RIYADH, Saudi Arabia — For two decades, Jason Greenblatt worked two doors down from Donald Trump — separated from his boss only by a supply closet and the office of Trump’s longtime assistant, Rhona Graff.
The chief attorney overseeing large transactions for the Trump Organization — including any involving Trump family members — the Queens-born father of six became a trusted negotiator for a fellow son of the outer boroughs, who built his entire brand on the concept of negotiating.
Greenblatt now has some new real estate — he works out of the Old Executive Office Building, across the street from the White House — and a new negotiation to oversee: he serves as the president’s lead envoy in the Middle East, figuring out how to deliver to the president “the ultimate deal,” peace between the Israelis and the Palestinians.
Greenblatt is the rare, old-school, Trump loyalist in a work environment where many of Trump’s top advisers are newcomers who date back only as far as his 2016 campaign. He reports directly to senior adviser Jared Kushner, and functions outside of the competing spheres of influence in the West Wing. “Jared brought in people he trusts and they are embracing the fact that they are not career diplomats but great listeners with deal-making experience who can try a new approach,” said spokesman Josh Raffel. In Riyadh, Greenblatt attended a bilateral meeting on Saturday between Trump and the deputy Crown Prince.
That description of a trusted newcomer certainly fits Greenblatt: In his previous life, the soft-spoken, sharp listener taught a class at Yeshiva University, entitled “The Anatomy of a Real Estate Deal,” which was capped off with a field trip to Trump Tower.
For his part, Trump has been broadcasting great enthusiasm about finding a deal between the Israelis and the Palestinians — despite warnings that now is not the right time coming from veteran diplomats and negotiators who have served in every administration since Ronald Reagan’s.
Foreign policy experts interpreted the Trump administration’s refusal to call the Western Wall part of Israel as motivated by a fear of alienating the Palestinians. They also viewed the administration’s hesitation to fulfill a campaign promise to move the U.S. Embassy to Jerusalem as another concession in the name of a potential peace deal.
“I think they seem to be too concerned it would upset the Palestinians, and they seem very eager for a breakthrough on the Israeli-Palestinian front, said Jeremy Bash, who previously served as chief of staff at the Defense Department and then at the CIA, referring to comments about the Western Wall. “It raises the question of whether the administration is as pro-Israel as it claims to be.”
But when Trump told Palestinian leaders visiting the White House that peace in the Middle East was “frankly, maybe not as difficult as people have thought over the years,” those experts on the region cringed.
Warnings from the conventional American players, however, have done little to mute the enthusiasm of the unorthodox, contrarian Trump, desperate for a win abroad that has eluded all of his predecessors.
And as Trump prepares to travel Monday from Saudi Arabia to Israel – where he will visit the Western Wall, the Holocaust Memorial in Jerusalem, Yad Vashem, and meet with Palestinian President Mahmoud Abbas in Bethlehem – he’s instead leaning on the sunnier assessment of Greenblatt.
Greenblatt, assistant to the President and special representative for international negotiations, has become the lead pointman in the White House on Middle East issues, in part because he didn’t need confirmation to start working when the Israeli Ambassador, David Friedman, was waiting for months in confirmation limbo. (Friedman only arrived in Israel in his official capacity last week.)
He’s compensated for his lack of experience by throwing himself into his work. He moved to Washington, leaving his family in New Jersey, though they visit on weekends for Shabbat.
In Washington and on an initial official visit to the Middle East in March, which included a stop at a Palestinian refugee camp, Greenblatt has impressed people with his open-minded attitude. “None of the American envoys have gone to a refugee camp,” said Dennis Ross, who served as the the Middle East envoy under President Bill Clinton. “This was a significant thing to do.” Greenblatt also attended the Arab League Summit in Jordan, and in May, he and Kushner met with Abbas for a two-hour breakfast at the White House.
