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The Unthinkable Handshake A Former Al-Qaeda Commander’s Path to the Oval Office

Monday, 10 November 2025 23:07

Summary

The meeting between United States President Donald Trump and Syrian President Ahmed al-Sharaa at the White House in November 2025 marked a profound and controversial shift in global counter-terrorism and Middle Eastern diplomacy. Al-Sharaa, once the leader of an al-Qaeda affiliate with a $10 million US bounty on his head, had his terrorist designation lifted just days before the historic visit, which was the first by a Syrian leader since 1946. His ascent followed a swift military offensive that toppled the long-time dictator Bashar al-Assad in December 2024. The diplomatic normalisation, driven by the Trump administration, is predicated on Al-Sharaa’s pivot away from Iran and Russia, his commitment to counter-terrorism, and the prospect of Syria joining the US-led coalition against the Islamic State. While the US suspended key economic sanctions, the full repeal of the stringent Caesar Act remains a contentious hurdle, highlighting the deep scepticism in Washington and among international allies regarding the long-term trustworthiness of the former militant-turned-statesman.

The Day the Terrorist Designation Fell

The arrival of Syrian President Ahmed al-Sharaa at the White House on Monday, November 10, 2025, represented a diplomatic and political reversal of a magnitude rarely seen in modern international relations [Ref: 1.2, 1.3, 1.6]. It was the first official visit by a Syrian leader to the White House since the nation gained independence in 1946 [Ref: 1.4]. The meeting with United States President Donald Trump was the culmination of a stunning year-long transformation for a man who, until just three days prior, had been officially branded an international terrorist by the US government [Ref: 1.3, 1.14]. The US Treasury Department removed the Specially Designated Global Terrorist (SDGT) designation on Al-Sharaa and his Interior Minister, Anas Khattab, on Friday, November 7, 2025 [Ref: 1.2, 1.13, 1.19]. This move followed a vote led by Washington at the United Nations Security Council to quash UN sanctions against the Syrian leader the previous Thursday [Ref: 1.4, 1.13]. For years, the US government had maintained a $10 million bounty on Al-Sharaa’s head, a reward that was quietly removed in December 2024 following the fall of the Assad regime [Ref: 1.3, 1.4, 1.9, 1.22]. The speed of this normalisation process has been described by some analysts in Washington as 'head-spinning' and 'unprecedented' given Al-Sharaa’s personal history [Ref: 1.14]. The White House meeting, which lasted nearly two hours in the Oval Office, was attended by a high-level US delegation, including Vice President J.D. Vance, Secretary of State Marco Rubio, Defense Secretary Pete Hegseth, and Joint Chiefs Chairman Gen. Dan Caine [Ref: 1.6, 1.14]. Despite the significance of the visit, Al-Sharaa was not greeted by President Trump at the main West Wing entrance, a protocol typically reserved for visiting foreign dignitaries, instead entering through a side door [Ref: 1.5, 1.6]. Following the talks, President Trump expressed his confidence in the new Syrian leader, stating that the US would 'do everything we can to make Syria successful' and that he believed Al-Sharaa could 'do the job' [Ref: 1.2, 1.6, 1.14]. The two leaders had first met in May 2025 in Riyadh, Saudi Arabia, on the sidelines of a Gulf Cooperation Council summit [Ref: 1.2, 1.4, 1.5, 1.15]. It was after that initial meeting that President Trump first praised Al-Sharaa as a 'young, attractive guy, tough guy, strong past' [Ref: 1.3, 1.4, 1.15]. The November meeting was the third between the two men [Ref: 1.3]. The last bilateral meeting between a US and Syrian president occurred 25 years ago when President Bill Clinton met with Hafez al-Assad in Geneva in 2000 [Ref: 1.5, 1.6, 1.18]. The White House visit cemented Al-Sharaa’s emergence as a central figure in Middle Eastern geopolitics, a remarkable achievement for a man who had been a pariah for over a decade [Ref: 1.22].

