As foreign policy luminaries rush to warn about the perils of a U.S. attack on Iran, there is widespread confidence in the White House that President Donald Trump can manage a strike’s fallout. This confidence reflects a years-long pattern that has shaped Trump’s thinking. Washington’s foreign policy establishment warns the president against some norm-breaking act. He ignores their advice and plows forward. And he faces no apparent repercussions. In 2018, when Trump broke with U.S. policy to move the American embassy in Israel to Jerusalem, I was serving in the State Department’s Bureau of Near Eastern Affairs. Our own bureaucratic experts predicted that the move would prompt widespread protests and violence against U.S. personnel, and we set up task forces and evacuation plans for a doomsday that never came. This dynamic repeated itself last June, when Trump joined Israel’s strikes on Iran’s nuclear program. Analysts warned that the decision would trigger a broader war and hasten Iran’s nuclear breakout. Once again, little happened. When the administration ousted Venezuelan President Nicolás Maduro in January, pundits insisted that his country and even the region would plunge into chaos, but nothing of the sort has yet occurred.
It is easy to see why Trump would believe that the warnings about another attack on Iran are overwrought and that he can repeat his formula of decisive action and a clean exit. But this time is different. I spent 18 years working on Iran in various U.S. government capacities, including as President Joe Biden’s Iran director and on Trump’s negotiating team in the spring and summer of 2025. From that experience, I can see that Trump fundamentally fails to grasp that Iranian weakness will not lead the country to capitulate at the negotiating table. On the contrary, Iran’s present fragility only narrows the space for meaningful compromises. Nor does Trump understand that Iran faces entirely different conditions than it did in June 2025, when it chose to de-escalate. The Islamic Republic now believes that Israel and the United States intend to repeatedly strike its ballistic missile program—the foundation of Iranian self-defense—and that it must be more aggressive to forestall the kind of perpetual assault that could topple it altogether.
Trump’s own behavior also increases the risk of escalation. The president’s ever-intensifying wish to be seen as a historic peacemaker has led him to an unnecessarily binary choice—strong-arm Tehran into a major new deal or use substantial force. And the nebulousness of his motives makes this flash point much more dangerous. Trump seems interested, in no particular order, in demonstrating the prowess of the U.S. military, strengthening his negotiating position, showing he was serious when he vowed in a January Truth Social post to protect Iranian protesters, and differentiating his approach from President Barack Obama’s. This mishmash of objectives contrasts with the focus he brought to his previous successful operations and will make him less prepared if a strike does not yield the expected, swift capitulation. All told, today’s conditions mean that an attack by the United States on Iran could result in unexpectedly deadly retaliation—and a much longer and potentially damaging conflict for Washington.
A SELF-MADE TRAP
Strategically speaking, Trump has no great reason to attack Iran. Tehran is a threat to Washington’s Middle East interests, yes, but it poses no immediate menace to the United States. In the aftermath of Iranians’ widespread protests and their subsequent brutal massacre, sustained economic and diplomatic pressure would have further weakened the regime without risking open conflict. But this president is rarely satisfied with quiet victories. As a result, he has made a major, flashier demand. Either the Iranian government agrees to a grand nuclear deal in which it gives up all nuclear enrichment and its missile program, or Washington attacks.
Launching a limited military strike on Iran to force it to meet U.S. requirements fits Trump’s playbook. It would afford him a spectacle. And he clearly wants either a surrender pact or a broad framework that validates his claim to have brought peace to the Middle East for the first time in several millennia. But Iran’s leaders are increasingly indisposed to offer him a big, symbolic victory. In general, Iranian negotiators like to focus on specifics and narrow, tit-for-tat concessions. Biden understood this, and as a member of his Iran negotiating team, I spent countless hours deliberating how to categorize nuclear-related sanctions.
At a round of negotiations with the United States in Geneva last week, Iran fronted Foreign Minister Abbas Araghchi, his full complement of official advisers, and a team of technical experts to hammer out fine specifics such as how Iran would export its uranium stockpiles and which U.S. executive orders would be rescinded. Trump, by contrast, sent just two people: his catchall special envoy, Steve Witkoff, and his son-in-law Jared Kushner. He does not care about technicalities or grasp their particular importance to Iran.
Iran’s leaders do not want to offer Trump a symbolic victory.
Instead, Washington is demanding sweeping public concessions while offering virtually nothing concrete in return. John Limbert, a former U.S. diplomat and, in 1979, a hostage in Iran, has wryly observed in his book Negotiating With Iran that “Iran doesn’t give in to pressure—only to a lot of pressure.” He notes how Iran, after years of fiery defiance, accepted in 1988 a humiliating UN-sponsored cease-fire with Iraq after finally concluding that continuing the devastating eight-year war threatened the Islamic Republic’s survival. Iran will not cave to major demands simply because of a bombing campaign. And by extension, the Iranian regime will not sign on to arrangements that, in its view, fundamentally undermine its viability, especially without concurrent guarantees. Insisting that Iran dismantle its missile program, for example, is almost certainly a nonstarter—the regime believes that the missile program undergirds its grip on power. Trump fails to comprehend that no matter how weak Iran is or how much force the United States deploys, Supreme Leader Ali Khamenei will never willingly negotiate the end of the Islamic Republic. He would rather die a martyr.
