Has Trump Thought Through the Endgame in Iran?
“All I want is freedom for the people,” President Donald Trump told a journalist, early on Saturday, not long after launching a joint military operation with Israel against Iran. Trump was talking about ordinary Iranians, subjected for almost half a century to a repressive theocracy—a regime that, just weeks prior, had carried out a brutal crackdown on Iranian protesters which possibly saw tens of thousands of people killed. Much like another U.S. President whose Middle East misadventures he often denounced, Trump was already styling himself as a liberator.
If not liberated, Iranians woke up on Sunday to a stark new reality, as Iranian authorities confirmed that the sweeping round of strikes had killed Iran’s Supreme Leader, Ayatollah Ali Khamenei, along with a cadre of other top officials. Khamenei, a clerical despot driven by rigid dogma and a ruthless instinct for survival, had been in power since the fall of the Soviet Union, his legacy shaped by years of geopolitical isolation, the shadow wars he waged abroad, and the uprisings he quashed at home. Trump cheered the news in a social-media post: “Khamenei, one of the most evil people in History, is dead.” In Iran, a state television anchor declared that “the leader of the great nation of Iran, the vanguard of the Islamic Ummah, his excellency Imam Khamenei drank the nectar of martyrdom and in the month of Ramadan ascended to the highest heaven.” A trio of surviving officials—President Masoud Pezeshkian; the judiciary chief Gholam-Hossein Mohseni-Ejei; and a jurist from the Guardian Council, Iran’s constitutional watchdog—will guide a transition.
For Trump and the Israeli Prime Minister, Benjamin Netanyahu, the decapitation of such a totemic figure as Khamenei marks a moment of triumph. It boosts Netanyahu’s warfighting image at home and will help Trump wave away any reminders of his own lengthy rhetorical record opposing costly regime-change wars in the Middle East. And it will further obscure hand-wringing over the apparent illegality of his intervention, which triggered an emergency session of the U.N. Security Council on Saturday and elicited a chorus of objections from congressional Democrats over the President’s misuse of war powers. After weeks of planning, the U.S. and Israel had decided to strike an Iranian regime that was already enfeebled by recent rounds of conflict, infiltrated by foreign intelligence assets, and vulnerable, more than ever, to U.S. and Israeli airpower. Fresh off the defenestration of Venezuela’s Nicolás Maduro, Trump also seemed convinced of his singular ability to dictate terms on the world stage. Trump whisperers in Washington appealed to his ego and his earlier declarations of support for Iranian dissent. “It is my strong view that history is watching every move we make,” Senator Lindsey Graham, an inveterate Iran hawk, wrote in a Fox News opinion piece, last week. “If we follow through by sending help to the protesters risking their lives, we will have a 21st Century Berlin Wall moment.”
For many Iranians, Khamenei’s exit is welcome, a symbolic end to an overly long chapter in the story of their country’s decaying revolution, and the first step toward a new political future. But it’s not a death knell for the Islamic Republic. Khamenei, an ailing octogenarian, frequently spoke of his willingness to be martyred, and regime officials have claimed that Israel already tried to target them last summer, when Israel and Iran traded strikes in what would become known as the Twelve-Day War. “This was coming, and the Iranians knew it was coming,” Vali Nasr, a professor of international affairs and Middle East studies at the Johns Hopkins School of Advanced International Studies, told me. “The U.S. has to go much farther than just killing Khamenei to paralyze the Islamic Republic.”
The U.S. and Israeli attack on Iran, on Saturday, convulsed the Middle East in a spasm of interstate violence. Iran launched retaliatory missiles and drone strikes against targets in Israel, while also striking Gulf metropoles, hitting civilian infrastructure—such as airports and luxury hotels in Dubai—and targeting U.S. military facilities in Bahrain, Qatar, and Kuwait. (These retaliatory strikes have resulted in at least four confirmed deaths: three foreign nationals in the U.A.E., and one person in Kuwait.) At least two hundred Iranians are dead, including many children, following the destruction of a school in southern Iran. At least nine people were killed in Israel, after an Iranian missile strike on the city of Beit Shemesh. On Sunday morning, U.S. Central Command confirmed that three U.S. service members had been killed, and five had been wounded, as part of the attacks on Iran, which are ongoing, with Israel carrying out more air strikes on Tehran. Trump warned that “heavy and pinpoint bombing” could continue through the week, if necessary, though he also told The Atlantic that he was open to negotiations with Iran’s reconstituted leadership.
“One should not be dazzled by the military advantage America and Israel have displayed in the early hours of this conflict,” Emile Hokayem, of the International Institute for Strategic Studies in London, wrote. “What matters is how the war ends—and Trump’s America is not likely to manage the long-term regional mess it is creating.”
