Donald Trump began with self-deprecating jokes and some friendly jabs at his presidential rival Hillary Clinton as normal at the annual Alfred E. Smith Memorial Dinner.
Even Clinton was laughing when Trump said, "I am told Hillary went to confession before tonight's event, but the priest was having a hard time . . . she said she could not remember 39 times."
But the crowd quickly turned on Trump when he said, "Hillary is so corrupt, she got kicked off the Watergate Commission."
It didn't get better.
"Now, if some of you have not noticed, Hillary is not laughing as much as the rest of us," Trump read from his notes, though no one was laughing at that point. "That's because she knows the jokes. All of the jokes were given to her in advance of the dinner by Donna Brazile."
That was a reference to leaked emails that showed the acting Democratic National Committee chair provided a question to Clinton ahead of a CNN town hall event.
There were more boos when Trump slammed Clinton over criticism the Clinton Foundation has used money intended to help earthquake victims in Haiti to enrich her friends.
"Everyone knows, of course, Hillary has believed that it takes a village, which only makes sense, after all, in places like Haiti, where she has taken a number of them," he said.
The dinner is a fundraiser for Catholic charities, and Trump even slammed Clinton over leaked emails that showed people who are now members of her campaign staff talking about spurring a "spring" within the conservative church.
"Here she is tonight in public, pretending not to hate Catholics."
Cardinal Timothy Dolan, who was seated between Trump and Clinton in at the dinner, looked uncomfortable and could be seen mopping his forehead with his napkin.
Clinton spoke immediately afterward, and though her jokes did not draw the same belly laughs as Trump's early jokes, even her sharpest barbs didn't bring boos and hisses.
Clinton closed her speech in a very different tone than Trump, noting Al Smith, the first Catholic to receive a major party nomination for president, fought discrimination.
In a clear reference to Trump's call for a temporary ban on Muslim immigration during the primaries.
"Don't forget, school boards sent home letters with children saying that if Al Smith is elected president, you will not be allowed to have or read a Bible," she said. "Voters were told that he would annul Protestant marriages. . . . Those fears of division can cause us to treat each other as the 'other.'"
Reaction was mixed. Political pundit David Gergen told CNN that Trump didn't seem to know the difference between being light-hearted and heavy-handed.
"I think there was a reason the boos were there," he said. "And that was that he went over the line on several occasions."
Fox News' Sean Hannity defended Trump, saying: "It's funny. A liberal crowd, liberal audience. It's New York. You got oohs and ahhs when Donald Trump crossed the line. They both gave as good as they got."
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