Come next month, in January 2021, the Israeli politician Gilad Erdan will be joining a long and storied list of characters, and heroes, who have had the job as Israel’s top representative in Washington. As Erdan both prepares for and settles into his new positions—he has already begun serving as Israel’s ambassador to the UN—it might behoove him, and the rest of us, to learn about his predecessors, and their experiences representing the Jewish state in the American capital.

Israel’s first ambassador to Washington, Eliahu Eilat (1948-1950), was not one of the better known of Erdan’s predecessors. He did, however, receive what may have been the most illustrious assignment: notifying President Harry Truman of Israel’s declaration as a state and requesting American recognition of that state. In a May 14, 1948 letter to Truman, signed with his not-yet-Hebraicized name of “Epstein,” Ambassador Eilat let the president know of Israel’s pending assertion of independence, and expressed “the hope that your government will recognize Israel and welcome Israel into the community of nations.” After a legendary internal struggle, and over the objections of Secretary of State George Marshall, Truman agreed to do so, beginning a long friendship between the two nations.

While Truman started a friendship between the United States and the nascent Israel, Marshall held a grudge against its ambassador. He would not deign to meet with Eilat—as we shall see, he would not be the last secretary of state to refuse such meetings—so Eilat looked for allies on the Hill. Eilat started a long Israeli tradition, taken up with special ingenuity by its ambassadors, of finding Congress to be more friendly territory than the State Department, and often more generous as well. Eilat successfully lobbied Congress to help Israel get a vital $100 million Export-Import Bank loan in 1949.

Eilat only had the job for a few years, but he was replaced by one of the longest serving and best known of the Israeli ambassadors to Washington, Abba Eban (1950-1959). On becoming ambassador, Eban went to the White House to present his credentials to Truman, a formal occasion typically steeped in protocol. Truman, however, would have none of it, grabbing Eban’s credentials from him and saying, “Let’s cut out the crap and have a real talk!”

If Eilat’s innovation was learning how to work Congress, Eban’s innovation was reaching the larger American public. He did this both through travel and via the relatively new medium of television. Eban charmed Americans with his posh British accent and his witticisms, becoming informally known as “The Voice of Israel.” To a Boston audience, he said, “If your tea is always like what I drank here this morning, I’m not surprised that you threw it into the harbor.” Eban, who had earned a rare “Triple First” at Cambridge, one of the highest designations possible there, had a quick wit. Once, when praised for his “Oxford English,” he retorted, “Cambridge actually, but in politics one expects to be smeared.”

Eban had a difficult assignment because advocating for Israel in Washington was an uphill battle. (He was ambassador to the UN as well, the last person to wear both hats until Erdan). There were vicious splits regarding Israel inside the Democratic Truman administration; the Republican Eisenhower White House was more unified, but unfortunately more hostile. As Eban wrote in his autobiography, “if there was anything to admire in America in the mid-fifties, it surely lay outside its Middle Eastern policies.”

Even though the Soviets were helping Egypt, the Eisenhower administration began by refusing to assist Israel. To try to change Eisenhower’s mind, Eban used a variety of tools, including eminent figures on the American scene. According to Emmanuel Navon’s new diplomatic history of Israel, The Star and the Scepter, Eban got the celebrated physicist Albert Einstein to weigh in on Israel’s side. Einstein died before embarking on the planned media tour on behalf of Israel, but the letter he wrote with Eban’s help on the issue was released after he died. It was one of the last things Einstein ever wrote.

Eban’s efforts in front of American audiences, Jewish and non-Jewish alike, helped improve Israel’s standing in Washington. But his charms worked better abroad than in Israel itself, where television was a rare luxury. In 1956, according to his biographer Asaf Siniver, Eban was more recognizable in America than he was in Israel. This sense of Eban as more of a foreigner, as “Mr. America” to Israelis, stunted his political ambitions at home. When his rival Golda Meir was told that Eban wanted to run for prime minister, she acidly asked, “Of what country?”

Another famous ambassador to the U.S. was the Israeli general and future Labor prime minister Yitzḥak Rabin (1968-1973). Rabin remains the only Israeli ambassador to the U.S. to rise to the top job in Israeli politics, although the current Israeli prime minister Benjamin Netanyahu did serve as the deputy chief of mission. While in Washington, Rabin befriended the Nixon speechwriter William Safire, and they both attended the 1970 Yom Kippur services at Washington’s Adas Israel Congregation. Regardless of their levels of religiosity, hitting the synagogue circuit was an important way for ambassadors to see and be seen in the American Jewish community.

