Mike Segar / Reuters

In February of 2015, Israel’s ambassador to the United States, Ron Dermer, was going through a rough period. Amid a contentious election in Israel, the Obama administration accused him of conspiring with Republican leaders on Capitol Hill to arrange an invitation for Israeli Prime Minister Benjamin Netanyahu to deliver a controversial speech on Obama’s diplomatic outreach to Iran before both houses of Congress, only 14 days before Israelis were set to go to the polls. Administration officials claimed that Dermer knew for two weeks that then-Speaker of the House John Boehner had invited Netanyahu to give a speech on this issue, yet didn’t share the information with anyone in the administration, leading to a situation in which they learned about it from the media. Democratic members of Congress lined up to boycott Netanyahu’s speech, and the Israeli opposition, capitalizing on the mess to improve its election prospects, blamed Dermer and Netanyahu for damaging the U.S.-Israel relationship.

As these events unfolded, rumors began circulating in the halls of the Knesset that Dermer was not long for Washington. “Whatever happens in the election,” one Likud minister told me at the time, “I don’t see how Dermer can stay the ambassador after everything that's happened.” The notion that Dermer had become persona non grata in the Obama White House and a partisan actor in the eyes of many Democrats prevailed, despite constant denials from the Israeli Embassy. Perhaps the only person in the Israeli government who refused to accept it was Netanyahu. “Ron is an excellent ambassador. … I see no reason to end his term in Washington,” he said at the time. Netanyahu went on to win the election, and stayed true to his word: Dermer remained his man in Washington, and there are no signs that he’ll be leaving any time soon.  

When Netanyahu arrives at the White House for his first meeting with President Donald Trump on Wednesday, even some of his strongest critics will agree that, at least for now, his bet on Dermer paid off. In a town where every foreign diplomat is scrambling to gain access to Trump’s inner circle, Dermer, according to recent reports, has already developed a close relationship with senior members of the Trump White House—most notably Jared Kushner, the president’s Jewish son-in-law and senior adviser. Dermer also met with members of Trump’s transition team at Trump Tower in Manhattan just days after the election, and also participated in Trump’s meeting with the head of Israel’s Mossad agency in December.

Dan Meridor, a former senior Cabinet member in two of Netanyahu’s governments, told me that he “did not like the confrontational approach” of Netanyahu and Dermer toward President Obama—but that now, with Trump in power, Netanyahu might need Dermer, whom he considers brilliant, more than ever. “This is an unexpected administration. No one knows what their plans are and how they want to execute them. So obviously, having access to his senior advisers … is something that any leader would like to have right now,” Meridor said. But he also added a note of caution. “I've seen reports saying he is very close to Jared Kushner. In any other administration, I’d immediately tell you that’s a great thing. With this administration, it’s harder to tell, because it’s not clear which people truly have the most influence,” he said.

Still, an open line to Kushner is better than what many of Dermer’s colleagues currently enjoy, four weeks into the Trump administration. “As a veteran ambassador that enjoys the trust of Israel’s prime minister and the close circle of the president, I would anticipate that he will play a pivotal role in building a strong, rich dialogue between the two administrations,” Josh Block, the CEO of The Israel Project, a pro-Israel organization based in Washington, told me. Indeed, Netanyahu seems to trust Dermer blindly. When the Israeli Cabinet convened last week to discuss a controversial piece of legislation to retroactively legalize illegal settlement outposts in the West Bank, Netanyahu told the ministers present that he doesn’t want to make any decisions before he has a chance to speak about the matter with Dermer.

Dermer grew up in a Jewish family in Miami Beach, Florida, where his father, a Democrat, was mayor in the late 1960s. He immigrated to Israel in the 1990s, and became involved in politics almost immediately. His first boss was Natan Sharansky, the famous Jewish dissident who fought for Soviet Jews’ right to immigrate to Israel. While working with Sharansky, Dermer was introduced to Netanyahu. Then, when Netanyahu was finance minister under Ariel Sharon, he appointed Dermer to serve as economic envoy at the Israeli embassy in Washington—an appointment for which Dermer had to give up his U.S. citizenship.

After three years in Washington, Dermer returned to Israel, just in time to become Netanyahu's senior policy adviser in the lead-up to Israel’s 2009 election. Netanyahu won, and Dermer, just over a decade after immigrating to the country, became his most-influential adviser. In that capacity, Dermer spent considerable time working with the Obama administration, and was involved in many of the diplomatic clashes between Israel and the United States. Headlines about tensions between him and members of Obama’s team began appearing as soon as 2009, and while some were exaggerated (“People in Bibi’s office were making up stuff and leaking it to the press in order damage colleagues they wanted to get rid of,” one former senior U.S. official told me), they created the impression that Dermer was constantly fighting with the administration.

