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The old men of Iran and America

Donald Trump wants to end America’s half-century conflict with Iran

February 5, 2026

An anti-U.S. mural is pictured at the former U.S. embassy in downtown Tehran, Iran, on January 20, 2026
THE year was 1988, and a businessman from New York and a cleric from the Iranian city of Mashhad were snarling at one another. Donald Trump said the American warships massed in the Persian Gulf should be “harsh” towards Iran. “One bullet shot at one of our men,” he said, “and I’d do a number on Kharg island,” the wedge of land that houses Iran’s main oil-export terminal. Ali Khamenei, then Iran’s president (though not yet an ayatollah), was undeterred: he vowed to make the waterway a “graveyard” for the Americans.
Almost four decades later their rhetoric is unchanged. Mr Trump has deployed what he calls a “beautiful armada” to the Middle East after the Iranian regime ignored his warnings not to massacre protesters last month. Mr Khamenei, in turn, has warned America’s president not to use it. “America should know that if it starts a war, this time it will be a regional war,” he said on February 1st.
Mr Trump wants this to be their last stand-off. Iran has never seemed more vulnerable. Through words or weapons, the president hopes to resolve America’s half-century-long conflict with the Islamic Republic. As for Mr Khamenei, he seems paralysed, committed to a worldview that is outdated. The showdown between these two cantankerous old men will shape the Middle East for a generation.
America’s growing military build-up suggests it is planning something big. The USS Abraham Lincoln, an aircraft-carrier, arrived in the region in late January. Extra refuelling tankers have landed in the Gulf. Fighter jets, destroyers and air-defence batteries have all been dispatched to help parry an Iranian counter-attack.
Yet even as Mr Trump talks up his armada, he seems hesitant to use it. Steve Witkoff, his all-purpose envoy, is due to meet Abbas Araghchi, Iran’s foreign minister, in Oman on February 6th. The meeting was scheduled after a frantic diplomatic effort by Egypt, Turkey and Gulf states, none of which wants a regional war. It suggests that any American strike is still days or weeks away—although the Iranians remember that last summer Mr Trump used the offer of talks as a feint before he bombed their nuclear sites.
Whether diplomacy can succeed will depend largely on the two leaders. Mr Khamenei’s goals have changed little since he became supreme leader in 1989. He wants to ensure the survival of Iran’s clerical regime. In his mind that requires swearing off any compromise, whether political reform at home or a less confrontational foreign policy towards America.
But after two years of tumult such rigidity has left him weakened. His allies have been humbled. His nuclear programme can no longer enrich uranium. His regime is despised at home, killing protesters while it presides over economic and environmental disaster. Mr Khamenei long feared that concessions would bring the regime to collapse—yet his refusal to make them has only undermined it further.
In many ways Mr Trump seems his opposite, a man of no fixed ideology. Still, he has a few bugbears (such as trade deficits) that have animated his politics for decades. Among them is a belief that Iran’s leaders keep getting the better of timid American leaders—“making us look like a bunch of fools”, as he put it in 1988. The Islamic Republic has vexed every president since Jimmy Carter. Mr Trump would like to be the one to settle matters. “It’s always the 1980s for Trump,” says a sympathetic foreign-policy hand in Washington.
He is flexible about how precisely to settle the conflict, though. The preternaturally optimistic Mr Witkoff hopes to make a deal. American officials insist it would have to go much further than the 2015 nuclear pact between Iran and world powers, or even the agreement they tried to negotiate before last summer’s Iran-Israel war. They say the regime would have to curtail not only its nuclear work but also its ballistic-missile programme and support for Arab militias.
Iran insists it will not discuss the latter two issues with America. On February 1st Mr Araghchi told cnn a deal was likely only if America did not chase “impossible” concessions on non-nuclear issues. Some diplomats in the region hope to find a creative workaround. Perhaps Iran could discuss its nuclear programme with America, and then discuss the other subjects with America’s allies in the region, whom America wanted to invite to the talks in Oman.
Yet Iran has balked at that idea, too: Mr Khamenei remains intractable. Any possible agreement with Iran would also be deeply unpopular in Washington, even with Mr Trump’s allies—particularly after the recent violence.
As America gears up for talks, then, the prevailing view in Washington is that those talks will fail. The question is not whether Mr Trump will strike Iran, but what he will strike and when. A few weeks ago it seemed likely that he would opt for a symbolic attack, largely to avoid unflattering comparisons to Barack Obama, who failed to enforce his red line on chemical-weapons use in Syria in 2013.
But the longer the stand-off, the greater the likelihood that the eventual American strike will be a big one. “Trump can’t move all these assets to the region only to bomb some empty Revolutionary Guard bases,” says a Western diplomat in the Gulf. Many observers now believe he may target Mr Khamenei and other top leaders. That could force political change. What sort is anyone’s guess.
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