Photo: Robert Patrick/Sipa

The last time Benjamin Barber saw Saif Qaddafi, in early December, they spent a cheerless evening together in London. Barber, a political scientist and board member of Saif’s Qaddafi International Charity and Development Foundation, was in town for a board meeting that was supposed to have taken place in Tripoli but, a week before, had been moved to England. Over an Italian dinner in Mayfair, he asked Saif why.

“I don’t feel comfortable in Tripoli,” the 38-year-old son of Colonel Muammar ­Qaddafi said. “I have too many enemies there right now.” Saif was in a desperate mood. For years he had pushed his way into his father’s chaotic political orbit, urging him to support reform in Libya. Muammar had obliged in the past—but recently he hadn’t. Allies of Saif’s had been arrested and businesses of his shut down. He had decamped and wasn’t sure he wanted to return. “He felt he was not welcome,” Barber says. “He’d been struggling for a long time.”

Barber urged him to push on. Libya was a vastly different country than it had been only a decade earlier, he assured him, thanks largely to Saif. It was a speech Saif had heard many times. He’d long worked with Barber and other academics, executives, consultants, and lobbyists to plot Libya’s future. They’d encouraged Saif, too, and had become partners in a campaign to revive his country and his family name, while he in turn worked with them to make Libya a supposed model of peaceful liberalization in the Arab world. He was what the region badly needed, his foreign boosters said. Saif sometimes agreed.

Two months after that dinner, with Libya in revolt, Muammar asked his favorite son to return home, which he did. Then, seemingly overnight, Saif became a new man: not the deliverer his supporters had hoped but someone indistinguishable from his father.

The second eldest of Muammar’s ­seven sons, Saif al-Islam Muammar al-Qaddafi was born in 1972, three years after his father took power in a military coup at 27. Little is known about Saif’s upbringing except for the brutal events surrounding it. When Saif was a child, Muammar went from a standard­-­issue strongman to the self-­described Brother Leader of the Great Socialist People’s Libyan Arab Jamahiriyah. It was a system he described as a perfect democracy but which others called a murderous autocracy (with televised executions). In 1986, following a terrorist attack in a German disco frequented by U.S. servicemen, Ronald Reagan ordered air strikes that killed, in the Qaddafis’ version, Saif’s younger sister. The U.N. imposed crippling sanctions on the country after Libyan agents were charged with aiding in the Pan Am 103 bombing, and by the end of the nineties, Libya was in shambles. According to a former State Department official, Muammar “knew he could not win this war” and began secret talks with the Clinton administration on compensating families of the Pan Am victims.

As Muammar entered his sixties, he began considering which of his sons might succeed him. His choices were under­whelming. Saif’s elder half-­brother, Mohammed, who ran the state telecom company, was uninterested in the mantle. Younger brother Al-Saadi was known for a failed professional-soccer career and little else, while Hannibal, the next in line, lacked certain statesmanlike qualities, as became clear when he was arrested in a Swiss hotel for beating two domestic servants. Khamis and Saif al-Arab were too young. Muatessem, an army officer five years Saif’s junior, had moved to Egypt after falling out of favor.

Saif, by contrast, had qualities his father admired: his own. Like Muammar, who quoted Rousseau and Madison to visiting diplomats, Saif was charming and well read. Like Muammar, he was confident. “He was absolutely sure what he believed was right,” says Jack Richards, an American businessman and early adviser of Saif’s. Most important, Saif developed ideas about Libya at an early age, including the realization that his father’s rule hadn’t been flawless. “It was implicit in everything Muammar did that Saif was not only the favorite son but the son who understood him the best, because he understood not the tyrant but the democrat,” Barber says. At the same time, there was a “profound Freudian tension.”

Saif showed, of all things, an affinity for America, the country Muammar had made his name maligning. After studying architecture and engineering in Tripoli, he earned degrees in Vienna and at the London School of Economics, and he became enamored of American political history and culture (His favorite movie, reportedly, is Saw). Says LSE professor David Held, who informally advised Saif, “He used to say that Arabs should have nothing to fear from American democracy promotion.”

His anti-authoritarian inclinations were so strong that Saif bristled—or made a show of bristling—at the mention of inheriting power. “The phrase heir apparent was abhorrent to Saif. But I think he secretly always harbored the hope he’d lead the country,” Richards says. Muammar, who held no official title and who spoke idealistically of a future Libya without a Qaddafi in power, seemed to admire his son’s stance, even if he wanted Saif to succeed him.

Photo: Marwan Naamani/AFP/Getty Images

So in 2002, as Libya secretly negotiated with the British government on dismantling its nuclear- and chemical-weapons programs, Muammar asked Saif to get involved. In London, Saif met with officials from Tony Blair’s cabinet and MI-6, and he is credited by some with broaching the idea of including Washington in negotiations. On the eve of the invasion of Iraq, the British contacted CIA assistant deputy director of operations Steve Kappes.

