Western intellectuals love Muammar Qaddafi’s hip, globe-trotting second son. Is he for real?

The seven sons of Libya’s longtime leader, Muammar Qaddafi, have each charted very different paths in life. Mohamad, the eldest and least favored, chairs the Libyan Olympic committee. Mutassim, the country’s powerful national security adviser, mostly operates behind the scenes, although, some years back, he was caught attempting to privately procure tanks for the army unit he commands. Then, there’s Saadi, a soccer enthusiast, who persuaded his father to make an exception to his edict that sports must be played by the people, not watched for fun. Naturally, once organized soccer was permitted, Saadi became captain of the national team; whenever he played domestic matches, his opponents would back away from him for fear that tackling him might be interpreted as an act of dissent. Saadi then signed on to play for Perugia, an Italian team, but his prowess didn’t translate outside Libya. And so, after a few seasons, he retired, returned home, and is now in charge of a tax-free zone that the government hopes will become North Africa’s Dubai. (Click here to view a slideshow of dictators who love big cats.)

Most infamous is Hannibal, who specializes in getting into trouble. He has made headlines for, among other things, assaulting two domestic servants in Switzerland. Some months later, his father declared jihad on that country. (Qaddafi’s only daughter, Ayesha, a lawyer who served on Saddam Hussein’s defense team, also threatened retribution.) Little is known about the two youngest sons: Saif Al Arab, a student, and the rather thuggish Khamis, a police officer who can often be spotted in his father’s bloated entourage. (Click here to subscribe to the TNR Society.)

The seven sons of Libya’s longtime leader, Muammar Qaddafi, have each charted very different paths in life. Mohamad, the eldest and least favored, chairs the Libyan Olympic committee. Mutassim, the country’s powerful national security adviser, mostly operates behind the scenes, although, some years back, he was caught attempting to privately procure tanks for the army unit he commands. Then, there’s Saadi, a soccer enthusiast, who persuaded his father to make an exception to his edict that sports must be played by the people, not watched for fun. Naturally, once organized soccer was permitted, Saadi became captain of the national team; whenever he played domestic matches, his opponents would back away from him for fear that tackling him might be interpreted as an act of dissent. Saadi then signed on to play for Perugia, an Italian team, but his prowess didn’t translate outside Libya. And so, after a few seasons, he retired, returned home, and is now in charge of a tax-free zone that the government hopes will become North Africa’s Dubai. (Click here to view a slideshow of dictators who love big cats.)

Most infamous is Hannibal, who specializes in getting into trouble. He has made headlines for, among other things, assaulting two domestic servants in Switzerland. Some months later, his father declared jihad on that country. (Qaddafi’s only daughter, Ayesha, a lawyer who served on Saddam Hussein’s defense team, also threatened retribution.) Little is known about the two youngest sons: Saif Al Arab, a student, and the rather thuggish Khamis, a police officer who can often be spotted in his father’s bloated entourage. (Click here to subscribe to the TNR Society.)

The odd one out is Qaddafi’s second-oldest son, Saif Al Islam. The 38-year-old Saif has his fiefdoms, too—he directs Libya’s sovereign wealth funds, worth some $70 billion, as well as much of its booming construction sector. But what sets him apart from his brothers is his unusual role as the quasi-official advocate for democracy in a nation that his father has ruled implacably for 40 years.

I met Saif this spring at his persimmon-colored villa in Tripoli. Although the house is surrounded by a security perimeter, four checkpoints, and a lawn that would pass muster at Wimbledon, Saif referred to it humbly as “the farm.” Inside, two stuffed Bengal tigers reclined on the marble floor. Until they died of natural causes some years ago, Fredo and Barney were Saif’s beloved pets. In a tiled atrium, he pointed to a photograph of the tigers. “Here they are younger,” he said. A coffee table was piled high with books, from John Kenneth Galbraith’s The Great Crash of 1929 to Hip Hotels. “I’ve read thousands of books,” Saif said, although, when I asked which he liked best, no particular title sprang to mind. Saif is also a keen artist. An exhibition of his expressionist paintings (his father and the tigers are popular subjects) opened this year in São Paulo and Moscow, although not to critical acclaim: An art writer for The Guardian declared that Saif’s “sentimentality is only exceeded by his technical incapacity.” We moved into the study, which was dominated by a large television. Saif had no trouble naming his favorite movie: the gory 2004 slasher flick Saw. He also told me that the American he would most like to meet is Dick Cheney, and then hastily added, “Just joking.” Throughout our conversation, he appeared anxious not to stray off message.

