Why Trump Keeps Getting Rolled in Negotiations

By David A. Graham

Tuesday, May 26, 2026

 

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. Hawkish Trump allies promptly criticized the deal, and despite histrionic pushback from Trump aides, the president had begun backing off claims of an imminent agreement by Sunday. “If I make a deal with Iran, it will be a good and proper one, not like the one made by Obama,” he posted. “Our deal is the exact opposite, but nobody has seen it, or knows what it is. It isn’t even fully negotiated yet.” 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. He has cycled through different rationales for the war, including regime change and stopping Iran’s nuclear program, but hasn’t landed on one. 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. (The president also seemed eager to have something to show for his weekend, because he skipped his eldest son’s wedding, ostensibly to work.) 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.

 

One of the ironies of The Art of the Deal, the book that made Trump’s reputation as a clever businessman, is that Trump himself didn’t write it. His ghostwriter, Tony Schwartz, has said that he cobbled the volume together after sitting at Trump’s elbow while he conducted his daily business. Unfortunately, it’s probably too late for Trump to hire a real professional to handle negotiations with Iran.