The Journey from Al-Qaeda to the Presidential Palace

The political journey of Ahmed al-Sharaa, born Ahmed Hussein al-Sharaa in Riyadh, Saudi Arabia, in 1982, is one of the most extraordinary narratives to emerge from the Syrian Civil War [Ref: 1.7, 1.10, 1.17]. He was raised in Damascus, where his family, originally from Daraa and the Golan Heights, had settled in the affluent Mezzeh neighbourhood [Ref: 1.10, 1.17]. His father, Hussein al-Sharaa, was an economist who had worked in the oil industry in Saudi Arabia and later opened a real estate office in Damascus [Ref: 1.7, 1.10, 1.15]. Al-Sharaa’s radicalisation began when he left his upper-middle-class life in Syria to join insurgent networks in Iraq following the 2003 US invasion [Ref: 1.9, 1.11, 1.15, 1.17]. He was captured by American forces in 2005 in Mosul during an operation targeting terrorists planting roadside bombs and spent six years imprisoned in US and Iraqi facilities, including Camp Bucca [Ref: 1.9, 1.10, 1.11, 1.17]. It was during his time in US custody that he met Abu Bakr al-Baghdadi, the future leader of the Islamic State [Ref: 1.9, 1.17]. Following his release in 2011, which coincided with the start of the Syrian Revolution against Bashar al-Assad, Al-Sharaa, using the nom de guerre Abu Mohammad al-Jolani, founded the al-Nusra Front in 2012 with the support of al-Qaeda [Ref: 1.2, 1.3, 1.7, 1.10, 1.11, 1.17]. The group quickly gained notoriety for its use of suicide bombings and its imposition of strict Islamist rule in areas it controlled [Ref: 1.17]. A major schism occurred in 2013 when Al-Sharaa refused Baghdadi’s demand to merge al-Nusra into the newly formed Islamic State, instead pledging allegiance to al-Qaeda’s central leadership [Ref: 1.9, 1.10, 1.17]. This break led to armed conflict between the two groups and defined Al-Sharaa’s subsequent path, as he focused his group’s efforts solely on the Syrian conflict [Ref: 1.10, 1.17]. In 2016, Al-Sharaa publicly announced that his group was severing all ties with al-Qaeda, renaming it Jabhat Fateh al-Sham, and later merging it with other factions to form Hayat Tahrir al-Sham (HTS) in 2017 [Ref: 1.7, 1.9, 1.10]. The US State Department formally revoked the Foreign Terrorist Organisation (FTO) designation for HTS in July 2025 [Ref: 1.19, 1.21]. HTS became the dominant opposition faction in northwestern Syria, and in November 2024, Al-Sharaa launched an 11-day offensive that saw the rapid collapse of the Assad regime [Ref: 1.7, 1.10, 1.11]. Bashar al-Assad fled to Russia on December 8, 2024, ending 54 years of the Assad family’s rule [Ref: 1.10, 1.11, 1.17]. Al-Sharaa was appointed president of Syria’s interim government in January 2025, having served as the de facto leader since December 2024 [Ref: 1.7, 1.10, 1.20]. Since taking power, he has sought to rebrand himself and his government, presenting a moderate image and promising an inclusive, transparent system to replace Assad’s repressive governance [Ref: 1.4, 1.16]. He has also engaged in international diplomacy, including a meeting with French President Emmanuel Macron in Paris and a visit to Moscow to meet Russian President Vladimir Putin in October 2025 [Ref: 1.11, 1.17, 1.22]. In September 2025, he became the first Syrian president in decades to address the UN General Assembly in New York [Ref: 1.4, 1.8, 1.16, 1.17].

The Geopolitical Calculus of Normalisation

The Trump administration’s decision to embrace Al-Sharaa is rooted in a complex geopolitical calculus that prioritises counter-terrorism, regional stability, and the strategic isolation of Iran [Ref: 1.12, 1.14]. A senior administration official confirmed that Syria is expected to join the US-led Global Coalition To Defeat ISIS, a significant policy shift that formalises expanded intelligence cooperation against the militant group [Ref: 1.3, 1.6, 1.14]. Al-Sharaa’s former militia, HTS, had already opposed ISIS during the latter years of the 14-year civil war [Ref: 1.3]. The new Syrian government has demonstrated its commitment to this partnership by carrying out nationwide preemptive operations targeting IS cells, resulting in 61 raids and 71 arrests in the month leading up to the White House visit [Ref: 1.4]. The US views Al-Sharaa as a pragmatic and potentially pliable leader who can secure Syria as a strategic bulwark in the region, particularly against the influence of Iran and its proxy, Hezbollah [Ref: 1.14, 1.18]. Al-Sharaa has aligned closely with Washington on the issue of Iran, which was a key supporter of the defunct Assad regime [Ref: 1.12, 1.14]. The US readout of the May 2025 meeting indicated that President Trump urged Al-Sharaa to take several bold steps, including joining the Abraham Accords with Israel, expelling foreign fighters, and deporting Palestinian terrorists [Ref: 1.12, 1.18]. Al-Sharaa, for his part, affirmed his commitment to Syria’s 1974 disengagement agreement with Israel and noted that Iran’s departure from Syria presented a significant opportunity [Ref: 1.12]. The US is actively brokering talks on a possible security pact between Syria and Israel, though the Israeli government remains wary of Al-Sharaa’s former militant ties and opposes a full lifting of US sanctions [Ref: 1.4, 1.5]. The normalisation also serves the US interest in addressing the issue of Islamic State detention centres in northeastern Syria, which are currently controlled by the Kurdish-led Syrian Democratic Forces (SDF) [Ref: 1.12, 1.14]. The Trump administration is seeking to integrate the SDF and its autonomous civil administration into the new government, a process that requires cooperation with Damascus [Ref: 1.12, 1.14]. Furthermore, the new Syrian leader is reportedly willing to accept a continued US military presence in the country, potentially including a new deployment of American forces to an airbase in Damascus, to facilitate the anti-ISIS fight [Ref: 1.14, 1.21]. This willingness to cooperate on security and pivot away from Assad’s traditional allies has been the primary currency for Al-Sharaa’s international rehabilitation [Ref: 1.22].

