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White House Correspondents’ Dilemma: Toasting the First Amendment as Trump Tramples Over It | Analysis

When President Donald Trump takes the stage on April 25 at the White House Correspondents Dinner, he’ll look out on a sea of journalists — some he’s mocked, others he’s sued, and at least one his administration has targeted for prosecution.

The Guardian has invited independent journalist Georgia Fort, who — along with former CNN anchor Don Lemon — was charged with conspiracy and interfering with the rights of worshippers while covering an anti-ICE protest in January at a St. Paul, Minnesota church. They each pleaded not guilty.

Guardian U.S. editor Betsy Reed told TheWrap that the outlet invited journalists like Fort and other press freedom advocates to “show their support for a free and independent press during a presidency that has seen unprecedented threats to journalists and numerous instances of capitulation to Trump by billionaire-owned media outlets.”

The White House Correspondents Dinner has long faced criticism for journalists appearing too chummy with the political leaders and administration officials they‘re expected to hold accountable. That’s why The New York Times opted nearly two decades ago to skip the annual soirée and has kept its distance ever since. “People already think the press is too cozy with government,” then-Washington bureau chief Dean Baquet said at the time. “And I think these events confirm that.” 

This year’s controversy goes well beyond chumminess, centering on the tension surrounding Trump’s presence at an event honoring the First Amendment after his administration’s assault on the press over the past 15 months. Trump has leveled numerous — at times ugly — jabs at the so-called “fake news,” while suing multiple news outlets and targeting NPR, PBS and Voice of America for funding cuts.  

In Trump’s second term, the White House barred the Associated Press from the Oval Office and took over the rotating press pool; the Pentagon imposed new restrictions that drove out dozens of outlets (which a federal judge ruled unconstitutional); FCC commissioner Brendan Carr has bragged about Trump “winning” his fight against the “fake news media” while threatening broadcasters; and the Justice Department pursued charges against Lemon and Fort and, along with the FBI, executed the search of a Washington Post reporter’s home in a leak investigation.

Lemon, for one, will not attend.

“This dinner is supposed to celebrate the First Amendment and honor the people who do the work it protects — the press,” he told TheWrap. “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.”

Weijia Jiang, a CBS News White House correspondent and the Correspondents Associations’ president, did not respond to an interview request. 

Several political reporters, who were not authorized to speak publicly, expressed concerns to TheWrap about this year’s dinner, including one who described the affair as “unseemly.”

“It looks like we’re having a weekend of fancy parties with the guy — and his administration — who are actively trying to take away our ability to cover them,” said the reporter, who suggested a number of journalists may quietly skip this year while others with qualms continue to attend to placate their organizations.

HuffPost announced it is skipping this year’s dinner —  “Trump’s second term is an affront to the free press,” said Editor-in-Chief Whitney Snyder — but most news organizations appear to be attending as usual.

A second political reporter said it is “farcical” for Trump to be the guest of honor at a dinner in honor of press freedom, yet this person acknowledged the White House Correspondents Association is in a bind and understood its decision. Not inviting the president — a break with long-standing tradition regardless of party — could be perceived as political snub, and potentially weaponized by the president’s allies to portray the press corps as anti-Trump. 

Barack Obama speaks next comedian Keegan-Michael Key playing “Luther, Obama’s anger translator” at the White House Correspondents’ Association Dinner in 2015. (Photo by YURI GRIPAS/AFP via Getty Images)

Presidents traditionally use the opportunity on stage at the Washington Hilton to take jabs at the news media and perhaps even their critics; former President Barack Obama famously roasted Trump in 2011 amid his birther crusade. But jokes at the press’s expense are typically accompanied by earnest appreciation for the work journalists do. And unlike past years, jabs from this sitting president would be coming alongside an assault on the press.

No one knows exactly what Trump will do. He may be affable and conciliatory in person — only to malign the press later on Truth Social. Or do something else entirely. But journalists run the risk of appearing on camera in tuxes and ball gowns and wearing tight smiles as the president unloads on them.

While the Correspondents Association has booked star comedians in the past — Jimmy Kimmel, Seth Meyers, Trevor Noah, Michelle Wolf — the organization instead tapped mentalist Oz Pearlman as this year’s entertainment, which means Trump won’t become a punchline like his predecessors. 

A third political reporter said the Correspondents Association was “chicken” for not hiring comedian, and considered it “bizarre” for Trump to be on stage at a First Amendment gathering as he’s actively suing news organizations. 

Last year, the Correspondents Association disinvited comedian host Amber Ruffin amidst the first months of Trump’s second term in a move to “ensure the focus is not on the politics of division,” it said.

DC party circuit

Trump allies will also be in attendance this year, with the David Ellison-owned CBS News inviting top White House adviser Stephen Miller and media-bashing Defense Secretary Pete Hegseth — even as the network is among those that exited the Pentagon last October in response to its restrictive new policies. (Ellison, the Paramount CEO, is also hosting a private dinner honoring Trump, according to Breaker.)

When Trump skipped the dinner last year and throughout his first term, few administration officials attended it or the four-day flurry of pre- and post-parties and boozy brunches. Media newsletter Status has specifically said Trump, Hegseth, Carr, Press Secretary Karoline Leavitt and others are not invited to its Thursday night event, but administration officials are sure to make the rounds elsewhere.

There’s no shortage of parties being thrown by media and tech companies, including Axios, Puck, Politico, CNN, NBC, MS NOW, Time, Vanity Fair, Semafor, Substack, Beehiiv and Grindr

Lemon said he may attend some events around Correspondents’ Dinner weekend, but that he’d “much rather be sitting across from Trump and members of his administration, asking real questions and demanding real answers.” 

“But they avoid that,” he continued. “The reason is clear — they don’t respect a free press, and they don’t want to be held accountable by one.”

Journalist Don Lemon looks on after issuing a statement to media outside federal court on January 30, 2026 in Los Angeles (Mario Tama/Getty Images)

Reed, of the Guardian, said her outlet’s journalists will be at the dinner “to cover any news out of the event, which is made more likely by Trump’s history of bullying and inappropriate comments toward reporters, in particular female ones.”

The Correspondents Association will also give out journalism scholarships and awards at the dinner — the latter which could make for an awkward moment on stage. 

The organization is honoring Wall Street Journal reporters for their coverage of Trump’s ties to the late convicted sex offender Jeffrey Epstein, a story that prompted the president to sue the paper, with a judge tossing the case this week.

Two of the journalists, Khadeeja Safdar and Joe Palazzolo, were personally sued by Trump, along with Journal owner Rupert Murdoch and News Corp. CEO Robert Thomson. 

In this instance, spotlighting critical reporting that Trump objects to — right in front of him — signals that the press, regardless of the president’s efforts to undermine them, will not be cowed. But the broader spectacle of Trump as an honored guest at a pro-press gathering may feed the perception that journalists, even amid unprecedented attacks, feel compelled to act as if everything is normal.

The post White House Correspondents’ Dilemma: Toasting the First Amendment as Trump Tramples Over It | Analysis appeared first on TheWrap.

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