NEW YORK — When Donald Trump takes the stage Monday at the annual policy conference of the American Israel Public Affairs Committee, the influential lobbying group known as AIPAC, he will be facing a wary crowd.
Trump’s ostentatious disregard for the sensitivities of various religious and ethnic groups has hit a nerve among Jewish organizations, inspiring a barrage of denunciations from across the ideological spectrum.
They cringed at his trafficking in Jewish stereotypes and recoiled when he hesitated before denouncing David Duke, the Ku Klux Klan figure.
On paper, Trump might be an unlikely candidate to raise eyebrows within the Jewish community. He is from the city with the country’s largest Jewish population, and he made his fortune working among the Jewish machers in New York’s real estate industry.
Trump’s Palm Beach club, Mar-a-Lago, was effectively marketed as a Jewish alternative to the town’s private clubs that had historically excluded Jews. His daughter Ivanka married an Orthodox Jew and converted. He endorsed Benjamin Netanyahu for prime minister of Israel (“Terrific guy, terrific leader”).
Yet, many Jews have said Trump’s comments about Muslims reminded them of when they had been singled out, and a group of rabbis said last week that it would walk out in protest from his AIPAC speech.
“What we’ve learned from our history is that we can’t stand idly by when a leader says those things,” said Rabbi Jesse M. Olitzky of South Orange, N.J., who plans to eject himself from the meeting.
Trump also stumbled when he waded into one of America’s most charged foreign policy issues, promising to remain a “neutral” broker between Israelis and Palestinians.
For the many Jews who side with Israel in its dealings with Palestinians — a number of whom are AIPAC members — “that was like fingernails across the chalkboard,” said Ari Fleischer, former spokesman for President George W. Bush. Trump later modified his position to be more pro-Israel, but his wavering left many unconvinced.
So while Trump has proved to be a master salesman at rallies and debates, the crowd he is addressing Monday might be his toughest sell yet.
“He’s said a variety of things over the years, much of it favorable to Israel, much of it ambiguous more recently,” said Josh Block, a former AIPAC spokesman who now runs a pro-Israel nonprofit in Washington. “The speech is an important opportunity for this audience to hear what he really thinks on these issues that matter a great deal.”
Three of the other four major presidential candidates are also addressing the conference, being held in Washington — Hillary Clinton, Ted Cruz, and John Kasich. Only Bernie Sanders declined to attend, saying he was going to spend the day campaigning in the West.
It is unclear how much the revulsion among Jewish voters over Trump’s comments and behavior matters in the voting booth. Little data exist on Jewish attitudes toward Trump, and because most American Jews are Democrats, they will not have a chance to weigh in on him unless he becomes the Republican nominee.
Bruce Balsam, 59, who was walking into Sabbath services Friday at Temple Emanu-El, the stately synagogue a few blocks north of Trump Tower on Fifth Avenue in New York City, said Trump’s shifting position on the Israeli-Palestinian conflict “really disturbs me.” But, he added, “I’d want to hear more about that.”
He said he considered Trump’s take on national security and Muslim immigration to be more “anti-Islamic” than “presidential,” but agreed that caution needed to be taken. “People who are coming from certain parts of the world, where anti-American sentiments are high, we should be highly cautious of,” Balsam said.
Balsam pointed to Temple Emanu-El, one of the largest Jewish institutions in the world, as an example. “You have armed guards outside,” he said, gesturing toward the New York Police Department’s counterterrorism officers. “You have armed guards inside.”
Hope Hicks, a spokeswoman for the Trump campaign, said Trump “looks forward to speaking to a group whom he has tremendous respect for.”
“Mr. Trump has said, as president, there will be no one stronger on Israeli-American relations than him, and his consistent support and advocacy for Israel over many years is proof of this,” she said. “Additionally, Mr. Trump is the only candidate to speak with clarity about the deadly threat of radical Islam. ISIS and other Islamic terror groups cannot be defeated if we are politically correct.”
That Trump has had to defend his pro-Israel credentials is something of a surprise, given his history. He has been honored by a variety of Jewish groups over the years, and, as he likes to point out, once served as grand marshal of the Salute to Israel Parade in Manhattan.
Trump has joked in the past that people assume he is Jewish because he owns so many buildings in New York. He has even claimed to be the victim of anti-Semitism.
Sheldon Adelson, the casino magnate and a major donor to Republican and Israeli causes, said recently that he would back Trump if he were the nominee.
But others see him as accommodating of bigotry. “The way he dillydallied with David Duke basically sent a message that was perceived by many in the Jewish community as he’s looking for any votes he can get from the hard right,” said Alan M. Dershowitz, the defense lawyer.
To Dershowitz, the problem is not simply Trump; it is the white supremacists who have rallied around his candidacy. “It’s quite frightening to see who supports him,” he said.