"I'm a negotiator like you folks, we are negotiators," Trump said, drawing laughter before pivoting to how he would renegotiate the Iran deal.
"Is there anybody that doesn't renegotiate deals in this room? This room negotiates them -- perhaps more than any other room I've ever spoken in."
The comments were largely met with laughter and smirks, and RJC spokesman Mark McNulty downplayed suggestions that Trump's comments pointed to Jewish stereotypes.
"Donald Trump is well aware of the composition of our board and our audience -- one that includes many successful businessmen and women as well as deal makers like him," McNulty told CNN.
But while Trump tried to win over the audience of wealthy Jewish Republicans
, the billionaire presidential candidate said he didn't believe the assembled crowd would support him.
"You're not gonna support me because I don't want your money. You want to control your politicians
, that's fine. Five months ago I was with you," Trump said, pointing to his recent past as a much sought-after political donor who filled the campaign coffers of both Republicans and Democrats. "I do want your support, but I don't want your money."
And while those comments also faced scrutiny, the Anti-Defamation League, a leading hate speech and anti-Semitism watchdog, said Thursday in a statement that "we do not believe that it was Donald Trump's intention to evoke anti-Semitic stereotypes."
"Here, context is everything," ADL CEO Jonathan Greenblatt said. "In this case he is speaking to a group of Jewish Republicans, a significant portion of whom are business people. We do not believe he intended his comments regarding negotiations and money to relate specifically to their Jewishness, but we understand that they could be interpreted that way."
Greenblatt noted that his group has not hesitated in the past to call out Trump over his comments about Mexican immigrants and Muslims. And he encouraged Trump "to clarify that this was not his intention, and that he rejects the traditional stereotypes about Jews and money."
Trump also faced boos from the crowd when in the question-and-answer portion of his appearance he would not pledge to keep Jerusalem as the undivided capital of Israel.
"I want to wait until I meet with Bibi," Trump said, referring to his upcoming meeting with Israeli Prime Minister Benjamin Netanyahu
when Trump is scheduled to visit the country later this month.
As he faced boos, Trump fired back at the crowd, singling out one man who booed Trump: "Who's the wise guy? Do me a favor, just relax, OK?"
As Trump leaned into elements of his standard stump speech, he came face to face with a very different reception than what he is used to on the campaign trail.
Instead of roaring applause, the candidate's lines touting his front-runner status in the polls and his great successes in business were met with chuckles. And his broad platitudes as to how he would handle certain issues were met with blank stares and not whoops and cheers.
Trump's refusal to vow Jerusalem would remain Israel's undivided capital -- a sticking point in negotiations with Palestinians -- came as Trump defended himself from remarks he made in an interview with The Associated Press.
Trump in that interview suggested the burden of peace rested largely on the shoulders of the Jewish state, saying a peace deal "will have to do with Israel and whether or not Israel wants to make the deal -- whether or not Israel's willing to sacrifice certain things."
Trump didn't back off that statement on Thursday, saying that he doesn't know whether "Israel has the commitment to make (a peace deal) and I don't know that the other side has the commitment to make it."
"It has to be said that Israel has given a lot," Trump said, adding, "I don't know whether or not they want to go along to that final step (of making a deal)."
Playing more to his audience of staunch supporters of Israel, Trump emphasized that Israel "has given a lot and hasn't gotten a lot of credit for it."
Trump also could not name which Arab leaders he would be able to work with effectively, saying simply that he hasn't "been working too much with the Arab leaders to be honest with you."
He added that the King of Jordan "seems like a nice man."
As he defended his pro-Israel credentials, Trump raised doubts about those of Democratic front-runner Hillary Clinton
when asked whether he believes she is a friend of Israel.
"Honestly, I don't' think anybody can say," Trump said, before raising doubts about Clinton's "strength" or "energy" to be president.
"Israel needs more than just our support. They need strength, they need real power behind that," Trump said.