One Thursday morning this past July, Ron Prosor, Israel’s ambassador to the United Nations, holed himself up in his office with his communications team. He was supposed to be chairing a staff meeting, but Iran and Syria had just announced their candidacies for the U.N.’s Human Rights Council, and Prosor wanted to make sure that the absurdity of two of the world’s most egregious human rights abusers running for its highest human rights body was not lost on the press. “The staff is still waiting for the meeting to start, and nobody has any clue what’s going on,” recalled Avishai Don, one of Prosor’s former speechwriters. “So, the crowd in his office slowly gets bigger, as we’re thinking of a funny way to say the inmates have taken over the asylum.”Finally, Prosor released a quote to the wire services: “Putting Iran and Syria on a Human Rights Council is like putting the Godfather in charge of a witness-protection program.” As far as Prosor was concerned, it wasn’t enough that Syria and Iran be condemned—they had to be mocked. And it worked: That night, Reuters included the line in its report about Syria’s decision to withdraw its candidacy.The incident is emblematic of the signature style of Israel’s unorthodox ambassador to the United Nations. For Prosor, who assumed the position in June 2011, humor is an essential tool for conducting diplomacy—and the often comical corridors of the U.N. are the ideal stage for his act. Prosor headed the Israeli Foreign Service from 2004 to 2007, but he doesn’t speak like your typical diplomat. Like any public official, he has his talking points. But rather than consisting of bureaucratic bromides, many take the form of wisecracks or cultural references. “It is in huge contrast to what you would see as classic diplomacy,” he admitted to me. But it has become Prosor’s calling card.It’s a style that contrasts with that of another noted Israeli ambassador to the U.N.: Benjamin Netanyahu, who held the post from 1984 to 1988. In his current stint as prime minister, Netanyahu has derided the U.N.’s “theater of the absurd” as well as lectured its delegates with the aid of a cartoon diagram of an Iranian nuclear bomb. For Netanyahu, ridiculing the U.N. is a publicity strategy—intended for external, not internal, consumption. Prosor, on the other hand, uses humor as an element of personal diplomacy. His goal is not so much to play to the crowd outside as to change minds inside—sometimes through shaming, sometimes through playful prodding. Having cultivated this skill throughout his career, long before he arrived at the U.N., Prosor is confident that he can subtly deploy it to shift the perspectives of others.Today, when the U.N.’s General Assembly opens its annual convention of world leaders, the 54-year-old ambassador will be in the arena coordinating high-level meetings between senior Israeli officials and their counterparts from other nations on issues like the Iranian nuclear program and the civil war in Syria. Prosor described the goings-on with characteristic bemusement, dubbing it “the No. 1 time during the year when heads of state can meet and talk to each other in one place, back to back—it’s like speed-dating.” It’s a quintessential Prosor riposte that showcases his ability to scale geopolitical encounters down to the more manageable level of human interaction.And if there’s one thing an Israeli needs at the U.N., it’s a sense of humor.***To say that the U.N. is biased against Israel is like saying Boston is biased against the Yankees. It’s technically accurate, but woefully understates the depth of the animosity. As Susan Rice, who spent five years as the U.S. ambassador to the U.N. before becoming President Obama’s national security advisor, said last May, “the U.N. isn’t at its best when it comes to Israel. In fact, it’s sometimes at its worst.” Nearly every branch of the U.N. is riddled with procedures and processes specifically designed to isolate and assail the Jewish state.Take the General Assembly, the plenary for all 193 U.N. member states: In 2012, it passed 22 resolutions against Israel and only four against other individual countries. One need not be a supporter of Israeli policies to recognize the perversity of repeatedly lambasting Israel while remaining silent on the abuses of China, Sudan, and Zimbabwe. But in an organization dominated by nondemocratic countries, Israel proves an easy target for repressive regimes seeking to distract from their own bad behavior. The 57 countries of the Organization of Islamic Cooperation and 120 members of the Non-Aligned Movement—which held its last conference in Tehran, where the group’s presidency was transferred to Iran’s former President Mahmoud Ahmadinejad—take advantage of their numbers to silence any nations that might defend Israel. “You have a hesitancy to be friends with or appear to be too close with Israel, for fear of being punished by an entire bloc of countries,” said Richard Grenell, who served as spokesman for the U.S. mission to the U.N. during the George W. Bush Administration.The U.N.’s specialized branches have likewise institutionalized the inquisition of Israel. Every year, the U.N. Educational, Scientific, and Cultural Organization (UNESCO), which counts Syria as a member of its human rights committee, passes a resolution condemning the Jewish state—and no one else. Similarly, the World Health Organization and International Labor Organization annually censure Israel alone. And the U.N. Human Rights Council, called “the shame of the United Nations” by the New York Times for its all-star membership of abusive authoritarians, reserves a permanent place on its agenda for Israel, guaranteeing that it will be condemned at every session. No other country or violation in the world—not genocide in Sudan, mass murder in Syria, or concentration camps in North Korea—has its own agenda item.Most diplomats would look at this situation and see a daunting challenge. Prosor, on the other hand, sees a gold mine of great material. Every instance of institutional hypocrisy becomes an opportunity. Thus, when the delegate from Iran—Israel’s chief adversary and the Middle East’s largest state sponsor of terrorism—bemoaned the influx of arms into the region, Prosor quipped in