By Michael Crowley
October 2, 2014

The Islamic Republic of Iran put its best face forward at the annual gathering of the U.N. General Assembly in New York City last month. In a room where Iran’s last President, Mahmoud Ahmadinejad, reliably delivered anti-American tirades, his successor, Hassan Rouhani, spoke in friendlier tones. The smooth-talking Rouhani called the 9/11 attacks a “criminal act” and condemned extremism. He also called for further dialogue with the U.S. over Iran’s nuclear program. The next day, Iran’s Western-educated Foreign Minister, Mohammad Javad Zarif, visited U.S. Secretary of State John Kerry’s suite at the nearby Waldorf-Astoria hotel, where the men, joined by the E.U.’s top diplomat, spoke for three hours about how to resolve the long-running nuclear standoff.

But the man who calls the shots remained at home. Whatever the diplomats in Western suits were saying in Manhattan, a powerful cleric in dark robes and a black turban–a man who never leaves Iran and rarely speaks to Western officials–was railing against the U.S. back in Tehran. The day after Rouhani spoke of dialogue, the official Twitter account of Iran’s Supreme Leader, Ali Khamenei, posted an infographic titled “The Result of Negotiations With U.S.” The text declared the nuclear talks both “useless” and “harmful.” A cartoon image featured Kerry in suit and tie, pounding a negotiating table with his fist hard enough to knock over a water glass as he threatened Iran with military action.

Other recent tweets from Khamenei’s account, @khamenei_ir, have called the U.S. a bully, a threat to peace and a supporter of terrorism. In a recent interview on Iranian television, the Supreme Leader, who wields ultimate power in Iran, called Kerry a liar and said the U.S. coalition against the Islamic State of Iraq and Greater Syria (ISIS)–a force that Iran opposes as well–is a mere excuse to dominate the Middle East.

Ten months into the slow-moving talks over Iran’s nuclear ambitions, it is clear that Khamenei is America’s real problem. Rouhani and Zarif may genuinely want a nuclear deal in which they would trade limits on Iran’s capacity to build a bomb for an end to economic sanctions. But they report to the Supreme Leader, who has the final say. And Khamenei loathes and distrusts the U.S. “The Supreme Leader is not prepared to accept our demands,” says Gary Samore, a key Iran nuclear-policy adviser in the Obama White House until last fall. “If Rouhani could actually make decisions, I think we could get a deal. But he’s not the decisionmaker–the Supreme Leader is.”

And unlike Rouhani, the Supreme Leader looks backward, not forward. Iranian reformers want to embrace modernity and the outside world, but Khamenei sees himself as the guardian of an Islamic revolution that rejects the influence of both. Khamenei is a spiritual man, a lover of hiking, poetry and the writing of Victor Hugo and John Steinbeck. But he despises America, which in his view has long subjugated a nation heir to the great Persian empire and which seeks to topple his government. For Khamenei, it may simply not be possible to do a deal with the devil.

Death to America

A few months after he took office in 2009, President Obama sent a secret message to Khamenei. It had been more than five years since the previous direct contact between America and Iran, and Obama wanted to restart a dialogue. The new President could only guess at whether it would work; U.S. intelligence on the Supreme Leader has never been very strong. “It’s really hard to know what he’s thinking,” says Kenneth Pollack, a former CIA analyst and author of two books about Iran. “There’s this real black hole around him.” The U.S. has tried to compensate for that, with limited results, with a National Security Agency surveillance program dedicated to Khamenei, called Operation Dreadnought.

Khamenei surprised some Obama advisers by responding to the President’s letter. But he did so in a “very ranty” written message, filled with grievances about America’s treatment of Iran, says Samore. Obama followed up with a second letter but received no reply.

Four years passed with no further communication, until Rouhani’s June 2013 election. By then Iran’s economy was groaning under the weight of international sanctions–GDP shrank by 5.8%, and inflation soared to almost 45%–and Rouhani signaled that Tehran was prepared to discuss a nuclear deal. He appointed Zarif, who counts many American journalists and politicians as personal friends, as his top envoy.

