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Journalists Brace for Trump Collision at White House Correspondents’ Dinner

April 25, 2026
in News
Journalists Brace for Trump Collision at White House Correspondents’ Dinner

As media personalities mingled across Washington on Friday night, one question hung over the festivities: Would President Donald Trump berate the press at the White House Correspondents’ Dinner?

“I’m more worried that he’s going to Red Wedding the Washington Hilton,” “Pod Save America” co-host Jon Favreau quipped to TheWrap at Crooked Media’s gathering at Washington’s Cafe Riggs.

A grim joke, for sure, but Trump’s upcoming speech — and the White House Correspondents’ Association’s decision to invite him — has fueled controversy and fears that he’ll bash journalists at Saturday night’s annual celebration of the First Amendment.

More than 300 journalists urged the organization’s members to confront Trump’s attacks on the press, while others have suggested a less antagonistic approach. Incoming WHCA president Jacqui Heinrich and Politico’s Dasha Burns, told TheWrap they’re eager for the president to honor tradition. “We have to all face each other,” said Burns. “I think sticking your head in the sand is not the answer for either the press or the president.”

The divide speaks to the unprecedented nature of reporters hosting a president so antagonistic toward the journalists assigned to cover him. The WHCA traditionally invites the president, who in the past has taken good-natured jabs at the media while also extolling the virtues of press freedom.

But any jokes at the press’ expense — never mind outright mockery — would come amid the backdrop of a 15-month assault. Trump — who turned down the WHCA’s invites during his first term, and last year – has personally sued news organizations, while his administration has threatened broadcasters, restricted access at the Pentagon and targeted journalists like Don Lemon, who faces federal chargesover his coverage of an anti-ICE protest.

“I’m not interested in dressing up in a tuxedo, sipping champagne, and pretending everything is normal with a president and a regime that spends every day attacking, undermining and trying to discredit journalists and journalism,” Lemon told TheWrap last week about why he would not attend Saturday night’s dinner.

Lemon didn’t rule out attending parties alongside the WHCD, and stopped by Grindr’s soirée, for one.

Grindr’s line went on for roughly an hour.
Grindr’s line went on for roughly an hour. (Credit: Tasos Katopodis/Getty Images for Grindr Inc.)

Over at beehiiv’s party with watchmaker Shinola, another TV news star-turned-independent journalist, Terry Moran, said he’d like to see Trump and the Correspondents’ Association come together to honor journalists — yet remains skeptical.

“I don’t think that’s what Trump is going to do, I think he’s going to trash the press, but I actually think it’s worth the price,” Moran said. “We will want this post-Trump, and post-Trump is coming, and so rather than both sides tearing the whole thing down, let him throw his tantrum, and the press hold on to this tradition.”

During the party at Shinola’s flagship D.C. store, guests chatted over mini lobster rolls and lychee martinis, as CNN’s Dana Bash caught up with colleague Brian Stelter, and podcaster Kara Swisher posed alongside beehiiv CEO Tyler Denk.

Former CBS News reporter and current member of beehiiv’s media collective Catherine Herridge told TheWrap it was “essential” reporters engage with the Trump administration, but she cautioned them to still “hold the powerful to account.”

“And that just doesn’t end when you walk into a dinner,” she said.

CNN’s Brian Stelter and Dana Bash.
CNN’s Brian Stelter and Dana Bash attend beehiiv & Shinola’s party on April 24, 2026 in Washington, DC. (Credit: Paul Morigi/Getty Images for Shinola)

As for what she makes of CBS News Editor-in-Chief Bari Weiss and Paramount CEO David Ellison’s mingling with Trump this week?

“I personally want to see CBS succeed,” she said. “I think Bari Weiss has a very tough job cut out for her.”

At Crooked Media’s party, a table featured chocolate bars promoting Crooked’s “CrookedCon” in November, nestled between folding fans from sponsor ActBlue and “for facts’ sake” buttons from The Guardian.

Favreau said he’s worried Trump will use the appearance at this annual press-focused event to unload on the media. “He’s like, ‘this is my chance to say what I want, get up, get off my chest what I want to [about] the press,” he said. “He could go for hours and hours, and if they play ‘The Rains of Castamere,’ then I would get the f–k out.”

The town’s hottest ticket Friday was Grindr’s inaugural WHCD party, held at a sprawling Georgetown estate. After waiting in line for upwards of an hour to get in — VIPs like former CNN anchor Jim Acosta walked right through the door — guests were treated to a martini of their choice, while servers passed French fries around a table of boxed cheeseburgers.

Guests scattered among the sprawling grounds included CNN’s Kaitlan Collins, “Real Housewives of Salt Lake City” star Bronwyn Newport in a pantsuit decked out in the word “Vote” and “holding space” journalist Tracy Gilchrist making her first WHCD circuit appearance. There was a floral arrangement and a projection onto a backhouse of Grindr’s logo, along with gifted hats that read, “0 Feet Away.”

By the time many of the guests made it to the night’s final party — UTA’s “Celebration of America’s Journalists,” where actor Zachary Levi spent the evening dancing near the DJ booth — some were ready for the drama around Trump’s dinner appearance (and the dinner itself) to end.

Kara Swisher attends beehiiv & Shinola's Celebration of Journalism on April 24, 2026 in Washington, DC. (Photo by Paul Morigi/Getty Images for Shinola)
Kara Swisher attends beehiiv & Shinola’s Celebration of Journalism on April 24, 2026. (Photo by Paul Morigi/Getty Images for Shinola)

“I don’t think it should exist,” Swisher told TheWrap. “It’s so perceptually [a] bad thing for the press to be sucking up to politicians and celebrities in that event, and as this administration is overly hostile to the press.”

What about tradition?

“So what? Big f–king deal,” Swisher said, invoking last year’s Oscar-winning movie “Sinners.”

“They don’t invite the vampires in,” she said. “What happens when they do? Everyone gets eaten. I’m sorry, you don’t invite these people in if they’re going the way they behave. They don’t deserve it, and it puts you in the worst ethical position.”

The post Journalists Brace for Trump Collision at White House Correspondents’ Dinner appeared first on TheWrap.

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