Trump's Syria gambit

Whether the President's Syria policy is brilliant or just plain reckless depends entirely on execution

Syrian President Ahmad al-Sharaa spent years as a detainee at Abu Ghraib. This weekend, he was at another undisclosed U.S. military location - this time shooting hoops with a U.S. admiral and nailing three-pointers. By Monday, he was walking into the White House for a meeting with President Trump as the first Syrian head of state to visit since 1946.

The optics alone are admittedly head-spinning, but think about what just happened: The same man who once led al-Qaeda’s Syrian affiliate and had a $10 million bounty on his head is now being welcomed as a partner.

You would be forgiven if you are experiencing a bit of whiplash. But before we dismiss this as yet another example of Trump’s chaotic dealmaking, it’s worth pausing to consider whether there might be method in what many consider madness.

Trump’s recent embrace of al-Sharaa represents a massive policy shift that speaks volumes about his transactional approach to Middle East diplomacy. It’s also, frankly, Saudi Crown Prince Mohammed bin Salman’s handiwork - a calculated power play designed to reshape regional dynamics while sending a not-so-subtle message to Israel about the limits of its influence.

The transformation of al-Sharaa from terrorist to statesman would strain credulity if we weren’t watching it unfold in real time. Less than a year ago, he led the Islamist militant group Hayat Tahrir al-Sham in a lightning offensive that toppled Bashar al-Assad’s brutal five-decade dictatorship. Now he’s trading military fatigues for smart suits, his nom de guerre Abu Mohammed al-Jolani for his given name, and jihadist rhetoric for promises of inclusive governance and reconstruction.

It’s the kind of plot twist you’d see oin Netflix’s The Diplomat - not quite at the level of the US Ambassador getting intimate with the British Foreign Secretary on his office desk during a work event, but close - the sort that makes compelling television precisely because it seems impossible in real life. Except here we are, living it.

Trump, characteristically, has latched onto the personal chemistry. “Young, attractive guy. Tough guy. Strong past, very strong past. Fighter,” the president gushed after their first meeting in Saudi Arabia in May - a meeting orchestrated by MBS himself.

One can only imagine what “very strong past” looks like in Trump’s mental Rolodex of acceptable résumé items. But the real story here isn’t Trump’s gut instincts about al-Sharaa’s character. It’s the strategic calculation - however unorthodox - that Syria under al-Sharaa could serve American interests in ways that Assad’s regime never could.

Consider what Monday’s meeting accomplished: Syria joined the U.S.-led coalition against ISIS, formally aligning Damascus with Washington after decades of hostility. The symbolism is obvious - a former al-Qaeda commander committing to fight ISIS alongside American forces. Yes, you read that correctly, and no, you haven’t slipped into an alternate timeline. Though honestly, at this point, who could tell?

The strategic logic becomes clearer when you examine what fell apart with Assad’s exit. Iran lost its crucial land corridor to Hezbollah. Russia’s Mediterranean access is now contingent on al-Sharaa’s goodwill. The entire Iranian axis of resistance has been fractured. Trump didn’t create this opportunity, but he’s capitalizing on it.

The sanctions relief is where Trump’s approach gets particularly interesting. He’s lifted comprehensive sanctions on Syria while maintaining them on Assad personally, human rights abusers, and Iranian proxies. It’s a carrot-and-stick approach that rewards al-Sharaa’s pivot away from Iran and Russia while keeping pressure on bad actors. The remaining hurdle - Congressional repeal of the Caesar Act sanctions, a punishing 2019 law named for a whistleblower who documented Assad’s atrocities - will be the real test of whether Trump can sell this gamble to skeptical lawmakers. The act remains waived but not repealed, creating what advocates call a “hanging shadow” that deters investment because companies fear sanctions could snap back at any moment.

