By: Abe Wertenheim – Jewish Voice News

U.S. Middle East envoy Steve Witkoff is expected to meet on Wednesday with senior Hamas operative Khalil al-Hayya in Turkey, according to multiple regional media outlets and officials cited in a report on Wednesday at The Jewish News Syndicate (JNS). The anticipated encounter marks a dramatic and controversial step in Washington’s efforts to implement President Donald Trump’s newly endorsed Gaza framework, a plan formally backed this week by the U.N. Security Council but rejected by Hamas over its central demand that the terrorist organization disarm.

The meeting, first detailed in part by The New York Times last Friday and now corroborated by Hamas sources speaking to Saudi Arabia’s Asharq Al-Awsat, underscores the extraordinary diplomatic channels being utilized by the Trump administration. As JNS has repeatedly noted, Hamas is a U.S.-designated foreign terrorist organization, and direct engagement between official American envoys and senior Hamas figures is exceedingly rare.

A Hamas official told Asharq Al-Awsat, as reported by JNS, that the organization intends to “listen to Washington’s plans” for enforcing Trump’s Gaza initiative in the aftermath of Monday’s Security Council vote. That resolution, a sweeping U.S.-drafted blueprint, outlines a detailed structure for Gaza’s postwar governance—including a transitional authority led by Trump and a mandate for Hamas’s full demilitarization. Hamas has rejected the plan outright, citing the demand that it give up its weapons.

Nevertheless, preparations for the latest round of talks appear to be moving ahead. According to media reports, the meeting between Witkoff and al-Hayya will take place in Turkey, where Hamas leadership has reestablished a significant presence in recent years.

Wednesday’s expected meeting follows a previous encounter on Oct. 10 in Sharm el-Sheikh, Egypt, where Witkoff and Trump adviser Jared Kushner met al-Hayya as part of urgent negotiations to halt escalating hostilities. That meeting ultimately led to the implementation of a ceasefire on Oct. 10 and the release of the final 20 living Israeli hostages, as well as the return of most of the bodies held in Gaza.

Officials characterized the October meeting as a pivotal moment in the rapid de-escalation that followed. This week’s engagement appears aimed at reviving what remains of that diplomatic opening, even as Hamas signals hardened opposition to the core components of Trump’s long-term plan.

The expected interlocutor, Khalil al-Hayya, is among Hamas’s most senior political officials and a prominent voice in the group’s international outreach. JNS reported that his record illustrates the profound tensions and moral hazards involved in the Trump administration’s current diplomatic approach.

Al-Hayya has repeatedly praised the Oct. 7, 2023, massacre—Hamas’s brutal cross-border attack that killed over 1,200 Israelis and constituted the deadliest day for Jews since the Holocaust—as a “military accomplishment” and a “source of pride.” His public justifications for the atrocities have made him one of the most visible defenders of Hamas’s campaign of mass murder, kidnapping, and war crimes.

For that reason, the notion of senior American envoys sitting across from al-Hayya remains jarring to many observers. Yet as officials have stressed, the Trump administration views the meeting as a necessary step to enforce the terms of the Gaza framework adopted this week by the Security Council.

In an interview with CBS’s 60 Minutes, Witkoff reflected on the earlier October meeting in Sharm el-Sheikh and described a deeply personal exchange that unfolded amid the high-stakes negotiations.

Witkoff told CBS that he had offered his condolences to al-Hayya over the death of his son, Himam al-Hayya, who was killed in a Sept. 9 Israeli airstrike targeting Hamas’s military leadership in Doha. Witkoff explained that his condolences drew on his own personal tragedy, sharing with al-Hayya that his son Andrew died of an opioid overdose in 2011.

“I told him that I had lost a son and that we were both members of a really bad club—parents who have buried children,” Witkoff said, according to the JNS report.

The admission highlighted the deeply human dimensions of a diplomatic process unfolding at the intersection of grief, conflict, and geopolitics.

As JNS makes clear in its coverage, the upcoming meeting takes place under complex and combustible circumstances. The U.N. Security Council’s overwhelming vote this week to support the Gaza plan has produced a rare moment of global alignment, with the U.S. pushing to implement a framework that would transition Gaza toward international administration and a demilitarized future.

Hamas’s rejection of the disarmament clause, however, threatens to derail the process from the outset. The group’s leadership has signaled that while it will listen to U.S. proposals, it has no intention of voluntarily relinquishing its military capacity—a position that directly contradicts the resolution’s foundational requirements.

Washington, meanwhile, is attempting to leverage international pressure, Arab-state engagement, and direct communication channels to ensure compliance with the new structure. Witkoff’s meeting with al-Hayya is intended to test whether Hamas is prepared to negotiate within the framework endorsed by the Security Council — or whether the group will remain intransigent.

For decades, U.S. policy has rejected direct engagement with Hamas leadership on the grounds that the group is a terrorist organization committed to the destruction of Israel and responsible for the mass killing of civilians. As the JNS report noted, the Trump administration’s willingness to pursue dialogue reflects both the urgency of the moment and the unprecedented complexity of shaping Gaza’s future after more than a year of war.

Diplomatic channels opened in Sharm el-Sheikh — and now continuing in Turkey — underline the White House’s determination to drive forward a controversial but sweeping reimagination of Gaza’s governance structure, security conditions, and regional integration.

Whether these talks can yield substantive progress remains uncertain. But the willingness of both sides to convene again signals that the battle over Gaza’s political fate has shifted decisively into the realm of high-level international negotiation.

As reported by JNS, Wednesday’s meeting could influence the trajectory of a postwar settlement plan now backed by much of the international community. It may also expose the depth of Hamas’s resistance to the central obligations imposed by the Security Council resolution, especially its requirement that the group disarm entirely.

With the Biden-era diplomatic framework dismantled and Trump’s newly endorsed “Gaza deal” taking center stage, Washington’s engagement with Hamas—even through indirect or unconventional channels—has become an unavoidable component of enforcing the U.N. plan.

The coming days will determine whether Hamas’s willingness to meet signals a serious negotiating posture or simply a bid to buy time, extract concessions, and retain its armed control over Gaza. For now, at least, the U.S. envoy’s mission continues — and the world watches whether a diplomatic pathway remains possible after one of the most devastating conflicts in modern Middle Eastern history.