Do Jewish Grandchildren Solve Trump’s Israel Problem?

It might be a quiet moment at the Western Wall or a walk through Jerusalem’s Old City — those were the seminal moments for Bill and Hillary Clinton on their first trip to the Holy Land after the future president lost his first bid for reelection as Arkansas governor.

Or it could be the helicopter flight Texas Gov. George W. Bush took over Israel when he fully realized how small the country was. Or the bomb shelters Sen. Barack Obama explored in Sderot, on Israel’s border with the Gaza Strip, when he thought of his daughters and how he would do anything to protect them from rocket fire.

Presidential candidates typically hold such an Israel moment in reserve for Jewish voters, a moment they connected with the Jewish state in their “kishkes,” their gut.

Donald Trump, the real estate magnate, reality television star and front-runner for the Republican presidential nomination, has an Israel moment he likes to cite. It just happens to have to taken place on Fifth Avenue in Trump’s native New York City. It was in 2004, when he served as grand marshal for the city’s Salute to Israel parade.

“First of all, there’s nobody on this stage that’s more pro-Israel than I am, OK. There’s nobody,” he said last Thursday night in Miami when his rival Sen. Ted Cruz, R-Texas, questioned his Israel bona fides. “I am pro-Israel. I was the grand marshal, not so long ago, of the Israeli Day Parade down Fifth Avenue.”

There was applause, but there also was some booing and tittering — a quintessentially Trump moment in this wild election season.

But the credential also was quintessentially Trump: a bit of sound and fury not so much about the subject at hand, Israel, but about Trump — and signifying not a whole lot. The Jewish organizations that put together the Salute to Israel parade name grand marshals not based on pro-Israel merit, but for the attention they attract. In 2014, there were at least three, including Gov. Andrew Cuomo and his Republican challenger in that election year, Rob Astorino.

It’s the kind of moment that has pro-Israel activists nervous, and watching closely for what he’ll say when he appears this week at Washington’s signature pro-Israel event, the annual American Israel Public Affairs Committee conference.

“He’s a wild card, and it’s very hard to figure out what he believes in and what he would do,” said Betsy Sheerr, a past AIPAC board member who is also on the board of my employer, the Jewish Telegraphic Agency, a wire service for Jewish media. “I think a lot of what he says is for show, but you can’t be sure. It’s going to be very hard for the pro-Israel community to approach this in a traditional way.”

How do you influence a candidate who, by making self-funding a hallmark of his campaign, has cut off the avenues of traditional influence, not just for the pro-Israel lobby but for other lobbies? Trump’s campaign is not susceptible to the dedicated volunteer from the outside who trades hard hours on the campaign trail for the candidate’s willingness to consider her pet issues. (His political director, Michael Glassner, worked in 2014 and 2015 at AIPAC’s Houston office; his path to Trump, however, was through Sarah Palin, the 2008 vice presidential nominee whom he is close to and who has endorsed Trump.)

And who — if anyone — is Trump’s Eddie Jacobson, the beloved Jewish partner and friend of Harry S. Truman who played the friendship card just once in his life: Meet with Zionist leaders, just hear them out, Jacobson implored Truman in March 1948, when Truman’s secretary of state, George Marshall, was advising him not to recognize the Jewish state. Truman heeded Jacobson’s advice, and two months later, on May 14, Truman recognized Israel 11 minutes after it declared independence.

Every president has an Eddie Jacobson, even — especially — the ones who have a tense relationship with Israel’s leadership. The guy who earns the president’s confidence by making his case to the Jewish community until it’s time for a quiet conversation with the president that starts: “You know, your Jewish critics may have a point.” It was Stuart Eizenstat for Jimmy Carter, Max Fisher for Ronald Reagan, Alan Solow for Barack Obama.

Who is Trump’s Eddie Jacobson? Does he have one? It’s emerging as a major question for a candidate who has departed from GOP orthodoxy on Israel by saying he would be adamantly neutral in brokering Israeli-Palestinian peace. Trump’s campaign spokeswoman, Hope Hicks, did not return a request for comment for this article.

A senior pro-Israel lay leader, who asked for anonymity so his organization is not identified with any candidate, said the pro-Israel community will be watching Trump closely at AIPAC, not just for what he says but for what he does before and after. “He can’t come to AIPAC and say ‘I’ll be even-handed’,” this leader said. “He has to put some policy out that will be one of his first big tests.”

AIPAC does not endorse or recommend candidates. But its major donors give money to campaigns, and they’re known to slip away from the conference, which is held at the massive Washington Convention Center, to meet individually with the candidates they favor at a nearby hotel. The invitations are often issued discreetly away from the conference — an email, a phone call — by the campaign staff.

Has Trump reserved a suite? Will he meet with potential donors? It was not yet clear on Friday, when he confirmed that he will speak at the conference. A clue: At the debate the night before, he would not count out fundraising for the general election.

“Trump and Israel is so out of the bell curve, you can’t even Google it,” said Ben Chouake, a New Jersey dentist who is president of NORPAC, the largest pro-Israel political action committee.

