He is one of four presidential candidates scheduled to appear at the American Israel Public Affairs Committee's three-day gathering, which kicked off with an address by Vice President Joe Biden
on Sunday night. The annual ritual is part love fest, with a parade of politicians reaffirming their pro-Israel bona fides, and wonk fest, with speakers getting deep into the weeds on the Israeli-Palestinian peace process and U.S. military and financial support for its closest Mideast ally.
In fact, Clinton slammed the billionaire businessman in her address Monday morning, attacking him for saying he would be "neutral" in the Israeli-Palestinian conflict.
She didn't name Trump, but it was clear she was referring to him when she said, "We need steady hands, not a president who says he's neutral on Monday, pro-Israel on Tuesday and who knows on Wednesday ... Israel's security is non-negotiable."
She continued, "We can't be neutral when rockets rain down on residential neighborhoods, when civilians are stabbed in the street. Some things aren't negotiable, and anyone who doesn't understand that has no business being our president."
While Trump has declared himself the most "pro-Israel" candidate out there, he hasn't offered much detail on his policies, and audience members on both sides of the partisan divide will be looking to his speech to see if he hits the notes they hope to hear.
"He hasn't taken any positions on Israel. He hasn't talked about specifics," said Nathan Wurtzel, a Republican and co-founder of the Catalyst Group, a political consultancy. "The Palestinian Authority won't even come to the table without concessions from Israel. What's his position on that? I don't know."
has said about Israel and issues of importance to the Jewish community hasn't always been well received.
Already, several Jewish organizations have slammed his rhetoric as hateful, condemned the violence at his rallies and criticized his inclusion at AIPAC; a group of rabbis has even called for boycotts of his speech
And his Israel policies -- particularly vowing to be a "neutral guy" on the Israeli-Palestinian peace process and suggesting that Israel lacks the commitment to make a deal -- haven't all sat well with activists who want the United States to be strongly on Israel's side.
Defending Trump's record
Trump's campaign, however, strongly defended his stance on Israel.
"Mr. Trump has a long history of being a strong supporter of Israel," said spokeswoman Hope Hicks in an email. "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 also pointed to him having "received numerous awards, participated in many events and made significant contributions to a variety of Jewish related causes over the years."
Trump was also the one who started the Republican stampede to AIPAC, announcing that he wouldn't be attending a debate in Utah on Monday night and would instead make "a very major speech in front of a very important group of people."
Still, Israel is a topic where Trump is a wild card, said Aaron David Miller, vice president at the Wilson Center and a former State Department peace negotiator.
"He is idiosyncratically different from any candidate seeking the Republican or Democratic nomination when it comes to how he talks about Israel," Miller said.
Greg Rosenbaum, chairman of the National Jewish Democratic Council, agreed that Cruz and Clinton are better-known elements when it comes to Israel.
"I think the stakes are very high for Trump, probably higher than they are for Cruz" or Clinton, he said.
Cruz vs. Trump
Cruz is certainly hoping to draw blood.
The Texas senator "will use his speaking opportunity to highlight Trump's positions -- or lack thereof -- in front of the thousands of AIPAC members in attendance," his campaign announced Wednesday, "Including Trump's recent comments that he would be 'neutral' in the debate between Israel and the Palestinians."
Cruz, a devout Christian and pastor's son, will be courting evangelical voters as much as Jewish ones. Evangelicals see the creation of Israel
as biblical prophecy and are adamantly against dividing the land in a peace agreement with Palestinians.
As a voting bloc, though, they have repeatedly favored Trump over Cruz as in Alabama
, where 43% of evangelicals backed Trump in the primary this month as opposed to 23% who supported Cruz. Cruz now lags in the delegate count by 418 to 678 of the 1,237 needed to secure the nomination.
Cruz might try to regain momentum among evangelical voters by touting his support for Israel, blasting Trump's vague positions and then "taking that position back on the trail to win back those evangelicals that he thought were naturally part of his support," Rosenbaum said.
Trump has a tricky line to walk, Rosenbaum added: "He is going to have a very difficult time winning over the crowd if he doesn't take a more pro-Israel stance, and if he does take a more pro-Israel stance, he's going to open himself up to charges of flip-flopping and pandering that may also give Cruz ammunition."
Questions about where Trump stands
Trump enters the room Monday night already having created concern among supporters of Israel on several fronts. Trump's declaration in a February town hall that he would be a "neutral guy" in negotiating a Mideast peace deal "made a lot of people uncomfortable," said Steve Rabinowitz, who runs a public relations firm and once served in the Clinton White House.
And a few things he has said have been controversial to the point of drawing boos from the Republican Jewish Coalition in December.
He questioned whether Israel really wants a peace deal, telling the coalition in December that he didn't know "if Israel has the commitment."
He's also engaged in "cringe-worthy" stereotypes, said Rosenbaum, pointing to Trump's quips about Jews and money at the event. Trump told the attendees he knew they wouldn't support him because he didn't want their money. "You want to control your politicians," he said. "That's fine."
But it was his refusal to tell the coalition whether he would move the U.S. Embassy to Jerusalem that drew jeers from the crowd.
Though a 1995 law calls for transferring the embassy from Tel Aviv to Jerusalem, Republican and Democratic presidents have consistently issued national security waivers to prevent the move until there's a peace agreement between Israelis and Palestinians, who both claim Jerusalem as their capital.
Others have pointed to Trump statements that aren't even about Israel, including his December suggestion that Muslims be barred from entering the United States.
The Union for Reform Judaism issued a statement earlier in the week that said Trump's rhetoric brought to mind the way Jews were blocked from entering America during World War II, "with deadly consequences."
Trump has batted back concerns about his commitment to Jewish issues and anti-Semitism by pointing to his family. His daughter converted to Judaism to marry the son of a New York real estate magnate, and his son married a Jewish woman.
Wurtzel, the Republican political consultant, said he sees no anti-Semitism in Trump himself but noted, "he's certainly attracted white supremacist, anti-Semitic followers."
Describing Trump's campaigning style as "power-hungry, nationalist, self-centered," Wurtzel added that "a Trump-led kind of government historically hasn't been friendly to Jews."