The Iranian Hedgehog vs. the American Fox

America’s most powerful military assets have now convened in the Middle East, encircling Iran and preparing to strike it from land, air, and sea. These assets include 10 advanced warships and dozens of fighter jets capable of flying at twice the speed of sound to deliver 20,000-pound payloads. Iranian officials have responded, with characteristic bombast, that they will “never submit,” have their “fingers on the trigger,” and are prepared to strike “the heart of Tel Aviv” and to harm thousands of U.S. soldiers in the Middle East.

Beneath this sabre-rattling is a test of wills between two men—President Trump, age 79, and Supreme Leader Ali Khamenei, age 86—with clashing personalities and worldviews. The best framework to understand them comes not from political science but from a short 1953 essay by the British philosopher Isaiah Berlin, called “The Hedgehog and the Fox.” Borrowing from the ancient-Greek poet Archilochus, Berlin divided “writers and thinkers, and, it may be, human beings in general” into two distinct categories. “The Fox knows many things,” he wrote, “but the hedgehog knows one big thing.”

Hedgehogs, he wrote, “relate everything to a single central vision, one system, less or more coherent or articulate, in terms of which they understand, think, and feel—a single, universal, organizing principle in terms of which alone all that they are and say has significance.” This describes Khamenei, whose four-decade reign has centered around the idea of “resistance”: against America, Israel, and now much of his own population.

Foxes, meanwhile, Berlin wrote, “pursue many ends, often unrelated and even contradictory, connected, if at all, only in some de facto way, for some psychological or physiological cause, related to no moral or aesthetic principle.” While his supporters and critics would disagree as to whether Trump should be commended for his agility or criticized for his incoherence, they might agree that he is the Jackson Pollock of grand strategy. No American president has kept both allies and adversaries on their toes more than Trump.

The two men are enigmas to each other, separated by far more than just language or geography. Trump, thrice-married and irreligious, was born into wealth and has lived a life of gold-plated opulence and publicity. Khamenei was born into poverty and outwardly disdains pomp, cultivating an image of pious frugality. He has been married for more than six decades to a woman the Iranian public has never seen—not even in a photograph.

Khamenei and Trump already have a tumultuous history. In 2018, Trump withdrew the United States from the nuclear deal his predecessor had struck with Iran and subjected Tehran to a maximum-pressure campaign to force either regime collapse or nuclear capitulation. Khamenei refused to compromise, calling instead for a “resistance economy” and killing thousands of citizens who protested their economic discontent.

In 2019, Khamenei engaged in a series of  provocations against the United States. Iran shot down a $100 million U.S. surveillance drone, and it launched a cruise missile attack on Saudi Arabia’s oil facilities, rattling global markets. In early 2020, Khamenei personally taunted Trump on Twitter, telling him he couldn’t  “do anything” and was “hated.” Days later, Trump, much to the surprise of even his own advisers, responded by assassinating Iran’s top military commander, Qassem Soleimani, in Iraq. This transformed a political rivalry into a blood feud. Since then, an account on X linked to Khamenei’s office has openly fantasized about killing Trump on the golf course, and in 2024 the FBI uncovered an actual Iranian assassination plot against him. Today, Trump may seek to kill Khamenei.

Most recently, this past summer, Trump dropped 14 30,000-pound bunker busters on Iran’s nuclear facilities. History will need more time to determine the efficacy of that decision, but Trump commonly touts it as a great example of his foreign policy’s success. For this reason, and because the strikes over the summer destroyed Iran’s air-defense systems, Trump may well choose to roll the dice again.

Trump warned Tehran on at least eight occasions that there would be consequences if Iran killed anti-government protesters. Khamenei drove a truck through Trump’s red line, giving his security forces the go-ahead to kill as many as 30,000 protesters over a 48-hour period, one of the worst massacres in modern history. “Resistance,” Khamenei has said, “unlike surrender, leads to the retreat of the enemy. When the enemy bullies you, if you take a step back, he will undoubtedly advance. The way to stop him from advancing is to resist.”

[Read: What are the chances Trump attacks Iran?]

During Trump’s first term, one of his senior advisers told me (confidentially, as he was not authorized to speak publicly on the matter) that the worst nightmare of the Iran hawks in the Cabinet was that Khamenei would offer Trump a meeting, much like the Singapore Summit Trump attended with Kim Jong Un. They knew that the president would jump at such an opportunity. But that opportunity never came. In Khamenei’s worldview, normalizing relations with the United States has always been kryptonite, an existential threat to a regime whose identity was premised on resisting America.

This philosophical asymmetry—Trump, the fox, has no fixed beliefs, whereas Khamenei, the hedgehog, has one fixed belief—is the engine of the current crisis. Trump thinks that everyone has a price; Khamenei holds that suffering is a price worth paying for his singular aim. Trump cannot understand why pressure and threats don’t break Khamenei. He assumes that every man can be bought and every nation has a breaking point. But Khamenei, who espouses resistance and martyrdom, and who believes that ceding to pressure projects weakness, cannot be persuaded with material blandishments.

“Khamenei’s motivation is no longer governing Iran,” a government-affiliated cleric in Tehran told me recently, “it is fighting ‘global arrogance’”—his moniker for America and Israel.

[Read: The collapse of the Khamenei doctrine]

Trump has spent the past week oscillating wildly between threats of war and offers of peace. “A massive Armada is heading to Iran,” he warned on social media, boasting that it is “ready, willing, and able to rapidly fulfill its mission, with speed and violence if necessary.” In the very same post, he wrote: “Hopefully Iran will ‘Come to the Table’ and negotiate a fair and equitable deal.” He has simultaneously threatened to “obliterate” the country, called Khamenei a “sick man,” and asked for a new accord. Given Trump’s track record, the supreme leader cannot dismiss these volleys as idle threats.

With Khamenei’s regime, and his life, on the line, the resistance instinct must be warring with the survival instinct beneath that black turban. Rather than watch his great-grandchildren at play, Khamenei is spending the twilight of his life like a curled-up hedgehog in his fortified bunker, his life at the mercy of a U.S. president whom he has called a “clown” and a “tyrant” who will be “overthrown.”

So who wins the battle between the fox and the hedgehog? According to Charles Darwin, survival belongs not to the strongest species, nor the most intelligent, but the one most adaptable to change. For Khamenei, abandoning his “one big thing”—resistance—would mean ideological suicide. But his refusal to adapt may now ensure his extinction.