President Donald Trump’s preference for short, sharp military operations is what got him into a bind in Iran; the same tactics won’t help him out of it.
Even as Washington signals restraint, the War in Iran is moving in the opposite direction.
On Monday, President Donald Trump gave Iran five additional days to reopen the Strait of Hormuz, or else he will authorize strikes against civilian energy infrastructure. The move, clearly aimed at calming oil and financial markets rattled by war, can be interpreted by Trump as an effort to de-escalate. Initially believing that Iran’s regime would quickly crumble in the face of relentless airstrikes and the killing of top leadership, including Supreme Leader Ayatollah Ali Khamenei, the Trump administration now sees that it is on the precipice of a quagmire. He needs an off-ramp. In other words, the delay in striking energy infrastructure signals a narrowing of options. Trump wants Iran to back down because he can’t find a way to end the war and save face.
On the one hand, the dilemma facing the Trump administration is a familiar one for states engaged in a war that has taken an unfavorable turn: quitting without appearing to concede. On the other hand, the dilemma Trump faces is even more difficult to simplify as a desire to save face: to end US participation in the war without triggering further escalation from Israel. This is because Iran is not going to surrender, and Israel is not going to allow the Iranian regime to survive.
Inside Iran, the war has intensified—but not in ways that suggest imminent collapse. Tehran and other major cities have endured repeated bombardment, with the threat of strikes on civilian infrastructure, particularly electricity, fueling widespread fear. Many residents report sleepless nights amid the constant shock of explosions. At the same time, the government has tightened its grip: restricting internet access, limiting international communications, and isolating the population from external scrutiny. The result is a society that is both exposed to violence and increasingly contained by the state.
These conditions help explain why Iran is unlikely to surrender under pressure alone. The regime has long demonstrated a capacity to absorb shocks while maintaining control through repression. Arrests of activists have intensified, death sentences continue to be issued, and the memory of past crackdowns has reinforced a climate of fear that discourages mass mobilization. At the same time, Tehran continues to project strength externally, targeting US positions and leveraging the Strait of Hormuz to signal its willingness to escalate.
And Iran’s current leadership, whether the new Supreme Leader Mojtaba Khamenei or the current Speaker of Iran’s Parliament Mohammad Bagher Ghalibaf, with whom the Trump administration was reportedly involved in talks before Ghalibaf himself dismissed such reports, are individuals deeply embedded within the Islamic Republic’s power structure and have records consistent with the hardline positions of Iran towards the United States and Israel.
For Israel, any outcome that leaves the current structure of the Iranian regime intact—even in a slightly altered form—risks being interpreted as a strategic failure. A younger leadership emerging from within the same system, combined with limited physical damage to infrastructure, would not fundamentally weaken the regime’s capacity to project power or sustain its policies. For that reason, Israel has strong incentives to resist any agreement that preserves the status quo.
Wars that do not end quickly not only last long but also become entrenched. This is exactly what has unfolded in Ukraine, where the failure of Russia’s initial early strike set in motion what will soon be the longest continuous interstate conflict in Europe since World War II. With the war in Iran, there is a danger that the US could soon reach the threshold beyond which ending the war quickly with any semblance of victory becomes impossible. To avoid either an unfinished war or an ignoble quick exit, it can become attractive to execute a large-scale, punishing strike in the hope that this will compel defeat.
The desire to execute such a singularly devastating strike is consistent with President Trump’s past actions, which show a consistent attraction to dramatic, high-impact operations designed to produce swift and visible outcomes. Last summer’s Operation Midnight Hammer and January’s Operation Absolute Resolve reflect a preference for climactic moments that promise resolution through quick applications of force rather than prolonged engagement.
Moreover, a decisive strike was exactly the initial goal of the February 28 airstrikes. When Trump posted a video that morning announcing the initiation of the strikes against Iran, he noted the possibility of US casualties but was vague on the duration of the operation. Recent reporting by Reuters indicates the desire was for the operation to be over quickly through a single decapitation strike. Though the Ayatollah was killed in an initial strike, that did not bring about the collapse of the regime.
With the initial decisive strike having failed, it seems the Trump administration simply hoped that a few more days, a week or two at most, of bombing military targets would compel surrender. That did not happen. Instead, the regime has doubled down with its closing of the Strait of Hormuz and strikes against Gulf neighbors.
This has left the administration under pressure to consider additional high-impact military options, a dynamic reflected in recent remarks by Defense Secretary Pete Hegseth, who stated that the United States “negotiates with bombs.”
The threat to energy infrastructure was clearly intended to be such a move. But having paused that action, it now seems to be considering other possibilities. Additional reporting—including from The New York Times—indicates that the Pentagon has been reviewing the rapid deployment of elements of the 82nd Airborne Division, likely aimed at executing a quick strike that can take control of Kharg Island, a critical hub for Iran’s oil exports.
Given the risks to US military personnel in an attempt to take and hold the island, the administration may opt for simply devastating the island, rendering it unusable for Iran. Indeed, while the US destroyed the military targets on the island, Trump has threatened to go further, destroying the oil infrastructure and ports on the island if Iran does not reopen the Strait of Hormuz.
But what if those, like the decapitation strike, fail once again to compel surrender? What’s next? The administration will then be grasping at straws. Could that lead it to go further, such as launching strikes on civilian buildings in Tehran, even to the point of rendering portions of the city uninhabitable? While the direct targeting of civilian infrastructure is a clear violation of the laws of war, the Trump administration could claim that this infrastructure is under the control of the Islamic Revolutionary Guard Corps as a means of plausibly stating that it is not deliberately targeting Iranian civilians.
While Trump and his team might seek a decisive strike to bring the war to a close (for which the Pentagon appears to be preparing), history suggests that such expectations are often misplaced. Even the most frequently cited example—the atomic bombings of Japan—remains deeply contested as a singular cause of surrender and occurred within the context of a prolonged and multifaceted war. In most cases, so-called decisive strikes fail to produce the political outcomes they promise, particularly when they do not fundamentally alter the underlying structure of the conflict. Instead, it can lead the adversary to double down.
The danger and the irony, then, is not only that a decisive strike may fail but also that it may deepen the very conflict it seeks to resolve. In a war defined by resilience, fragmentation, and competing objectives, there are few clean endings. The allure of a final blow is powerful. What makes the idea so compelling is precisely what makes it so dangerous: the illusion that one final blow can resolve what is, in reality, a deeply entrenched and evolving conflict.
But it is precisely that allure that makes it so dangerous.
About the Authors: Paul Poast and Pegah Banihashemi
Paul Poast is an associate professor in the Department of Political Science at the University of Chicago, where his research and teaching focus on international relations. He is also a senior nonresident fellow at the Chicago Council on Global Affairs and a foreign affairs columnist for World Politics Review. Paul is the author or co-author of four books: The Economics of War(McGraw-Hill Irwin, 2006), Organizing Democracy(University of Chicago Press, 2018), Arguing About Alliances(Cornell University Press, 2019), and Wheat at War(Oxford University Press, 2025).
Pegah Banihashemi is a JSD candidate at the University of Chicago Law School, where she also completed an LLM in 2022. Pegah is currently working on the history of the formation of the Iranian Constitution, both before and after the Islamic Revolution of 1979. She has worked extensively on the analysis of international law and international human rights and is a regular expert legal analyst for many global media outlets and non-profits.
