Republican front-runner Donald Trump’s speech to an influential pro-Israel lobby on Monday offers a prime opportunity for him to assuage concerns over his commitment to the Jewish state and, perhaps, make inroads into a normally Democratic constituency.

The New York billionaire regularly proclaims himself to be the most pro-Israel candidate in the race and touts his daughter Ivanka’s marriage to a Jewish man and her conversion to Judaism. But he drew boos in December during an awkward appearance at the Republican Jewish Coalition in response to his ambiguity over whether the U.S embassy in Israel should be relocated to Jerusalem. And he has drawn fire over statements that he would be neutral in trying to broker peace in the Middle East.

Trump has a high-profile platform Monday at the American Israel Public Affairs Committee’s 2016 policy conference, which also features addresses from four other presidential candidates.

“The problem right now is that he has been unclear about his Israel policy,” said Jeff Ballabon, a lobbyist and lawyer and who is active in the Orthodox Jewish community. “Other Republicans have been explicit … It would be good to see an unequivocal statement of clarity that Israel is our primary ally in the region.”

Jack Brach, a Republican Jewish activist from New York, said a rhetorical style that benefits Trump can also make trouble for him.

“Unlike other candidates, he doesn’t measure his words so carefully and he speaks off the cuff,” he said, adding that Trump brings a businessman’s penchant for setting broad directives and letting experts work out the details. “He doesn’t do specifics because he’s a negotiator. He’s a dealmaker … I don’t think we can expect more from him on the U.S.-Israel relationship.”

[lz_third_party includes=”https://www.youtube.com/watch?v=vB02qlU4-lY”]

Brach said Trump’s deal-making reputation, while attractive in many contexts, could be concerning to Israel backers since it is so outnumbered in the region.

“He may find it more practical to leave Israel out,” he said. “Having said that, I think he’s been learning every step of the way.”

Ballabon said appearing to endorse a two-state solution for Israel would hurt Trump with Orthodox Jews without helping him with the large mass of American Jews who overwhelmingly lean Democrat.

Who do you think would win the Presidency?

By completing the poll, you agree to receive emails from LifeZette, occasional offers from our partners and that you've read and agree to our privacy policy and legal statement.

“In the general, I’m not sure what the profile is of a Jewish Democrat who is moving from Hillary to Donald,” he said.

Trump’s moderation on social issues could give him an opening that conventional Republicans do not have.

But Brach said Trump’s moderation on social issues could give him an opening that conventional Republicans do not have.

“There’s a New York angle,” he said. “Trump’s a New Yorker. He speaks to New Yorkers. He speaks like a businessman … He’s less scary (than other Republicans) to Jews who are left of center.”

Trump will have more than skeptics to deal with Monday. He will have to contend with what has been a regular fixture at his events — protesters. A pair of rabbis launched a group called Come Together Against Hate, which is organizing a demonstration at AIPAC. Rabbi David Paskin, one of the leaders, said some participants will skip the speech altogether and demonstrate outside. Others plan to listen to Trump’s introduction and then silently file out as he takes the podium.

“We’re going to counter what he’s offering with a Torah of love,” he said. “Our issue is with the tenor of his campaign.”

[lz_related_box id=”117832″]

Paskin said he is troubled by Trump’s appeal and hopes he does not gain steam in the general election if he becomes the GOP nominee. He said he has gotten positive feedback to his anti-Trump initiative but also has heard from many Jewish people who support the real estate mogul. He said they talk about immigration, making American great and other issues.

“A lot of what they say to me is what I would expect to hear from him,” he said. “He has done a phenomenal job leading our country down a very dangerous path.”

Jonathan Greenblatt, CEO of the Anti-Defamation League, declined in a prepared statement to condemn AIPAC for inviting Trump.

“Having said that, we believe that those attendees who might be offended by Mr. Trump’s message have every right to walk out on him should they choose to do so because they believe that his offensive statements deeply clash with their Jewish values,” he said.