While the New York fundraiser for Catholic charities always includes the two candidates getting laughs at their rival’s expense, Trump’s lines stuck closely to his campaign’s antagonistic rhetoric after an initially positive start.
 
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The boos first began when Trump made a joke based on the debunked theory that Clinton had been fired from the Watergate Commission.
 
“Hillary is so corrupt that she got kicked off the Watergate Commission,” he said. "She got kicked off the Watergate Commission. How corrupt do you have to be to get kicked off the Watergate Commission? Pretty corrupt."
 
And they deepened when he pivoted to the hacked emails of her top aides.
 
“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 remark drew loud cries from the audience, to which Trump responded, “That’s okay. I don’t know who they’re angry at, Hillary, you or I.”
 
He prompted another round of booing when he referenced comments from those same leaked emails in which aides wrote dismissively about prominent Christian conservatives in the media. 
 
“Here she is in public pretending not to hate Catholics,” Trump said, pressing on through his prepared remarks.
 
At that line, Clinton turned to New York Cardinal Timothy Dolan with her eyebrows raised. 
 
Trump leaned in once more on the emails, chiding Clinton for an email in which then-Democratic Party vice-chair Donna Brazile appeared to send her campaign a town hall question in advance.
 
“If some of you haven’t noticed, Hillary isn’t laughing as much as all of us,” Trump said.
 
“That’s because she knows the jokes — all of the jokes were given to her in advance by Donna Brazile.”
 
That’s not to say the jokes were all contentious. Trump drew rounds of laughter at the start of his speech with more light-hearted barbs.
 
At the top of his remarks, he acknowledged that the dinner traditionally includes a healthy mixture of self-deprecating jokes from the nominees as well as jabs at their opponents.
  
"They say when you do this kind of event, you always start out with a self-deprecating joke," he said. 
 
"Some people think this would be tough for me, but the truth is I'm actually a modest person. In fact, many people tell me modesty is perhaps my best quality, even better than my temperament." 
 
Trump joked that the dinner shows that the two candidates can be cordial to each other even after a rough debate. 
 
“Hillary accidentally bumped into me and she very civilly said: ‘Pardon me,'" he said. "And I very politely replied, ‘Let me talk to you about that once I get into office.’” 
 
And turning to his wife with a smile, Trump said “this one’s gonna get me in trouble, but not with Hillary,” before launching into a joke about the revelations that his wife’s Republican National Convention speech had been plagiarized in part from a previous speech by first lady Michelle ObamaMichelle LeVaughn Robinson ObamaElection Countdown: GOP worries House majority endangered by top of ticket | Dems make history in Tuesday's primaries | Parties fight for Puerto Rican vote in Florida | GOP lawmakers plan 'Freedom Tour' Dems ready to move past Michelle Obama’s ‘go high’ message Obamas greeted by screaming fans at Martha's Vineyard MORE
 
“The president told me to stop whining, but I have to say the media is more biased this year than ever before,” he said. 
 
“You want the proof? Michelle Obama gives a speech and everyone loves it, it’s fantastic, they think she’s absolutely great. My wife Melania gives the exact same speech and people get on her case. I don’t get it, I don’t know why.”