Donald Trump at the Alfred E. Smith Memorial Foundation Dinner, where he made what were nominally jokes about Hillary Clinton. PHOTOGRAPH BY BRENDAN SMIALOWSKI / AFP / Getty

“You know, last night I called Hillary a nasty woman,” Donald Trump said at the Alfred E. Smith Memorial Foundation Dinner, at the Waldorf-Astoria, on Thursday night. Hillary Clinton, who was sitting on the dais with him, separated only by Cardinal Timothy Dolan, of New York, tilted her head with a neutral expression, as Trump continued, "But this stuff is all relative. After listening to Hillary rattle on and on and on”—his voice descended into a groan—“I don't think so badly of Rosie O'Donnell anymore. In fact, I’m actually starting to like Rosie a lot.” Clinton laughed, and the crowd did, too, with the slight hesitation of wondering where this was going, and if it was going to be all right. It wasn’t. It’s hard to know when Trump reached the point at which a great number of the people in the audience started to feel dirty. But once he did he never got out of the mud.

The Al Smith dinner, which takes place each year, raises money for Catholic charities. It is also supposed to be the space in which, even in the most partisan years, the two major-party Presidential candidates are allowed to smile at each other; their supporters allow them to do so in exchange for jokes. Here is one that Trump told last night: “Hillary believes that it’s vital to deceive the people by having one public policy and a totally different policy in private.” This was a reference to WikiLeaks. Trump continued, “For example, here she is tonight—in public—trying to pretend she doesn’t hate Catholics.” That, somehow, was the punch line.

In its contorted way, Trump’s joke was about an e-mail in which Jennifer Palmieri, a Clinton aide who herself is Catholic, referred to Catholicism as “the most socially acceptable politically conservative religion.” The Trumpian translation turned this into evidence that Clinton was a religious bigot—an anti-Catholic in a room full of Catholics. His schoolyard instinct was not only to mock but to get everyone else present to feel ashamed of being seen as close to the target of his scorn. She doesn’t even like you. It didn’t work; he got booed before the joke was half told. “I don’t know who they’re angry at, Hillary, you or I,” he said, seeming to forget that he wasn’t at one of his rallies, and that the people who had gathered there were not about to start chanting, “Lock her up!” At another point, he said, “Last night, they said that was the most vicious debate in the history of politics.” His voice caught on a small laugh as he continued, "And, I don’t know, are we supposed to be proud of that, or are we supposed to be unhappy?” He seems to have decided to go with “proud."

It hadn’t started so badly. Trump made what may have been meant to be a self-deprecating joke about his “beautifully formed hands”—he extended them to the audience, wiggling his fingers—although he only managed to suggest that they were not as powerful as God’s hands, “and nobody can compete with God—is that correct?" (The premise had to do with Trump Tower and St. Patrick’s Cathedral both being on Fifth Avenue.) He more or less acknowledged the evening’s spirit when he said, "Just before taking the dais, Hillary accidentally bumped into me. And she very civilly said, ‘Pardon me.’ ” Clinton laughed at that, as Trump went on, “I very politely replied, ‘Let me talk to you about that after I get into office.’ ” And he was still roughly in Al Smith territory when he told this joke about the media being unfair: "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. And I don’t get it.” Melania did. She glowed with an air of good humor as her husband told her to stand up and be acknowledged. "She took a lot of abuse. Oh, I’m in trouble when I go home tonight,” he said. "Cardinal, please speak to her.” But it is notable that the closest Trump came to a successful self-deprecating joke was one that had as its target not himself but his wife. Then he went back to insulting the other woman at the center of the dais.

"Hillary is so corrupt, she got kicked off the Watergate commission,” Trump said. "How corrupt do you have to be to get kicked off the Watergate commission?” Real jokes have many layers, which is about the only way in which Trump’s lies resemble them. First, it is not true, according to fact checkers who’ve looked into it, that Clinton was fired at all from her job as a young lawyer in the Watergate investigation, let alone for corruption. Then there’s Trump’s straight-talk assumption that you’d have to be pretty corrupt—laughably corrupt—to be exiled from the investigation into Watergate. Maybe he’s under the impression that the “Watergate commission,” and not Richard Nixon’s operatives, broke into the D.N.C. office in 1972—or that any group of lawyers trying to restrain a Republican President must be a den of thieves.

There is supposed to be a point when these speeches turn serious, or reflective. It is, after all, a charity event, in honor of a great New Yorker, Al Smith, who served as governor in the nineteen-twenties and was the first Catholic to be nominated as a major-party candidate for President. Trump did say that he was impressed that the dinner had raised six million dollars (“net!”). And he threw in a reference to the “culture of life,” which Dolan, who had been looking increasingly anxious, was able to applaud. As the clapping died down, the cardinal took the opportunity to wipe his forehead with his napkin. (The next morning, Dolan told NBC that he, Trump, and Clinton had prayed together before the dinner.)

At one point, Trump said that Clinton was laughing less than others in the room. But, really, there were times, even when he was speaking, that she seemed to be smiling more than most people on the dais. She seems, in an essential way, to have stopped worrying about him. There were exceptions, as when Trump made a crack that suggested that the Clintons were looting Haiti—there was a pun about “taking villages." At that, she couldn’t repress a stone-cold glare.

When Clinton spoke, one of her jokes was about how it took a village to help her write a funny speech. Some of her jokes were funny—or funny enough, as Barack Obama might say. She was surprised that he’d given her the mic; "I didn’t think he’d be O.K. with a peaceful transition of power.” And there was plenty of self-deprecation, with references to her “rigorous nap schedule.” She added, "Usually, I charge a lot for speeches like this,” and said that she loved the people there so much that she wanted to put them in a “basket of adorables.” There was also a slightly forced joke about Trump rating the Statue of Liberty a four or a five, and about how she, personally, preferred the number forty-five. (She’d be the forty-fifth President?) Melania squinted at that one.

But she turned the knife, too. Gesturing to Rudy Giuliani, who was present, she said that he’d begun his career prosecuting tax frauds and then decided, “If you can’t beat them, go on Fox News and call ’em a genius.” Giuliani sulked at that. Speaking of the nominees’ medical records, she said, “Donald really is healthy as a horse—you know, the one Vladimir Putin rides around on.” (She also said that Trump’s speeches were translated from “the original Russian,” and told Trump that she’d enjoyed his and that "I will also enjoy listening to Mike Pence deny that you ever gave it.”) It was more than fair, but it was also a little grim.

What really illustrated the distance between Clinton and Trump was a quality in keeping with the spirit of the evening: a turn toward redemption. She told the story of Al Smith, and the vicious anti-Catholic bigotry with which his campaign was met in certain quarters. “Those appeals, appeals to fear and division, can cause us to treat each other as ‘the other,’ ” she said. "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 neighbors as ourselves.” The tone in the room seemed to shift, as the Presidential campaign has in the past few weeks, toward a more confident rejection of Trump and of Trumpism. "This is a hell of a dinner,” Trump had said just after he rose to speak. It’s been a hell of a Presidential race. It’s almost over.