After President Trump brought global economics to the brink of meltdown with his erratic unilateral tariff decrees, Tyler Page and Maggie Haberman reported in the New York Times that Trump told Republicans “I know what the hell I’m doing!” and, after reversing himself, his press secretary, Karoline Leavitt, said he was acting “instinctively, more than anything else.”
What explains this and other behavior that goes alarmingly beyond what most of his closest supporters expected of him?
Counterintuitively, one of the greatest dangers to which a political leader’s inner circle must pay attention is when the leader experiences significant success. Against the odds, Trump recovered from an electoral loss and a slew of lawsuits to regain the presidency for a second time, with larger margins, and watched the lawsuits disappear as a cloak of immunity wrapped around him. Impressive successes! Two things then occur.
First, the leader takes these favorable outcomes to reinforce any existing sense of specialness, superior acuity, or messianic mission. Increasingly, they tune out the counsel of others and trust their own gut, which has so far proven to be brilliantly right, regardless of mounting evidence to the contrary.
Second, those in his inner circle of confidants and in the near inner circle of elites become cautious about contradicting him. The leader is too successful, has too much power, and is too darn sure of himself. When a leader veers off course, their most intimate followers share culpability for retreating from giving counsel based on good data and judgment. They see that truth-telling is unwelcome and become self-censors, valuing their position and access more than their obligation to be trusted advisors.
The confluence of these two tendencies is a recipe for disaster in governance. The leader is rolling the dice. When they come up 7s or 11s in successive rolls, they become addicted to risk and the rush they get when they beat the odds. They forget that the odds will sooner or later turn against them.
To use a historic case, not because it is analogous, but because it is well known, when Adolph Hitler overruled the cautions of his political and military advisors and took the risks of occupying the Rhineland, marching into Austria, and annexing Czechoslovakia, the successes created a sense of invincibility. This spell continued when he invaded Poland, though the allied forces responded with a declaration of war. His rapid subjugation of Poland, the “low countries” and France reinforced his sense of invincibility. By then, no advisors could stop him when he made the fatal error of invading Russia.
The losers in that case were not just tens of millions of Europeans who forfeited their lives, but the German people themselves, whose country was decimated under the counteroffensives of the Allied forces.
This is a crucial lesson for those who support President Trump. There is no question he has proven to be an exceptional political figure who won the trust of a majority of American voters. They placed their faith in his promise to create a government that would be more responsive to their needs. To do this, he must disrupt the status quo, which, inherently, will produce voluminous objections to his policies. This would still be within the framework of a dynamic political process that may give his supporters something of what they expect.
In contrast, by becoming obsessively self-referential, Mr. Trump, like highly successful leaders before him, risks nullifying whatever benefit he might bring to his supporters. No human being on earth, no matter how messianic they claim their mission, can be trusted to single-handedly control the vast powers of the US presidency without seeking a range of viewpoints to inform their decision making. The effect of their blind spots, personal peccadillos, or biases is magnified tenfold and threatens to nullify the value they may otherwise bring to the office.
In my book, To Stop a Tyrant, I discuss three types of followers: conformists, colluders, and courageous followers. If those who most intimately surround the political leader are conformists (sycophants) or colluders (who amplify his worst impulses), the political leader will continue to become more extreme, exposing themselves and their country to far greater risk. The antidote is courageous followers who will stand up and report the truth as they see it, regardless of the displeasure this evokes in the leader. It is courageous followers who, in fact, are the most loyal to the leader.
In the recent event, when the US Treasury bond market began to behave erratically, his advisors finally found their voice as courageous followers and got through to the President. He suspended the market-shaking tariffs for ninety days. Let’s hope they do not wait quite as long to effectively intervene when “his instincts’ next tell him to play chicken with the world economy or its democratic institutions. And neither should you wait to speak up wherever you can make your voice heard.
Ira Chaleff is the author of To Stop a Tyrant: The Power of Political Followers to Make or Brake a Toxic Leader and The Courageous Follower: Standing Up To and For Our Leaders.
image of U.S. President Donald Trump is displayed on a digital billboard in Times Square in New York on April 8, 2026.
