Cartoon by Daniel Boris

What Is Ayatollah Ali Khamenei Thinking?

Mardo Soghom

Middle East Forum: Iran’s 86-year-old dictator has faced a series of dangerous moments since 2018, when President Donald Trump withdrew from the Obama-era nuclear agreement and reimposed sanctions on the Islamic Republic. Khamenei gambled with Iran’s economy and succeeded in destroying it. He faced four protest movements since 2017 during successive national uprisings and survived each one by crushing protests, sometimes killing thousands, all without provoking any serious international backlash.

Khamenei then took an even greater risk by backing Hamas’s October 7, 2023, rampage in Israel. His top officials calculated the likelihood of a backlash against Tehran and its regional allies, but Khamenei chose to discount those risks. He doubled down, encouraging the Houthis in November 2023 to join the war against Israel. He simultaneously refused to make concessions on the nuclear issue to the Biden administration, which had adopted a far softer posture toward Tehran.

His latest gamble has been to challenge Trump directly after massacring up to 20,000 protesters in January 2026, daring Trump to respond. In a January 17 message, Khamenei accused Trump of fomenting unrest and said, “The U.S. president openly encouraged the rioters, and behind the scenes, the U.S. and the Zionist regime provided them with assistance; therefore, we consider the U.S. president a criminal, both for the casualties and damage, and for the slander he leveled against the Iranian nation.”

Many Iranians on social media, however, blamed Trump for doing too little while people were being killed in their thousands. In fact, Trump canceled the air operation that protesters had hoped would stop Khamenei’s murder brigades.

Why is Khamenei taking so many risks at the twilight of his life, gambling everything to defy the United States? He easily could have cut a deal in the past five or six years, won sanctions relief, regained a measure of international legitimacy, and reduced the risk of revolution.

There is little doubt among both Iranian analysts and ordinary people that he is a stubborn man. Protesters hurl the harshest insults at him because they hold him personally responsible for policies that have produced economic misery and social degradation.

Khamenei’s mind is wired like that of the semi-educated, anti-imperialist leftists of the 1960s, fused with an Islamist worldview saturated in hostility toward Jews and the West. Two ideologies converge in him: resentment toward Western power, and the medieval antisemitism embedded in political Islam. Together, they give meaning to his life and mission.

An unnamed Iranian official reportedly remarked years ago, “If we can’t make peace with Barack Hussein Obama, who preaches mutual respect every week and sends us Nowruz greetings, then it becomes obvious the problem lies in Tehran, not Washington.”

Iranians in the streets understand this reality. That is why they chant “Khamenei is a murderer, his rule is illegitimate,” and “Khamenei, have some shame, leave this country alone.” On January 20, exiled Crown Prince Reza Pahlavi called out Khamenei on X: “You are an anti-Iranian criminal. You have neither honor nor humanity. Your hands are stained with the blood of tens of thousands of Iranians.”

There are rumors among Iranians that Khamenei visited the Soviet Union in his youth and has always been a closet communist. Whatever the truth of that, one thing is clear: He is not an ordinary conservative Shi’ite cleric. He is a vintage twentieth-century leftist Islamist, trying in the final years of his life to fulfill what he sees as a sacred ideological mission.

In the same January 17 speech, he repeated his familiar rhetoric: “Islam and faithful, devout Muslims can steer today’s world away from the abyss of ruin and corruption toward the peaks of righteousness, salvation, and honor, from the direction of hell toward paradise—provided they act with deep and widespread faith.” These words reveal either stunning obliviousness or willful blindness to the economic and moral corruption inside his own system, now documented by countless scandals.

Khamenei will not compromise with the United States at the end of his life, especially if that means accepting Israel’s existence. The real question is whether, after him, other strongmen inside the Islamic Republic will be more flexible.

Reports that thousands of Shi’ite militiamen from Iraq and elsewhere were brought into Iran to help suppress protests show that not only Khamenei, but the entire clerical-security establishment, now survives through force alone. With almost no legitimacy left among the public, it depends on a “Khameneist” ideology that sanctifies repression and treats permanent revolution as a moral duty. That ideology, in turn, empowers them to silence those who want a normal life, good relations with the West, and a secular future.