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Steve Witkoff is a 68-year-old self-made billionaire, a Bronx-born real estate attorney who parlayed a penchant for deal-making and debt-leveraging into an international real estate empire.
Jared Kushner is a third-generation nepo baby, the millennial heir to the multibillion-dollar Kushner Companies and — in the apocryphal lore of the romances of American royalty — the man who beat Tom Brady for the hand of the famously beautiful and equally wealthy Ivanka Trump.
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And in a repudiation of everything American fables teach about the merits of hard work and the sloth stoked by a life of easy luxury and superfluous privilege, it was the lanky and soft-spoken Kushner who succeeded in tidying up the mess created by the charismatic and aggressive Witkoff in Israel. Despite President Donald Trump granting Witkoff the unprecedented dual appointments of United States special envoy to the Middle East and for peace missions, Witkoff was seemingly no closer to a peace in either Gaza or Ukraine, nearly a year after Trump was elected to a second term as president. So to seal the deal in Gaza, Trump went to Kushner.
In a follow-up act to cement Trump’s first term Abraham Accords into Middle East legend, Kushner resurfaced from his comfortable sabbatical hobnobbing with Beyoncé and Jeff Bezos to return to public service. When Israeli Prime Minister Benjamin Netanyahu made his fourth pilgrimage to Washington, D.C., since the start of Trump’s second term in office, Kushner was conspicuously front and center in photos released by the White House. Within the week, he was deployed to Egypt for peace talks to bring the carnage in Gaza to a close at last. A fortnight into nearly every regional stakeholder signing on to the Trump peace deal, and a tenuous but unparalleled ceasefire has held strong enough to qualify the war as truly ended, at least for now.
And it is arguably in spite of, not because of, the shockingly and, at times, embarrassingly witless Witkoff.
During a victory lap on 60 Minutes with the execrable Lesley Stahl, Kushner and Witkoff were technically in agreement in their assessment of the run-up to October’s peace deal, but reading between the lines, the divergence between their understanding of the facts on the ground is clear. Kushner said he and Witkoff were both dismayed over Israel’s strike on senior Hamas officials in Qatar, but his subsequent actions indicated a lot less daylight between the Trump delegation and Israel than he would publicly admit to.
“And so at that point — Steve and I basically sat together and said, ‘We need to take a whole new approach. And perhaps with all of this chaos can come an opportunity,’ and so we decided to take the previous ceasefire proposal and then the end of war proposal that we’d been working on, and merge it together into one document, and then focus on seeing if we can get the Qataris and the Arab world onboard,” Kushner said. “And so we put that together, spoke with the Qataris, made a lot of progress, brought it to the president, and he said, ‘I love this idea. Let’s go all in, and let’s push very hard to get the Arab world aligned. And then we’ll figure out how to get Israel onboard and turn this whole negotiation around.'”
Kushner, a self-described student of Trump’s “pragmatic realism,” clearly understood that Israel’s show of strength — a signal that it could indeed end the war through force — could be used to push for peace. His language would be considered almost sociopathically amoral if used in a social context; used to end the bloodiest war in the region in decades, Kushner’s realpolitik was likely, once again, lifesaving.
Witkoff possesses no such emotional distance, effusively lauding the Qataris as “peacemakers” while reinterpreting diplomatic decisions as personal grievances and lamenting that he felt “betrayed” by Israel’s Doha strike. One exchange between Witkoff and Stahl is worth reading, not just hearing, in its entirety.
STAHL: People should understand that Netanyahu, the Israelis, bombed the peacemakers, bombed the negotiating team.
WITKOFF: And by the way, Lesley, it had a metastasizing effect because the Qataris were critical to the negotiation, as were the Egyptians and the Turks. And we had lost the confidence of the Qataris. And so Hamas went underground, and it was very, very difficult to get to them. And …
STAHL: And they were the … your link to Hamas?
WITKOFF: Absolutely.
STAHL: You were dealing through the Qataris to make your proposals to Hamas.
WITKOFF: And it became very, very evident as to how important and how critical that role was.
STAHL: But there was something that happened that brought the Qataris back in. And that was this phone call that I think President Trump actually forced Netanyahu to make to the Qataris.
