Donald Trump brings up Doug Emhoff's alleged affair to roast Kamala Harris during Al Smith dinner speech

NEW YORK CITY, NEW YORK: Speaking at the decorated Al Smith dinner in New York City on Thursday, October 17, former president Donald Trump landed a barrage of zingers on Vice President Kamala Harris—and also made a risque joke about her husband Doug Emhoff.

Trump made a pointed joke about Emhoff's past affair with family nanny Najen Naylor which reportedly led to a pregnancy. Emhoff has previously admitted to the affair, though he didn't delve into details about the situation.

Doug Emhoff catches some shrapnel

At the Al Smith dinner, Trump admitted that one of his jokes was a bit harsh — but he couldn’t resist. "A major issue in this race is childcare, and Kamala has put forward a concept of a plan," he began, offering some self-deprecating humor on his own "concept of a plan" statements.

But then he went in for the jugular. "The only piece of advice I would have for her in the event she wins would be not to let husband Doug anywhere near the nannies," he quipped. "That's that nasty one. That's nasty. That's too tough," he admitted, as quoted by The Telegraph.

Trump couldn’t resist reflecting on his infamous 2016 Al Smith dinner speech, where he famously roasted Hillary Clinton. He recalled how he thought it was supposed to be a roast and came prepared with material that even had his own supporters wincing.

"I was running against crooked Hillary. And I did it, and I thought it was a roast. So I was told it's a roast. And I had the meanest guy you've ever seen write stuff up. And man was the room angry," he recounted.

"I went overboard don’t you agree? I was like terrible. Even my own side was angry at me. They said it's too much. But I did it anyway," Trump joked.

"Catholics, you've got to vote for me. You better remember I’m here and she’s not. I could have done that too," he added.

Trump takes aim at Kamala Harris and Tim Walz for missing dinner

Kamala Harris was notably missing from the dinner as she chose to campaign in Wisconsin instead. Her absence made her the first major party candidate to skip the event since Walter Mondale in 1984. Trump seized on this. “It shows you there is a God,” he quipped, suggesting that her no-show might be a good sign for his campaign.

He also called it “disrespectful” to the Catholic community and reminded the audience of Mondale’s crushing defeat to Ronald Reagan.

"My opponent feels like she does not have to be here, which is disrespectful to the event and in particular to our great Catholic community – very disrespectful," Trump said, adding, "The last Democrat not to attend this event was Walter Mondale and it did not go very well for him."

Trump also had some barbs reserved for Harris’ running mate Tim Walz, poking fun at various missteps. He joked about Walz’s service with the National Guard. "Unfortunately, Governor Walz isn't in here himself. But don't worry, he'll say that he was," he cracked, earning a round of laughs.

He then took a shot at Walz’s support for a Minnesota law allowing feminine products in boys' bathrooms. "I used to think the Democrats were crazy for saying that men have periods, but then I met Tim Walz," he quipped. "This guy is calling us weird. But this is weird that the Democrat candidate is not with us tonight," he continued.

"I guess I just don’t see the point of taking shots at myself when other people have been shooting at me for a long time," the former president said at one point.

Trump even threw in a dig at President Joe Biden: “If Dems really wanted to have someone not be with us this evening they would have just sent Joe Biden.”

The room was packed with several well-known figures, including Timothy Cardinal Michael Dolan, Senate Majority Leader Charles Schumer, New York Mayor Eric Adams, and state Attorney General Letitia James.