In his memoir, former CIA director George Tenet describes Saif’s presence in the meeting: “[He] started to play the role of tough-guy negotiator, telling Steve and his British colleague what the Libyans expected from us before anything would happen on their end. Steve and the Brit allowed the leader’s son to go on for a while and then cut him off.” By the time Kappes and his MI-6 counterpart went to Libya, Tenet says, Saif had calmed down. After they met with Muammar in Tripoli, Saif invited them to a late dinner at his beach house, where he apparently sat by patiently and listened.

Days after Saddam Hussein was captured, Libya announced it was abandoning its WMD programs. A jubilant Bush administration pointed to the chastening effect of the Iraq war. Those aware of the negotiations knew better, but even they were astonished at Qaddafi’s rapid about-face. Saif bore much of the credit. According to Randa Fahmy-Hudome, a lobbyist who worked for him, “Saif was a ‘no man,’ as opposed to a ‘yes man,’ for his father,” she says. Now Muammar was “testing Saif to see if he had what it took to lead the country.”

With sanctions lifted and signs pointing to the regime coming off the White House’s list of state sponsors of terrorism, the country was suddenly fertile ground. ­Executives from ExxonMobil, ChevronTexaco, Caterpillar, Halliburton, Dow Chemical, and Boeing, to name a few, went to Libya, eager to get at its reserves of light crude and a $100 billion development fund. Now that oil revenue could be invested with foreign banks, Wall Street came calling.

Saif and his father were at the center of the deal-making, and Saif made a few invest­ments of his own. He brought in the K Street consultancy C&O Resources to represent Libya to the Bush administration. He signed the Livingston Group, run by former House Speaker Bob Livingston, to a $2.4 million contract to lobby Congress. For $1.2 million a year, he hired Fahmy-Hudome, a former Department of Energy official, to entice business, and he hired communications firm Brown Lloyd James, along with a former White House special assistant, to handle press relations.

The most ambitious courtier was the Monitor Group, a Cambridge, Massachusetts, consultancy that assists countries with economic reform. Co-founder ­Michael Porter, a professor at Harvard Business School, began traveling to Tripoli to meet with Saif, bringing with him energy consultant and Pulitzer Prize–winning author Daniel Yergin. In June 2004, Porter, Yergin, and Fahmy-Hudome attended an economic forum Saif was overseeing at Tripoli’s Corinthia Hotel. Saif, the Americans found, was a refreshing change from Muammar, who, dressed in one of his quasi-military getups, was known to provoke visitors by decrying the hypocrisies of the West. In a natty suit, with shaved head and eyeglasses gleaming, Saif directed the proceedings with the efficiency of an executive. “It was the seminal meeting of launching the new Libya. This was the team that was going to help him do it,” says Fahmy-Hudome.

That night, Saif sent cars to collect the team and bring them to his beach house for a seafood dinner. Having changed out of his suit, he received them in a flowing white thaub and traditional taqiyah cap. They toasted to the future of Libya.

Two years after that toast, in 2006, Porter presented the Qaddafis with a plan for the rehabilitation of the country that called for a “unique model of ‘popular capitalism’ ” starting with the energy sector, which would revive the economy and, eventually, Libyan society. Muammar could do all this, they promised, by 2019, the 50th anniversary of his coup.

For a yearly fee that reached $3 million, Monitor also mounted an international public-relations campaign to “enhance international understanding and appreciation of Libya and the contribution it has made and may continue to make to its region and to the world,” according to a memo. This entailed bringing to Libya a who’s-who gallery of public intellectuals, including Harvard’s Robert Putnam and Joseph Nye and former LSE director Anthony Giddens. Some, like Barber, were paid consulting fees. Others wrote glowing stories about the new Libya in the press, and Monitor offered, for an additional $2.4 million, to ghostwrite a book under Muammar’s name.

Photo: Buljubasic/Cropix/Sipa

Saif didn’t completely rely on Monitor for connections—he was a skilled roving diplomat in his own right. He developed ties with State Department officials and congressmen from both parties. He spoke at the Council on Foreign Relations and the World Economic Forum, where he announced his intention to create an organization devoted to tracking human-rights abuses in the Middle East. According to a former Bill Clinton aide, Saif called the ex-president from time to time for advice.

As he grew more comfortable on the international stage, Saif further distinguished himself from his father. At a dinner meeting in London, he requested to be seated between a Jewish congressional aide who worked for a leading pro-Israel congressman and a member of a prominent Jewish lobbying association. (Saif was rumored to be dating an Israeli actress at one time.)

He even openly criticized the regime. At the same dinner, the congressional aide asked him what Libya needed most. His one-word answer: democracy.

“You mean Libya needs more democracy?” the aide asked.