Despite the overtures, skeptics warned Obama not to trust either Rouhani or Zarif. Israeli Prime Minister Benjamin Netanyahu, who says an Iranian bomb would threaten his country’s existence, insisted that Rouhani was “a wolf in sheep’s clothing,” noting that Khamenei is “the real power in Iran, the dictator known as the Supreme Leader.” There were concerns in Washington as well, including on the part of then Secretary of State Hillary Clinton, who writes in her recent memoir, Hard Choices, that she watched Rouhani’s outreach with “a healthy dose of skepticism.” The Supreme Leader, as she puts it, “still held all the real power.”

And then there was history: several American Presidents have been burned by trusting Iranian “moderates.” Ronald Reagan wound up with the Iran-contra scandal. George H.W. Bush once spent half an hour on the phone with a man he believed to be Iran’s President–only to discover afterward that he’d been duped, likely by a hard-liner trying to subvert the moderate Iranian leader. In the late 1990s Bill Clinton exchanged overtures with the moderate President Mohammed Khatami, only to see the Supreme Leader abruptly halt the process and rebuke Khatami.

The doubters also worried that Iran was mainly waging a public relations effort to reverse the malevolent image fostered by the acidic Ahmadinejad. Perhaps by showing a friendlier face to the world, Iran could get the sanctions lifted without making major concessions on its nuclear program. Whatever the motive, the new look worked, up to a point. Last fall, Rouhani and Obama had the first phone conversation between the Presidents of Iran and the U.S. since the 1979 revolution. That November, Kerry and Zarif, along with diplomats from five other major powers, struck a temporary deal that froze the progress of Iran’s nuclear program in exchange for eased sanctions. Expectations soared as some foreign policy experts imagined a new U.S.-Iranian partnership in the Middle East. Obama spoke of giving Iran “a dignified path to forge a new beginning with the wider world.”

In the Shah’s Dungeon

Notably, however, the Supreme Leader never spoke in such cheerful terms. Khamenei was born in 1939 in the northeastern Iranian shrine city of Mashhad. The second of eight children, he followed in the footsteps of his father, a religious scholar, and studied in the holy Shi’ite city of Qum. (The Persians converted to Shi’ism 500 years ago, and Iran is home to the world’s largest Shi’ite population–a fact that has put it at odds with the Sunni Arab world.) It was there that he met his predecessor and mentor, Ayatullah Ruhollah Khomeini, the leader of Iran’s Islamic revolution and the first man to hold the title of Supreme Leader.

It was Khomeini who branded America “the Great Satan” and instilled a hatred for the West among his followers. Khamenei didn’t need persuading. By the time of the revolution, he had already been jailed six times by Iran’s pro-American monarch, Shah Reza Pahlavi. While the Shah had a glamorous image in the West, he was a thug at home, reinstalled in a 1953 CIA-led coup and protected by a U.S.-trained secret police with a record of brutal torture–torture that Khamenei experienced firsthand. Visitors to a former interrogation center at a prison where he was held in solitary confinement–now an anti-Shah museum–can see a portrait of a young Khamenei with a black beard, shortly cropped hair and thick glasses, and a video in which he describes how an interrogator for the secret police, known as SAVAK, once poured alcohol on his beard and set it afire.

A plaque indicating Khamenei’s old cell now bears a telling quote from him: “Unless you are faced with such brutal and vicious circumstances, you will not have any true and deep understanding of those hardships and difficulties.” Khamenei likely holds the U.S. at least partly responsible for this misery, says the Iranian-American journalist Hooman Majd. “He saw the U.S. support someone he considered a vicious dictator in whose jails he spent time.”

Almost every speech Khamenei delivers is shot through with that animosity. His rhetoric suggests a man who doubts that the U.S. could ever strike a deal in good faith. “America,” he said in a 2009 address, “appears with a deceitful smile but has a dagger behind its back … That is its true nature.” Even ostensible allies cannot trust Washington, he warned an audience recently. “When America has the opportunity,” he said, “it will stab them in the back and tear their hearts open.”

The Uncertain Ayatullah

Khamenei’s acolytes speak of him like a deity. “Understanding the complete character of the Senior Leader is a hard thing,” says Hossein Shariatmadari, editor of the government-owned newspaper Kayhan and a frequent visitor with Khamenei. “He has a very high and enhanced heavenly characteristic.”

