This May Be Trump’s Biggest Error in the Iran War

For 2,500 years, military commanders have heeded the injunction of Sun Tzu, the great Chinese military strategist: Know your enemy. Yet the Trump administration’s greatest mistake in the Iran war may be its persistent failure to understand Tehran’s priorities and motivations—and how much punishment the regime is willing to absorb to prevail.Iran’s decision Tuesday to launch ballistic missiles at U.S. troops in Jordan was a prime example. It befuddled Washington. U.S. officials had come to expect that their actions would drive the war, and Iran would react. But here was Tehran, escalating matters just after the United States had suspended its 13-day barrage of strikes against Iranian defenses and infrastructure. U.S. Central Command, which is responsible for military operations in the Middle East, described the move as a “surprise attack.”Tehran characterized the missile strikes as self-defense against what the regime saw as the Trump administration’s broadening of the war. Around the same time as the Iranian attack, U.S. and Saudi forces launched joint strikes on Iran-backed militias in Iraq, Riyadh’s first publicly acknowledged military strikes of the conflict. Turki al-Maliki, a Saudi defense-ministry spokesperson, said in a statement that the militias had attacked the kingdom’s oil facilities and that Riyadh reserved the right to respond “at the appropriate time and place.”This week’s events hardly represented the first time that the two sides had misread each other’s intentions. The convoluted and complicated war has swung almost weekly between peace overtures and fighting. Those misinterpretations appear set to continue, especially amid signs that others may be dragged into the fight. Egyptian officials earlier this week confirmed that a drone had set two gas vessels ablaze at Damietta, a port city on the Mediterranean near the Suez Canal. No group has claimed responsibility, but the attack raised fears that Iran has expanded its list of nations to target.The memorandum of understanding that Washington and Tehran signed in the middle of last month quickly devolved into one of the war’s signature misunderstandings. The very first clause of the agreement promised to end the fighting, but the two sides had fundamentally different interpretations of their obligations.The memorandum did not end the dispute over the Strait of Hormuz but rather, it papered over it. Washington believed it had secured 60 days of open, toll-free commercial navigation. Tehran read the agreement as preserving its authority to manage traffic through the waterway. As the dispute erupted, some Iranian officials believed that the U.S. had purposely drafted a vague agreement to trigger a violation that could be used as a predicate to resume strikes, a person familiar with their thinking told us. And the U.S. sought to use financial incentives, such as sanctions waivers and investment, to entice a government that was preoccupied with the assassination of its supreme leader. Was anyone really surprised that the pact fell apart? Certainly not President Trump, who professed that he “couldn’t care less” after each side had walked away.Read: War by any other nameEven before the war began, in late February, the two governments were talking past each other. The U.S. believed that Iran was fragile and the regime susceptible to collapse after nationwide protests. The regime believed that nothing short of its total capitulation to U.S. demands would prevent a war. Trump ordered the war to begin while talks were still under way, and his administration believed that the death of Iran’s supreme leader, Ayatollah Ali Khamenei, on the conflict’s first day would quickly be followed by the collapse of the state. Instead, five months in, the regime remains intact and seems to have enough confidence to endure any U.S. response.This could put the two sides on a path to escalation, each remaining convinced that more military pressure will force the other to abandon its objectives. “America’s calculation is that escalation would lead to surrender. Iran’s calculation is that escalation would lead to deterrence,” Vali Nasr, a professor of international affairs and Middle East studies at the Johns Hopkins School of Advanced International Studies, told us.Trump promised on Fox News earlier this week to “beat the fucking shit out of them.” Iran’s Islamic Revolutionary Guard Corps, meanwhile, said that the base in Jordan would remain a target because “as long as threats against Iran persist, resistance will persist.” (The Jordanian military said that all five missiles fired Tuesday were intercepted.) But neither side seems able to answer the question that matters most: What if escalation doesn’t work?Escalation is “a means to an end, but we don’t know what the end is,” Danny Citrinowicz, a former Israeli intelligence officer who specializes in Iran, told us.Part of the confusion may stem from the fact that Trump himself appears to be of (at least) two minds about how he wants to proceed. He has vacillated between backing more military action and giving peace talks a chance. The U.S. cannot begin to understand its enemy if it has yet