The Sanctions Hurdle and the Cost of Reconstruction

The most immediate and pressing issue for the new Syrian government is the lifting of crippling economic sanctions, which have severely hampered the country’s ability to rebuild after 13 years of civil war [Ref: 1.4, 1.5, 1.15]. The World Bank estimated the conservative best cost of Syria’s reconstruction at $216 billion in October 2025 [Ref: 1.4, 1.8]. Al-Sharaa’s primary objective during his Washington visit was to push for the full repeal of the Caesar Syria Civilian Protection Act of 2019, a punishing set of sanctions imposed over human rights abuses committed by the Assad regime [Ref: 1.4, 1.6]. While President Trump had announced the lifting of most US sanctions in May 2025, and issued an executive order in June formally removing the comprehensive sanctions program, the Caesar Act remains a major stumbling block [Ref: 1.5, 1.6, 1.19]. The Caesar Act’s stringent sanctions require a vote by the US Congress to be permanently removed [Ref: 1.4, 1.5, 1.6, 1.14]. On the day of the White House meeting, Secretary of State Marco Rubio announced a new waiver, suspending the imposition of Caesar Act sanctions in part for another 180 days, replacing the waiver issued in May [Ref: 1.6, 1.19]. This suspension halts the imposition of sanctions except for certain transactions involving the governments of Russia and Iran, or the transfer of Russian-origin or Iranian-origin goods, technology, software, funds, financing, or services [Ref: 1.19]. The threat of the Caesar Act being reimposed remains a deterrent to US and foreign companies considering investment in Syria [Ref: 1.2, 1.4]. The US Treasury Department has, however, facilitated the approval of licenses for exports to Syria related to telecommunications infrastructure, sanitation, power generation, civil aviation, and other civil services [Ref: 1.19]. Al-Sharaa’s government is seeking to unlock billions of dollars in reconstruction funds and attract American companies to invest in Syrian oil and gas [Ref: 1.8, 1.12]. The Syrian leader has argued that the economic restrictions are no longer justified and that economic empowerment is key to stabilising the country [Ref: 1.4, 1.9]. Despite the sanctions relief, the US government continues to review Syria’s State Sponsor of Terrorism designation, and sanctions remain on Bashar al-Assad and his associates, human rights abusers, and captagon drug traffickers [Ref: 1.19]. The ongoing debate in Congress over the Caesar Act reflects the deep division and scepticism among lawmakers who are wary of granting unconditional relief to a former al-Qaeda affiliate leader [Ref: 1.6, 1.14].

Conclusion

The White House meeting between President Trump and President Al-Sharaa represents a watershed moment in the post-Assad era, fundamentally rewriting the rules of engagement between the West and a nation long defined by civil war and extremism. The speed of Al-Sharaa’s transformation, from a US-designated terrorist with a $10 million bounty to a legitimate head of state hosted in the Oval Office, is a testament to the transactional nature of contemporary geopolitics [Ref: 1.3, 1.14, 1.15]. The US administration has made a clear calculation: that the strategic benefits of securing a counter-terrorism partner, isolating Iran, and potentially brokering a security arrangement with Israel outweigh the moral and political hazards of rehabilitating a former al-Qaeda commander [Ref: 1.12, 1.14, 1.18]. For Al-Sharaa, the handshake is a critical step toward ending Syria’s international isolation and unlocking the massive reconstruction funds needed to rebuild his devastated country [Ref: 1.4, 1.8, 1.15]. The temporary suspension of the Caesar Act sanctions provides a crucial, albeit time-limited, window for economic re-engagement [Ref: 1.6, 1.19]. However, the long-term success of this policy hinges on Al-Sharaa’s ability to deliver on his promises of an inclusive, stable, and democratic Syria, while navigating the complex domestic challenges of integrating rival factions and protecting minority groups [Ref: 1.11, 1.16]. The enduring opposition in the US Congress and the continued wariness of regional actors like Israel underscore the fragility of this new diplomatic reality [Ref: 1.4, 1.6, 1.14]. The question remains whether the former militant’s political intelligence and ambition can truly transform a war-torn state into a reliable partner, or if the embrace of a former extremist will ultimately prove to be a profound miscalculation [Ref: 1.15, 1.17].

References

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