“He lives very simply,” says Kazem Jalali, a member of Iran’s parliament. “He lives more simply than the new Pope.” That’s hard to say. No public photos seem to exist of his home or even his wife. But Khamenei is typically seen working in his modest Tehran offices or delivering speeches in traditional clerical robes, his black turban signifying direct descent from the Prophet Muhammad.

After the Shah fled Iran, Khomeini assumed power and oversaw a new Islamic constitution which named him Supreme Leader, a position charged with ensuring that Iran’s parliamentary government complied with Islamic law. The startling overthrow of an oil-rich Middle Eastern ally, the hostage crisis and chants of “Death to America!” in Tehran quickly made Khomeini a household name in the U.S. Khamenei took a barely visible backseat role as Iran’s President, serving from 1981 to 1989. He spent much of that time managing Iran’s ghastly eight-year war with Iraq–in which, in another well-remembered grievance, Iraq received U.S. backing even after Saddam Hussein employed chemical weapons against Iranian troops.

Before his death in 1989, Khomeini gave his blessing for Khamenei to be his successor. But it was not a simple choice. One problem was that Khamenei lacked his predecessor’s religious credentials. Because he was not a marja, or grand ayatullah, as Iran’s new Islamic constitution required, the document had to be amended before Khamenei could become Supreme Leader. “Had the revolution never happened, Khamenei would have likely been a modest clergyman today, not one of the most powerful men in the Middle East,” says Karim Sadjadpour of the Carnegie Endowment for International Peace.

Beyond religious credentials, Khamenei also lacked the raw charisma of his mentor. Even when his speeches are harsh–and they usually are–his delivery is dull. His face is blander than that of the scowling, wild-eyed Khomeini. “He is a weak man in a very powerful job,” says Pollack.

As a result, Khamenei consolidated his power by forming a close alliance with Iran’s hard-line Revolutionary Guard. “Because Khamenei lacked Khomeini’s religious credentials, he sought legitimacy in the barracks rather than the seminary,” Sadjadpour says. “Whereas Khomeini was a clerical dictator, Khamenei is more of a military dictator.”

He did have the Iranian equivalent of street cred, thanks to his time in the Shah’s prisons. Khamenei also narrowly survived a 1981 assassination attempt in which a Marxist opposition group planted a bomb in a tape recorder at a press conference. The explosion crippled his right arm. As a result, says one person who recently met with Khamenei in Tehran, he has developed a peculiar handshake: “He lifts both of his hands and almost picks up yours in the wedge between them,” says this person, who describes the 75-year-old as alert and otherwise in good health. (Khamenei was recently hospitalized for what is thought to have been prostate surgery.)

Khamenei may lack his predecessor’s magnetism, but he does seem to be more open-minded. He is devoted to poetry and literature, including the works of Western authors. According to a recent Foreign Affairs article by the Iranian journalist Akbar Ganji, Khamenei extols Tolstoy, Balzac and Steinbeck’s Grapes of Wrath–if only for its bleak portrait of capitalism. Hugo’s Les Misérables is “the best novel that has been written in history,” he once said, “a miracle in the world of novel writing.” And when it comes to Western music–which Khomeini despised–he has drawn a distinction between “decadent music for dancing and debauchery” and music that “a wise transcendental person can enjoy.”

Unmovable

Despite his taste in French romantics, Khamenei upholds a strict Islamic law. In May, six young Iranians posted a YouTube video of themselves dancing around Tehran to Pharrell’s hit song “Happy.” For the crimes of women without headscarves dancing with men, they were arrested and sentenced to 91 lashes and six to 12 months in prison. (A court later suspended the sentences.) Khamenei likely did not order the arrests, but he does see cultural liberalization as a dire threat to Iran’s Islamic purity–and therefore to his own power. In a 2005 speech on state television, he said Iran’s enemies want to “arouse sexual desires” and “spread unrestrained mixing of men and women” in Iran. If they did, he concluded, “there will no longer be any need for artillery and guns” to overthrow his government.

He also oversees a regime of censorship and repression that stifles open debate. Most Iranians are unable to access Twitter, which is ironic, given how frequently Khamenei himself tweets. In late September, 11 Iranians were arrested for the crime of sharing jokes about the late Khomeini.

