After Killing Iran's Supreme Leader, Trump Faces the Hard Question

For the first time in 47 years, Iran's Supreme Leader is dead. But regime change? That's still anyone's guess.

President Trump launched the largest U.S. military operation in the Middle East since the 2003 Iraq invasion today, killing Ali Khamenei in coordinated airstrikes with Israel. In a Truth Social video posted in the early hours, Trump urged Iranians to "take over your government," calling it "probably your only chance for generations."

Yet even with Khamenei eliminated—whom Trump labeled "one of the most evil people in History"—the harder question remains: What happens next?

The "Maximalist" Gamble

This wasn't a unanimous decision. Some of Trump's closest advisers, including Vice President Vance, Joint Chiefs Chairman General Dan Caine, and Pentagon official Elbridge Colby, expressed reservations about the operation. Caine privately warned about the complications of any move against Iran, questioning whether airstrikes alone could undermine the regime.

Chief of Staff Susie Wiles, architect of Trump's 2024 comeback, didn't take a personal position but made sure Trump heard concerns about "unpredictable consequences." Republican midterm strategists are already anxious about foreign military adventures turning off voters who want leaders focused on the economy.

Even yesterday, there was a last-ditch diplomatic effort. Oman's foreign minister met with Vance, hoping to buy more time for U.S.-Iran negotiations that Oman has mediated. This week's Geneva talks had shown progress, but Iran wouldn't accept Trump's demands: destruction of primary nuclear sites, delivery of all enriched uranium to the U.S., and no sunset clauses.

Steve Witkoff, Trump's lead negotiator, concluded further talks were futile. The two sides couldn't even agree on a basic framework.

The Optimistic Assessment

Trump was convinced the odds wouldn't improve over time. Benjamin Netanyahu urged him to act, believing that with Khamenei and Iran's president eliminated, "mid-market businessmen" within the Islamic Revolutionary Guard Corps could be persuaded to work with Americans rather than remain zealots.

History suggests that's probably overly rosy. But Trump wasn't deterred. His past success with limited strikes on Iran's nuclear facilities last summer, plus last month's operation removing Nicolás Maduro from power in Venezuela, may have convinced Trump that the U.S. military is "an almost biblical force that can accomplish anything," one adviser told reporters.

The problem? Iran is far bigger and more complicated than Venezuela.

The Ground Truth

Prospects for popular revolt seem dim, at least short-term. Iranians are unarmed, facing security forces that recently killed an estimated 30,000 civilians after December protests. The IRGC has a decentralized hierarchy trained to maintain control despite strikes.

Within 12 hours, Iran is expected to move to close the Strait of Hormuz, through which roughly one-fifth of the world's oil flows. Iran has already fired back at regional targets today, though many missiles were intercepted with limited damage reported.

Military planners have rehearsed this "maximalist" option for years. After initial bombardment of hundreds of targets, the decisive phase comes in the following days. If Iran responds with ballistic missiles, the U.S. must strike launchers, storage sites, and transportation routes. Each Iranian missile launch forces Washington to expend costly, limited air-defense interceptors.

The Timeline Problem

Trump offered no timeline for how long the U.S. would wait for Iranians to overthrow their government, later saying on Truth Social that attacks could last "a week or more." Military planners concluded that strikes alone wouldn't produce regime change—which explains Trump's direct appeal to Iranian people.

But stopping too soon could leave the current regime intact and foreclose future nuclear negotiations. Continuing until costs become unbearable might force Iran to negotiate from weakness. "The next time we sit down with Iran, it must not be as equals," one former defense official said. "It must be as victor and vanquished."

Achieving that outcome could require weeks of sustained attacks—risking a failed state with enriched uranium, destabilized oil routes, threatened Gulf allies, refugee crisis, and global economic disruption.

The Diplomatic Window That Closed

Ironically, hours before the first American bombs fell, Oman's Foreign Minister Badr Albusaidi told CBS that the U.S. and Iran were close to the "heart" of an agreement. "If the ultimate objective is to ensure forever that Iran cannot have a nuclear bomb, I think we have cracked that problem through these negotiations by agreeing a very important breakthrough that has never been achieved any time before."

Trump never made a public case—as Bush did with Iraq—for why negotiating wouldn't yield results. Unlike Bush's decision to invade Iraq, no ground troops are expected in Iran. Trump wants to avoid a quagmire while still achieving regime change.

Legacy on the Line

Trump has told confidants he believes his legacy could be defined by overthrowing regimes in Venezuela, Iran, and potentially Cuba—redrawing global maps and doing what predecessors couldn't. But the record of success in regime-change initiatives is sparse, especially when engaging only from a distance.

If the ayatollah-led regime collapses, the IRGC would be best positioned to step in—and could prove even more hostile to Washington. Alternatively, Trump could redefine success mid-operation and declare victory after degrading Iran's defenses.

Dana Stroul, former deputy assistant secretary of defense for the Middle East, outlined a more hopeful scenario: Opposition leaders emerge from prison to unify the country, assuming sustained strikes dismantle the regime's religious and security apparatus. But that's a big assumption.

With at least 150 aircraft and drones, more than a dozen destroyers, and two aircraft carriers at his disposal, Trump may still find it difficult to achieve his ultimate goals. "I worry that the lesson he's taken is he can do this, and that the blowback won't be that bad," said Jonathan Panikoff, a former U.S. intelligence official.