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Trump’s ‘gut’ let him down in Iran — and we’re all paying the price of his failed diplomacy

Washington’s brand of dealmaking seems unable to handle a determined enemy that seeks its own survival by imposing maximum pain on others.

By Ivo Daalder

Ivo Daalder, a former U.S. ambassador to NATO, is a senior fellow at Harvard University’s Belfer Center and host of the weekly podcast “World Review with Ivo Daalder.” He writes POLITICO’s From Across the Pond column.

When it comes to war and diplomacy — much like in business — U.S. President Donald Trump doesn’t sweat the details. Nor does he rely on the kind of policy process, in-depth analysis and expert advice that’s been the norm for other presidents. He is a leader who goes with his gut, which, he has said, “tells me more sometimes than anybody else’s brain can ever tell me.”

Until now, Trump had gotten away with relying on his gut. His use of force has been quick, achieving results in Iran last June and in Venezuela just three months ago. He’s also helped end conflicts, though most of the eight wars he claims to have brought to a close — among which, ironically, he counts the war between Israel and Iran in June — were either on the verge of being settled or, in the case of the Congo, never really ended.

In Iran, his gut finally let him down.

Four weeks of bombing hasn’t produced the swift change in Iran’s regime or behavior that Trump’s gut had expected. Instead, Tehran has turned the tables by targeting Gulf states and closing the Strait of Hormuz, imposing rapidly growing costs on the region and the world. And in doing so, it has finally given Trump an adversary unwilling to submit to his whims — even after bombing 10,000 targets and counting.

For many — including Trump’s last three predecessors — this was all too predictable. It’s why they, in their times, had all opted for diplomacy over war when seeking to prevent Iran from acquiring nuclear weapons. But Trump didn’t steep himself in the details or the analyses that swayed former presidents George W. Bush, Barack Obama and Joe Biden to forego the pressure to bomb Iran — including from Israel.

And now, his instinct that a bombing campaign would eliminate a threat that all U.S. presidents since Jimmy Carter have faced, is falling short. His desperate attempts to force a deal by claiming Tehran “is begging” for one, and his serial extension of deadlines when threatening to bomb power plants, are signs he recognizes that he’s increasingly caught between two bad options: the unpalatable need to escalate with ground troops, or accepting a deal he probably could have secured without a war.

Rightly, many have pointed to the multitude of shortcomings in the preparation, planning and execution of the war against Iran to explain why Trump has found himself in this position. The president himself admitted he had been surprised that Iran hit back, attacked Gulf allies and closed the Hormuz Strait — despite being repeatedly warned it would do so.

But the diplomacy, both in the run-up to the war and now, also leaves much to be desired.

Rather than relying on diplomats with the necessary negotiating skills and background to engage with Iranian counterparts — who, even he admits, are “great negotiators” — Trump has relied on friends and family who lack the required experience and know-how.

The president, his son-in-law Jared Kushner and his friend and Special Envoy to the Middle East Steve Witkoff are all convinced their private sector experience as dealmakers make them perfect diplomats. But the skills needed for those two jobs are very different — and not easily transferable.

In the private sector, dealmakers settle on the broad points of an agreement, leaving the details to lawyers. But in diplomacy, strategic and historical context matter — as does knowledge of what drives the other side, which is very different than simply making a buck.

We can see all this in Witkoff and Kushner’s go-to approach: putting down a term sheet, or rather a multi-point plan — 28 points for Ukraine, 20 for Gaza, 15 for Iran — and then trying to bamboozle the other side into accepting it. Meanwhile, the points are often vague, open to multiple interpretations and almost always divorced from the context of the conflict they seek to address.

The idea is that if one side “holds the cards,” the other side must fold. But that’s not how diplomacy works.

In Ukraine, the 28 points were mainly drawn up by Russia, and were roundly rejected by Kyiv. Then a new 19-point plan worked out with Ukraine was, predictably, rejected by Moscow. Today, the much-heralded negotiations that were supposed to end the war in one day have been suspended, and the conflict has entered its fifth year.

In Gaza, a ceasefire was eventually reached, and the hostages were all released — major goals for both Israel and the U.S. Yet, there is still no peace. The Gaza strip is partitioned in two, with Israel controlling one side and Hamas the other. Hamas hasn’t demilitarized, and Israel violates the ceasefire on an almost daily basis.

The prospects for reaching a peace deal with Iran anytime soon are no better. The much-discussed 15-point plan is a list of maximalist demands — including complete denuclearization, strict limits on missiles and an end to the support of regional proxies — which Iran has consistently rejected.

And even if the bombing campaign were to ultimately convince those now in power in Tehran to negotiate an end to the war, their country’s experience with the Trump administration will make reaching any kind of agreement extremely difficult. After all, this is the same U.S. president who walked away from the 2015 nuclear deal Iran had signed with the Obama administration, even though it had complied with the terms. Moreover, Tehran twice agreed to enter indirect talks after Trump returned to office — and twice those talks were cut short by Israel and the U.S. bombing their country and leadership.

Indeed, before the war started, Iran had engaged in serious discussions to limit its nuclear program. But Witkoff and Kushner apparently didn’t understand the concessions it was seemingly prepared to make—concessions that included pausing enrichment, down-blending and possibly removing its stockpile of enriched uranium, and more. Witkoff also wrongly thought Iran’s insistence on an inalienable right to enrichment and possession of 440 kilograms of uranium — which was widely known — somehow meant it wasn’t serious about a deal.

Now, Trump is stuck in a situation of his own making. His gut let him down. His negotiators don’t know how to deal with a determined enemy that seeks its own survival by imposing maximum pain on others. And we’re all paying the price.