But Khamenei’s battle against modernity may be a losing one. Many Iranians, especially young urban ones, don’t share his stern morality. Iranian women increasingly stretch or ignore the Islamic dress codes that require “modesty.” Private parties in Tehran can be just as festive as those in Brooklyn. Millions of Iranians own smartphones, listen to Western music, watch American movies and are well informed about the outside world. “Most Iranians have no firsthand recollection of the [1979] revolution,” says one Obama Administration official, who notes that almost two-thirds of Iranians were born after the Shah’s fall. “They’re probably the most pro-American people in the region, after Israel.” American visitors to Tehran are typically welcomed warmly.

That tension helped to produce an unprecedented challenge to Khamenei’s power. In June 2009, a wave of street demonstrations in cities like Tehran and Isfahan erupted after Ahmadinejad won re-election in a seemingly rigged vote. In what became known as the Green movement, thousands of protesters denounced the Supreme Leader with chants of “Death to the dictator.”

Khamenei declared the protests the work of “espionage machines working for Zionists and the Americans.” Nonsense, perhaps, but revealing of his mind-set. For years American politicians and pundits have talked about overthrowing Iran’s Islamic government, either by force or by supporting democratic reform. “He is convinced that the U.S. raises concerns over the nuclear program as a fig leaf for the hidden goal of regime change,” says a former Obama Administration official.

The demonstrations were soon brutally suppressed by Iran’s hard-line security services. Khamenei’s son and close adviser Mojtaba reportedly helped oversee a violent crackdown by paramilitary forces. In Washington, Obama officials concluded that Khamenei felt he could give no ground. “He has this view that any hint of weakness is the beginning of the end,” says the Administration official.

The Nuclear Clock

Khamenei may have drawn mixed lessons from the Green movement, however. His tolerance for a reformer like Rouhani likely reflects anxiety that the sanctions could produce more social unrest. By the time of Rouhani’s 2013 election, sanctions expanded by the West into Iran’s oil and banking sectors had badly stunted the country’s economy, and Iranians were eager for relief.

At the same time, a nuclear deal that lifts the sanctions could trigger investment, growth and accompanying cultural ferment that Khamenei may not welcome. “The world will flood into Iran” when sanctions are lifted, the top State Department Iran negotiator, Wendy Sherman, recently told Voice of America. That’s meant to be a promise, but to Khamenei’s ears, it could sound like a threat.

To succeed, Rouhani and Zarif must persuade Khamenei that his real worry, in a region where economic stagnation has recently fueled revolution, should be about sanctions and isolation. “The Supreme Leader has to become convinced that not to do a deal is the greater threat,” says Dennis Ross, a former top Middle East policy adviser in the Obama White House.

So far, he doesn’t seem convinced. Khamenei seems to believe that the benefits of a military nuclear capability outweigh the risks. Like North Korea’s Kim Jong Un, he may believe a nuke is the only thing that can protect him from a hostile U.S.

In July, Khamenei delivered a speech calling for an industrial-scale uranium-enrichment program well beyond proposed Western limits. Many analysts saw it as a death knell. “The notion of getting a good agreement is over, in my view,” says the Council on Foreign Relations’ Ray Takeyh.

Last month, Secretary of State Kerry suggested another path for cooperation, saying that Iran could join the international coalition against ISIS. But Khamenei has dismissed America’s ISIS campaign as a new excuse for domination of the Middle East. He may also fear that the ultimate goal is to topple Iran’s longtime ally Syrian dictator Bashar Assad.

Khamenei clearly has no interest in being America’s partner anyway. But U.S. officials warn against assuming that means he won’t strike a deal of convenience. It’s also possible that if no agreement is reached in November, the talks will be extended. “The Supreme Leader plays a long game,” says a senior Administration official. “A lot of Iran watchers believe he’ll always whack the Great Satan, even if he knows he needs to do a deal. We’ll see. The important lesson about the Middle East is to watch what they do, not what they say.”

But what he’s saying doesn’t give much reason for hope. Instead of a new partnership with Iran, the U.S. could be headed for a new conflict, one that the Supreme Leader may always have thought was inevitable.

–WITH REPORTING BY ARYN BAKER AND KAY SERJOIE/TEHRAN

Contact us at editors@time.com.

This appears in the October 13, 2014 issue of TIME.

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