There’s little evidence that the Trump Administration has thought through the endgame. Analysts contend that Israel can live with a fragmented, weak Iranian state, whose military assets it can destroy when it sees fit, as is the case with Israel’s periodic bombardments of Syria. But the United States and, moreover, its Gulf allies don’t want to see a total collapse of a country of more than ninety million people. “What regional states and European states are fearing, but not talking about, is an exodus of Iranians from a very unstable post-Islamic Republic Iran, and infighting around Iran’s borders that certainly can also spill over into neighboring countries like Turkey, Pakistan and Afghanistan,” Sanam Vakil, the director of the Middle East and North Africa Programme at Chatham House, a British think tank, told me.
There are few useful precedents to help chart the path forward. Trump may hope for a similar outcome to what followed Maduro’s extraordinary rendition from Venezuela, with the once hostile regime in Caracas reconfiguring itself, under acting President Delcy Rodríguez, into a quasi-clientelistic arrangement with Washington. But, as Vakil told me, “there are no Delcy-like figures in Iran.”
The air campaign over Iran also recalls the NATO-led intervention into Libya in 2011, which led to the ouster and killing of the long-ruling dictator Muammar Qaddafi. But, unlike in Libya, there’s no major rebellion under way inside Iran, nor even a coherent opposition and, absent mass defections from the security forces, little prospect of an armed challenge to the regime gaining significant ground on its own. And then there’s the legacy of the calamity that followed in Libya, with Qaddafi’s ouster paving the way for more than a decade of failed governance and prolonged civil strife.
Outside Iran, some of the diaspora and opposition groups have coalesced around Reza Pahlavi, the son of the Shah dethroned by the 1979 Revolution. Pahlavi has cast himself as a figure of unity who can shepherd Iran’s political transition. But he is already a divisive character outside the country and has minimal influence within. As Ervand Abrahamian, a historian of Iran and professor emeritus at the City University of New York, noted in a recent conversation that we had, history offers few happy examples of monarchical restorations after a long revolutionary interlude. The most recent example, he suggested, could date as far back as the Bourbons being installed in Paris after Napoleon’s defeat in 1815—but that required the deployment of hundreds of thousands of Prussian, Russian, and other Allied troops to buttress the royalist return. Neither Trump nor Netanyahu nor any Middle Eastern leader would want to participate in such an occupation.
For now, with Iran’s regime backed into a shrinking corner, the potential for a destabilizing conflagration is real. “There is a danger of a regional war in which Iran attempts to destroy the positive things that have been built in the Gulf and to go after oil installations to spike the price of oil,” Karim Sadjadpour, a senior fellow at the Carnegie Endowment for International Peace, said in an interview with Foreign Affairs. “Israel is better equipped to defend itself because of its military prowess and its distance from Iran, but those Gulf countries are more vulnerable.”
The scenes of chaos in expat-clogged places like Doha and Dubai represent a kind of worst-case scenario for leaders of the Gulf monarchies, who want the world to see their glittering kingdoms as oases of stability and prosperity, Kristian Coates Ulrichsen, a Middle East expert at the Baker Institute for Public Policy at Rice University, told me. It also complicates the Trump Administration’s own significant dealings with wealthy Arab royals, which include major rounds of investment in U.S. tech companies and some of Trump’s own family enterprises. A prolonged conflict has “consequences for U.S. credibility as a mediator, as a negotiator,” Ulrichsen said. “We saw after the Iraq invasion in 2003 how credibility takes a long time to be restored when something of this magnitude happens.”
Until the weekend, it seemed there was an off-ramp. Oman’s Foreign Minister, Badr Albusaidi, conducted a last-ditch mission to Washington, meeting with Vice-President J. D. Vance and appearing Friday on CBS’s “Face the Nation,” where he said that a substantive agreement between Iran and the United States was “within our reach.” He suggested that Israeli and American fears over a potential Iranian nuclear weapon would be assuaged, that Iran’s stockpiles of enriched uranium could be secured, and the parties in dispute could settle terms “peacefully and permanently.”
The indirect talks staged between Trump’s envoys and Iranian counterparts now seem something of a smoke screen for what was already in motion: a concerted U.S.-Israeli plan to hit Iran, not dissimilar from the strikes in June that also happened during ongoing negotiations with Tehran. Amid the fog of war, Albusaidi recognized that the diplomatic track he had been trying to furrow as an intermediary had come to an end.
“I am dismayed. Active and serious negotiations have yet again been undermined,” Albusaidi wrote on X, on Saturday morning. “Neither the interests of the United States nor the cause of global peace are well served by this. And I pray for the innocents who will suffer. I urge the United States not to get sucked in further. This is not your war.” For Trump, having taken this course, the war is very much his own. ♦