Now al-Jolani, 42, seeks to seize the moment yet again, leading his fellow insurgents in an offensive that has put them in control of Syria’s largest city, reigniting the country's long civil war and raising new questions about President Bashar Assad’s hold on power.

Al-Jolani's success on the battlefield follows years of maneuvering among extremist organizations while eliminating competitors and former allies.

Along the way he moved to distance himself from al-Qaida, polishing his image and his extremist group in an attempt to win over international governments and the country’s religious and ethnic minorities.

Putting himself forward as a champion of pluralism and tolerance, al-Jolani's rebranding efforts sought to broaden his group's public support and legitimacy.

Still, it had been years since the militants in Syria, based in the country's northwest, made any substantial military progress against Assad. 

The Syrian president's government, with backing from Iran and Russia, has maintained its control of about 70 percent of the country in a stalemate that had left al-Jolaniand his Islamist militant group Hayat Tahrir al-Sham, or HTS, out of the spotlight.

But the militants' descent on Aleppo and nearby towns, alongside a coalition of Turkish-backed armed groups, has shaken up Syria’s tense detente and left the war-torn country’s neighbors in Jordan, Iraq, and Lebanon worried about this flareup spilling over.

Al-Jolani's beginnings in Iraq
 

Al-Jolani’s ties to al-Qaida stretch back to 2003 when he joined extremists battling US troops in Iraq. The native of Syria was detained several times by the US military, but remained in Iraq.

During that time, al-Qaida usurped likeminded groups and formed the extremist Islamic State of Iraq, led by Abu Bakr al-Baghdadi.

In 2011, a popular uprising against Syria's Assad triggered a government crackdown and led to an all-out war. 

Al-Jolani's prominence grew when al-Baghdadi sent him to Syria to establish a branch of al-Qaida called the Nusra Front, which the US labeled as a terrorist organization. That designation still remains in place and the US government has put a $10 million bounty on him.

The Nusra Front and the Syrian conflict
 

As Syria's civil war intensified in 2013, so did al-Jolani’s ambitions. He defied al-Baghdadi’s calls to dissolve the Nusra Front and merge it with al-Qaida's operation in Iraq, to form the Islamic State of Iraq and Syria, or ISIS.

Al-Jolani nonetheless pledged his allegiance to al-Qaida, which later disassociated itself from ISIS. 

The Nusra Front battled ISIS and eliminated much of its competition among the militant groups opposed al-Assad. 

In his first interview in 2014, al-Jolani kept his face covered, telling a reporter for Qatari network Al-Jazeera that he rejected political talks in Geneva to end the conflict. He said his goal was to see Syria ruled under Islamic law and made clear that there was no room for the country's Alawite, Shia, Druze, and Christian minorities.

Consolidating power and rebranding

In 2016, al-Jolani revealed his face to the public for the first time in a video message that announced his group was renaming itself Jabhat Fateh al-Sham and cutting its ties to al-Qaida.

“This new organization has no affiliation to any external entity,” he said in the video, filmed wearing military garb and a turban.

The move paved the way for al-Jolani to assert full control over fracturing militant groups. A year later, his alliance rebranded again as HTS as the groups merged, consolidating al-Golani’s power in northwest Syria’s Idlib province.

Afterward HTS clashed with independent Islamist militants who opposed the merger, further emboldening al-Jolani and and his group as the leading power in northwestern Syria, able to rule with an iron fist.

With his power consolidated, al-Jolani set in motion a transformation that few could have imagined. Replacing his military garb with a shirt and trousers, he began calling for religious tolerance and pluralism. 

He appealed to the Druze community in Idlib, which the Nusra Front had previously targeted, and visited the families of Kurds who were killed by Turkish-backed militias.

In 2021, al-Jolani had his first interview with an American journalist on PBS. Wearing a blazer, with his short hair gelled back, the now more soft-spoken HTS leader said that his group posed no threat to the West and that sanctions imposed against it were unjust.

“Yes, we have criticized Western policies,” he said. “But to wage a war against the United States or Europe from Syria, that’s not true. We didn’t say we wanted to fight.”

* This story was edited by Ahram Online.