MBS’s role in orchestrating this rapprochement deserves special attention. By facilitating Trump’s meeting with al-Sharaa, the Saudi crown prince has added Syrian sovereignty to his list of demands before normalizing relations with Israel. It’s a shrewd move that strengthens Saudi leverage over both Washington and Tel Aviv while positioning Riyadh as an important regional broker.

For Trump, betting on al-Sharaa allows him to claim he’s ending American military commitments in the Middle East while actually securing indefinite U.S. presence on more favorable terms. American forces will remain in eastern Syria - protecting oil fields and managing ISIS detention facilities - but now with Damascus’s blessing rather than as an illegal occupation force. Plus, let’s face it - there isn’t exactly a plan B Syrian government waiting in the wings.

The risks are enormous. Al-Sharaa’s government has been implicated in sectarian violence that’s killed thousands since Assad’s fall. His promises of inclusive governance ring hollow to many Syrians who’ve watched power concentrate among his loyalists. The massacres in Syria’s coastal region and the south, where security forces under al-Sharaa’s command were directly involved, raise serious questions about whether he can unite a fractured country. And then there’s the elephant in the Oval Office: Will al-Sharaa revert to his jihadist roots, bringing his old terrorist network back into Syria’s power structure? Or will he invite foreign fighters back into the country once he’s consolidated power?

Israel views this entire enterprise with alarm. Since al-Sharaa took power, Israel has bombed Syria more than 1,000 times and seized additional territory beyond the Golan Heights. Netanyahu reportedly begged Trump not to lift sanctions. Yet remarkably, al-Sharaa has largely refrained from retaliation, keeping communication channels open while allowing the Trump administration to broker indirect negotiations. Some Syrians suspect al-Sharaa made an accommodation with Israel long ago - that Israel helped HTS survive in Idlib and is now being rewarded. Whether that’s paranoia or prescience remains to be seen, but al-Sharaa’s restraint is certainly convenient for Trump’s goal of brokering regional deals.

Syria’s reconstruction challenge is staggering. Estimates range from $216 billion to nearly $900 billion after 14 years of civil war. Al-Sharaa needs international investment, and that requires American blessing. Trump holds the keys to unlock Gulf money, European engagement, and global finance.

The conventional foreign policy establishment recoils at the spectacle of an American president embracing a former jihadist. But conventional approaches to Syria have failed spectacularly for more than a decade. Obama’s “red line” became a punch line. Biden’s policy was to ignore Syria entirely. Trump is attempting to shape outcomes rather than merely react to them.

What makes this moment genuinely perilous - or potentially transformative - is that Trump is making one of the biggest Middle East bets of his presidency with insufficient attention to the details and guardrails that determine success or failure. Will al-Sharaa’s government protect religious minorities? Can he integrate Kurdish forces without triggering renewed conflict? Will Syria become a genuine partner in counterterrorism or simply another client state managing American prisons?

The ultimate test isn’t whether al-Sharaa’s journey from Abu Ghraib to the Oval Office offends our sensibilities. It’s whether this partnership advances American interests, stabilizes Syria, and demonstrates that even former adversaries can be integrated into a regional order that constrains Iran and ISIS while preventing the humanitarian catastrophe from worsening.

Trump’s Syria policy may be transactional, personality-driven, and improvised - but it’s also potentially groundbreaking. Whether it’s brilliant or just plain reckless depends entirely on execution, and we’re only in the opening act. What’s become clear over Trump’s first year back in office is that shredding the old Middle East playbook isn’t a bug - it’s the feature. For better or worse, we’re writing a new one in real time.

Cosmopolitics was founded on the belief that foreign policy coverage deserves better than partisan talking points and editors who treat substance, context, and issues-driven reporting as boring and unnecessary.

But this kind of journalism can’t survive on good intentions alone - I need your support. Becoming a paid subscriber is the best to keep this newsletter thriving and prove there’s an appetite for a smarter approach to covering international affairs. Subscriptions start at just $7 a month or $70 a year.

Click the button below, and thank you for supporting independent journalism that treats you like an adult.