“No. ‘More democracy’ would imply that we had some,” Saif said.

In 2007, after persuading his father to free a group of Bulgarian medics in Tripoli, he publicly admitted that they had been tortured into confessing, falsely, to having spread HIV in their hospital. He brought in Human Rights Watch to prepare a report on the notorious Abu Salim prison, where Muammar had ordered the killing of more than a thousand inmates. He initiated a program to rehabilitate Libyan jihadists and worked behind the scenes to help American intelligence break up the network of Pakistani scientist A. Q. Khan, who had provided Libya with nuclear materials. “We wanted to know if [Saif] could take an idea and work it through the Libyan system,” the former State Department official says, and it seemed he could.

His Al-Ghad media group provided non-state-controlled news in Libya. His Qaddafi International Charity and Development Foundation sent students abroad. With a Libyan committee and the Monitor Group, he wrote the first and only constitution Libya has ever known.

In 2008, the U.S. posted its first ambassador to Libya in 37 years. That November, Saif was rewarded with his first visit to Washington, a city his father had never seen. In reaction, Qaddafi’s old guard accused Saif of acquiescing to American demands and profiting from economic reforms. Like his brothers, he enjoyed a steady income from the national oil company, but he also seems to have held special sway over state coffers. “It was crony capitalism, not a real market,” says former Libyan immigration minister Ali Errishi, who claims it was common knowledge in Libya that Saif took generous fees for foreign deals.

His personal expenditures didn’t go unnoticed, either. While at the LSE, he lived for a time at the Lanesborough hotel, before buying a $16 million house in a London suburb (since the uprisings, the house has been occupied by anti-Qaddafi squatters). There were birthday parties in Monaco and St.-Tropez, hunting trips in Europe and New Zealand, and a pair of pet Bengal tigers in Tripoli that figured in his surrealist paintings, which he shipped to galleries around the world. (“Everyone admired them because it would have been disruptive to your commercial relationship with Libya not to,” Richards says of the artwork.)

“Occasionally I’d meet him in London, and he’d be in a leather suit with a beautiful Polish girlfriend on his arm. It would be a completely different Saif,” Barber says. “I’d go to meet him at a restaurant, and he’d be sitting at a table with a group of girls and friends, partying.”

But Muammar gave Saif tacit approval and sometimes more. He took to speaking publicly about the need for reform, even promising elections. He provided Saif with cover from hard-liners and put some of his reform-minded allies into government positions.

One thing Saif would not accept, which Muammar repeatedly pressed on him, was an official post in his father’s government.

In August 2008, Saif, at the height of his popularity, was preparing to go to Washington. Before he left, he gave a speech at an annual youth gathering, as he had done for the past three years. But this speech would prove to be his most infamous. He claimed that Libya had been in “stagnation for decades.” In a swipe at his father, he said, “we want to have an administrative, legal, and constitutional system once and for all, rather than change … every year.” Referring to George Orwell’s Animal Farm, he called Arab countries with their ruling families a “forest of dictatorships.”

It’s unclear why Saif took his criticisms so far. Some think he was flush with recent diplomatic successes. Others, however, believe he was beginning to realize that changing Libya was a fool’s errand. Most of his family, content with their fiefdoms, still seemed indifferent to the problems. “There wasn’t much evidence of reform,” says Sandra Charles, the head of C&O Resources. “There were too many people around Qaddafi who had more persuasion.”

Photo: Louafi Larbi/Reuters

After the speech, Saif either was advised or chose to leave Libya. Perhaps knowing this would happen, Saif had prearranged his exit, saying in the speech that he would leave politics now that his reforms were under way. His announcement was met with well-orchestrated protests demanding he stay—a bit of political theater that must have impressed Muammar.

As it turns out, his exit couldn’t have come at a better time. His brother ­Muatessem had returned from Egypt in 2006 and cast his lot with the hard-liners. Because he was disenchanted with Saif or because he wanted to test the brothers against one another, Muammar appointed Muatessem ­national-security adviser, a position he readily accepted. Months after Saif’s speech, Muatessem traveled to Washington to meet with the new secretary of State, Hillary Clinton, and accompanied Muammar to U.N. meetings in New York. Their father had never brought Saif on a state visit of this stature.

When they returned, authorities seized Saif’s Al-Libiyya satellite-television channel and his Al-Ghad media group. His political allies were arrested. As his father shut him out, Saif came to believe the Obama administration was doing the same. In a meeting at the family compound, he upbraided the new American ambassador, Gene Cretz, telling him he was “fed up” with the White House’s slow pace of reengagement. According to the cable that Cretz sent to Washington afterward, Saif pointed out how important he’d been to the U.S. agenda and warned, “If something goes wrong, people will blame me, whether I am in a certain official position or not.” Then he complained of his father’s treatment in New York, where he had been forbidden from pitching his customary tent in Central Park.

