Damascene Folly

In embracing a former jihadist as Syria’s leader, Donald Trump is risking the future of West Asia.

U.S. President Donald Trump has always fancied himself a dealmaker. But his latest diplomatic coup in form of a sudden decision to lift all U.S. sanctions on Syria and embrace its new president, Ahmed al-Sharaa, veers less toward shrewd statesmanship and more toward reckless romanticism. Al-Sharaa, better known by his nom de guerre Abu Mohammed al-Jolani, was once a commander in al-Qaeda’s Syrian affiliate, Jabhat al-Nusra. Now, he is feted by Trump as a “strong past” fighter with a “real shot” at national redemption. This is geopolitics with a reality-TV script and nuclear stakes.

Al-Sharaa’s path from jihadist leader to head of state would stretch credulity if it weren’t true. Captured two decades ago by American forces in Iraq and incarcerated in the infamous Camp Bucca, the breeding ground of the Islamic State, he returned to Syria to wage war against Bashar al-Assad’s regime. Over time, and after multiple bloody schisms among the opposition, al-Sharaa emerged as the de facto ruler of Syria’s Idlib province. A tactical break with al-Qaeda in 2016 helped distance him from global jihadism, but did not erase his past.

Still, his victory over Assad late last year with quiet assistance from Turkey and tacit nods from Gulf states, propelled him from warlord to powerbroker. Al-Sharaa’s regime, forged from the embers of civil war and bolstered by Islamist networks, may not resemble a Western liberal democracy. But in Trump’s eyes, it represents something far more alluring: a ‘winner.’

The timing of Trump’s pivot is as cynical as it is symbolic. Less than seven months after the collapse of the Assad regime - long one of the world’s most sanctioned - Trump’s Treasury Secretary, Scott Bessent confirmed that Washington would unwind all sanctions. This effectively ended the ‘Caesar Act’ regime of pressure imposed on Syria since 2020, which sought to hold the Assad government accountable for war crimes and deter reconstruction partnerships with malign actors like Iran and Russia.

Syria today is a wasteland. Fourteen years of civil war have devastated its cities and decimated its economy. A third of the country’s buildings are uninhabitable. Aleppo, once a cosmopolitan beacon of Levantine life, is now a shattered skeleton. The country’s institutions are either non-functional or in the grip of armed militias, some linked to criminal syndicates. The currency is worthless, the middle class has vanished, and even survival is a luxury.

Trump’s decision to lift sanctions, then, is not born of humanitarian concern. It is transactional. In exchange, Washington expects Syria to evict foreign fighters, expel Palestinian factions and take full responsibility for Islamic State (ISIS) detainees in the northeast. Trump also wants al-Sharaa to sign the Abraham Accords by normalising ties with Israel. It is a maximalist wishlist, implausible and delusional given Al-Shaara’s past.

And yet, al-Sharaa is playing along. His government is cooperating in operations against ISIS, reaching out to former American proxies such as the Kurdish-led Syrian Democratic Forces, and even allowing quiet talks with Israel’s intelligence agencies. Turkey’s President Recep Tayyip Erdogan and Saudi Arabia’s Mohammed bin Salman, long hostile to Assad but pragmatic in their realpolitik, have pushed for al-Sharaa’s recognition. Trump, ever impressionable, is listening.

None of this sits well with America’s national security establishment. Figures like Joel Rayburn and John Bolton are aghast. Rayburn, a former special envoy for Syria and a seasoned military officer, warns that al-Sharaa is a jihadist in presidential clothing.

Al-Sharaa’s ideological reformation remains suspect. His rule over Idlib was marked by brutal repression, religious policing, and the marginalisation of women and minorities. The infrastructure of jihadism may have been papered over, but it is not dismantled. With militias still armed and civic peace tenuous, the chance that Syria backslides into war or exports instability, is high.

History may remember this as Trump’s Syrian folly, or his most audacious diplomatic bet. Either way, it is a reminder of how personal charisma, power and the illusion of strength often seduce American presidents.