Trump’s High-Stakes Gamble: What Does Trump Really Want?

On 14 May 2025, in the gilded halls of Riyadh’s King Abdulaziz International Conference Center, history appeared to bend once again to the force of Donald Trump’s will. Standing beside Syrian President Ahmed al-Sharaa, Trump beamed before the cameras, grasping the hand of the man once known for his militant ties and battlefield leadership of Hayat Tahrir al-Sham (HTS)—a group formerly affiliated with al-Qaeda. It was the first direct encounter between a sitting US president and a Syrian leader since Bill Clinton’s 2000 meeting with Hafez al-Assad in Geneva. But this time, the symbolism was more jarring than diplomatic.

Trump’s words were characteristically provocative. Describing al-Sharaa as a “young attractive tough guy,” he ignited a media firestorm and left policy analysts around the globe struggling to interpret what, exactly, had just happened—and what it might mean for international security, US strategy in the Middle East, and the shifting sands of global order.

The Making of a Trump Doctrine?

To understand the magnitude of this moment, one must first understand Trump’s instinctual approach to foreign policy. While traditional US presidents have often spoken the language of values—human rights, democracy, alliances—Trump speaks the language of deals. His worldview is transactional, his methods unpredictable, and his messaging driven by a cocktail of gut instinct, media impact, and political calculus.

His reversal on Syria is emblematic. In December 2024, Trump had taken to X (formerly Twitter), proclaiming, “Syria is a mess, but is not our friend. THE UNITED STATES SHOULD HAVE NOTHING TO DO WITH IT.” It was a message of withdrawal, of strategic detachment. Fast forward to May 2025, and not only is Trump involved, he has unilaterally lifted all US sanctions on Syria, citing the need to “give peace and prosperity a chance.”

This isn’t simply policy whiplash—it’s the clearest signal yet that Trump is building what could be dubbed a “Trump Doctrine 2.0”: a raw, unapologetic strategy that blends shock diplomacy with unconventional alliances to shift global power dynamics.

From Pariah to Partner: The Al-Sharaa Gamble

The rise of Ahmed al-Sharaa is itself a geopolitical anomaly. Once a commander of a militant insurgency, al-Sharaa has reinvented himself as Syria’s civilian president, consolidating power and projecting stability in a country still licking the wounds of over a decade of civil war. Many Western leaders remain deeply skeptical of his transformation. But Trump, ever the contrarian, has seized the moment.

What does Trump see in al-Sharaa? Perhaps a mirror image: a man vilified by the establishment, but unapologetically bold. Or perhaps Trump believes that a “clean slate” approach could redraw regional lines of influence—an audacious attempt to flip Syria from Iranian orbit to American favor.

For Trump, this is not simply about Syria. It is about disrupting the status quo, sidelining bureaucratic diplomacy, and asserting American relevance in an increasingly multipolar world.

A Global Audience

Trump’s meeting with al-Sharaa was not just for Middle Eastern eyes. It was a global broadcast aimed at several key audiences:

Russia and China: Trump’s move can be read as a warning shot, a sign that America is willing to outmaneuver them in regions they thought firmly within their sphere.

Europe: The traditional transatlantic alliance has been frayed by Trump’s isolationist tendencies. His Syria pivot only widens the gap, reminding European allies that Trump charts his own course.

Africa and Latin America: For leaders in developing nations, the message is clear: the US is open to business—regardless of past affiliations—if the deal is good.

Risks and Realities

Yet the gamble is immense. Al-Sharaa’s legitimacy remains contested. His past cannot be easily erased, and his government’s human rights record is under intense scrutiny. Trump’s decision to lift sanctions without extracting any public commitments on reforms or democratic governance risks emboldening authoritarian tendencies, not reversing them.

Moreover, Congress has already begun pushing back, with bipartisan voices warning that Trump is overstepping the boundaries of presidential authority. The move may face legal and political challenges, especially from those who see it as undermining years of multilateral efforts to isolate violent extremism.

What Does Trump Really Want?

At his core, Trump appears to seek legacy and leverage. He wants to be seen as the man who broke the deadlock on Syria, who made the impossible handshake happen, and who outmaneuvered America’s rivals at their own game.

This is not about ideology; it’s about impact. Trump is playing a high-stakes game of geopolitical poker, with Syria as the latest wild card.

Whether this gamble results in a grand bargain or a catastrophic misfire remains to be seen. But one thing is certain: the Trump era is not just back—it’s rewriting the rules again, one handshake at a time.

Dr Brian O. Reuben is the Executive Chairman of the Sixteenth Council.