The failed attempt to secure a peaceful resolution with Iran has not shaken the president’s faith in the two men he put in charge of making peace around the world.
Special envoy Steve Witkoff and Jared Kushner, the president’s son-in-law, are in charge of solving some of the world’s most intractable conflicts and even as the war with Iran expands, the president insists his top diplomats are the best men for the task.
“I think they're doing a great job,” President Donald Trump told POLITICO in a brief phone interview Friday. “People like that you can't hire.”
The unprecedented dynamic of two men leading negotiations with Iran, Israel and Hamas and Ukraine and Russia – sometimes all in one afternoon – underscores how the Trump administration believes peace deals should be forged. It views diplomacy like a real-estate venture, requiring a business mindset and a small team tasked with securing a big development deal, according to two administration officials granted anonymity to explain how the president’s closest advisers think about their mission.
And if negotiations with one party fail as they did with Tehran, use the failure as leverage for another deal.
Trump, on Friday, did just that, suggesting that the war with Iran may prove a boon for Kushner’s notable first-term achievement – the Abraham Accords, which normalized diplomatic relations between Israel and the United Arab Emirates, Bahrain, Sudan and Morocco.
“A lot of people are going to be joining the Abraham Accords,” Trump said. “Now that Iran is decimated, because you know that was always a fear over that.”
Adding more countries to the Abraham Accords has long been a goal of the president to bring larger regional stability and peace to the Middle East.
Trump’s optimism comes as critics accuse the president of placing overwhelming trust in underwhelming men. While Kushner and Witkoff, a New York and Miami real estate developer, are widely lauded for shepherding the deal that brought home Israeli hostages, their brokered ceasefire remains fragile and Hamas is still a force in Gaza. Negotiations to end the Ukraine war have not produced a ceasefire. And attempts to persuade Iran to give up its uranium enrichment program were unsuccessful.
The breakneck pace leads to a “risk of overextension,” said former State Department negotiator Aaron David Miller, who served in both Republican and Democratic administrations. The volume of detail required to handle three negotiations at once is too much to place on two businessmen, and there is a risk that the administration’s top negotiators lack a sufficient understanding of history and psychology, “which is critically important to how the combatants in these conflicts actually see matters,” Miller said.
The Joint Comprehensive Plan of Action, the Iran deal the Obama administration negotiated and Trump has widely panned, was 159 pages long and took two years to hammer out.
But Trump’s confidence is unwavering. “They don't have too much,” he said. “They actually have -- they have capacity for more, to be honest with you.”
The idea of working on three deals at once with only two men at the helm is unprecedented. And Trump’s use of “peace envoys” goes beyond usual practice, as he hand picks his top negotiators without congressional confirmation.
The Trump administration insists that a small team handling multiple fires around the world has a better chance of success than a phalanx of diplomats and experts tackling various regional conflicts, comparing high-stakes diplomacy to the kinds of projects the Trump family has long been associated with.
Witkoff and Kushner keep their teams small when negotiating major business deals and approach the world stage in a similar way. One of the administration officials noted that real estate deals begin at the top with a select few who have a vision.
“Then after that comes constructive managers and coordinating with engineers and architects and so forth,” the first official continued. “So I just think that we're very good at understanding what the complicating features of a deal are. We talk about it, we address it, then we figure out how we're going to solve it.”
Global negotiations, like development deals, have "similar rhythms for transactions,” said the second administration official.
“Some of these conflicts, they all move the same way,” said the first administration official, noting that the “game plan” receives input from Trump, Secretary of State Marco Rubio, CIA Director John Ratcliffe and chief of staff Susie Wiles. There is also a working relationship with Vice President JD Vance, Secretary of Defense Pete Hegseth and Chairman of the Joint Chiefs Gen. Dan Caine.
“We've had people say, ‘How can you have such a small team?’ Well the beginning of the decision making here on the game plan doesn't require a big group,” the first administration official said.
Witkoff and Kushner’s one-size fits all approach was most evident last month in Geneva when the duo met with the Ukrainians, the Russians and the Iranians in one day, attempting to secure separate deals to end the four-year-war in Ukraine and halt Iran’s nuclear capabilities.
They met with the Iranians from 9 a.m. to 12:30 p.m., met with the Ukrainians from 1 p.m. to 5:30 p.m. and spoke to the Russians after that, the second administration official said. That was followed by a dinner with the Ukrainians and regional partners, including Germany, the United Kingdom, France, Italy and Switzerland. The dinner was followed by another meeting with the Russians from 9:30 p.m. to 11 p.m.
Witkoff and Kushner have “tried to take the approaches that work [in Gaza] and then bring them to these other conflicts. And obviously [they] have to modify them to the personalities and the dynamics,” said the second administration official.
The countries and actors may be different, but the general idea – that this is similar to a business deal – is the same.
That business approach doesn’t sit well with everyone, especially those accustomed to a traditional diplomatic approach with experts and fixed administration channels.
“A business mindset can be desirable for diplomatic negotiations – clear-eyed, no nonsense, results oriented,” said a State Department official in Trump’s first term, granted anonymity to express their views on the current administration. “But that should mean understanding with whom you’re doing business. Business experience is no substitute for understanding the region, Islam, and the interests of Hamas and Iran as they understand their interests.”
The two administration officials say a small team avoids damaging leaks and pushed back on the idea that Witkoff and Kushner don’t avail themselves of subject matter experts. The National Security Council staff worked on negotiations between Israel and Hamas and State Department officials are involved in negotiations around the Russia-Ukraine war.
“We always consult with Marco and his team and [deputy national security adviser] Robert Gabriel in terms of who the right team is in the government to support these efforts,” the second administration official said.
For the Iran negotiations, Witkoff and Kushner consulted with the CIA, DOD and State Department nuclear experts, the first official said.
But at other times, it’s just the two close friends of Trump, “sitting at a keyboard for a couple of hours” and typing up sensitive materials like the 20-point Israel-Gaza peace plan, per the second administration official.
“Their main asset, which is necessary but not sufficient, is their relationship with the president, and as a consequence of that relationship, their capacity to get through all of the bureaucratic hurdles that are imposed by our partners,” said Miller, currently a senior fellow at the Carnegie Endowment for International Peace.
A Biden administration official, granted anonymity to speak candidly about the Trump administration, agreed that Kushner and Witkoff have a leg up because everyone knows they are among a select few Trump listens to.
The modern geopolitical arena responds better to negotiators close ties to the president who can think outside the box, the person said, rather than textbook expertise in the issue -- something that can be gathered from experts working under them.
The administration contends that Witkoff and Kushner have had more success than they get credited for – pointing to Gaza, specifically. There was also a large prisoner exchange last week between Russia and Ukraine that Witkoff credited to their sustained diplomatic efforts.
With Iran, the administration notes, Tehran simply wouldn’t negotiate.
“They said, ‘we have the inalienable right to enrich,’” Witkoff said Saturday night aboard Air Force One. “They bragged about having 60 percent enriched fuel, enough for 11 bombs. They told me and Jared, ‘we’re not going to give you diplomatically what you take militarily.’”
And in Ukraine, officials insist that a breakthrough is just a matter of when, not if, and random events can become inflection points for a deal.
“These things are so mercurial. Things are changing all the time,” the first official said, explaining that the "inflection point” for the Israel-Hamas negotiations was Israel striking Qatar, not something that the U.S. planned or approved of.
That gives them faith that there is a chance — however slim — that something will break their way with Russia and Ukraine — and force Putin or Zelenskyy to change their political calculus.
Cheyenne Haslett contributed to this report.
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