On this occasion, Rabbi Stanley Rabinowitz gave a blistering sermon attacking “those who would use alliteration to polarize our society”—an unsubtle allusion to the famous speech Safire penned for Vice-President Spiro Agnew criticizing “the nattering nabobs of negativism” in the American media. Safire, who had made a serious effort to stop traveling with Agnew and return to Washington for the holiday, squirmed uncomfortably during the sermon; he wrote later that this was not the sin he had come to atone for. Rabin comforted Safire about the slight and, according to Safire, “probably” chided the rabbi about it afterwards. Safire was forever grateful for Rabin’s commiseration, and they long remained friends, despite frequent ideological disagreements.

Besides his friendship with Safire, Rabin’s tenure in Washington had other lasting effects. He had developed a good relationship with President Nixon, which was helpful when Nixon pushed through crucial arms shipments to a beleaguered Israel in the 1973 Yom Kippur War. And on a personal level, Rabin recalled picking up a love for both tennis and whiskey during his Washington tenure, two habits that remained with him. He also picked up an American bank account, in his wife’s name, which was illegal at the time and later caused him to step down from the premiership in 1977.

Even more involved in the 1973 Yom Kippur War was Rabin’s successor at the embassy, Simcha Dinitz (1973-1979). Dinitz was in constant contact with the U.S. national security adviser Henry Kissinger throughout the war, both on the rearmament issue and on the complex negotiations governing a ceasefire. Once Israel had turned the tide and was on the offensive against the Egyptians, Kissinger was desperate to get the Israelis to stop their advance, both to facilitate a ceasefire and to reduce the risk of the Soviet Union entering the conflict. He called Dinitz from the White House Situation Room to stress the point, eventually exclaiming, “Jesus Christ, don’t you understand?” Suddenly remembering to whom he was speaking, Kissinger stopped, and said, “Oh.” Dinitz, in response, told Kissinger that he might be more persuasive if he would cite a different prophet.

Kissinger, typically, gave back as good as he got. During a spring 1974 “shuttle diplomacy” trip to the Middle East, Kissinger saw Dinitz speaking to some reporters. Referring to the good press Israel used to get in those long-ago days, Kissinger joked, “See, Dinitz is now handing his instructions to the press,” adding “Simcha is reviewing his troops.” Kissinger may have been irked, but, in working the media, Dinitz was doing his job.

Despite his squabbles with Kissinger, Dinitz was happier dealing with the Nixon administration than with Jimmy Carter’s team a few years later. The administration’s hostility started at the top with Carter, but also with National Security Adviser Zbigniew Brzezinski and Secretary of State Cyrus Vance. Brzezinski and Vance were rivals who disagreed on nearly every key foreign policy issue, but they presented a united front when it came to being critical of Israel. At one point, Dinitz went to Carter’s domestic policy adviser, Stuart Eizenstat, to complain about the negativity, saying, “I would like to take away [Carter’s] anger at Israel. He is dealing with an ally.”

Moshe Arens (1982-1983) would encounter a friendlier environment when he served as the Israeli ambassador to Washington during the Reagan administration. Arens, one of three Israeli ambassadors to Washington to have grown up in the U.S., was well regarded in Reagan world. He developed close friendships with Reagan’s two secretaries of state, Alexander Haig and George Shultz, as well as Reagan’s vice-president and successor George H.W. Bush. Another important Arens friendship was with then-Congressman and future Housing and Urban Development Secretary Jack Kemp. Kemp was an advocate for free-market economics and influenced both Arens and Arens’s protégé, a man by the name of Benjamin Netanyahu, on the benefits of the market system. Kemp’s teachings would have huge implications for Israel, since Netanyahu as both finance minister and prime minister would later help drag Israel away from its socialist origins and transform it into the “startup nation” that it is today.

Arens also helped develop the relationship between Israel and America’s evangelical Christian community. He befriended the Israel supporter and Moral Majority founder Jerry Falwell, Sr. during his tenure as ambassador. Later, as defense minister, he spoke to Falwell and a group of 600 evangelical leaders visiting Israel. In helping to convert Israel away from its socialist past and in cultivating Christian Zionists, Arens was instrumental in developing two of the key drivers that transitioned the Republican party from its anti-Israel past to its current incarnation as a staunchly pro-Israel party.

Another ambassador during the Reagan years was Meir Rosenne (1983-1987), who was known for his sharp sense of humor. When the lights went out at a dinner at his residence with Secretary of State Shultz, the dinner guests sat in near darkness as the security people went on alert. Rosenne, however, used the situation to his advantage, telling Shultz, “You see we need economic assistance. . . . I couldn’t pay the electric bill.” The line was particularly resonant given that Israel was in the midst of real economic misery at the time, with 400-percent inflation, and Shultz was an important figure in helping reshape U.S economic aid to benefit the struggling Israeli economy. A tougher Cabinet secretary to woo was Defense Secretary Caspar Weinberger. Weinberger was so incensed over the U.S. Navy analyst Jonathan Pollard’s spying for Israel that he told Rosenne that he thought that the U.S. should have executed Pollard instead of imprisoning him.

