Is Syria's new president a U.S. ally or an enemy?

President Donald Trump met Wednesday with Syria’s new leader, Ahmad al-Sharaa, in an effort to forge a new relationship with the country, the first time a U.S. president has met with its leader in decades. But what kind of relationship the U.S. will have with a person it once called an Al Qaeda terrorist remains unclear. 

“We’re living in a very unusual world where suddenly people who professed hatred of the West and in particular the United States are now being accepted as potential allies and partners,” said Sajjan Gohel, international security director at the Asia Pacific Foundation.

Al-Sharaa, whose nom de guerre is Abu Mohammad al-Jolani, has long been on the U.S.’ radar because of his associations with Al Qaeda’s former branch in Syria, his efforts to unite that faction (called the Nusrah Front) with the Islamic State terrorist group, or ISIS, and his initial introduction to the U.S. when he was taken into custody in Iraq. 

Al-Sharaa pledged allegiance to Al Qaeda as part of the Iraq insurgency in 2003 and was jailed at the infamous Abu Ghraib prison in Iraq. In the nearly two decades that followed, he shifted his allegiances and alliances to head up Hay’at Tahrir al-Sham (HTS), which after years of stalemate, overthrew Bashar al-Assad's regime in December, according to al-Sharaa’s published statements and experts on the region. 

His clothing style has changed from wearing military fatigues surrounded by weapons, to a more plain military uniform, and now to business suits standing side by side with Saudi Crown Prince Mohammed bin Salman and Trump, according to publicly available photos. 

Now the U.S. is asking him to recognize Israel, deport Palestinian terrorists, tell foreign fighters to leave Syria and help America stop any ISIS resurgence in the region. The U.S. has a history of negotiating over time with leaders once deemed by the American government to be terrorists or associated with terrorists, from PLO leader Yasser Arafat to Sinn Fein leader Gerry Adams.

White House spokesperson Anna Kelly said that President Trump wants Al-Sharaa to remove foreign fighters from Syria. “President Trump was clear that this is Syria’s opportunity to achieve greatness and removing foreign fighters is a bold step in that direction," she said. "Any foreign fighter returned from Syria to the U.S. would be prosecuted to the fullest extent of the law and we would expect the same from our partners.”

Jonathan Schanzer, the executive director of the Foundation for Defense of Democracies, said that the U.S. had lifted the sanctions on Syria too quickly. “It was too early,” he said in a social media post. “Not enough known.”

But Persian Gulf states, and some Trump administration officials, see Syria’s new president as a leader who can at last deliver stability to a country that has been a source of regional instability for years. They are willing to gamble that the Syrian president will fulfill his pledges to avoid a return to dictatorship and civil war, experts say.

Saudi Arabia says it is ready to cancel Syria’s outstanding debt to international institutions and Qatar has promised to pay the wages of the country’s civil servants. 

Experts wonder just which version of al-Sharaa will lead Syria and whether his choices for his Cabinet foreshadow discriminatory policies against women and minorities in his country. 

“The best analogy to describe al-Sharaa is that he’s like a transistor radio, that he can tune his message,” Gohel said. “He can move from engaging with jihadists who are concerned he is getting to close to the West, and he can equally pivot to people in the West who have concerns about his associations with jihadists.”

Al-Sharaa’s first introductions to the U.S. in the Middle East occurred in 2003 when he traveled from Syria to Iraq in advance of the U.S. invasion. According to public records and his own statements, al-Sharaa was picked up by Iraqi authorities during the second Gulf War.

He was imprisoned at the notorious Abu Ghraib prison at the same time Omar al-Baghdadi — the now deceased leader of ISIS — was held prisoner there.

That arrest came, according to al-Sharaa, after he pledged allegiance to Al Qaeda and was a part of the Iraqi insurgency against U.S. forces. Ultimately, he fell under the command of Abu Musab al-Zarqawi — the notorious terrorist leader who was responsible for the deaths of more than 700 Americans in Iraq (according to previous NBC News reporting), with many lives lost to bombings. 

After leaving Iraq, al-Sharaa spent time fighting the Syrian regime while also fighting alongside and with the different factions fighting against Syria’s regime

In a 2021 interview in a documentary film that aired on PBS’ “Frontline,” al-Sharaa spoke about the terrorist attacks of Sept. 11, 2001, and what he felt after them.

“First of all, anybody who lived in the Islamic world, in the Arab world at the time who tells you that he wasn’t happy would be lying to you,” he said, “because people felt the injustice of the Americans in their support of the Zionists, their policies towards Muslims in general, and their clear and strong support of the tyrants in the region.” 

He added, “But people regret the killing of innocent people, for sure.”

Since taking power, al-Sharaa has promised that Syria’s minority groups including women, Christians and the Alawites would be protected under his government.

“Ahmad al-Sharaa optics matter a great deal,” Gohel said, adding, “he has tried to frame his regime as supportive of women’s rights, he’s keen to get specific perceptions of his intentions that are seen as palatable to the West.”

But a close examination of the people he’s chosen for leadership positions and their views raise questions about the seriousness of those efforts, experts say.

When HTS first took power in Syria, Gohel said, there were no women in government leadership positions until al-Sharaa appointed Aisha al-Dibs to be the head of women’s affairs; she is also the only Christian in government. 

An education minister, though, has been accused of instituting a policy that would portray women historical figures from the Levant not as people who lived but as fictional characters. Another minister in al-Sharaa’s government has a history of sentencing women to death on allegations that they made blasphemous statements. 

“There are people in his administration that are extremely misogynistic," Gohel said.

Based on his experience in studying hundreds of terrorist attacks and terrorist groups around the world, Gohel said al-Sharaa’s tolerance of misogyny does not portend well for U.S. counterterrorism efforts. 

“Any entity that does not condemn misogynistic practices or allows misogyny to become part of the state apparatus are not going to be allies to the counterterrorism effort,” he said. 

Schanzer, of the Foundation for Defense of Democracies, said that the stakes are enormous. If al-Sharaa can stabilize Syria, it could aid Syrians, the region and the U.S. If not, Syria could re-emerge as a major security threat.

“If things go badly, Schanzer said, “today paved the way for a Muslim Brotherhood-Sunni jihad state in the heart of the Levant.”

A White House readout of Trump’s meeting with al-Sharaa on Wednesday suggested that for the relationship to strengthen, the U.S. would like to see the Syrians assist U.S. counterterrorism efforts.

Syria still has detainee camps filled with large numbers of ISIS prisoners. U.S. and European counterterrorism leaders would like to see them imprisoned and monitored so that ISIS does not have a resurgence in Syria and the region and again conduct attacks in the West. 

The U.S. has also asked that al-Sharaa expel foreign fighters, according to the White House memo. 

 The question for al-Sharaa and for the U.S. is just where those foreign fighters should go.

“I am really concerned about this foreign fighter dynamic,” Gohel said.