Steve Witkoff, President Donald Trump’s Middle East peace envoy, is set to meet with Khalil al-Hayya, the chief negotiator for Hamas, in the coming days. This meeting, confirmed by sources familiar with Witkoff’s plans, is expected to focus on ongoing discussions regarding a ceasefire in Gaza following the violent escalation that culminated in the October 7, 2025 massacre.
Witkoff’s willingness to engage with al-Hayya illustrates the Trump administration’s strategy of maintaining dialogue with Hamas, despite the group’s designation as a foreign terrorist organization by the United States. This approach signals a complex balance between diplomacy and security concerns in a region marked by prolonged conflict.
The timing of this meeting remains uncertain, as adjustments to Witkoff’s travel plans could still occur. This meeting is not the first encounter between the two; they previously met in Egypt in October, just prior to a significant ceasefire agreement. That agreement facilitated a hostage exchange, wherein Hamas released all 20 Israeli hostages in exchange for nearly 2,000 Palestinian prisoners.
During the October meeting, Jared Kushner, Trump’s son-in-law and senior advisor, played a pivotal role in brokering the deal. The negotiations at that time represented a critical moment in U.S. involvement in the region, underscoring the complexities of international diplomacy surrounding the Israeli-Palestinian conflict.
Witkoff, who has personal experience with loss—having tragically lost his son, Andrew, to an opioid overdose in 2011—has exhibited a unique perspective in his diplomatic engagements. He has publicly expressed condolences to al-Hayya following the death of the Hamas leader’s son during an Israeli air strike on a meeting in Qatar in September.
A representative for Witkoff declined to comment on the forthcoming meeting with al-Hayya, maintaining a level of discretion typical of diplomatic discussions. As the situation in Gaza evolves, the implications of this summit could be significant, impacting not only U.S.-Hamas relations but also the broader dynamics in the Middle East.
The international community continues to watch these developments closely, as they may influence future peace efforts in a region that has long been defined by conflict and a search for resolution.