By 2009, Muammar seemed unsatisfied with Muatessem’s performance, and he asked Saif, not his brother, to aid in negotiations going on in Britain for the release of Abdel Basset al-Megrahi, the convicted Pan Am 103 conspirator. Megrahi was, Scottish doctors claimed, stricken with terminal cancer. He was freed, and Saif’s preening delivery of him to Tripoli could not have come off worse in the West. Congress was incensed, and Obama wanted Megrahi placed under house arrest until his death. In Muammar’s eyes, though, it may have signified Saif’s renewed allegiance. But Saif still chose to stay away.

He may have been preparing to leave the maelstrom of Libyan politics for good. By 2010, he’d begun plans to move Al-Ghad out of Libya, and, having completed his Ph.D., he was asked by Oxford University Press to write two books on, ironically, the subject of creating civil institutions in countries like Libya. When he had dinner with Barber in December, he still had no plans to return. “It’s much easier for me to be outside of the country,” Saif said.

In February, as protests in ­Benghazi—where Muammar had started his coup four decades ago—turned into a civil war and government security forces went on the offensive, Colonel Qaddafi asked his son to come home. Liberal Libyans and Saif’s supporters were convinced he could be the peacemaker.

But when Saif finally did emerge, in a speech on state television on February 20, those hopes vanished. He talked for almost an hour, appearing at times disoriented, baffled, or bored. Wearing a suit and sitting in front of a map of Africa, he blamed tribal factions for the fighting, then Islamists, then foreigners. He promised reforms and warned of civil war, and closed with “We will live in Libya and die in Libya.”

His subsequent appearances only got worse. In interviews, he informed the world that there was no war, but if there were, its real villains were not the Qaddafis but terrorists, drug dealers, Washington, the U.N., Prime Minister David Cameron, or the very news networks talking to him at that moment. By March, when footage of Saif toting an assault rifle and rallying pro-Qaddafi troops leaked onto the Internet, it was clear not only that Saif wouldn’t be Libya’s visionary but that he’d become the new spokesman for a congenital strain of Qaddafian dementia. Slouching in an armchair in a luxury hotel suite, looking tired and impatient, he scolded a SkyNews interviewer: “There is a big, big gap between reality and illusion,” he said, the reality being his and the illusion that of Westerners. The latter were “living in their own world … They have no idea what is going on in Libya.”

But of course Saif knew better than anyone that this was a lie. Certain Westerners had a very good idea of what was going on in Libya—because of him. “A whole passel of people are thoroughly surprised and unhappy and very confused about Saif,” a lobbyist who worked closely with him says. Some have urged Saif to abandon his family. One sent him a text: “You’re better than this.” But most have washed their hands of him. “They all liked him then, but they’ll all say he’s terrible now,” Fahmy-Hudome says.

Photo: Morvan/Sipa

In May, Monitor co-founder and director Mark Fuller resigned. A former dean of Harvard College said that Porter had disgraced the university, and the director of the LSE, Howard Davies, stepped down in March. The school is now investigating allegations that Saif plagiarized portions of his dissertation. Barber, who has taken to comparing Saif to Michael Corleone and who resigned from the board of Saif’s foundation soon after the fighting began, has been called to testify before the House of Lords in the matter.

Only one person I spoke with has remained in touch with Saif since the revolt began. During the first weeks of the uprising, he says, Saif tried in vain to counsel Muammar and his brothers to negotiate and find a way out. Now they shuttle secretly between safe houses. Saif laments that his work was for naught and that reformers he recruited have turned on him and are leading the uprising. His brothers accuse him of having given their enemies an opening with his insistence on reform.

Any possibility of negotiation between the Qaddafi government and Western forces likely ended on April 30, when a NATO airstrike killed Saif’s younger brother, Saif Al-Arab, almost 25 years to the day after his sister was allegedly killed. “The Qaddafis all believe that NATO only wants their deaths now,” says Barber. Last week, the International Criminal Court requested arrest warrants for Muammar and Saif—but none of his brothers—for masterminding the murderous crackdown.

“I don’t think there’s any way he’ll leave. He’d only leave with his father and brothers, or he’ll go down with them,” Jack Richards says. He adds, “He really could have been the savior.”

Others believe that a savior can only be found elsewhere and that Saif’s true nature has finally emerged. “His father told him this is a tough country, and once in a while, you have to kill some people,” Ali Errishi says. “Saif didn’t have that in him. But now that it’s been taken away from him, he wants to show his father that he’s tough enough to win a war—against their own people.”

Correction

In the original version of this article, it should have been noted that C&O Resources was brought on to advise Saif Qaddafi and Libyan officials about Bush-administration policy; while Sandra Charles visited Libya in June 2004, she did not attend an economic conference Saif hosted.