On Saturday night, President Donald Trump has dinner plans with an unlikely group of tablemates.
For the first time in his two terms as president, he will attend the White House Correspondents’ Association Dinner, a tradition dating back to 1921 that was intended to build relationships between the president and reporters, as well as champion the First Amendment and press freedom.
But the president’s debut comes at a time when that relationship with the press is more combative than ever. In the year since Trump returned to the White House, he has waged war on press freedom and the rights of journalists, the battles of which are sometimes so ugly they resemble hand-to-hand combat, all playing out in federal courts across the country.
For over a decade, one of Trump’s signature strategies has been to lob insults and threats at the press at nearly every opportunity, from campaign rally stages to the Oval Office — and just last week, the White House briefing room.
In a press conference following reports that a second pilot was missing from a shot-down American fighter jet in Iran, the president vowed not only to find the person who leaked the story, but he threatened to jail journalists at the news organization that first reported it.
“We think we’ll be able to find it out,” Trump said. “Becuase we’re going to go to the media company that released it, and we’re going to say, ‘national security. Give it up or go to jail.’”
The threat to jail journalists for protecting sources was a clear escalation in Trump’s crusade against news organizations, but the gauntlet was thrown on the day he was inaugurated for the second time in January 2025.
Hours after he was sworn in, Trump signed an executive order renaming the “Gulf of Mexico” the “Gulf of America.” Shortly after, The Associated Press declared that the new name did not meet its editorial standards and that it would continue to refer to the body of water by its globally recognized name.
The White House retaliated, limiting the AP’s access to the Oval Office and press pool.
“It is alarming that the Trump administration would punish AP for its independent journalism,” the AP’s executive editor, Julie Pace, wrote in a statement at the time. “Limiting our access to the Oval Office based on the content of AP’s speech not only severely impedes the public’s access to independent news, it plainly violates the First Amendment.”
The AP sued the Trump administration and a federal judge in Washington initially ordered the White House to restore the news wire’s access, calling the restrictions a violation of the First Amendment. But an appellate court later largely sided with the administration, finding that spaces like the Oval Office are not public forums and the White House may control access. The case remains ongoing.
In July, the president sued The Wall Street Journal’s parent company for defamation after the newspaper published a report saying Trump wrote a note coupled with a doodle of a naked woman for the Jeffrey Epstein “birthday book.”
A federal judge dismissed the suit, finding the president failed to show The Journal acted with actual malice, which is the standard for defamation claims by public officials.
“The complaint comes nowhere close to this standard,” wrote U.S. District Judge Darrin Gayles. “Quite the opposite.”
The wielding of the courts against journalists by the Trump administration is not limited to the president, either.
The FBI director followed suit this week, filing a complaint against The Atlantic for defamation and demanding $250 million over its explosive reporting that his job could be in jeopardy due to what the article described as excessive drinking and lack of attentiveness to his duties. In his complaint, Patel says the reporting was “replete with false and obviously fabricated allegations designed to destroy Director Patel’s reputation and drive him from office.” In a statement, The Atlantic said, “We stand by our reporting on Kash Patel, and we will vigorously defend The Atlantic and our journalists against this meritless lawsuit.”
The administration has also targeted independent journalists. In January, Trump’s Justice Department arrested former CNN anchor Don Lemon and Georgia Fort for their actions while covering an anti-Immigration and Customs Enforcement protest in St. Paul, Minnesota.
Lemon and Fort have pleaded not guilty to felony charges of conspiring to violate religious freedoms at a house of worship and injuring, intimidating and interfering with the exercise of religious freedoms at a place of worship.
Multiple federal judges previously blocked Lemon’s arrest, finding prosecutors did not show probable cause that the journalist committed a crime.
But Lemon’s legal team said this action is about more than just their client.
“Don Lemon has been a journalist for 30 years, and his constitutionally protected work in Minneapolis was no different than what he has always done,” his lawyer, Abbe Lowell, said in a statement. “The First Amendment exists to protect journalists whose role it is to shine a light on the truth and hold those in power accountable.”
And in January of this year, a chilling message was sent by the administration to all journalists who utilize confidential sources, a common and sometimes necessary practice in newsgathering. Granting a source anonymity is regarded as an essential tool in reporting matters of public interest when the source of the information might face danger or retribution for coming forward.