Zalman Shoval (1990-1992 and 1998-1999) would have a tough time as ambassador during the George H.W. Bush administration. The Bush team fought with Israel on the issue of $10 billion in loan guarantees for housing for refugees from the Soviet Union, which the American administration wanted to condition on their exclusive use within the “Green Line,” demarking Israel’s 1948-1949 armistice lines. Israel would not commit to the ban. This blowup led to the notorious incident in which Bush, complaining about pro-Israel lobbying on the issue, especially from Hadassah, publicly grumbled that, “I heard today there was something like 1,000 lobbyists on the Hill working on the other side of the question. We’ve got one lonely little guy down here doing it.”

Shoval was one of those complaining about the Bush administration’s approach, both to the American Jewish community and in the press, which irked the Bush team even further. As part of his efforts to work the media, Shoval had given an interview to Reuters in which he criticized the Bush administration for its delay on the loan guarantees and also for noting that Israel had yet to receive “one cent in aid” for Iraqi Scud missile attacks. The Bush administration was furious with Shoval over his comments, with the president himself calling them “outrageous.” Shoval had to apologize, saying, “I did say some things which diplomats are supposed not to say, and I am sorry for that.”

One exception to the hostility to Israel in Bush-world was Vice-President Dan Quayle, a longtime Israel supporter dating back to his days in Congress. In the midst of the loan guarantee tiff, both Shoval and Quayle appeared before the Miami convention of the National Jewish Community Relations Advisory Council. The 1,000 attendees gave Shoval multiple standing ovations in a show of support. Quayle did not say anything, but embraced Shoval to convey that he still stood with Israel. Shoval was appropriately diplomatic about Quayle’s signal, smiling and saying, “I think the message got across. I will now prove my diplomatic proficiency and expertise by not adding any comment.” Quayle’s support was also indicative of the rising pro-Israel sentiment in the GOP, which would be evident both in Congress and in subsequent Republican administrations.

Shoval found the Bush administration difficult, but he also got to appreciate the challenge his predecessor Dinitz had faced with the Carter administration. When he and his wife Kena met Carter’s national security adviser Zbigniew Brzezinski, now a private citizen, they were dismayed to find out how little he knew about Israel. Brzezinski expressed surprise at learning that Kena’s parents arrived in Palestine in 1921. “What?” Brzezinski asked, “There were already Jews there?”

Shoval left for a number of years but returned to Washington during the Clinton administration. He recalled being surprised when he first saw the youthful-looking Bill Clinton and Al Gore, remarking that they looked like a “couple of bar-mitzvah boys.” Later, he would visit Clinton and give him a copy of Psalms, telling him, “Mr. President, you will find the solution to all your problems in this book.” What Shoval did not know at the time was the extent of the Monica Lewinsky scandal. Later, after all of the lurid details came out in Independent Counsel Kenneth Starr’s report of the Clinton affair, Shoval was afraid that Clinton might not have taken the gift in the way it was intended. In Shoval’s mind, Clinton was thinking, “Not only did that Jewish girl get me into this bind, the Jewish ambassador comes along to make fun of me.”

Shoval also accompanied Clinton to the Israel-Palestinian negotiations that took place at Wye Plantation on Maryland’s Eastern Shore in October 1998. While there, he got into a golf cart with then-Minister of Trade Natan Sharansky, which, Shoval recalled, Sharansky “operated like a race car.” (Interestingly, Shoval was not the only Israeli ambassador to have a scare in a motorized vehicle while visiting an American president. Ephraim Evron [1979-1982] recalled visiting Lyndon Johnson’s ranch in the 1960s, long before becoming ambassador, and driving around with Johnson in his jeep. Johnson, who liked to scare passengers with his aggressive driving, ended up flipping the jeep with the two men inside it. Nervous Secret Service agents had to  rescue them from a ravine.)

Shoval’s replacement, David Ivry (1999-2002), had previously served as head of the Israeli Air Force during Israel’s successful raid on the Iraqi nuclear reactor at Osirak. The U.S. issued an obligatory condemnation of the raid at the time, but when George W. Bush came to office, there was a newfound appreciation for this bold act. Vice-President Dick Cheney, who had served as defense secretary under Bush senior during the first Gulf war, was particularly appreciative of Ivry. Cheney gave Ivry a signed satellite photo of the destroyed Iraqi reactor, which the latter proudly displayed in his embassy office: “For Gen. David Ivry, with thanks and appreciation for the outstanding job he did on the Iraqi nuclear program in 1981—which made our job much easier in Desert Storm.”