Saif is more than six feet tall, with a shaved head and hip, rimless glasses. He juggles his two identities—traditional Arab leader and Western-educated modernizer— with care. When I met him, he sported a royal blue kurta with a goldenrod- hued rug tossed over one shoulder; in public, however, he favors bespoke business suits, with three-pointed handkerchiefs tucked in the breast pockets. Saif’s friends include Nat Rothschild, scion of a powerful British banking family, and he’s acquired an enthusiastic following among certain Western intellectuals. Benjamin Barber, the author of Jihad vs. McWorld and an adviser to the Libyan government, told me, “I don’t think there has ever been a young political leader in a ruling family who’s had such extraordinary insight into Western political thought.”

Saif’s polish and prestigious friends make for a conspicuous contrast to his father, who was, for many years, shunned by the Western world for harboring terrorists and for bankrolling notorious despots such as Charles Taylor and Idi Amin. In recent years, however, Libya has swiftly shed its pariah status. The United Nations lifted sanctions in 2003, the United States followed suit in 2004, and, in 2006, the Bush administration removed the country from its list of states that sponsor terrorism. Saif, who is often presumed to be his father’s successor, has played a prominent role in this rehabilitation. Last year, in an event that marked Libya’s improved standing in the world, he negotiated the release from prison of Abdelbaset Al Megrahi, who was convicted for the 1988 bombing of Pan Am Flight 103 over Lockerbie, Scotland. And Saif has ambitious plans. He wants to end Libya’s economic dependence on oil, rewrite its repressive penal code, and draft a constitution, which the country has lacked since 1977. The question, however, is whether it’s really possible for a man named Qaddafi to bring democracy to Libya.

To drive through the streets of Tripoli is to take an architectural tour of nearly 2,000 years of absolute rule, from the arch constructed by Marcus Aurelius in 163 C.E. to the gleaming petrodollar towers stretching skyward. Downtown, between the Mediterranean Sea and Green Square, stands a red castle built on the remains of an old Roman settlement. In 1790, as legend has it, one crown prince named Yusuf Karamanli invited his two brothers to discuss succession in the castle’s study. After they reached an agreement, he ordered a servant to fetch the Quran so they could swear on it. The servant returned with a pistol. The crown prince murdered his brothers and went on to rule Libya for nearly 40 years.

Muammar Qaddafi did not seize power with quite the same élan—he ejected Libya’s monarchy in a bloodless coup in 1969—but he has maintained his authority for even longer than the crown prince. He governed according to a system he called “Islamic socialism,” which he outlined in his 1975 revolutionary manual, the Green Book. This eccentric document combines Qaddafi’s political philosophy with musings on breast-feeding and horse racing and maintains that the country is ruled not by Qaddafi— whose official title is “brotherly leader and guide of the revolution”—but directly by the people. In truth, Qaddafi’s power has been absolute. Opposition was crushed ruthlessly at home; during the 1980s, the government dispatched hit squads to murder dissidents abroad. As foreign pressure mounted on his regime, Qaddafi remained defiant—through the blowback from the Lockerbie bombing in 1988, nearly two decades of tough economic sanctions, and an attempted ouster by the administration of Ronald Reagan, who famously dubbed Qaddafi the “mad dog of the Middle East.”

In the 1990s, however, Qaddafi appeared ready to emerge from the doghouse. In 1999, he sent the suspected Lockerbie bombers to The Hague for a trial. American and British officials soon held their first direct talks with Libya in 18 years. Not long afterward, American oil executives returned to Libya, where billions worth of frozen assets awaited them. The U.K. restored full diplomatic ties; Libya was opening for business.

