In a dramatic and unexpected turn of diplomacy, Steve Witkoff, acting as the U.S. Special Envoy to the Middle East, and Jared Kushner, son‑in‑law of Donald Trump and a central figure in U.S. Middle‑East policy, disclosed that they helddirect, face‑to‑face meetings with senior Hamas officials. These meetings mark a substantial break from longstanding U.S. policy of not engaging directly with Hamas, designated by the U.S. as a terrorist organisation. The details they revealed show how high the stakes are, how fragile the peace process remains, and how much risk the U.S. is willing to take.

What Was Revealed: The Key Details

From multiple sources and interviews, including with 60 Minutes and media outlets, the following startling points emerge:

The meetings took place in Sharm el‑Sheikh, Egypt, with Witkoff and Kushner meeting a senior Hamas delegation led by Khalil al‑Hayya (also spelled al‑Khaya) along with intelligence mediators from Qatar, Egypt and Turkey.

Prior to the meeting, the Trump administration gave the envoys explicit authorisation to engage Hamas directly if needed. One source: “President Trump quietly gave permission for Witkoff and Kushner to meet Hamas leaders if necessary to finalize the deal.”

During the meeting, one of the core messages delivered was that the hostages Hamas held were increasingly a liability rather than an asset—a psychological shift aimed at persuading Hamas to release them. Witkoff told them: “The hostages have become more of a burden than a leverage tool.”

Kushner and Witkoff also conveyed a U.S. guarantee: that if Hamas fulfilled its commitments, Israel would not immediately resume hostile operations. According to sources: “President Trump’s message is that you will be treated fairly and he stands behind all 20 points of his peace plan.”

A remarkable emotional moment reportedly occurred when Witkoff expressed condolences to al‑Hayya over the loss of his son in an Israeli airstrike—Witkoff himself had lost a son. That humanising moment is said to have broken a deadlock.

The talks reportedly lasted around 45 minutes, after which mediators declared that an agreement had been reached.

These disclosures open a rare window into how high‑level diplomacy sometimes looks: risky, personal, unconventional.

Why This Is So Significant

Departure from precedent

It has long been official U.S. policy not to negotiate or meet directly with Hamas, given its designation as a terrorist organisation. The fact that Washington allowed direct contact signals a major shift—driven by urgency to end hostages standoff and war in Gaza.

Back‑channel leverage and trust‑building

The meeting shows how diplomacy increasingly relies on personal trust and guarantees rather than purely formal state‑to‑state communications. The personal stories (loss of sons) and the guarantee from the U.S. carrying weight reflect how “soft” diplomacy is as important as the “hard” terms.

The hostages as pivot point

The revelation that U.S. envoys convinced Hamas the captives were a burden flips the narrative: from hostages as leverage to hostages as liability. That shift appears to have been a critical lever.

Implications for the broader peace process

By engaging directly, the U.S. is effectively buying time and making negotiations more real: a cease‑fire, hostages released, and the first steps for Gaza’s stabilisation are in play. The deal reportedly aligns with Trump’s 20‑point plan for Gaza.

The Risks & Controversies

Even as the disclosures impress, they’re fraught with risk:

Domestic political backlash: Some U.S. and Israeli officials believe any direct engagement rewards terrorism. The fact that these meetings happened without full transparency may breed distrust.

Hamas credibility and motives: Witkoff himself admitted Hamas “may have duped me” about acceptance of his proposal. If Hamas uses the pause to rearm, the deal could collapse.

Enforcement and verification: The guarantees given to Hamas hinge on U.S. and Israeli ability to enforce commitments. If these fail, the U.S. credibility suffers.

Moral and strategic ambiguity: Critics question dealing with a group with a record of terror, and worry that helping Hamas politically or leaving them partly intact undermines Israeli security.

Regional spill‑over: The agreement involves multiple regional players (Qatar, Egypt, Turkey). If any backslide, the stability of the deal is threatened.

What They Said: Key Quotes & Moments

The hostages have become more of a burden than a leverage tool.” — Steve Witkoff.

What did Hamas gain by keeping these hostages? You had tens of thousands of Palestinians who were killed in these wars.” — Jared Kushner.

I think we were able … to convince people that a hostage release was a good thing.” — Witkoff, regarding phase one of negotiations.

These statements underscore the mindset: to shift incentives, break stalemates, and create a path forward.

Timeline and Stakes

Earlier in 2025, Witkoff proposed a “bridge” cease‑fire extension linked to hostage release. Hamas rejected or stalled the deal.

By October 2025, the high‑level meeting in Sharm el‑Sheikh occurred, convening Witkoff and Kushner with Hamas leaders and regional mediators. The breakthrough happened quickly thereafter.

Simultaneously, the U.S. and others sought to broker the next phase: disarmament of Hamas, stabilisation of Gaza, and major reconstruction funding.

The bigger picture: If successful, the deal may reshape Gaza’s governance, rebuild the Strip, reduce the threat of future war, and reintegrate the region economically and diplomatically.

What Happens Next: The Unfinished Business

Despite the deal’s breakthrough, the next phase is far from certain. Key hurdles remain:

Disarmament: How does Hamas relinquish its arms? What enforces it? The U.S. has indicated “disarm or we will disarm them.”

Gaza governance: Who governs Gaza after Hamas’s military structure is dismantled? The role of the Palestinian Authority, technocrats, regional actors is still unclear.

Aid & reconstruction: With tens of billions of dollars needed and massive devastation in Gaza, delivery of reconstruction and aid is essential—and fraught with corruption risk.

Hostages & verification: Ensuring all hostages are freed, accounting for the bodies of the fallen, and ensuring Israel’s security guarantees.

Durable ceasefire: The truce is fragile. Any resumption of hostilities, breach of terms, or collapse in trust could unravel the deal quickly.

How U.S., Israel, Egypt, Qatar, Turkey and Hamas manage this next phase will determine whether the breakthrough lasts.

My Take

The disclosures by Witkoff and Kushner reveal a bold diplomatic gamble. By meeting directly with Hamas, they acknowledged that nothing short of high‑risk engagement might crack the deadlock. The personal dimension—condolences, human stories, guarantees—suggests they believed they needed to transcend normal diplomacy.

The implications are enormous: if this deal holds, the U.S. will have brokered one of the most significant mediated outcomes in decades for the Israel‑Gaza conflict. The Gulf states and Egypt stand to gain stability; Gaza stands to be rebuilt; Israel may gain security; Hamas… well, its role is up in the air.

But the gamble is high. If the peace collapses, the U.S. stands to lose face; Israel may feel betrayed; Gaza could plunge back into war; Hamas may rearm; and the next crisis could be worse than the last.

In short: This is one of those historic moments where strategy, personality, risk and policy all converge. Witkoff and Kushner may well be credited as peacemakers—or blamed as enablers.