And if temperamentally, he can come across like a soft-spoken Trump foil, he shares some qualities with the boss. Like Trump, Greenblatt harbors a deep mistrust of the mainstream media, and a general feeling that the Trump administration is being treated unfairly by the press. “Someone who cares about Israel would never rely on the mainstream media sources to obtain their information,” he told the independent Orthodox Jewish newspaper Yated Ne’eman. “We seek out our own research on alternative websites or from alternative papers to get the true stories.”
Trump friend and ally Ronald Lauder, a longtime leader of the American Jewish community, is also in regular contact with Greenblatt, advocating for his belief in the possibility of a peace deal now.
But the experts who have tried, and failed, before are warning Greenblatt to temper expectations — largely because they believe conditions outside of Trump’s control make a peace deal impossible right now. At 82 years old, Abbas is in succession mode, and he lacks an electoral mandate. Israeli Prime Minister Benjamin Netanyahu, meanwhile, is reliant on the right-wing parties in his coalition to maintain power, preventing him from making any territorial concessions in the West Bank.
Ross has taken his concerns directly to the Trump administration, as has Elliott Abrams, a neoconservative foreign policy expert who worked for Reagan and President George W. Bush, and was briefly considered for the role of Secretary of State Rex Tillerson’s no. 2 at the State Department.
“I’ve told Jason that I do not think a final status agreement is possible now,” Abrams said in an interview. “I’ve urged him to be looking at positive steps that really benefit Israelis and Palestinians and make life better. That’s more realistic, and if you’re an optimist, it lays a foundation for a possible agreement later.”
That view is echoed by John Hannah, a former policy adviser to Vice President Dick Cheney, who wrote in a recent policy paper that it would be a waste of improved relations between Israel and some of its Arab neighbors to try to “solve a maddeningly intractable conflict that has defied resolution for nearly 70 years — and whose current prospects for progress are probably as bleak as they’ve been in a generation.”
Martin Indyk, who served as ambassador to Israel under Clinton, agreed, telling POLITICO: “It’s dangerous to raise expectations and then have them dashed again.”
But foreign policy experts said they doubt Trump’s has the patience to accept small wins that could set the stage for peace down the line. “You can see him going for the big deal, and the situation is just not ripe for an agreement right now,” said Ilan Goldenberg, a former State Department official under John Kerry.
As for Greenblatt, many of the experts who have met with him said they don’t have a strong sense of what he transmits back to the president, or whether he agrees with them. “He holds his cards very close to his vest,” said Ross.
“He can come off as a cipher, and typically no one knows what Jason is thinking,” said an American expert on the region who has met with Greenblatt on multiple occasions. “I think there’s a reason he is so guarded – because he, like many in the administration, knows that Trump ultimately does what he pleases. Predicting administration policy exposes oneself to the likelihood of later embarrassment.”
A White House official pushed back against the idea that Greenblatt couldn’t speak truth to the power of Trump.“The President is eager for information on all sides and his optimism is a great asset as it helps bring people to the table,” the official said.
The truth, however, is that Greenblatt, in large part, agrees with Trump, according to interviews with White House officials. He sees the experts trying to persuade him that peace is out of reach as having an outdated view of the region. He has described the current moment as a “once in a lifetime opportunity” to broker peace, echoing Trump’s own words – in part because of his deep belief in Trump’s powers of negotiation, in part because of the shared threat of Iran to both the Israelis and the Palestinians.
His success in Trump’s orbit has also made some skeptical of his ability to contradict the boss. “His job isn’t to listen to everyone and then come back to Trump and say here is what is possible and here is what is not,” said one outside adviser who has spoken extensively with Greenblatt. “Trump has said getting a deal is easier than it looks, and we’re going to do it. My impression is it’s not really possible to go back to him and say, “it can’t be done, not now.’”
The fear is that when it comes to a peace deal, the stakes are too high to fail — for Israel, for the Palestinians and for Trump. As they head to Israel, Trump and Greenblatt might be the most optimistic people involved. “Maybe we can end that journey and start a much better journey,” Trump told Abbas, while seated next to him in the Oval Office earlier this month, of the long failure of the peace process.
In response, Abbas simply put his hands up in the air and shrugged.