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Why Trump Keeps Getting Rolled By Iran

Another day and the Strait of Hormuz remains closed, oil prices are rising again, and no end to the Felon's war of choice appears in the offing as Iran and the USA trade strikes on each other despite the supposed cease fire.  By all reports, the Felon is desperate to find an exit strategy as gas prices and inflation continue to be the largest concerns of many voters, including within the MAGA base. Unfortunately, as a piece in The Atlantic lays out, the Felon is actually a lousy negotiator who has surrounded himself with bootlickers who lack the experience, knowledge and competence to steer the Felon in the right direction, assuming he even listens to them.  The Iranians seem to understand who they are up against and appear happy to keep the Strait closed and allow the Felon to twist on the rope of his own making.  Meanwhile, Americans increasingly believe that the war will continue and seem less and less inclined to believe the Felon's lies about progress in negotiations.  Here highlights from the article that underscore the Felon's poor negotiating position:

Donald Trump’s reputation and political career were built on his dealmaking prowess, yet the president keeps demonstrating that he is a terrible negotiator.

Repeatedly over the past nine years, Trump has gotten rolled by counterparts during high-stakes exchanges. North Korea, Russia, Russia again, China, and China again have gotten the better of the United States. Trump has had to slink back to Washington without much to show except empty talk about friendship with whatever dictator has just run circles around him.

He’s had some success in brokering agreements when acting as a third party (though not nearly as much as he pretends) but much less luck when his own government is a participant. The one glaring exception came when he was effectively negotiating with himself, getting his own administration to set up a $1.8 billion slush fund for his political allies.

The newest example of Trump’s artlessness is Iran. Let’s review the past few days: Trump posted on Saturday that he was close to striking a deal with Tehran that would end the war he started earlier this year and reopen the Strait of Hormuz. As the outlines of the agreement began to emerge, it looked both incomplete and bad: Trump had postponed discussing the hardest issues—matters, such as nuclear weapons, that led him to go to war—in exchange for opening the strait, which was open before Trump started the war. . . . . despite histrionic pushback from Trump aides, the president had begun backing off claims of an imminent agreement by Sunday.

Yesterday, in a sign that a deal might not be near at all, the U.S. military conducted what it called “self-defense strikes” against Iranian targets—directly contradicting the administration’s previous claims about having wiped out any threats to the United States in Iran.

The situation demonstrates a few reasons that Trump is such a bad negotiator. My colleagues Tom Nichols and Robert Kagan have all written illuminating articles on the specific failures inherent or likely in any deal with Iran. But the incident also shows the structural problems with the president’s approach.

First, Trump is unprepared. Some effective presidents (Dwight Eisenhower, George H. W. Bush) came to the White House with a history of deep engagement in public affairs and foreign relations, which made them ready to handle sensitive foreign negotiations. Others brought a formidable work ethic and a ruthless intellect (Barack Obama, Bill Clinton). Both types surround themselves with smart advisers whose input they take seriously. Trump is 0 for 3 on these conditions, which is one reason he wrote off the risk of Iran closing the strait in the first place: He both surrounds himself with less qualified aides than past presidents did and refuses to heed their counsel.

The same failure of preparation extends to the frontline negotiators. Even after many of its top officials were killed in the war, Iran has maintained a hard-nosed corps of diplomats who have long been involved in foreign policy. Trump, by contrast, has dispatched a real-estate pal and his nepo-baby son-in-law. Secretary of State Marco Rubio, perhaps the best informed of Trump’s aides, has been largely invisible.

Second, as the roller-coaster weekend demonstrates, Trump is mercurial. Keeping one’s bottom line ambiguous in a negotiation is canny, but Trump doesn’t appear to have any bottom line in his own mind. . . . Lacking a goal in the war means he also lacks a goal in the peace talks. Iran may be able to use that to its advantage, but even if its leaders are eager to make a deal, they will be understandably reluctant to agree to anything that requires a leap of faith, because Trump may change his mind at any moment, as appeared to happen amid Republican backlash in recent days.

Third, Trump is desperate for a deal, and everyone knows it. His misjudgments have led him to corporate bankruptcies and cheap sales in business, and he’s in a similar situation now. Every conflict between an autocracy and a democracy (however fragile this one may be) is asymmetric: Trump has to be concerned about public opinion, whereas Iran’s leaders have shown not only that they are indifferent to the suffering of their people; they are willing to massacre them by the thousands. But as the war drags on with no positive resolution in sight, and the U.S. economy looks shakier, Trump has become visibly more frantic to reach a peace agreement. . . . Iran, sensing Trump’s need for a deal, has maintained a hard line.

All of these factors combine to mean that Trump is ill-equipped to win any negotiation, much less one that is the result of his own blundering into war. Trump is likely to muddle through, as he has so many times in his career, and reach some sort of agreement with Iran. He will surely say that it’s a great triumph, but reality will be harder to ignore than it was when Trump’s failures merely hurt his own bank accounts.

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Trump's Impending Defeat in Iran

The Felon and his mouthpieces are claiming that negotiations with Iran toward a peace agreement are progressing.  As usual, much of the media is merely parroting the Felon's claims without close examination and oil prices have fallen slightly.  In reality, as reported by the New York Times the only piece seemingly being negotiated is the opening of the Strait of Hormuz while ballistic missiles and uranium enrichment would be addressed at a later date. As for the purported reasons for the Felon's launching his war of choice - regime change, ending Iran's nuclear program, and weakening Iran's influence in the Middle East - none have been achieved. Much of the debacle could have been avoided had the Felon listened to competent advisers and not cavalierly ignored warnings about Iran closing the Strait of Hormuz.  A piece at The Atlantic by a former Republican looks at what in reality is the Felon's impending loss in the war and why, given the Felon's temperament and personality the impending loss was predictable.  Here are article highlights:

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 June 2025, U.S. and Israeli air strikes 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 June 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?

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 not to wage 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 endgame 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? . . . 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. . . . . 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 signaling 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.

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.

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