Things got a little awkward when Trump roasted Clinton at a swanky New York dinner

‘And then I said: ‘If I win…”. Picture: Getty Images

Donald Trump started off on a good note of lighthearted jokes at a charity dinner in Manhattan on Thursday, but the mood turned once he started attacking Hillary Clinton more heavily.

The Catholic charity dinner brought both presidential nominees together for an evening of cracking jokes, and some of Trump’s initial blows landed well with the crowd.

But the audience turned on him once his jokes got too serious.

“Now I’m told Hillary went to confession before tonight’s event, but the priest was having a hard time when he asked her about her sins and she said she couldn’t remember 39 times,” Trump said.

He then called Clinton “corrupt,” which drew a chorus of boos from the crowd.

“Hillary is so corrupt, she got kicked off the Watergate commission,” he said, to continued boos. “How corrupt do you have to be to get kicked off the Watergate commission? Pretty corrupt.”

Trump then cracked a joke about Wikileaks, which has been publishing hacked emails from Clinton campaign chairman John Podesta.

“I wasn’t really sure if Hillary was going to be here tonight because I guess you didn’t send her invitation by email,” Trump said. “Or maybe you did, and she just found out about it through the wonder of Wikileaks.”

The crowd laughed at that joke, but soured once Trump referenced a speech Clinton had made to a bank behind closed doors. A partial transcript of that speech was included in the Podesta emails posted on Wikileaks.

“We’ve learned so much from Wikileaks,” Trump said. “For example, Hillary believes that it’s vital to deceive the people by having one public policy and a totally different policy in private.”

The crowd booed loudly at that, to which Trump said, “That’s OK, I don’t know who they’re angry at, Hillary, you or I.”

He continued: “For example, here she is in public tonight pretending not to hate Catholics.”

Shocked boos rose up from the audience, but Trump pressed on.

Hands on the table please. No, really. Picture: Getty Images

“Now, if some of you haven’t noticed, Hillary isn’t laughing as much as the rest of us,” Trump said. “That’s because she knows the jokes, and all of the jokes were given to her in advance of the dinner by Donna Brazile.”

That got more boos and heckling. Trump was referring to emails that hinted that Democratic National Committee interim chairwoman Donna Brazile gave the Clinton campaign a debate question in advance.

He then continued on this course to more boos.

“Hillary has been in Washington a long time,” Trump said. “She knows a lot about how government works. And according to her sworn testimony, Hillary has forgotten more things than most of us will ever, ever know.”

Clinton’s speech, which included more self-deprecating jokes, was more well-received by the audience.

Despite the tension between the two candidates in recent weeks, Clinton and Trump shook hands at the conclusion of the dinner.

NOW WATCH: ‘America has lost’: The Philippines president just announced that he’s allying with China, wants to talk to Putin

Business Insider Emails & Alerts

Site highlights each day to your inbox.

Follow Business Insider Australia on Facebook, Twitter, LinkedIn, and Instagram.