President Donald Trump once remarked that his intuition and instincts were the key factors separating him from the mere mortals trying to negotiate good deals. “I have a gut, and my gut tells me more sometimes than anybody else’s brain can ever tell me,” the president said at one point during his first term.

And in many cases, Trump’s words have proved to be prophetic — prioritizing his gut over the traditional advice of his political advisers has earned him two presidential election victories and a core base of support that sticks with him regardless of what decisions he makes.

Yet on war, peace and Iran, the insightful gut Trump claims to possess is looking more and more like a cesspool of adolescent-level judgment. The president and his allies will continue to give interviews about how wonderful the military operation against Iran is going and how Tehran, humbled and confused, is either on its last legs or desperate to make an agreement to save itself.

Yet we shouldn’t fall for public relations strategy. The United States is in the position it’s in today because Trump’s predilections on Iran have failed consistently since his first term. Every assumption he’s carried has been dead wrong on every level.

The list is far too long to extrapolate on comprehensively in a single column, but consider this.

In May 2018, after campaigning in part on how horrible the Barack Obama-era Iranian nuclear deal was, Trump issued an executive order to officially pull the United States out of the accord and reinstate all of the economic sanctions previously lifted on the Iranian economy. The aim, he said at the time, was to pressure the Iranians so hard that they would be forced to crawl back to the negotiating table and settle on a new deal with tougher terms. In Trump’s own words, “The fact is (the Iranians) are going to want to make a new and lasting deal, one that benefits all of Iran and the Iranian people.”

How did that assumption work out? Not very well. Iran took the U.S. withdrawal as an insulting breach of an agreement it negotiated only a few years prior. Even as Iran’s banking channels were isolated from the international financial system and more Iranian oil barrels came off the market, Supreme Leader Ayatollah Ali Khamenei refused to authorize a renegotiation with Washington. Instead of caving as Trump expected, Iran acquired leverage of its own by installing more centrifuges, churning out uranium at higher grades and increasing its stockpile of nuclear fuel. The decision to leave the old nuclear deal simply added to Trump’s problems.

Those faulty assumptions have continued to the present day. During the opening hours of the war, Trump, convinced by Israeli Prime Minister Benjamin Netanyahu that killing Khamenei would cause chaos in the Iranian ranks, targeted the supreme leader’s office partly in the hope that the regime itself would be decapitated. Khamenei and some of his closest longtime advisers were killed during the first day of the conflict, which was no doubt a stellar military success on the tactical level.

However, the weakening of the Iranian regime that Trump and Netanyahu were betting on missed the mark. There were no mass demonstrations by the Iranian people against the regime, the Islamic Revolutionary Guard Corps continued to fight even more ferociously, and Khamenei’s death did nothing to bring Iran’s negotiating position onto a more reasonable plane. Trump thought he could rerun the playbook in Venezuela, where taking out a dictator at the top would lead to a more pragmatic replacement. Nothing like that has occurred.

The Strait of Hormuz, the Middle East’s most important chokepoint for oil, natural gas and other exports, is the sight of another Trump miscalculation. Despite being warned that Iran could shut the waterway during any prospective war with the United States, the president apparently believed Tehran would capitulate before that scenario happened. Why he was so confident things would shake out as he predicted was a mystery.

Of course, we know how the story has proceeded. The Strait of Hormuz, through which about one-fifth of the world’s crude oil flows to market, is now essentially an Iranian-controlled lake. Shipping traffic has declined by an astounding 95% from prewar levels, increasing the price of crude by more than half over the last month and forcing the Trump administration to relax sanctions on Iranian crude to ensure adequate global supply. The Economist magazine found that Iran is now earning twice as much from its own oil sales as it did before the U.S. and Israeli bombs started falling, a direct consequence of Tehran’s decision to turn maritime traffic in the Persian Gulf on and off virtually at will.

Finally, Trump continues to assume that if he drops enough bombs on enough Iranian targets, kills enough senior-level Iranian officials and lobs enough rhetorical threats on Truth Social — the latest being a post on Monday threatening to wipe out Iran’s electricity infrastructure — Iran will capitulate out of fear. Yet we should keep in mind that the U.S. has already bombed Iran more than 10,000 times over the last month, and when you add Israel’s strikes to the equation, the number goes up even further.

Even so, Iran is determined to continue stringing out the war for as long as it takes to get Trump to quit out of economic desperation. Iran’s strategy could very well work. After all, the last thing Trump needs is even higher gas prices and inflation at a time when the midterm elections will hinge on which party is doing a better job tackling cost-of-living issues.

Being a leader sometimes means having the humility to admit when your previous belief system was incorrect. The other path is pressing on in your delusions, hoping you will eventually be vindicated.

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Daniel DePetris is a fellow at Defense Priorities and a foreign affairs columnist for the Chicago Tribune.

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