to settle on its own aims—or how to achieve them. Trump has repeatedly sought to back away from the conflict, but during a meeting with senior advisers last Friday, he seriously considered ramping up attacks. He opted not to, but the plans remain on his desk, a senior White House official told us. A pause in U.S. strikes that began Saturday was over by midweek following Iran’s attack on the base in Jordan.The U.S. is seeking to understand an enemy that is changing and adapting. Iran appears intent on reintroducing the element of military surprise, driven by the belief that it can outlast Trump and that negotiations no longer present a viable path. The regime operates differently under its new supreme leader, Mojtaba Khamenei, who replaced his late father. Iran is no longer content to let proxies across the region fight for its interests. It wants to use its missiles and drones to fight for its long-term security. And it is willing to endure strikes by the U.S. to the point that American military commanders are running short on viable targets it can hit to stop attacks on the strait.“They are willing to sacrifice themselves and the public for the future of the regime,” Citrinowicz said. He doesn’t believe that Iran wants to fight an endless war any more than Trump does. But Tehran thinks Trump faces constraints, including the economic damage stemming from the strait’s continued closure and the tepid response of Gulf States. Iran’s position, in contrast, has been strengthened by support from the Houthis in Yemen, who recently began targeting Saudi interests and threatened to close the Bab al-Mandab Strait to commercial shipping. Iranian leaders, Citrinowicz said, “believe at the end of the day, they are able to shape the situation on the ground to their own benefit.”A number of influential MAGA allies—including Laura Ingraham and Steve Bannon—have publicly and privately called for the White House to rapidly wind down the war, believing that the conflict has demoralized Trump’s base and will hurt the GOP in the midterms. Republicans facing tough reelection fights have expressed fears to the West Wing that an escalation in the conflict would lead to even higher gas prices, which could doom their November chances. Yet at same time, Persian Gulf allies have made clear that they find Iran’s control of the Strait of Hormuz untenable—especially if the regime charges tolls. That would, in effect, mean that the same countries battered by Tehran’s missiles would be stuck paying for Iran to rebuild.Perhaps as a result, Washington has lurched among military, diplomatic, and economic strategies, hoping that one, or some combination of them, would compel Tehran to yield. Yesterday, the Trump administration announced a new round of sanctions that aim to put economic pressure on Iran by targeting companies and tankers tied to its maritime trade. The U.S. also hopes that an escalation of military strikes will do enough to tip the regime either into collapse or capitulation. But even the threat of escalation can come with a cost: Brent crude climbed nearly 8 percent after Trump’s profanity-laden remarks, briefly breaking $91 a barrel yesterday.Officials told us that Trump was noncommittal when Israeli Prime Minister Benjamin Netanyahu, during his Tuesday visit to the White House, urged the president to ramp up attacks on Iran (among the ideas being considered is to strike the land routes that Iran has been using to resupply its forces). Netanyahu expressed deep skepticism that Iran would ever agree to a reasonable peace deal. U.S. officials believe that some factions in the Iranian power structure favor making a deal, but whether they have the authority to do so is not clear. The officials also believe that Iran’s economy will continue to weaken to a point at which Tehran will be forced into a deal.For now, there are no good options for Trump and there is no clarity as to how two sides in a widening war can find off-ramps, particularly if they continue to misinterpret each other’s actions.Graeme Wood: The U.S. is subtly shifting its Iran strategyTrump could declare victory, noting that the U.S. and Israel killed the ayatollah, and vow to attack again should Iran resume its quest for a nuclear weapon. Or he could try to return to the terms of the MOU. But the administration would likely have to sign on to some aspects of Iran’s interpretation of it, such as its retention of control of the Strait of Hormuz. Or Trump can escalate, hitting Iran’s missile capabilities to make the targeting of U.S. bases and Gulf partners more difficult. But he would have to do so at a rate faster than Iran can reconstitute its forces. And he faces political opposition to a more prolonged conflict: A CBS News/YouGov poll released earlier this week found that a majority of Americans are not optimistic about the war and feel that its objectives are not clear. More than two-thirds of respondents said the Trump administration should end the war now.Both sides seem to agree on one thing: There is no end in sight to the war. U.S. defense officials told us that they believe conflict will continue into 2027. Iran is signaling that it plans for a fight even longer than that.