But the real turning point came on September 11, 2001. The threat of radical Islam was old news to Libya—it had been the first nation to issue a warrant for Osama bin Laden’s arrest, in 1998, after Muslim militants had attempted to assassinate Qaddafi. Following the attacks, the government was eager to share with the United States intelligence on terrorist networks. Bigger concessions followed. In August, Libya agreed to pay reparations to the families of victims of the Lockerbie bombing, and, in December, Qaddafi gave up his nuclear weapons program and renounced terrorism. In 2008, the United States sent its first ambassador to Tripoli in more than 35 years. Libya had transformed from one of the most reliable villains on the world stage to a U.S. partner in the war on terror.

When I met Saif at “the farm,” he regaled me with a practiced narrative of his formative years, in which Libya’s outcast status had inspired him to end its isolation. “I had a very hard life,” he began. We were standing in the grounds, outside an enclosure that housed a fluffy orange tiger cub scuffling playfully in the dirt. Saif described a night when he was 14 years old and awoke to the sound of U.S. F-111 fighter jets dropping 2,000- pound bombs on his house. His mother dragged him to a secret underground bunker, where he huddled with his father and siblings. “The whole world was closed to me,” he said, recalling the times that he was denied visas to study in Switzerland, France, and Britain and, then, briefly admitted to a university in Austria, only to be ejected from the country by its head of security. “I was very upset, but I decided that I would change this sad picture.”

Saif initially studied architecture in Belgium but gravitated toward politics after his father began to seek out brand-name scholars to advise Libya on reform. (Benjamin Barber said that Muammar Qaddafi contacted him after reading about him on the Internet.) With his father’s blessing, Saif became the country’s most high-profile proponent of liberalizing Libya. He obtained a Ph.D. from the London School of Economics, where he read Rousseau, Locke, and Weber, and wrote his dissertation on comparative democracy.

Saif has championed numerous innovations, including a watchdog organization that polices corruption. Under his watch, Libya plans to invest $124 billion in new infrastructure projects, in an effort to build an economy that runs on more than crude. The results are visible: Along Tripoli’s washed-out skyline, red building cranes swing in wide arcs above sandy plots of earth.

Saif told me that he considers the writing of a constitution to be his flagship initiative. Despite the many changes that have come to Libya, its political system remains constricted. “There’s no freedom of the press. You cannot freely choose your leaders. It’s still a cult of personality,” said Daniel Byman, the director of Georgetown University’s Center for Peace and Security Studies. I asked Saif how the constitution project was progressing, and he said a draft exists but had not yet been made public. “My father is not very enthusiastic about this project,” he admitted. “Hopefully, one day, he will accept it.”

Despite his zeal for democratic institutions, so far, Saif has used the authority of the state to advance his cause. He runs the only domestic human-rights organization permitted in the country—the Qaddafi International Charity and Development Foundation. I was first invited to Libya last fall by the foundation to witness its efforts to reform the Libyan Islamic Fighting Group (LIFG), a militant outfit that has repeatedly tried to overthrow Qaddafi’s government.

During the 1990s, the LIFG, like Al Qaeda, found safe haven in Afghanistan and Sudan. But its mission has primarily been to build an Islamic state in Libya, not to join Al Qaeda’s global jihad. After September 11, many of the group’s leaders were arrested by the United States and detained at Bagram Airfield in Afghanistan and other international facilities. (One of these senior members, a religious scholar named Abu Yahya, escaped from Bagram in 2005, linked up with Al Qaeda, and is now regarded as its most senior leader after bin Laden and Ayman Al Zawahiri.)

In 2005, the United States returned LIFG leaders to Libyan custody, as part of an effort to send detainees back to their home countries. Saif claims that the Americans asked his foundation to “monitor” these prisoners, although he won’t say who made this request. (The State Department did not return calls seeking comment.) In 2007, Saif met Noman Benotman, a charismatic former LIFG leader, in London. He asked Benotman to discover if his former associates would be willing to renounce their jihad. When Benotman visited the LIFG leaders in Libya’s Abu Salim prison, they told him they were ready to stop fighting. This meeting launched two years of discussions between the LIFG and the Libyan government, in which the Qaddafi foundation served as the go-between.