Trump does have some Jewish backers, including colleagues and friends who knew him as a businessman in New York. In addition to embracing his moderation on social issues like gay marriage and abortion, they tend to cite his recording of an ad supporting Netanyahu’s 2013 reelection bid as a pro-Israel credential (although, notably, Netanyahu has condemned Trump’s rhetoric on Muslims this election season). Moreover, they say his critics miss the point: Trump is a businessman, not a politician. “People are bent out of shape because he won’t take sides. I’m a negotiator myself; that’s how you do things,” Gedaliah Shaps, an entrepreneur, told JTA recently. “But I believe he truly has Israel’s best interests at heart. He says Israel is going to love him, and I believe that.”

But that leaves open the question of Trump’s views about the Jewish faith. Chouake, who has endorsed Cruz for president, ran through the on-the-one-hand, on-the-other-hand litany that he says has been preoccupying him since Trump emerged late last year as a force to be reckoned with.

On the one hand, his daughter Ivanka converted to Judaism and is married to Jared Kushner, the son of real estate magnate Charles Kushner, who has been prominent in pro-Israel circles. His son Eric is also married to a Jewish woman, Lara Yunaska.

“His daughter is sending the kids to Ramaz,” a premier private Jewish day school on New York’s Upper East Side, said Chouake, who is also active in AIPAC. “His son-in-law and his in-laws are the Kushners. … He’s going to have to be pro-Israel or spend a lot more time alone with his wife.”

On the other hand — and this is the level of agonizing that Trump has induced among the pro-Israel crowd — what is Trump’s relationship with his daughter and son-in-law? They campaign for him, he employs her at The Trump Organization, but what are his thoughts about their Jewish faith?

This is what pro-Israel Republicans have been reduced to analyzing in the absence of any specific evidence of the front-runner’s policies on the Middle East.

“He doesn’t have position papers,” Chouake said. “He doesn’t have to; he’s the front-runner.”

Trump has kidded Jewish Republicans that it annoys him that he is unable to call his daughter on the Jewish Sabbath. There are even whispers among pro-Israel leaders about his weird tendency to hypothesize that he might date Ivanka, were she not his daughter — where does that leave poor Jared?

“The in-law thing cuts both ways,” said a prominent Jewish figure who spoke anonymously because of the sensitivity of the issue. Meaning: He could adore the Jewish son-in-law. Or maybe hate him. Who knows?

And then there was his jokey-hostile appearance at a candidates forum organized in December by the Republican Jewish Coalition.

“You’re not gonna support me even though you know I’m the best thing that could ever happen to Israel,” Trump told the crowd, eliciting nervous laughter. “And I’ll be that. And I know why you’re not going to support me. You’re not going to support me because I don’t want your money. Isn’t it crazy?”

America’s conservative pro-Israel community, of which RJC is a part, has always been at a loss at how to deal with the indifference, if not hostility, toward Israel of a certain portion of the Republican base. That was evident in the way that RJC’s director, Matt Brooks, squirmed at a Las Vegas forum last week when the subject of Trump came up.

“It’s a ‘We’re going to have to wait and see’ answer,” he said when asked if the RJC would endorse Trump if he become the candidate. “Our track record in speaking up — and we will have plenty of opportunity once we have a nominee to speak up or speak out as the case may be — if you step back and you look at the history of the organization, whether it’s Pat Buchanan or others, even speaking out and taking on our own president when we had fundamental differences of opinion.”

Buchanan, a former Republican presidential candidate whose rhetoric Jewish groups believed veered into anti-Semitism, was a telling citation.

Much of the #NeverTrump campaign on social media is driven by Jewish conservatives like Max Boot, the Council on Foreign Relations scholar who was a top advisor to John McCain’s 2008 candidacy, and Jennifer Rubin, the Washington Post columnist. They’re motivated not just by his professed “neutrality” on Israel and the Palestinians. His broadsides against Muslims also are galling for many Jews, who recall how America’s foreign policy isolationism in the early 20^th century sought to keep Jews out of the United States and the United States out of World War II.

It’s an opening his Republican rivals have tried to seize. Sen. Marco Rubio, R-Fla., chose a synagogue to deliver a broadside against Trump on Friday, four days before the Florida primary, a must-win for Rubio. “Trump is no ally to Israel” was the subject line on an email his campaign blasted during Thursday’s debate.

Fred Zeidman, a Texas businessman who was George W. Bush’s Eddie Jacobson and who backed Jeb Bush until he dropped out of this campaign, said he believed a trusted Jewish advisor to Trump would soon emerge, perhaps among his many fellow New York Realtors who are Jewish.

“You’ve got to count on people that he knows, that he trusts and that have good relationships with him to carry the message,” Zeidman said. He added that he will back Trump if he gets the nomination, because he believes keeping a Democrat out of the White House overrides other considerations.

Chouake scoffs. “He’s not Truman. Truman was a tremendous person with tremendous personal moral character,” he said. “I don’t know about Trump. I don’t know if Trump has Truman’s character and integrity.”