If anything, Iran’s negotiators have less flexibility now than they did a year ago. At this juncture, Khamenei should have authorized his negotiating partners to break with their traditional approach and offer Trump the appearance of a major win. Six weeks ago, the mere fact that Trump held off on his promise to retaliate on behalf of Iran’s protesters and offered negotiations created a huge opportunity for Tehran. But it squandered the opening when it rejected the Trump administration’s first proposal—a regional summit in Istanbul between foreign ministers, which could have differed enough from Obama’s negotiating framework to give Trump political cover. Iran simply couldn’t bring itself to let Trump save face and score a symbolic win. In truth, Khamenei is just as obsessed with appearances as Trump is, and he is increasingly catering to his most hard-line supporters. He has made it impossible for his negotiating team to offer even minor compromises, much less the kinds of big concessions Trump is demanding.
POINT OF NO RETURN
Iran knows that it cannot win an outright war with the United States or Israel. In theory, if Trump strikes, Tehran would be best off seeking a quick de-escalation—as it did with Israel in April and October of 2024 and with both countries in June 2025. But Iran is facing a very different situation now than it did then. Today, Israel and the United States both perceive Iran as a paper tiger. The proxy militias that it used to deter Israel and terrorize the Middle East for years have largely been neutralized. Its nuclear program is in ruins. Its air defenses are in tatters: the June strikes destroyed most of its surface-to-air missile sites and punched massive holes in its early-warning radar network. And in December, Israeli Prime Minister Benjamin Netanyahu went to Mar-a-Lago and got Trump’s permission to strike Iran’s ballistic missile program, the keystone of the country’s defense, at a time and place of Netanyahu’s choosing. This development threatens the very existence of the Islamic Republic. The program is Iran’s only remaining means of threatening Israel. (Iran also mostly makes these missiles domestically, so Israel would have to strike Iran every six months or so to keep the arsenal sufficiently degraded.)
The ambiguity of Trump’s current intentions also changes the Iranian calculus. The U.S. president is not threatening to attack Iran because of any imminent threat or in response to any act of Iranian aggression. His motives are various and unclear: he is disappointed by the negotiations’ progress, he feels compelled to defend the redline he established with his Truth Social post, he is desperate to avoid unflattering comparisons to Obama, and he believes he can undertake major operations with minimal consequences. From Iran’s perspective, both Israel and the United States appear to have concluded that they can strike without any direct provocation and when doing so serves domestic political needs; Iran even thinks the two countries will be tempted to strike frequently. As a result, Iranian officials feel they need to give Trump a bloody nose or they will perpetually be at risk.
In a speech last week, Khamenei threatened to sink a U.S. aircraft carrier and close the Strait of Hormuz. Tehran is unlikely to do either of these things, given the current U.S. military buildup in the region. But it could more easily inflict U.S. casualties. Killing Americans may be a particularly appealing option: Iranian leaders remember that in 1983, U.S. President Ronald Reagan withdrew all U.S. forces from Lebanon after the Iran-backed suicide bombing of a Marine barracks there, despite initially claiming he would not be cowed by terrorism.
Iran may seriously consider targeting the Gulf Arab states’ energy infrastructure.
The United States has roughly 40,000 troops positioned across 13 regional bases, not including the significant naval and air power it has recently deployed to the Middle East. On February 19, Iran’s ambassador to the UN warned the body that if the country were attacked, all nearby “bases, facilities, and assets of the hostile force … would constitute legitimate targets.” Although Tehran’s regional proxies are degraded, Iraqi and Houthi militias still have the capacity to add to any Iranian response. According to a mid-January Quinnipiac poll, 70 percent of Americans—and a majority of Republicans—oppose military intervention in Iran. Trump will struggle to justify any American deaths in a conflict of his own making. Iran could also intensify its missile strikes on Israeli civilian targets, straining Israel’s defensive capabilities and challenging the United States to pour resources into bolstering its ally.
Finally, Tehran could target global oil flows and international shipping, sending energy prices up and creating a serious political liability for Trump. Iran may well encourage the Houthis to resume attacking ships transiting the Red Sea. The country’s Islamic Revolutionary Guard Corps has also been preparing to selectively seize adversary ships in the Strait of Hormuz. If conflict with the United States deepens, Iran may seriously consider targeting the Gulf Arab states’ energy infrastructure directly. In 2019, during Trump’s last “maximum pressure” campaign, Iran directly attacked Saudi Arabia’s Abqaiq oil processing facility, the world’s largest. That assault appeared to be designed to damage easily replaceable components, thus limiting the consequences to the global energy supply. But if Tehran instead assaulted infrastructure that it knows would take longer to repair, the results would be much more damaging. The relationships between Iran and the Gulf Arab states are stronger now than they were then, but Tehran knows that Gulf leaders carry real influence with Trump and could appeal to him to back down if they came under pressure.
Iran may be weak. But it still has ways to inflict real pain on the United States—and much more incentive to try than it did before. If Trump wants to maintain the playbook that has worked for him, he will need a decisive and low-cost end to this saga. But powerful forces, both within him and external to him, have led him to dismiss the many off-ramps he already had. Iran hawks such as Senator Lindsey Graham are urging Trump not to “talk like Reagan and act like Obama,” a comparison Trump hates and fears. It may seem implausible that Trump, who promised his supporters an end to forever wars, would take out Iran’s leaders or commit ground troops to regime change and nation building. Yet he has come this far. He may well be pushed onward, regardless of the cost.
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