Then, last fall, Abu Yahya’s brother, Abu Idris, along with five other LIFG leaders, issued a 400-page-plus document titled “Corrective Studies”—essentially a religious argument against global jihad. The leaders denounced the killing of innocents, including “women, children, elderly people, priests, messengers, traders.” Jihad, they wrote, was only lawful for Muslims whose countries were being occupied by foreign forces. “Corrective Studies” was hailed as the most significant theological repudiation of Al Qaeda by Muslim militants. Saif, as is his habit, claimed the document was his idea. “I told them, ‘You should write this.’ It helped me with my father.”

In late March, Saif held a conference for a small group of high-level Western counterterrorism analysts to demonstrate the progress his foundation had made with the lifg. One crisp morning, the attendees were taken by minivans to Abu Salim prison, a low-slung, sandcolored, stucco building in a dusty Tripoli suburb. Saif had a surprise in store.

For Libyans, Abu Salim evokes grim memories. In 1996, according to Human Rights Watch, some 1,200 prisoners were killed here—many of them executed by impromptu firing squads. Most had been accused of being Islamists intent on plotting to remove the Qaddafi regime. For nearly a decade, families didn’t know if their sons were alive. Saif has promised to investigate the massacre, but his report is more than a year overdue.

After arriving at Abu Salim, we walked a quarter of a mile down a macadam driveway. Suddenly, inmates dressed in crisp white kurtas and shiny black nylon vests began pouring out of the prison, cheering, “Thank you to my friend Qaddafi and his son Saif Al Islam.” The men made their way toward white plastic lawn chairs that had been placed under a nearby tent. Then, more people began pushing their way through the prison gates—the prisoners’ families. Mothers squeezed their sons’ cheeks and wept.

Not everyone was won over by this joyful scene. “How do you like my uniform?” one man walking next to me muttered sarcastically in English. He was clad in rough cotton and a shepherd’s vest. “I spent thirteen years on your West Coast. I’ve dressed this way to look like a stupid old man, so they won’t track me.” He looked away from me, barely moving his mouth as he spoke. “Please, we are looking to you for help. This is not a country; it’s an asylum. This is not a government; it’s one man. The father is simply trying to appoint the son. There are thousands of young men in prison. Look, they’re filming everyone you talk to.” Sure enough, a tall man in sunglasses was following me with a video camera, posing as a TV journalist. When I glared at him, he swung the lens away.

Nearby, I saw two men hugging each other. One said he’d received a phone call the previous night, informing him that his brother would be released after being held incommunicado for three years. “He is a student. They came and took him at 5 a.m. saying he had dangerous books about Islam,” he said. The newly released man shrugged. “I’m out today. I may be back in tomorrow.” His brother was more hopeful. “Saif is better than Qaddafi,” he insisted. “Saif’s not a soldier, at least. He has a doctorate.”

That afternoon, Saif held a press conference in a brand-new luxury hotel in downtown Tripoli. Two-hundred and fourteen inmates had been released. Thirty-four belonged to the LIFG, including three of its six top leaders. One hundred more were former jihadists who’d fought against the United States in Iraq. The remaining handful belonged to other Islamic groups suspected of plotting to overthrow the Libyan government. Thanks to Saif, they were now free men.

The prisoner release was an ingenious move. Saif had demonstrated that a militant group could be persuaded to publicly denounce its former terrorist allies. “The implication is pretty radical,” said Jarret Brachman, the former director of research at West Point’s Combating Terrorism Center. “The Libyans might hold one of the keys of success to the war with Al Qaeda.” But, while the members of the LIFG had ostensibly gone through “demobilization”—which at least included perfunctory meetings with religious teachers and prison officials—no one, including Saif, knew whether the other freed prisoners had been rehabilitated. “What matters to the international community is not just are [the released prisoners] targeting Qaddafi and his family,” said Jessica Stern, a lecturer at Harvard’s Kennedy School of Government. “What matters a lot is if they’ve given up fighting jihad against the West.” Of that, there was no guarantee.

