From the heir apparent to Muammar Qaddafi's rule in Libya to a decade of living in captivity and obscurity before launching a presidential bid, Saif Al Islam Qaddafi was one of the country's most prominent figures.
He was killed during a “direct confrontation” with unknown gunmen, his office and local media announced on Tuesday.
Despite never holding an official position in Libya, Saif Al Islam, 53, was seen as the most powerful figure in the country after his father who notoriously ruled for more than four decades. He led talks on Libya abandoning its weapons of mass destruction and negotiated compensation for the families of those killed in the bombing of Pan Am Flight 103 over Lockerbie, Scotland, in 1988.
He also engaged with the West and championed himself as a reformer, calling for human rights to be respected and for a constitution.
Educated at the London School of Economics and a fluent English speaker, he was once seen by many governments as the acceptable, western-friendly face of Libya.
But the situation changed in 2011 when a rebellion broke out against his father's long rule. He remained prominent throughout the violence that engulfed the country in the wake of the Arab Spring protests.
Allegations emerged of torture and violence committed against his father's opponents. In March, Nato launches strikes on Libya and in June, Saif Al Islam announced that elections would be held and that his father would step down if he did not win. Nato rejected the offer and continued the bombardment of the country.
He warned that rivers of blood would flow and the government would fight to the last man and woman and bullet.
“All of Libya will be destroyed. We will need 40 years to reach an agreement on how to run the country, because today, everyone will want to be president, or emir, and everybody will want to run the country,” he said, wagging his finger at the camera in a TV broadcast.
After rebels took over the capital Tripoli, he attempted to flee to neighbouring Niger dressed as a Bedouin tribesman.
The Abu Bakr Sadik Brigade militia captured him on a desert road and flew him to the western town of Zintan about a month after his father was hunted down and summarily shot dead by rebels.
He spent the next six years detained in Zintan and in 2015 was sentenced to death by firing squad by a court in Tripoli for war crimes. He was also wanted by the International Criminal Court in The Hague, which issued an arrest warrant against him for “murder and persecution”.
Saif Al Islam spent years underground in Zintan to avoid assassination after he was released by the militia in 2017 under an amnesty law.
Wearing a traditional Libyan robe and turban, he appeared in the southern city of Sabha in 2021 to file his candidacy for the presidential elections, a move viewed as controversial and opposed by many.
Powerful armed groups that emerged from the rebel factions that rose up in 2011 rejected it.
He was disqualified because of his 2015 conviction, and when he tried to appeal the ruling, fighters blocked off the court. The ensuing arguments contributed to the collapse of the election process and Libya's return to political stalemate.
He was one of the last remaining figures of the Qaddafi dynasty. His brother, Hannibal, was released in November on bail after being detained in Lebanon for almost a decade without trial.
Hannibal had left in 2011 and lived in exile in Syria but was abducted and taken to Lebanon where he was accused of withholding information about the fate of Musa Al Sadr, an influential Lebanese Shiite cleric who disappeared during a trip to Libya in 1978.