According to an Israeli embassy official, that impression wasn't always true. “Dermer worked closely with White House officials throughout the entire [Obama] term,” the official told me. The official noted that in January 2016 President Obama, “in an unprecedented gesture,” attended a Holocaust Remembrance Day ceremony at the Israeli Embassy in Washington, less than a year after Netanyahu’s speech to Congress. The official also added that top administration officials like Joe Biden and Susan Rice attended the embassy’s Israeli Independence Day receptions. Dermer also played a key role in convincing Netanyahu to extend a gesture of goodwill to Obama during his March 2013 visit to Israel, by agreeing to apologize to Turkish President Erdogan for an Israeli raid on a Turkish flotilla that tried to break the Israeli naval blockade of Gaza. Senior members of the Obama administration appreciated Dermer’s push for this gesture to take place during the visit.

And yet, many saw Netanyahu’s appointment of Dermer to serve as his ambassador to Washington in late 2013 as a sign that he was preparing for a confrontation: Dermer was seen by many liberal and left-leaning American Jews as affiliated with neo-conservative Republicans, who were highly critical of Obama’s foreign policy. “Bibi always needs an external enemy to fight against, it's part of his way of conducting politics,” explained one former senior Israeli official, who worked closely with Netanyahu for more than a decade. “When he sent Ron to Washington, it was clear that he was getting ready for a big fight with Obama.”

The controversy over Netanyahu’s speech to Congress was the low point of Dermer’s relationship with the Obama administration. Dermer, like Netanyahu, seems to feel no regrets: He believed it was the prime minister’s duty to speak up on the dangers posed by Iran, and has rejected accusations that it was all part of a political ploy meant to boost Netanyahu’s standing ahead of the Israeli election.

Robert Danin, a former U.S. diplomat who worked with Dermer in Jerusalem when the latter served as Netanyahu’s political adviser, said that both men seem to believe that Israel is being unfairly piled on by a hypocritical world, and that it must stand up for itself. “They don't think about it in terms of hasbara [the Hebrew word for explaining, used by Israelis to describe attempts to better explain Israel's positions and complexities to the rest of the world], but as a national security issue, almost an existential one. [They think] Israel is involved in a war of ideas, requiring it to speak strongly against unjust critics, to help ensure the country’s survival.”

The belief in speaking up, even at the expense of alienating allies and supporters—such as pro-Israel Democrats who agonized over the speech in 2015—has recently brought Dermer into friction with left-leaning supporters of Israel. In November 2016, after Dermer’s meeting with the Trump transition team, he publicly defended Trump's senior adviser Stephen Bannon, who has been accused of making anti-Semitic remarks. One month later, Dermer accepted an award from the Center for Security Policy, a right-wing think-tank that has been accused of racism and Islamophobia by the Southern Poverty Law Center. Dermer lashed out against those accusations in his speech and offered a strong defense of the Center’s founder, Frank Gaffney, just like he did for Bannon. One public figure with staunch pro-Israel views told me that by making these statements, Dermer gave “legitimacy to people who hate some of Israel's best friends in this country.”

The downside, and danger, of such an approach, is the effect it could have on Israel's relationship with the Democratic party going forward. “The most urgent task for an Israeli ambassador in the U.S. right now is to preserve bipartisan support for our country,” Danny Ayalon, Israel’s ambassador to Washington from 2002 to 2006, told me. “It's not an easy task, when the entire political system in the United States is drifting towards extreme partisanship. It’s something that will require caution and calculation at every step of the way.” People close to Dermer like to emphasize that he enjoys good working relationships with many prominent Democrats in Washington, and that he regularly sits with Democratic members of Congress, just as he does with Republican ones. Yet even senior Israeli officials acknowledge that the battles of the last eight years have created a rift between Israel and large parts of the Democratic Party—a rift that Dermer must be careful not to widen further, as he works to create a close working relationship with Trump.

Dan Shapiro, who until recently was the U.S. ambassador to Israel, told me that he has conveyed a similar message to Dermer. “As a friend, I've advised him that one of his big challenges will be, while working closely with the Trump administration, to maintain Israel as a point of bipartisan consensus and to be attentive to progressive communities who aren't going anywhere and who Israel will need in the future. It's going to take a lot of effort to strike that balance.” In other words: Even if Dermer indeed becomes a favorite of the Donald Trump White House, it would be wise of him not to forget that unlike him and his boss, many supporters of Israel in the U.S. are currently longing for Barack Obama.  

We want to hear what you think about this article. Submit a letter to the editor or write to letters@theatlantic.com.