If Donald Trump’s campaign has been defined by going where no candidate has gone before, on Thursday the real estate mogul went even further: getting himself roundly booed at a Catholic charity dinner that is usually a moment of bipartisan good cheer in the presidential race.
The Republican nominee encountered a chilly reception at the Alfred E Smith dinner, an annual Catholic fundraiser for needy children in New York City, where Hillary Clinton was also in attendance.
Presidential candidates have long traditionally addressed the white-tie affair, roasting themselves while throwing in a few good-humoured jabs at their opponents.
At first Trump did earn some laughs with his speech inside the famed Waldorf Astoria Hotel. But it quickly deterioriated into an attack on Clinton that prompted jeers from the audience and shouts for him to stop speaking.
“Hillary believes it’s vital to deceive the people by having one public policy and a totally different policy in private,” Trump said, invoking the emails of her campaign chairman John Podesta that were illegally hacked and published on the website WikiLeaks.
“That’s okay,” 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 a few feet away from the Archbishop of New York, Timothy Dolan, who served as the evening’s host.
“For example, here she is tonight in public, pretending not to hate Catholics,” Trump said.
While the charity event is known for self-deprecating jokes, the genuine contempt between the two nominees overshadowed proceedings.
Upon being introduced Trump and Clinton settled into their seats on a dais without so much as an acknowledgement of each other’s presence.
Clinton shook the hand of Trump’s wife, Melania, but only later were she and Trump spotted leaning across Dolan, who sat between them, to have a chat that appeared to last all of 30 seconds.
Trump was the first to speak and initially seemed to embrace the spirit of the evening.
“Some people think this would be tough for me,” he said, “but the truth is … I’m actually a modest person, very modest.
“Many people tell me that modesty is perhaps my best quality, even better than my temperament.”
In a riff on what he has dubbed bias within the media, Trump brought the house down by poking fun at his wife’s partly plagiarised speech 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 at a Trump campaign rally – fell flat.
“This is the first time that Hillary is sitting down and speaking to major corporate donors and not getting paid for it,” Trump said.
“Hillary is so corrupt she got kicked off the Watergate commission.”
The audience of roughly 1,500 clad in tuxedos and ballroom gowns were not laughing. Nor were they amused when Trump made light of his assertion in the final presidential debate, held less than 24 hours earlier in Las Vegas, that Clinton was “a nasty woman”.
“This stuff is all relative,” he said. “After listening to Hillary rattle on and on and on, I don’t think so badly of Rosie O’Donnell any more. In fact I’m actually starting to like Rosie a lot.”
Clinton’s speech was less bitter in its tone but also included 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 and its president, 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.”
Both candidates laughed along for parts of one another’s remarks, but in other moments sat stoney-faced. The frostiness was uncharacteristic of previous election cycles but then so has been the tenor of the 2016 contest.
As Trump focused on Clinton’s trustworthiness, the former secretary of state honed in on his behavior toward women.
“Donald looks at the Statue of Liberty and sees a four,” Clinton said, “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.
Her roast also nodded to the previous night’s debate, in which Trump refused to endorse the US democratic process, leaving open whether he would accept the outcome of the 8 November election.
“It’s amazing I’m up here after Donald. I didn’t think he’d be OK with a peaceful transition of power,” Clinton said, before tossing in a dig at Trump’s running mate: “After listening to your speech I will also enjoy listening to Mike Pence deny you ever gave it.”
Clinton’s remarks were met with occasional groans but not the open show of distaste that greeted Trump. Relishing her standing with less than three weeks remaining until election day, Clinton made sure to capitalize on the moment by calling out her opponent for saying she should be drug tested prior to the final debate.
“I am so flattered that Donald thought I use some sort of performance enhancer,” she said. “Actually I did – it’s called preparation.”
Throughout the evening the collective toll of an election distinct in its ugliness separated the event from previous years’.
Even Nicholas DiMarzio, the reverend who conducted the invocation at the start of the ceremony, deadpanned: “I think most of us, including Secretary Clinton and Mr Trump, are praying for this election to be over soon. So let us pray.”
Al Smith IV, the great-grandson of the late Al Smith in whose memory the dinner earned its name, cautioned the candidates in his own introduction: “Tonight we’re all friends.”
But even Smith couldn’t help himself when commenting on a race that with each passing day has never ceased to shock the public.
“Donald went up to Hillary and asked her how she was doing,” Smith joked.
“Hillary replied: ‘I’m fine. Now get out of the ladies’ dressing room.’”
Just a few breaths later he skewered Trump again over the allegations of assault and a lewd tape.
“Don, even though there’s a man sitting next to you in a robe, you’re not in a locker room,” Smith told the New York developer in his hometown. “So please watch your language.”