the Security Council that “this is like the mafia complaining that the crime rate in New York is too high.”Likewise, when Syrian Ambassador Bashar Jaafari claimed last year that his government was not responsible for the massacres taking place in his country, Prosor took him to task. “If lying was an Olympic event, I have no doubt that the Syrian regime and its representatives could easily win a gold medal,” he told the General Assembly in August 2012. (He also presciently warned that Syria’s Assad would use chemical weapons against his own people.) There is certainly no love lost between Prosor and his Syrian counterpart. “When Jaafari snores, he lies,” he told me. “But this was really absurd. And not only did I react, but you should have seen the Arab ambassadors—the Saudis and the Qataris and the Kuwaitis. They’re used to lying anyhow, but he really went way beyond the call of duty.” Prosor’s derision here is instructive—far from gratuitous grandstanding, it enabled him to appeal to even some of Israel’s most inveterate opponents, because they shared his disgust with Syria’s conduct.Continue reading: “We were never going to be boring.”Needless to say, this is not a traditional approach. “U.N. speeches are written by people who don’t write English and read by people who don’t speak it. They’re endlessly boring,” said Nate Miller, who served as the Israeli mission’s chief speechwriter from 2010 to mid 2013. “Ron was very clear that we were never going to be boring.” The unofficial credo of the speech-writing team became “What would Togo think?” That is, would the representative of a country like Togo, unfamiliar with Israel’s situation, leave the speech with a greater appreciation for the challenges faced by the Jewish state? Or would they find the rhetoric convoluted and stultifying, filled with legalese and diplomatic digressions?Prosor’s style certainly makes his words stand out. Before he arrived at the U.N., he served as Israel’s ambassador to the United Kingdom, where he was dubbed the “king of the diplomatic quip,” and his one-liners peppered the local papers. In one memorable instance, Prosor responded to a proposed boycott of Israeli dates during Ramadan. “Israel will continue to successfully export dates, whilst others choose to export hate,” he told the Guardian. “We encourage Muslim shoppers to ignore this nonsense, and instead double the quantity they usually purchase, to help bring about a two-date solution.”Prosor isn’t the first Israeli ambassador to the U.N. to use humor as a diplomatic weapon. In 1976, after Israel’s daring hostage rescue operation at Entebbe, Chaim Herzog cracked up the Security Council when he pointed out the blatant hypocrisy of the Soviet Union accusing Israel of violating another country’s sovereignty. “On these subjects, I defer to [them], having regard to the Soviet Union’s very considerable record in these respects in Hungary, in Czechoslovakia, and in other countries in Eastern Europe,” he said, eliciting laughter from the assembled delegates. But while Prosor’s predecessors have occasionally resorted to mockery as messaging, he is the first to make it a defining feature of his diplomacy. “I believe personally that you can’t win without playing offense,” he told me.Of course, there’s a reason most ambassadors favor discretion and understatement over straight-talk and sarcasm. The latter may make Israel feel better in the short run, but it runs the risk of impeding genuine diplomatic progress by alienating potential partners. But Prosor, says Arthur Lenk, Israel’s ambassador to South Africa, is a special case. “It’s a personality,” he explained. “If you can’t do it lightly, and with some humanity, and you just come across as sarcastic and angry, it’s going to blow up in your face.” The trick is to use humor not simply to ridicule others—though that can have its place—but to playfully prod them into understanding your own perspective. Lenk is no stranger to fraught affairs of state, having served from 2005 to 2009 as his country’s representative to Azerbaijan, one of Israel’s only Muslim allies. “Ron’s style works,” he said. “Humor’s a good tool if you do it right. And Ron Prosor is one of the best diplomats the state of Israel has.”If anything, Prosor’s willingness to speak his mind has gotten him into more trouble with his own government than with the U.N. At a December 2012 conference in Jerusalem for Israel’s ambassadors, Prosor questioned the timing of the government’s recent announcement that it would build in the controversial E1 corridor in the West Bank. The move, taken in response to the Palestinian declaration of statehood at the U.N., had evoked broad international condemnation, and Prosor inquired as to the strategy behind it. His question was reportedly greeted with “a torrent of applause from the assembled ambassadors,” but it received a stern rebuke from Netanyahu’s national security adviser, Yaakov Amidror. “Gentlemen, do not be confused. You are representatives of the government. If it’s inconvenient for you, go into politics or resign.” (Prosor maintained to me that he was seeking a messaging strategy, not challenging the policy, which he has vigorously defended at the U.N.)Of course, Israel has a tough time at the U.N. even when it doesn’t have a controversial policy to uphold. But despite the many challenges the Jewish state faces in the international arena, Prosor is confident he can make progress at the U.N. “I’m very optimistic in who we are and what we are,” he said. “All I need is for the world to look at us with open eyes, and not through fun-house mirrors that distort our image.”This is why humor is so critical to Prosor’s diplomatic enterprise: Deployed correctly, it can shift perspectives. More than making people laugh, Prosor hopes to make them reconsider Israel’s precarious place in the community of nations. But does he ever worry that he’ll run out of jokes and snappy metaphors to encapsulate the U.N.’s dysfunction and hypocritical stance toward Israel? “No,” he laughed. “Believe me, we come up with new ones all the time.”***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Yair Rosenberg is a senior writer at Tablet. Subscribe to his newsletter, and follow him on Twitter and Facebook.