Saif’s account of his work makes for a compelling tale, in which the idealistic son persuades his father to open his country to the West. But Libyan insiders have a different interpretation of these events. They say Qaddafi was motivated by the knowledge that Libya’s oil is expected to run dry in 30 years— and by the unsettling experience of watching the downfall of his friend Saddam Hussein. Qaddafi didn’t want to “end up in a hole,” said Mahmoud Jibriel, chairman of the Economic Development Board, a governmental think tank. And even Saif ’s boosters concede that his proposals owe a debt to his father. “Whatever their relationship... none of this could happen against [Qaddafi’s] wishes,” said Barber. Hafed Al Ghwell, a Libyan intellectual based in Washington, D.C., offered a different assessment: “Saif is being used in many ways by the system,” he said, “to give a Westernized feel to it.”

Among Qaddafi’s sons, Mutassim is thought to pose the most serious challenge to Saif. He is allied with the security apparatus and the aging, conservative members of his father’s regime. However, last October, Muammar Qaddafi instructed the regime to find his son a government position, like general coordinator of the people’s committees, the equivalent of secretary of state. This was the clearest sign yet that Qaddafi intended Saif to succeed him. But Saif told me that he had declined his father’s offer—and he dismissed my questions about family succession. “All the time, people are trying to create enemies for me, the old guard, my brother—to sex it up,” he said. He has repeatedly insisted that he’ll only serve in the government if he’s elected. “We want to have a democracy and constitution and institutions. It’s not my goal to be part of the political machine. My goal is to create a better life for the Libyan people,” he insisted. “Has there been a shift in Libya? The answer is yes, definitely,” said Heba Fatma Morayef, a researcher for Human Rights Watch. But, she added, “What if Saif is out of favor tomorrow? Do these new freedoms apply to anyone whose name isn’t Qaddafi?”

A few days after the prisoner release, I paid a visit to Ahmed Rahal, the news editor at Al Ghad, Libya’s only “semiindependent” news company—which, inevitably, is owned by Saif. The newsroom looked like newsrooms everywhere. Rahal, a heavyset man with the weary gait of an overworked editor, was interrupted every few minutes to take calls from correspondents covering the Arab Summit that week in Qaddafi’s home town of Sirte. He spoke with a slight Manchester accent—he had only recently returned from London, where he’d worked for the U.K.-based independent Libyan news site Al Youm. The Libyan government periodically blocks access to Al Youm, and has sometimes shut down Al Ghad’s two newspapers, claiming they owe the government hundreds of millions of dollars in printing costs.

I asked Rahal if he thought the prisoner release was significant. “This was a very big deal,” he said. Two months earlier, Muammar Qaddafi had called the Islamists “terrorists” and vowed that they would never leave prison. The release proved that Saif could stand up to his father. But Rahal was more circumspect when it came to Saif’s political reforms. “It’s not an easy question,” he said. That he’d felt safe to come back to Libya after working for Al Youm was in itself a sign that something was different. Admittedly, internal security had hauled him in for questioning not long after his return. The agents asked him whether or not he’d read the Green Book and what he thought of the brotherly leader’s ideas. Rahal told them, “When I lived in Libya, and you forced me to read it, I didn’t read it. When I went to London and was free not to read it, I read the Green Book and found that the leader had some very good ideas, but that the people around him have used them to destroy the country.” After the interview, he was still permitted to go back to work.

“Twenty-five years ago, this would have meant prison,” he pointed out. Now, his news agency was beginning to take on human rights issues. Recently, it had been investigating the brutal abuse of women who are found guilty of “crimes of honor” and sent to so-called rehabilitation centers that operate more like prisons. But, when I asked him whether Al Ghad could report freely, he answered that there were limits, of which Libyans are well aware. “Saif has said there are four red lines: Islam, splitting up the country, national security, and the fourth and the last is Muammar Qaddafi.”

Eliza Griswold, a fellow at the New America Foundation, is the author of The Tenth Parallel, which will be published this August.

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