“Let’s try this again,” outgoing White House Correspondents’ Association president Weijia Jiang told a ballroom filled with reporters on Friday night. “Because one thing about this press corps is that we always have a follow-up.”
That kicked off the second correspondents’ dinner of the year – and for me. In April, I had just accepted a job offer from RealClearPolitics and went to the dinner with my soon-to-be colleagues. Hours later, I and nearly everyone else in the room were covering yet another apparent assassination attempt against Donald Trump while our salads sat on our plates. That same night, President Trump pushed to resume the dinner. When he was told it could not continue, Trump promised to reschedule it. During a subsequent White House press conference that night, the president said he might not be able to deliver his original speech, noting that the would-be assassin was trying to hijack the American principle of freedom of speech.
The kumbaya moment did not last the three months until the repeat dinner, this time at the Waldorf Astoria in Washington (formerly, the Trump Hotel). White House Press Secretary Karoline Leavitt teased that the speech would be “unifying and vicious.”
Ultimately, it was mostly just long. The president spent over an hour weaving between telling genuinely funny quips, some of them self-deprecating, and airing his frustrations at the coverage of his presidency. He thanked reporters for their hard work and then dismissed them as stupid and dishonest.
There’s nothing Washington loves more than drama, political power, irony, and a good steak and lobster dinner. The correspondents’ dinner provided all in spades.
The do-over looked quite different. I was one of the few reporters nervous enough about long security lines to arrive a full hour early. Despite verifying my name, receiving a wristband, scanning a QR code twice, and going through security, I was at the ballroom entrance within five minutes of walking through the hotel’s front door.
There was a mini red carpet, but no photographers or press line as there is at the traditional – and much larger – dinner at the Washington Hilton. It was either the reduced square footage or a noticeable increase in security or both, but Secret Service agents were stationed every few feet, in front of every door and bathroom, and dogs patrolled along the security line.
Some other reporters and I stood around talking and waiting for the rest of the attendees to show up. We also watched for VIPs coming down the staircase. At one point, Health Secretary Robert F. Kennedy Jr. walked down, surveyed the sparse ballroom, and walked right back out. Other administration officials, including Dan Scavino and new wife Erin, walked out with a security detail to take photos on the red carpet and then returned to a secured room.
Each table was decked out with a layered centerpiece of macarons, which would be our dessert for the evening. Each table also received a bottle of red and white wine, though a special glass of Diet Coke was brought out at the head table for the president. Because the attending outlets had already paid for the first dinner, the second one was gratis, but it also meant that the wine did not last nearly long enough for the night we were in for.
Once I finished the peach burrata salad, I thought, “Hey, we’ve already made it farther than the first time.” The steak and lobster main course was nothing to write home about, so I won’t.
Many of us in the room still spent the evening on edge, remembering just how quickly the night’s fun changed at the first dinner. In the days before, some reporters wondered whether the Waldorf would be safe, or if the rooms would also be hosting a domestic terrorist. When some dishes clattered, every head instantly turned. This time, it was only clumsiness.
After Jiang’s welcome remarks, we all watched a video compilation of an AI-generated James Madison telling us about the importance of the First Amendment and then current White House reporters explaining what a privilege it is to ask questions of the leader of the free world.
The awards portion alone lasted over an hour as the association honored student journalists, White House reporters, local reporters, the Washington Hilton staff who hosted the first dinner, the Secret Service officer who took a bullet to his vest, and more. I craned my neck from the back of the room to see if the president would shake hands with the reporters who published the most damaging stories of his term thus far. And to his credit, he did. When the Wall Street Journal accepted an award for publishing a letter to Jeffrey Epstein, allegedly written by Trump (which he disputes), Trump walked over and shook each reporter’s hands, throwing up his own with a shrug as he went back to his seat.
Then the moment we all had waited for: Trump took the podium for the first time at a correspondents’ dinner.
“Just like my presidency, the second time is always better,” he quipped of the rescheduled event.
For the first 10 minutes, Trump brought his brand of humor and showmanship to the stage. He joked that Kennedy personally ran over the cow for our steaks that night and how he’s learned never to be sarcastic with gullible reporters.
The long evening needed a laugh break, and the president seemed pleased to fill the role of comedian-in-chief. Until he wasn’t. President Trump loves to feed off crowd energy, and it’s one reason why he’s been energetic on the campaign trail for the past decade. But speaking to this particular audience did not give him the feedback he wanted, and that’s when the speech seemed to deteriorate.
At one point, Trump tried some crowd work by asking Fox News’ Peter Doocy who has been the most transparent president in U.S. history. Doocy declined to respond. Trump joked about former New Jersey Gov. Chris Christie’s weight, CBS News president Bari Weiss’s sexuality and leadership, and how Bruce Springsteen’s anti-Trump music tour is ruining Springsteen’s legacy. None were met with much laughter.
When he did not get the applause lines, Trump broke the fourth wall and told us he was simply reading from the teleprompter: “Who the hell wrote that line?” he rhetorically asked his speechwriting staff.
Then he turned to one of his favorite subjects: the media itself.
“But of course, this evening, it’s really all about the fake news media, and your handling of prizes, writing, and producing and performing made-up stories,” Trump told the room full of people who had worked on those stories.
Almost every president has a love-hate relationship with the press. They know they need reporters to convey news, along with the policies and views, to the rest of the country. They also know that the presidency is under a spotlight like no other, and they are often frustrated with how the press uses that spotlight. Trump is no different – but much more vocal about his dissatisfaction.
He called WSJ’s Josh Dawsey unhireable. He called CNN’s Kaitlan Collins attractive but said she should smile more. At that point, every woman sitting on the main stage stopped smiling, except for White House Press Secretary Karoline Leavitt.
Despite how much Trump might hate the stories coming out of the mainstream news, he reads and watches them religiously. He even shared with us his displeasure at finding out that his staff had been screening press calls. Normally, reporters work to bypass press secretaries. This time, Trump did it himself.
“They said nothing. That’s over a week I haven’t received a call. So I said, ‘You know, I’m going to give the press my phone number.’ Oh, that was the stupidest thing I ever did. I’m getting a call every 3.7 minutes,” Trump laughed. “I always find that when you don’t speak to the press, you always get a bad story. When you do speak to the press, you have a shot at getting a good story.”
That part did get him an applause break.
At another point, he teased that he might run for a third term, something he has publicly ruled out and said was only a joke. Nevertheless, Trump pulled out a “Trump 2028” hat toward the end of the speech and wore it for the rest of the night. The White House social media accounts have used a photo with cryptic messages to try to stir up attention at the stunt. No one appears to be falling for it.
And that should please the president. After 10 years of covering him, reporters are finally weighing how seriously to take what he says in the context of an event like Friday night. And now they call multiple times every day to get his thoughts on a variety of issues.
Overall, I thought the night was full of history. In video remembrances for White House correspondents who had passed, I learned of their legacy of hard work and harder questions. And during the president’s speech, several of us had our timers out to see how long he would go (64 minutes and 22 seconds, per my recording, shattering the record for modern presidents).
After the dinner, the media did what they love to do best: analyze what the president had just said. In the end, it was indeed a celebratory night for the First Amendment.
