Republican presidential nominee Donald Trump drew boos near the end of his speech at the 71st Annual Alfred E. Smith Memorial Foundation Dinner in New York on Thursday night.
The event, which featured Trump and Democratic presidential nominee Hillary Clinton, is typically a lighthearted affair where the two candidate poke good fun at themselves and each other. It has been a staple on the calendar for presidential candidates for decades, offering a chance for them to show off their sense of humor and take a break from the grind of the campaign.
But Thursday night’s dinner turned a bit awkward.
Trump, speaking before Clinton, started off strong, drawing hearty laughs from the white tie-clad crowd and Clinton.
He joked about his humility.
“Modesty is perhaps my best quality,” he said, “even better than my temperament.”
Trump got in a quality joke about “my own beautifully formed hands.”
Trump admitted, “this is corny stuff.” The event benefits Catholic Charities, and Trump said that those in the audience “already have a place in your heart for a guy who started out as a carpenter working for his father.”
Trump got one of his biggest laughs when he said that Clinton had bumped into him backstage before the event.
“She very civilly said, ‘Pardon me.’ And I very politely replied, ‘Let me talk to you about that after I get into office,” Trump said.
After joking that Clinton gave him his choice of ambassadorships to Iraq or Afghanistan, Trump brought up calling Clinton “a nasty woman” at Wednesday night’s debate between the candidates.
One of his other big laugh lines came when he made a joke at the expense of his wife Melania. He said that Michelle Obama gave a speech “and everyone loves it. They (the media) says she’s absolutely great. My wife Melania gives the exact same speech and people get on her case and I don’t get it.”
Trump was referencing Melania Trump’s speech at the Republican National Convention where she took several lines from Michelle Obama’s 2008 Democratic National Convention speech.
It was after that joke that things turned a bit darker and brought unusual boos from the crowd.
Trump said Clinton “was so corrupt she got kicked off the Watergate commission.” He said the “economy is busted, the government is corrupt.” He said he was she may have only found out about her invitation to the dinner “through the wonder of WikiLeaks.”
The crowd began to tighten up with some booing audible on the television broadcast.
Trump said Clinton is totally different in private than she is in public. “Tonight in public she is pretending not to hate Catholics,” a reference to some campaign staffer emails discovered through WikiLeaks.
He also made a joke about Haiti. Saying Clinton knows it takes a village — the title of her book — Trump said “in places like Haiti, where she’s taken a number of them.” The reference is to emails about the Clinton Foundation and donations to earthquake-ravaged Haiti.
Clinton spoke second. No one booed during her speech, but she did cut a bit close to Trump on a joke about the Statue of Liberty.
She said while the Statue of Liberty was a beacon of hope and freedom to many, Trump looks at the statute as a “four, maybe a five if she ditches the torch and tablet and changes her hair.” Trump has drawn criticism from Clinton and others for his treatment of women and their looks.
Clinton joked, “After listening to your speech, I will also look forward to listening to Mike Pence deny that you ever said it.”
Clinton also took some shots at herself. She opened by saying she had taken “a break from my rigorous nap schedule to be here.”
Four years ago, President Barack Obama and Mitt Romney set aside their differences to trade (mostly) warm jokes. Romney, scanning the well-heeled crowd in the gilded Waldorf-Astoria ballroom, joked that the event's white-tie attire finally gave him a chance to publicly don what "Ann and I wear around the house." Obama, meanwhile, used his speech that year to look ahead to an upcoming debate on foreign policy, previewing his argument by saying "Spoiler alert: we got Bin Laden."
This is the first time that both party's nominees hail from New York State as a crowd of about 1,500 gathers for the distinctly Gotham event, held each October. Attendees pay between $3,000 and $15,000 to attend the dinner, which raises about $5 million to provide services for impoverished children.
The dinner is named after the former New York governor, who was the first Catholic to receive a major party nomination for president when he unsuccessfully ran in 1928. And fittingly for an event named after a man nicknamed "The Happy Warrior," the occasion has produced dozens of memorable presidential jokes.
In 2000, then-Texas Governor George W. Bush gazed upon the glitzy gathering and declared: "This is an impressive crowd, the haves and the have-mores. Some people call you the elite. I call you my base."
That same year, Vice President Al Gore touted his campaign trail ability to weave in stories "of real people in the audience and their everyday challenges."
"Like the woman here tonight whose husband is about to lose his job," Gore continued. "She's struggling to get out of public housing and get a job of her own. Hillary Clinton, I want to fight for you."
And in 2008, John McCain joked about the exalted manner in which the media venerated Obama, noting that "'Maverick' I can do, but 'Messiah' is above my pay grade." But he wound down his remarks with a note of grace that, to this point, has been largely absent from the 2016 campaign.
"I can't wish my opponent luck," McCain said, turning toward Obama, "but I do wish him well."
The Associated Press contributed to this report.