In an offhand remark about Iran at the White House on Tuesday, President Donald Trump showed how much his approach to foreign policy differs from his predecessors’.

“We killed all their leadership,” he said. “And then they met to choose new leaders, and we killed all of them. And now we have a new group and we can easily do that. But let’s see how they turn out.”

Apart from its bluntness, the comment reflected what analysts call a “decapitation strategy” — a brutal metaphor for targeting or sidelining a powerful political figure in the belief that it can reshape the country they led.

It’s not just Iran, either. Trump has also sought to reshape Venezuela and Cuba by targeting their leaders as part of his deeply personalized approach to foreign policy.

It’s a far different approach than what’s typically favored in Washington, where teams of analysts look at countries as complex systems driven by institutions, history and culture.

Instead, in Trump’s second term, diplomacy has become less about painstaking negotiations and more about high-impact moves aimed directly at those in power. Traditional foreign policy tools — sanctions, alliances and multilateral agreements — often take years to produce results. Trump’s strategy, by contrast, seeks speed and visibility, promising immediate, headline-grabbing outcomes.

In practice, however, the outcomes have been far more complicated — and far less successful.

In Venezuela, years of U.S. pressure — including sanctions and diplomatic backing for opposition leader Juan Guaidó — were aimed at dislodging Nicolás Maduro and triggering a political transition. While Guaidó briefly gained international recognition, the effort failed to produce any changes on the ground, as Maduro maintained support from the military and key state institutions.

Trump took a more dramatic approach, sending the military to capture Maduro and saying that “we’re going to run the country” until a transition. But even as Delcy Rodríguez has served in an acting leadership role during a transitional phase, the country’s underlying political system remains largely intact. Core institutions such as the military and government heads continue to work in much the same way, and basic governance in Venezuela is pretty close to how it was under Maduro. Trump succeeded in changing the leaders but not the system.

In Iran, Ali Khamenei was killed in a major U.S.-Israeli strike aimed at crippling the regime’s leadership. Within days, Iran’s ruling institutions installed his son, Mojtaba Khamenei, as the new supreme leader. The system held together, the military and political elite remained loyal and Iran’s regional posture persisted — if anything, becoming more confrontational. Even the removal of the most powerful figure in the system did not dismantle the system itself.

When asked what he considered the “worst-case scenario” for Iran, Trump seemed to grasp the limitations of the strategy.

“I guess the worst case would be we do this and then somebody takes over who’s as bad as the previous person, right? That could happen,” he said in early March. “We don’t want that to happen. That would probably be the worst. You go through this and then in five years, you realize you put somebody in who is no better. … I would say that would be about the worst.”

Cuba tells a quieter but equally revealing story. The Trump administration tightened sanctions and sought to isolate Havana, aiming to pressure the leadership into political change. Yet even after the transition from the Castro era to Miguel Díaz-Canel, the core political system endured. Trump’s own rhetoric captured his maximalist ambition, declaring, “I do believe I’ll be having the honor of taking Cuba. It’s a big honor, I mean, whether I free it, take it. I think I can do anything I want with it.” But Institutional continuity, national identity, and decades of centralized governance proved resistant to external pressure. Only the names at the top are different.

These cases highlight a core flaw in Trump’s approach: Governments are not just individuals. They are systems, held together by institutions, networks and ideological foundations that do not disappear when a single figure is removed or targeted. In Venezuela, the system protected Maduro. In Iran, it absorbed the shock of leadership loss and reconstituted itself quickly. In Cuba, it outlasted leadership transition with little structural change. Like the hydra of Greek myth, “decapitation” only made it stronger.

This approach to foreign policy reflects a high-risk, high-visibility bet: that global politics can be reshaped by targeting those at the top. But in Venezuela, Iran and Cuba, the results tell a different story. Leaders were pressured, targeted or replaced — but the systems beneath them held firm.

Trump may yet succeed with this strategy in another country that is more ripe for change. But for now, his record is a sobering reminder of the limits of personalized diplomacy.

This is a preview of MS NOW’s Project 47 Newsletter. As President Trump continues implementing his ambitious agenda, get expert analysis on the administration’s latest actions and how others are pushing back sent straight to your inbox every Tuesday. Sign up now.

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