The first surprising thing about President Trump’s impending defeat in the 2026 Iran War is that he already fought and won a successful war against Iran last year. In August 2025, U.S. and Israeli airstrikes badly damaged the Iranian nuclear program in 12 days of bombardment. Exactly how badly remains controversial. But they didn’t do nothing. If Trump had quit while ahead, he could have banked his gains from last August as a solid if imperfect win.The second surprising thing about Trump’s impending defeat is that he does not seem to have cared at all about the only evident reason to resume fighting in 2026: the Iranian people’s rebellion against their brutal oppressors. Trump has never given any evidence of caring about Iranian democracy or human rights. He promised the Iranian people, “help is on the way” on January 13, but military operations did not commence until thousands were dead and the rebellion was already effectively crushed. During military operations, Trump made clear that he sought a deal with the existing regime. He made no effort to support or cooperate with Iranian dissidents before, during, or after the uprising.The third surprising thing about Trump’s impending defeat is that even he himself seems never to have understood why he went back to war against Iran. What exactly did he think he would achieve? He kept saying that he wanted to ensure that Iran never developed a nuclear weapon. He also insisted that he had effectively prevented it from doing so in August. He seemed genuinely to believe that claim. If so, why resume the fighting? If, on the other hand, those words were wrong, then why not simply hit the nuclear sites again? Why the need for this bigger war?Trump started the February 28 war for reasons of personality, not strategy. He is on his way to losing the war for the same reasons of personality.Trump is arrogant. Think how often Trump mocks his predecessors as “dumb” and praises himself as “smart.” Those predecessors, from Jimmy Carter through Ronald Reagan to Joe Biden, all had to ponder military responses to Iranian terrorism and aggression. They all ultimately decided against waging a major war against Iranian national territory. Among the prime deterrents to action: the Strait of Hormuz problem. Trump apparently decided that a problem that was too hard for everybody else would magically disappear for him, because he is tough and growls in his official photographs.Trump is reckless. Trump is not a plan-ahead guy. He plunges into desperate adventures without any clear end game in mind. What really was Trump’s plan on January 6, 2021? After Mike Pence was seized by rioters and forced at gunpoint to recite the magic words Trump wanted him to say, what was supposed to happen then? The 81 million American majority who’d voted against Trump in 2020 would submit? The military, CIA, and FBI would follow blatantly illegal orders? In 2021, Trump provoked violence and hoped it would all somehow work out. He followed the same approach again in 2026.Trump hates procedure. A lot of the apparatus of the modern presidency exists to force confrontations with unwelcome realities. Cabinet officers are confirmed by the Senate to assure the country that major offices are filled by people of character and competence. The National Security Council is supposed to process challenging data to ensure that the president receives necessary information. But to run the Department of Defense, Trump nominated and the Senate approved Pete Hegseth. Instead of choosing a national security adviser to replace Mike Waltz after Waltz’s resignation on May 1, 2025,, Trump tapped Secretary of State Marco Rubio to take on the role. But to double up that particular job dooms the job not to be done at all, especially since Trump has shriveled the NSC’s staff and subjected it to loyalty tests demanded by his most screwball supporters.Trump is panicky. For all his bluster and boasting, Trump cannot take the heat. Presidents who believe in their decisions ride out bad polls. Trump panics and reverses course. Trump has been signalling since mid-March that he wants an end to the Iran War at almost any price. The Iranians have read those signals. For all the damage the U.S. military inflicted on Iran, the Iranians seem to have gambled that they could outlast Trump. They’ve been proven right.Trump is gullible. As Trump’s present secretary of state observed back in 2016, Trump is most fundamentally a con artist. But Trump is often a self-defeating con artist who falls victim to his own con. Trump demanded “unconditional surrender” from Iran. Instead, he’s negotiating an exit that concedes most of Iran’s demands and leaves Iran in a more dominant position over Persian Gulf oil traffic than it occupied before the war. But Trump seems genuinely to have convinced himself that he’s won a mighty victory, and he seems truly baffled that others decline to endorse his flim-flam.Trump can’t lead. Trump’s method of governance is command. He cannot work across party lines, and he cannot speak to any part of the American nation beyond his MAGA base. A war leader, however, must be a national leader. War imposes costly sacrifices. Leaders who take the nation to war must explain those costs and inspire those sacrifices. Trump simply cannot do any of that work, and he has no idea how it could be done.For three years in his first term, Trump benefited from the strong economy that he inherited. Then the pandemic struck, and his first instinct was to hunt for someone to blame. In this second presidency, his main work has been spectacular self-enrichment, even as the economy has sagged under the weight of his catastrophic trade wars. He made no case for an Iran War to the public and never sought approval by Congress. There are some Iran hawks on the Democratic side, especially in the Senate. Trump never tried to ally with them.Trump’s vision of the presidency is authoritarian and kleptocratic: issue orders, grab money, luxuriate in flattery, erect monuments to oneself. That’s no way to lead a nation through the hazards and difficulties of war. Now the war is ending on disadvantageous terms for the United States. Trump’s old methods will be turned to a new task: trying to deceive the American people and the world into believing that the war he lost was really a big win, the biggest ever, so big you cannot believe it. He’s likely to discover that, indeed, nobody does believe it.