Trump is stuck between two realities. Neither serves the American people
Normally, I worry that events may overtake a column. But not so with the Iran war.
I don’t worry about running afoul of a headline or Truth Social post from the president because what is said about the situation is no longer very relevant to the reality.
On April 8, Nick Catoggio, my Dispatch colleague, dubbed an earlier stoppage with Iran “Schrödinger’s ceasefire.” This was a reference to the famous thought experiment by the physicist Erwin Schrödinger, who was trying to explain the weirdness of “superpositionality” in quantum physics. A cat in a box is both dead and alive at the same time until you open the box. Schrödinger meant to illustrate the absurdity of the idea that particles aren’t any one thing, but a “cloud of probabilities.”
The Trump administration is stuck in a word cloud of probabilities of his own making. The war is over. The war is on. The war isn’t a war. We have a deal, but we don’t have a deal, but we’re about to have a deal. We destroyed Iran’s military. No, we left it intact. We want regime change. No we don’t. We already accomplished it. We “obliterated” Iran’s nuclear program a year ago. We had to go to war in February to prevent nuclear war. The Strait of Hormuz is open, closed, or something in-between. No deal without “unconditional surrender.” Let’s make a deal!
This everything-all-at-once vibe can be disorienting, particularly since most Americans didn’t have a war with Iran on their bingo cards until the shooting had already started. President Trump didn’t prepare the country or consult with Congress beforehand because he thought it would all be a smashing success in a matter of weeks.
The miscalculation that started it all: killing Iran’s Supreme Leader, Ayatollah Ali Khamenei, and much of Iran’s senior leadership, on the first day of the war. To “the great proud people of Iran, I say tonight that the hour of your freedom is at hand,” Trump announced on Feb. 28. “When we are finished, take over your government. It will be yours to take. This will be probably your only chance for generations.”
I support regime change in Iran and shed no tears for Khamenei or his goons. But when you start a war by killing the regime’s top leaders, it’s not unreasonable for the remaining ones to conclude that you really intend regime change.
Khamenei was a murderous fanatic, but he was a fairly cautious one. He liked to threaten closing the Strait of Hormuz or attacking our regional allies, but he was reluctant to actually do it, fearing it would invite a regime change war. The mullahs and IRGC goons believed, not unreasonably, that if they lost their grip on power, they’d be lynched by the Iranian people they’ve brutalized for decades.
By starting with a regime change war, Trump removed any reason for the regime not to go for broke. When you have nothing to lose — particularly when you are a millenarian religious fanatic — a Persian Alamo strategy makes a lot of sense.
So Iran closed the Strait of Hormuz and attacked its neighbors.
But it turns out this wasn’t the Alamo. In the contest of wills, Trump blinked. The Iranian regime’s tolerance for punishment proved — so far — to be greater than Trump’s and that of our gulf allies. Militarily we could finish the job, but that would require ground troops and much greater economic turmoil. In a conflict Trump launched unilaterally without the prior support of Congress, NATO or the American people, Trump doesn’t have the political capital for that.
But that’s only half the problem. Trump wants the war over, but he doesn’t want to pay — militarily, economically, politically — what that would cost. So he wants to make a deal that ends it. But there is no deal available that wouldn’t come at an equally undesirable cost. Any deal that looks like what President Obama struck with the Iranians would be too embarrassing to bear. But the Iranians are convinced that they can get just such a deal, and they’re willing to drag things out as long as it takes.
The result: Trump’s in a box of his own making. He thinks he can talk his way out by simply asserting a reality that doesn’t exist. When the financial markets get nervous, he announces a breakthrough that is, at best, a possibility. When the Iranians agree to a deal that looks similar to one Obama might negotiate, Trump goes back to his threats.
It can’t go on forever. But I’m sure it’ll last until long after this column is forgotten.
Jonah Goldberg is editor-in-chief of The Dispatch and the host of The Remnant podcast. His Twitter handle is @JonahDispatch.