22:44

If Donald Trump’s campaign has been defined by going where no candidate has gone before, on Thursday the real estate mogul added a new feather to his cap: being roundly booed at a Catholic charity dinner.

The Republican nominee encountered a chilly reception at the Alfred E. Smith dinner, an annual Catholic fundraiser in New York City, with Hillary Clinton also in attendance. Presidential candidates have long graced the white-tie affair and roasted themselves while throwing in a few jabs at their opponents.

But after earning a few laughs, Trump’s remarks quickly devolved into a stinging indictment of Clinton that prompted jeers from the audience.

“Hillary believes it’s vital to deceive the people by having one public policy and a totally different policy in private,” Trump said, nodding to the emails of her campaign chairman John Podesta that were published by WikiLeaks.

“That’s OK,” Trump responded to the audible boos that followed. “I don’t know who they’re angry at, Hillary, you or I?”

“You!” a voice cried out from the crowd.

Trump pressed on, standing at a podium mere feet away from Cardinal Timothy Dolan, who served as the evening’s host: “For example, here she is tonight in public, pretending not to hate Catholics.”

Trump did bring the house down with a rejoinder poking fun at his wife’s dabble with plagiarism during the Republican National Convention in July.

“Michelle Obama gives a speech and everyone loves it, it’s fantastic,” Trump said. “My wife Melania gives the exact same speech, and people get on her case. I don’t get it.”

But the barbs he subsequently threw at Clinton, delivered as though the venue was a Trump campaign rally, fell flat.

Clinton’s speech, albeit less bitter in its tone, was similarly crafted with a series of jokes not far removed from the attack lines she has employed against Trump on the stump.

The Democratic nominee needled her opponent over his admiration for Russia, remarking of Trump’s refusal to disclose his health records: “Donald Trump really is as healthy as a horse – you know, the one Vladimir Putin rides around on.”

Of his inability to stick to teleprompters, Clinton quipped: “I’m sure it’s even harder when you’re translating from the original Russian.”

The former secretary of state also homed in on his behavior toward women. “Donald looks at the Statue of Liberty and sees a four, maybe a five, if she loses the torch and tablet and changes her hair.

“You know what would be a good number for a woman? 45,” she added, in reference to the number marking the next president’s place in US history.