The FBI searched the home of a Washington Post reporter in connection to a criminal case involving a leak of classified information and in the process, seized her electronic devices, including a cellphone, two laptops and a Garmin watch. The reporter, Hannah Natanson, had been writing a series of stories about Venezuela based on leaked classified information, according to federal prosecutors who indicted her alleged anonymous source. She also filed reports about the massive firings by the Trump administration, relying on scores of accounts from government workers, some whom were confidential sources. Three months later, Natanson has neither been charged with a crime, nor has her property been returned by the government.
The Reporters Committee for Freedom of the Press called the search “a tremendous escalation in the administration’s intrusions into the independence of the press.”
The search and seizure came after then-Attorney General Pam Bondi rolled back a Biden-era policy that prevented officials from searching reporters’ phone records when trying to identify government employees who shared sensitive information to news outlets. That rollback was one of the many Trump administration initiatives to systematically curtail press freedom.
Last fall, the Pentagon instituted a new, restrictive press policy aimed at “preventing leaks that damage operational security and national security.” The policy blocked journalists from reporting any information without approval from department officials, and it gave Pentagon officials discretion to immediately suspend or ultimately revoke the press credentials who violated those restrictions.
The New York Times sued, arguing that the policy violated the First Amendment, and a federal judge agreed, finding the policy unconstitutional.
“Those who drafted the First Amendment believed that the nation’s security requires a free press and an informed people and that such security is endangered by governmental suppression of political speech,” U.S. District Judge Paul Friedman wrote. “It must not be abandoned now.”
Following that order, the Department of Defense issued a new, equally restrictive policy that closed “Correspondents’ Corridor,” the workspace inside the Pentagon that reporters have occupied for decades, and implemented a mandatory escort around the Pentagon grounds. In a scathing opinion, Friedman called the policy “a blatant attempt to circumvent a lawful order.” The administration is currently appealing the case.
It has not been just about targeting individual journalists or impeding their work, either — in some cases, Trump’s administration has attempted to completely dismantle news organizations by cutting their funding and staff.
Last May, the White House issued an executive order titled “Ending Taxpayer Subsidization of Biased Media.” The order cut public funding for NPR and PBS, which rely on both government and private funding to operate. A federal judge last month found the executive order was unconstitutional on First Amendment grounds.
“The message is clear: NPR and PBS need not apply for any federal benefit because the president disapproves of their ‘left-wing’ coverage of the news,” U.S. District Judge Randolph Moss wrote. “The First Amendment, he continued, “does not tolerate viewpoint discrimination and retaliation of this type.”
In a separate executive order last spring, the White House took steps to restructure and dismantle the Voice of America, a government-funded broadcaster aimed at countering global propaganda. The Trump administration laid off nearly the entire staff and largely halted operations. The director of Voice of America sued to prevent what he called the “wholesale destruction” of the 84-year-old organization.
In March, a federal judge ruled Kari Lake, the Trump ally who led this initiative, was appointed illegally. The order made her actions, including the mass layoffs, null and void. That same judge also canceled all actions the Trump administration took to dismantle the organization, including ordering more than 1,000 full-time employees return to work. The administration appealed that ruling.
All of this could make the president’s appearance at Saturday night’s White House Correspondent’s Dinner a bit awkward. Traditionally, the evening is a celebration of the First Amendment, full of speeches that extol the virtues of press freedom and awards handed out to journalists who have exposed wrongdoing within the current administration. Given the number of skirmishes currently playing out between the press and Trump, there has been surprise that he accepted the invitation at all, something he did not do during his first term.
For its part, the WHCA is pleased he’s coming.
“For more than 100 years, the journalists of the White House Correspondents’ Association have enjoyed an evening with the president, a dinner that celebrates the First Amendment while supporting the work we do including awards and honoring excellent journalism and scholarships to help the next generation of reporters who someday will be the ones asking the questions at the White House,” WHCA President and CBS White House Correspondent Weijia Jiang said in a statement.
Eyes will surely be on the crowd, and the guest of honor, for any seat-squirming, but perhaps his mere attendance signals a detente.
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