Danny Ayalon (2002-2006) benefited from strong relationships with top members of the George W. Bush administration, as well as members of Congress from both parties. A much chillier reception greeted his successor, the historian-turned-diplomat Michael Oren (2009-2013). He repeatedly asked for a meeting with Secretary of State Hillary Clinton, only to be consistently rebuffed, reminiscent of Eilat’s failures to get a meeting with Secretary of State Marshall. In one instance, Oren ran into Clinton while both of them were attending the same event and she mocked his failure to get a meeting with her. According to Oren, Clinton “approached me and socked me in the arm, laughing, ‘Michael Oren! I’ve been calling you and calling you but you never return my messages!’”

Clinton’s snubs were far from the only indignity he encountered in the Obama years. President Obama’s famously profane chief of staff Rahm Emanuel, unhappy with Prime Minister Netanyahu’s challenging of Obama at a White House visit, made his displeasure clear to Oren. As Oren recalled, Emanuel “pump[ed] a half finger into my chest . . . and bark[ed], ‘You do not f–king come to the White House and f–king lecture the president of the United States!’”

But perhaps the worst indignity that Oren suffered was after Israel announced the building of housing in eastern Jerusalem while Vice-President Joe Biden was visiting Israel. After Clinton berated Netanyahu over the announcement, Deputy Secretary of State James Steinberg summoned Oren to the State Department for his own talking to. As Oren recalled, “Steinberg added his own furious comment—department staffers, I later heard, listened in on our conversation and cheered—about Israel’s insult to the president and the pride of the United States.” Little wonder that Oren would write Ally, a revealing memoir about the Obama administration’s treatment of both him and Israel.

Given his challenges with the administration, Oren had to diversify his efforts, doing a lot of media, outreach to the American Jewish community, and work in Congress. But he had to walk a careful line while doing so. Once, when scheduled to appear on Fox News, Oren found out that the appearance would be in a split-screen interview with the Obama critic and outspoken Israel ally John Bolton. This put Oren in a quandary of either having to defend Obama or join with Bolton in piling on him. Neither option was appealing, and so he demurred and asked that the interview be solo. Bolton, however, was unhappy with Oren’s Solomonic approach. When they met in person after the interviews, Bolton “physically lunged” at Oren, he wrote, “so fiercely that my security detail stepped in to restrain him.” In addition to the physical assault, there were words as well, as Bolton told Oren, “You’re afraid to go on a split screen! You know what you are? You’re a weenie!’”

With the Jewish community, Oren made a special effort to highlight Israel’s increasing disquiet with Iran. In 2010, Oren did the Yom Kippur trifecta, speaking to Conservative, Orthodox, and Reform synagogues over the course of the one-day holiday. In his visits, he conveyed the message that Iran was the key issue facing Israel, over and above the challenges of Gaza and peace with the Palestinians.

When it came to Congress, Oren found himself working increasingly closely with Congressional Republicans. He worked with House Speaker John Boehner on setting up a speech by Prime Minister Netanyahu in front of Congress, something that infuriated the Obama administration. Boehner had a ready explanation for why the conversations took place without involving the administration, saying, “There’s no secret about the animosity that this White House has for Prime Minister Netanyahu. I frankly didn’t want that getting in the way.” Unsurprisingly, this explanation failed to assuage the administration, and the Obama team warned that no administration officials would receive Netanyahu on his visit.

Like Oren, the current ambassador Ron Dermer (2013-2020), Erdan’s immediate predecessor, also had his troubles with Democratic policymakers. The biggest disagreement, in 2015, stemmed from another address by Netanyahu to a joint session of Congress, in which he denounced the Obama administration’s Iran deal. Once again, many Democrats blamed Dermer for his role in setting up the visit in conjunction with the GOP leadership in Congress and without, they claimed, first consulting with the White House. Both Oren and Dermer saw firsthand the increasing challenges Israel was facing with a Democratic party that was becoming increasingly split over the issue of Israel.

Dermer would find things easier in the current White House, where he was a frequent visitor. He had a particularly close relationship with Vice-President Mike Pence, with whom he attended an Indiana Pacers-Miami Heat basketball game when Pence was governor of Indiana. Dermer, a Miami native and sports fanatic, bet Pence on the outcome of the game, which the Pacers won. The next day, Dermer, a good sport, was seen wearing a Pacers yarmulke in payment for his loss. It remains unclear what Pence would have had to wear had the Heat won.

Regardless of different approaches, these emissaries have all had the same basic mission: to represent the state of Israel in the capital of its most important ally. To navigate the challenging waters of Washington, Erdan will have to deploy humor and straight talk, cultivate relationships with the media, maintain good ties on both sides of the aisle—an increasing challenge these days—tend to the demanding splits and fissures within the American Jewish community, and keep his government at home happy as well. It’s a difficult job, but there’s no better way to figure out how to do it than to look to the example of his impressive predecessors.

Barak Eisenman assisted with research for this article.