The fancy 2016 dinner that changed everything about American politics

Former President Donald Trump’s dominant victory in Iowa on Monday has begun the shift in media coverage toward an inevitability — a third consecutive general election campaign featuring the favorite foil of the corporate press. From the moment Trump was elected in 2016, he has served as the chief antagonist to a large portion of a media apparatus that previously at least attempted objectivity. But when it came to Trump, objectivity was no longer even the goal, much less the reality.

It was bad during his first term; worse during the 2020 cycle. In 2024? We’ve reached a new low, with an activist media hyperbolizing Trump’s threats to American democracy — so much so, they assure us, that we must essentially destroy democracy by removing Trump from the ballot in order for democracy to be saved. We’ve gone off the journalistic ethics reservation.

What started the shift?

There are many possibilities, but if we wanted to explain it all with a single moment, you might look to October 20, 2016. On that night, at the famed Waldorf Astoria hotel in New York City, the highest of high society gathered for a “white tie” dinner (even more fancy than “black tie,” Wikipedia tells me!), ostensibly to raise money for charity. The Al Smith Dinner is a regular yearly festivity, and while money is raised for Catholic charities, it has really been the ultimate “see and be seen” event.

The Al Smith Dinner has also typically been a stop for political candidates to deliver comedic roasts of themselves and each other, and 2016 was no exception. Fresh off the final presidential debate of the cycle just the night before — a brutal and serious battle moderated by Chris Wallace — Donald Trump and Hillary Clinton made their way from Las Vegas to NYC for the dinner. What transpired that evening truly has to be seen to be believed — an incredible artifact of a past political and cultural moment.

The “media elites” were there: Katie Couric, Gayle King, Charlie Rose, Chris Matthews. Even Maria Bartiromo, from the other side of the TV aisle. Politicians in attendance included Sen. Chuck Schumer, then-Gov. Andrew Cuomo, Mike Bloomberg, then-Mayor Bill de Blasio. And so many more — that’s just a sampling of who was visible on the dais itself, let alone sitting in the audience of the pretentious gathering.

Trump went first. He described the audience as Clinton’s “largest crowd of the season,” and joked that she had bumped into him before sitting down and said “pardon me,” to which he replied, “let me talk to you about that after I get into office.”

Remember, back in 2016, it was Clinton and her email server that was the political liability potentially crossing over into the criminal arena — long before the series of Trump’s indictments and trials. But what’s most incredible about this line is the reaction — uproarious laughter not just from the crowd, but from Clinton herself. She was in on the joke.

Some in the audience, no doubt from the media themselves, didn’t like when Trump welcomed the “heads of the media” who had been “working overtime to get Hillary elected.” But they all enjoyed the joke aimed at Trump’s wife Melania, referencing her plagiarism of a speech by Michelle Obama.

When it was Clinton’s turn, she was totally up for the game. “I took a break from my rigorous nap schedule,” she said, and added, “usually I charge a lot for speeches like this.”

But it wasn’t just the self-deprecating humor — taking place, incredibly, at the absolute height of a particularly harsh campaign. “It’s amazing I’m up here after Donald,” she said. “I didn’t think he’d be okay with a peaceful transition of power.” Laughter from the crowd — can you imagine what the Jan. 6-obsessed left would think of this joke today?

And as serious as we were told the Russian collusion story was even at the time, it was not above a good one-liner from the Democratic nominee. “Donald really is as healthy as a horse,” Clinton said. “You know, the one Vladimir Putin rides around on.”

After the dinner, there were a few news stories about the mixed reaction from the crowd for Trump — some boos with the laughs. There was very little about the reality, which was that Clinton got about the same reaction.

But what’s most telling about this moment is that it truly could only exist because most of the people in that room — from the press to the politicians on the left — hated Trump but thought he was surely going to lose a few weeks later. This was all fun for now, because the country would never let this reality star-turned-“bad thought” demagogue actually get into the White House.

But then Trump won. And suddenly, sitting there yukking it up with the guy was a monumental, embarrassing mistake.

This is what was behind the way the establishment treated the Hunter Biden laptop story, which I wrote about in great detail in my book, “Uncovered.” The Acela media — like those media elites in that room that night — felt guilty about how they covered Trump, treating him so cavalierly during the campaign. They were fearful of getting the same backlash they got after the election by progressives who said the media contributed to his victory. Moments like the Al Smith Dinner, right after that heated debate, made it all look fake.

The media was not going to make that mistake again.

And that brings us to 2024, and a replay of all the media’s worst instincts, and worst neuroses, brought on by their permanently damaged psyches after being so incredibly wrong about how The Clinton-Trump race would end.

The 2016 Al Smith Dinner, and moments like it, are the scar tissue of a press that has been attempting to repent for its original sin for nearly eight years. As we look ahead to New Hampshire, this is just the beginning of what promises to be a truly hysterical year.

Steve Krakauer, a NewsNation contributor, is the author of “Uncovered: How the Media Got Cozy with Power, Abandoned Its Principles, and Lost the People” and editor and host of the Fourth Watch newsletter and podcast.