Both Stahl and Witkoff have it backward. Israel didn’t like the negotiators, so it bombed the negotiating team in the country that was providing said terrorists safe sanctuary, proving to Hamas that its days were numbered and to Qatar that it was no longer off limits in its complicity. Netanyahu was always available to Trump on speed dial; it was Hamas, through its partners, the Qataris, that even Witkoff complained had “duped” him.
To understand just how backward Witkoff understood the situation, consider the timeline. Since Trump won office last year, Witkoff has been backchanneling with stakeholders in the region to no avail. As recently as Sept. 2, Qatar was publicly refusing Israel’s condition that any peace necessitated a release of all the remaining living hostages in Gaza.
The Israel Defense Forces struck Doha on Sept. 9. Though the U.S. publicly denied supporting the attacks, ample evidence suggests that Trump knew about the strike beforehand and did not stop Netanyahu from going through with them, and the use of Saudi airspace belies the kingdom’s public tut-tutting of the strike.
Within two weeks, Witkoff and Kushner had Trump’s draft of a Gaza deal in the hands of the Qataris. Directly contradicting Witkoff’s assertion that “we had lost the confidence of the Qataris” is the fact that, rather than rejecting the deal, Qatar accepted and brought the rest of the regional stakeholders to the table.
All in all, Trump publicly announced the peace deal fewer than three weeks after Israel’s Doha strike, and it was signed exactly one month after the attack. A rational interpretation of the events is not that Trump forced a long-willing Netanyahu to the table, but that Netanyahu gave Trump the final piece of leverage to force the rest of the world to bend the knee to America’s will.
The witlessness of Witkoff is not the same as the deep state within the Trump administration that is indeed actively and perniciously undermining the president’s agenda. While War Secretary Pete Hegseth seems more obsessed with punishing the press corps rather than the leakers within the Pentagon actively working against the White House, Trump seems to have recognized this internal deep state and begun to sideline them accordingly. In a scoop within a scoop, the Wall Street Journal reported that Trump has removed long-range missile authorization entirely from the purview of Elbridge Colby, the undersecretary of defense for policy in the Pentagon, who has repeatedly disobeyed the president’s direct orders to arm allies such as Ukraine.
Witkoff, a genuine friend and fellow billionaire of Trump’s, is hardly in the same category as charmless career swamp monsters like Colby. But there is increasing evidence that Trump has knowingly embraced Witkoff’s deficiencies and deployed him as his useful idiot.
Recall that Trump kept Witkoff out of the loop over the summer, allowing Witkoff to earnestly believe he was renegotiating some tacky redux of the JCPOA while the U.S. military was clandestinely planning to decimate Iran’s nuclear weapons capability with operation “Midnight Hammer.” And the 60 Minutes double act provided a fleeting glance at the good cop, bad cop routine that Witkoff might not have fully understood he was being cast into to catch Hamas off guard to Kushner’s machinations.
But that hasn’t mitigated the risk that Witkoff remains a liability elsewhere in the world. Witkoff, who has already beclowned himself with the Russians by attending diplomatic talks solo and mistaking a Kremlin translator for a U.S. State Department official, continues to undermine Trump’s ceasefire goals in Ukraine. When a now humbled and gracious Ukrainian President Volodymyr Zelensky beckoned Trump for Tomahawk missiles on bended knee last week, he was reportedly met with Witkoff’s insistence that he hand over the entire Donbas to Russia simply because — in a direct parroting of Russian President Vladimir Putin — the Kremlin incorporated Russian sovereignty over the Donbas in its constitution. Contrary to initial reporting, it seems that Trump wisely did not echo Witkoff’s talking point, instead reiterating his hope that a peace would compromise territory along the war’s current front lines, but an overly confident Kremlin quickly rejected Trump’s proposal over the weekend.
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It’s too soon to definitely say whether Trump, Kushner, and the first son’s 25 books he read on the Israel conflict will have brought a permanent peace to Gaza. The media has already joked that Witkoff and Kushner have been deployed to the region as “Bibisitters,” even though Saudi Arabia and the United Arab Emirates have warned it is Hamas that could cause the deal to fall apart if it does not disarm in accordance with Trump’s terms. Implicit in the critiques of the moderate Sunni states is that Qatar seems less interested in taking out Hamas than rebuilding it.
For the sake of world peace, Witkoff would be wise to wake up to the risk of his friends in Qatar, but it’s fully possible that the pure pragmatism of Trump’s realpolitik overrides all of this, and Trump takes matters back into his own hands.
