When US President Donald Trump traveled to the Middle East in May, few expected the trip to produce a diplomatic turning point between Washington and Damascus. Fewer still imagined that Trump would personally meet Syria’s new president, Ahmad Al-Sharaa – a figure whose past ties to Al-Qaeda and Hayat Tahrir Al-Sham (HTS) once made him an untouchable outcast in Western capitals. But under pressure from two of Washington’s closest regional partners, Saudi Crown Prince Mohammed bin Salman and Turkish President Recep Tayyip Erdogan, Trump agreed to meet the Syrian leader. What began as a bold gesture quickly transformed into one of the most consequential diplomatic gambles of Trump’s second term.

The real shock came months later, when Trump extended a personal invitation for Al-Sharaa to visit the White House – the first such invitation ever extended to a sitting Syrian president. On Nov. 10, Al-Sharaa arrived in Washington for hours of closed-door discussions with senior Cabinet officials. Unlike the grand pageantry surrounding other state visits, including the high-profile ceremony held for the Saudi crown prince the following week, Al-Sharaa’s welcome was low-key. Yet its significance was unmistakable.

Trump’s public praise for the Syrian leader was unprecedented. Standing beside him, the president described Al-Sharaa as “a very strong leader,” adding: “He comes from a very tough place … I like him. I get along with him … He has had a rough past. We’ve all had a rough past.”

For American political observers, it was astonishing. For the first time, a US president openly voiced support for a man who once held a senior position within extremist movements the US spent decades fighting. Trump insisted that Al-Sharaa’s militant history was “a thing of the past,” and that the Syrian president could become a stabilizing force in the region. Al-Sharaa echoed the sentiment, focusing on shared priorities such as regional stability and counterterrorism cooperation.

But the praise came at a steep internal cost. Rumors circulated that several senior advisers warned Trump against legitimizing Al-Sharaa. Those advisers, according to multiple reports, are no longer in their posts.

Trump’s Republican allies have not been uniformly supportive. Some, particularly those active in conservative media circles, have rejected Trump’s embrace of Al-Sharaa. Commentator Laura Loomer became one of the most vocal detractors, accusing the Syrian leader of........

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