started this war: fully reopening the strait of Hormuz to commercial shipping so that oil prices can stabilize. Under a draft agreement being circulated to US allies, Washington would also lift its blockade of Iranian ports and allow Tehran to access about $12bn in frozen assets. Once again, Trump seems to be aiming for a limited deal with Iran that defers the most difficult questions to future talks, which could drag out for months or even years.
Iran's Resilience: Military Strength Preserved
In some ways, Iran has emerged stronger after a war intended to decimate its military capabilities. A CIA report sent to Trump earlier this month found that Tehran had managed to retain a significant part of its missile capabilities. The analysis said Iran preserved about 70% of its prewar stockpile of missiles and about 75% of its mobile launchers. The report also concluded that Iran was more resilient than US officials had claimed, and it could survive a naval blockade for months.
Political Calculations: Midterm Elections and Trump's Dilemma
At his cabinet meeting, Trump said he didn't care about the midterm elections and wasn't in a rush to reach a deal. "It's got to be perfect," Trump told reporters, adding: "I didn't do this to get a crummy agreement." Despite his weak position, Trump insists that he will strike a better deal with Iran than the one negotiated by the Obama administration in 2015. That agreement provided Tehran with relief from international sanctions in exchange for limits on its nuclear enrichment.
The Unintended Consequences: Strengthening the Adversary
Trump could have avoided starting a regime-change war that failed, leaving the world to deal with its consequences. Instead, the master negotiator handed Iran a new economic weapon – and more leverage to extract a favorable deal. The worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood, and then you're dead. Trump wrote in his famous book. The best thing you can do is deal from strength, and leverage is the biggest strength you can have.