The fate of Muammar Gaddafi's son wasn't inevitable. There was a choice and a decidedly better one. In February, as the Arab Spring unfolded, he dispatched an op-ed to several American newspapers, expressing a willingness to move toward a more open Libya. Every paper rejected it. But if that lost piece had been published, perhaps the dictator's son, Saif al-Islam, would have found a place among the rebels. After all, other Gaddafi loyalists, such as the minister of justice, and Mahmoud Jibril, chairman of the National Economic Development Board, switched sides to pursue what Saif said he wanted: a Libyan constitution.
"Saif was the best hope the Libyan government had," says Sarah Leah Whitson, a Libya researcher for Human Rights Watch. "But when push came to shove, he abandoned even his pretend principles and chose to stand by his father to retain power, no matter how brutal and ruthless the cost."
Perhaps the decision wasn't surprising, given Saif's upbringing and temperament; in some ways, the road had already been chosen. Like his other six siblings, Saif, 39, was a puppet of his father, who ruled his family like he ruled Libya's tribes: playing one against the other. The Gaddafi children, for their part, carved up the country's wealth.
Muhammad, the oldest son, controlled telecommunications. Hardliner Mutassim served as -national-security adviser until he lost his father's favor and was shipped to Egypt. Saadi, perhaps the best-known brother, captained the national soccer team. Aptly named Hannibal earned infamy for beating his model wife to a pulp in a suite at the posh Claridge's hotel in London. His sister, Aisha, served as a lawyer not only for Hannibal but also for Saddam Hussein, a family friend. The two youngest brothers, Khamis and Saif al-Arab, got lost in the shadows of their older siblings.
Of them all, it was Saif al-Islam, the self-styled artist, who enjoyed life outside Libya the most. His father used him as a slick ambassador to the West. And Saif loved this role, which allowed him to travel abroad and hang out with his Israeli girlfriend.
When Jessica Stern, a Harvard University professor, traveled to Libya last year as a guest of the Gaddafi Foundation to observe Saif's pet project of deradicalizing jihadis, she noticed a Hip Hotels guidebook on a coffee table at Saif's villa. "I felt strongly that we were being manipulated to see him as the last hope for Libya," Stern recalls, "even as I also wondered whether he might be just that."
A cosseted son of a billionaire father intent on ensuring the empire's future, Saif might seem the Libyan version of James Murdoch, Rupert's 38-year-old son. But whereas Murdoch the Younger still has a shot at redemption (phone hacking after all isn't a crime against humanity), Saif is in more dire straits. On Feb. 21, he told horrified Libyans that "rivers of blood"—their blood—would soon run in the streets. In spring, the International Criminal Court issued an arrest warrant "for his alleged criminal responsibility for the commission of murder and persecution of civilians as crimes against humanity." Gone are the days in which he partied with Nathaniel Rothschild, dabbled in falconry with Arab princelings, and frolicked on the lawn with his Bengali tiger cub—a live version of his stuffed favorite tigers, Fredo and Barney, which he kept in his villa. And to the parade of policy wonks, businessmen, and journalists who'd lately trooped through Tripoli to see the "new Libya," Saif's enthusiastic embrace of his father's destructive mission is mystifying. How, in a matter of months, did Saif devolve from ardent democracy promoter to religious conservative?
When I met him last year at the Rixos hotel in Tripoli, Saif wore George Clooney stubble and a debonair air that vanished when he found himself off a practiced point. He seemed more confused than crazy when pushed on reform specifics or on why, despite talk about human rights, no one had been tried for a massacre at the Abu Salim prison. On TV last week, Saif looked less like a hedge funder and more like a fist-pumping militant in fatigues, as he brandished an AK-47 and taunted his fellow citizens as "rats."
Geoffrey Robertson, a prominent U.K. based human-rights lawyer, who faced off with Saif during a 2002 libel case in London, wasn't surprised by the transformation. "I'll never forget I got hold of his thesis for which he got highest of honors ... and it began with a dedication to his father, almost a prayer of love. I cross-examined him on that, and he got very angry," he said. "I've cross-examined a lot of mass murderers, but he was a nasty piece of work."
Various explanations have been offered for why Saif would give up the high-flying life to become a warrior for his father's lost cause. It's well known that he's a notoriously bad decision maker, who makes rash choices or stalls at critical moments. But there's also the theory that perhaps Saif is as mentally unsound as his father. He "can wax eloquently over dinner one minute and spout nonsensical threats the next," says Jarret Brachman, a counterterrorism expert who went to Tripoli last year. "Saif is lucid and clearheaded at times," he added, "and bonkers the next."
To any Libyan, the tyrant's overthrow was unthinkable. The brutal regime was simply a fact of life: the sun rises, you wake up, and Gaddafi is still in power. And just as this seeming fact of nature disheartened many Libyans, it bred a sense of untouchability in the dictator and his children. And ultimately for this son, being a Gaddafi trumped all. "Saif tried to prolong the life of his father's regime by giving limited freedoms to the media, releasing political prisoners, and calling for 'reform,'?" says Omar Ashour, a University of Exeter lecturer who knows him. "But once a real chance emerged, Saif chose mass murder and repression." Now, with the conflict headed for its bloody conclusion, Saif clearly doesn't grasp the gravity of what's befallen him. Telling the International Criminal Court to "screw" itself, he still believes he's in control of a world that has decisively turned against him.