In May 2025, U.S. President Donald Trump embarked on a high-profile tour of the Middle East, visiting Saudi Arabia, Qatar, and the United Arab Emirates. The trip, marked by lavish receptions and multibillion-dollar business deals, signaled a bold shift in U.S. foreign policy toward the region. At its core was a surprising move: Trump’s meeting with Syria’s interim president, Ahmad al-Sharaa, a former al-Qaeda-affiliated militant once designated a terrorist by the U.S. with a $10 million FBI bounty on his head. This encounter, alongside Trump’s announcement to lift decades-old sanctions on Syria, has sparked intense debate about the direction of his diplomacy—whether it represents a pragmatic realignment for stability or a risky embrace of a volatile figure. This article examines Trump’s Middle East strategy, the implications of his engagement with Sharaa, and the broader geopolitical consequences for the region.
A Transformative Tour: Business and Diplomacy Intertwined
Trump’s four-day Middle East tour was a spectacle of opulence and deal-making. In Saudi Arabia, he announced a $600 billion investment agreement and a $142 billion arms deal, described by the White House as “the largest defense cooperation agreement” in history. In Qatar, a $1.2 trillion economic exchange included a Boeing aircraft purchase, while the UAE secured over $200 billion in commercial deals focused on AI, energy, and defense. These agreements underscored Trump’s view of diplomacy as a “worldwide hunt for deals,” prioritizing economic leverage over traditional strategic visions like those of past presidents.
Yet, the tour’s most striking moment came in Riyadh on May 14, 2025, when Trump met Sharaa, the first U.S.-Syria presidential summit in 25 years. Hosted by Saudi Crown Prince Mohammed bin Salman, with Turkish President Recep Tayyip Erdogan joining virtually, the 37-minute meeting was a diplomatic bombshell. Sharaa, once known as Abu Mohammad al-Jolani, led Hay’at Tahrir al-Sham (HTS), a group still listed as a Foreign Terrorist Organization by the U.S. State Department. His rapid transformation from jihadist to Syrian leader, following HTS’s December 2024 overthrow of Bashar al-Assad, set the stage for this unprecedented engagement.
Engaging a Former Terrorist: A Calculated Move?
Trump’s decision to meet Sharaa, a man who fought U.S. forces in Iraq and spent five years in U.S. detention, reflects his willingness to break with conventional foreign policy. Sharaa’s past is steeped in militancy: he joined al-Qaeda in Iraq in 2003, was detained at Camp Bucca, and later led al-Nusra Front, al-Qaeda’s Syrian affiliate, orchestrating attacks until severing ties in 2016. Despite his efforts to rebrand as a pragmatic leader—trading fatigues for business suits and pledging moderation—Sharaa remains a U.S.-designated terrorist. The Biden administration removed the $10 million bounty in December 2024, paving the way for engagement, but skepticism persists about his intentions.
Trump’s rationale appears rooted in pragmatism. He urged Sharaa to join the Abraham Accords, normalize ties with Israel, expel foreign militants, manage ISIS detention centers, and counter the Islamic State’s resurgence. In return, Trump promised to lift U.S. sanctions, imposed since 1979 when Syria was designated a state sponsor of terrorism. The sanctions, intensified by the 2019 Caesar Act, have crippled Syria’s economy, with 90% of its population living in poverty and economic losses from the civil war estimated at $800 billion. Lifting them could enable humanitarian aid, foreign investment, and trade, offering Syria a lifeline to rebuild.
The White House framed the move as a step toward regional stability, with Press Secretary Karoline Leavitt noting Sharaa’s interest in positioning Syria as a trade hub and inviting U.S. investment in its oil and gas sectors. Trump himself praised Sharaa as a “young, attractive guy” with a “strong past” and “real potential,” downplaying his jihadist history. This aligns with Trump’s broader philosophy, articulated in Riyadh: his job is not to “dispense justice” for past sins but to promote “stability, prosperity, and peace” through trade deals.
Regional Realignment: A Sunni-Led Order
Trump’s diplomacy signals a realignment toward a Sunni-led Middle East, anchored by Saudi Arabia and supported by Qatar and the UAE. The meeting with Sharaa, brokered by Gulf powers, reflects their growing influence in shaping Syria’s future. Saudi Arabia, in particular, has emerged as a regional leader, leveraging its economic clout to counter Iran’s diminished “axis of resistance.” The fall of Assad, a key Iranian ally, and the weakening of Hezbollah and the Houthis have tilted the balance toward Sunni states. Trump’s sanctions relief and engagement with Sharaa aim to integrate Syria into this orbit, reducing Russian and Iranian influence.
However, this approach has sidelined Israel, a traditional U.S. ally. Israel opposes lifting sanctions, fearing Syria could become a base for Hamas or other groups. Since Sharaa’s rise, Israel has escalated airstrikes on Syrian military targets, seizing a buffer zone established in 1974. Prime Minister Benjamin Netanyahu, stunned by Trump’s pivot, reportedly urged him not to lift sanctions. Israeli media highlighted a growing disconnect, with Trump’s focus on Gulf deals and diplomacy with Iran and the Houthis leaving Israel feeling isolated.
Risks and Criticisms
Critics warn that Trump’s embrace of Sharaa is a gamble. HTS’s authoritarian governance in rebel-held areas raises doubts about Sharaa’s commitment to moderation. Recent violence against Syria’s Alawite minority, with over 1,400 civilian deaths reported, underscores the fragility of his rule. Analysts like Caroline Rose of The New Lines Institute question whether HTS’s shift is a genuine change or a tactical maneuver to secure legitimacy. Former U.S. Ambassador Robert Ford, who placed Sharaa on the terrorist list in 2012, described him as an “authoritarian by nature” leading a weak government.
The move has also drawn scrutiny from U.S. lawmakers, with questions about implementation, particularly regarding the Caesar Act, which requires Congressional approval to repeal. Concerns persist about Syria’s stability and whether Sharaa can deliver on promises to counter extremism and foster inclusive governance.
Conclusion: A New Middle East or a House of Cards?
Trump’s Middle East diplomacy, exemplified by his meeting with Sharaa, is a high-stakes bet on economic incentives and regional partnerships to reshape a volatile region. By engaging a former terrorist-turned-president, he seeks to stabilize Syria, counter Iran, and bolster Sunni allies, all while securing lucrative deals for U.S. companies. The lifting of sanctions could unlock Syria’s economic potential, but it hinges on Sharaa’s ability to deliver on promises of moderation and security—a tall order given his past and Syria’s fractured landscape.
For now, Trump’s approach has reshaped the diplomatic map, elevating Saudi Arabia and sidelining Israel. Whether this ushers in a “new golden era” of stability, as the White House claims, or sows the seeds of future conflict remains uncertain. As one regional source noted, “Iran had the leading role; now Saudi Arabia has entered with other tools: the economy, money, investment.” The question is whether Trump’s transactional diplomacy can hold this new order together—or if it will collapse under the weight of its contradictions.
