Well, that was awkward.

If you’ve ever squirmed through a mean-spirited, ill-advised wedding toast delivered by somebody’s inappropriate drunk uncle, then you’ll have some sense of the feeling in the room at New York’s Waldorf-Astoria hotel Thursday night, where Donald Trump and Hillary Clinton attended the annual fundraiser for Catholic charities known as the Al Smith Dinner.

The event has become a regular stop near the end of the presidential campaign cycle over the past decade, though its history stretches back more than 70 years. Over time, nominees have been invited or excluded based largely on their relationships with the Catholic Church. But under the leadership of New York Cardinal Timothy Dolan, a famously gregarious churchman, during the last three elections all have been welcome for an evening away from the campaign trail, to relax and poke some fun at themselves.

That may change after this year.

Not quite 24 hours after they left the debate stage in Las Vegas, Clinton and Trump sat just a cardinal away from each other on the dais at the Al Smith Dinner, named for the New York governor who was also the first Catholic major party nominee for the White House in 1928. Trump won the coin toss to speak first – if he hadn’t, joked Al Smith IV, he would cried foul about the “rigged” coin – and quickly made clear that there wasn’t going to be much self-deprecating humor this year.

“A special hello to all of you in this room who have known and loved me for many, many years,” Trump began. “I’d become their best friends. They asked for my endorsement.” But, he continued, since he began running for president, “Now they think I’m a no-good rotten disgusting scoundrel.” It wasn’t a joke. It was Trump’s lifelong bitterness over the ridicule he’s endured from the New York elites who have never accepted him.

With the crowd confused, Trump moved along to a few light jokes aimed at his opponent — “I’m sure Hillary is going to laugh a lot tonight. Maybe even at an appropriate moment.”

Story continues

Another line got a huge laugh from the crowd, including Clinton herself — “I bumped into Hillary backstage and she said, ‘Pardon me.’” But it would have been funnier if he hadn’t threatened to put her in jail during their second debate.

Trump even delivered one jibe at the expense of his wife, admitting that she didn’t know about it in advance — “Michelle [Obama] gives a speech and everyone loves it, it’s fantastic. My wife Melania gives the exact same speech and people get on her case.”

And then the evening went off the rails. Dropping the pretense of humor, Trump began lobbing attack lines from his campaign rallies, calling Clinton “so corrupt – so corrupt – she was fired from the Watergate committee.” On the dais behind him, the eyes of dinner guests bulged and to his left, Clinton, who had been gamely playing along with a broad smile and laugh, froze.

The crowd began booing, an almost unheard-of occurrence at these generally clubby dinners. Jimmy Carter found himself booed when he appeared with Ronald Reagan in 1980, but that was based on policy differences. Conservative Catholics who thought the evangelical Carter would be a fellow abortion opponent when he was elected in 1976 had lost faith in him after four years in the White House and were furthered angered by his White House conference on families, which they saw as threatening the definition and structure of traditional families.

When Trump brought up Wikileaks, the boos and hisses increased in volume and he stopped to acknowledge them. “That’s okay. I don’t know who they’re angry at,” he said, turning to Clinton. “You or I.” From the audience, someone hollered “You!”

Undeterred, Trump continued, saying of Clinton: “Here she is now in public, pretending not to hate Catholics.”

Nothing underscored the unprecedented nature of Trump’s performance than the stony face of Cardinal Dolan, who at one point during the GOP nominee’s remarks sat with his chin in his hand, and didn’t applaud even when Trump closed by praising the dinner’s charitable purpose.

Clinton’s turn at the podium was less awkward but her barbs were still more cutting than those of past candidates. She delivered the inevitable pantsuit joke, and acknowledged that she’s not seen as the life of the party. The closest she got to addressing Trump’s women problems was a joke about the Statue of Liberty – “Donald looks at the Statue of Liberty, and sees a 4.”

The few burns she let loose were scorchers. Pointing out Michael Bloomberg on the dais, Clinton said, “It’s a shame he isn’t speaking tonight. I’m curious to hear what a billionaire has to say.” And noting that Trump suggested she be drug-tested before the final debate, she joked, “I am so flattered that Donald thought I used some sort of performance enhancer. And looking back, I did. It’s called preparation.”

The crowd seemed more at ease with Clinton, groaning only when she suggested that Trump was the horse Vladimir Putin famously rides. And Trump appeared to take the ribbing mostly in stride, smiling occasionally. But the tension of this long, bitter, ugly campaign permeated the event. The two opponents did not shake hands when they entered the ballroom, although they did exchange a few words during dinner. And it was unclear until last week if both candidates would in fact attend.

Clinton got the last word, camouflaging a few of her toughest jabs in a more somber closing reflection on the history of Catholics in America. “There are a lot of people in this room tonight who themselves or their parents or grandparents came here as immigrants,” she said before touching on the anti-Catholicism they faced and that dogged Smith’s presidential campaign.

“Those appeals to fear and division can cause us to treat each other as the other,” she continued. “Rhetoric like that makes it harder for us to see each other, to respect each other, to listen to each other, and certainly a lot harder to love our neighbor as ourself.”