A red “Trump 2028” baseball cap emerged in the closing moments of the White House Correspondents’ Association dinner on Friday night, July 24, placed atop the head of 80-year-old President Donald Trump as he joked about launching another White House bid despite the constitutional two-term ceiling. The stunt capped an evening that drew widespread criticism and left much of the formally dressed crowd at the Waldorf Astoria in near-silence.
Scattered jeers and muted reactions greeted large portions of what Trump’s team had previewed as a “unifying yet vicious” performance during the July 24, 2026, gathering in Washington. The venue itself — a building the president once ran as his own branded hotel — hosted the rescheduled affair after a gunman had forced postponement of the original April event.
Jokes That Missed Their Mark
Tepid applause followed the hour-long remarks. CBS News correspondent and outgoing president of the association Weijia Jiang rose to speak as Trump’s departure music began, visibly startled by the spectacle. When someone had asked her beforehand how much time the president planned to take, she recalled responding that they ought to already have the answer. “You’re White House Correspondents, you should know,” Jiang said, before expressing thanks.
Trump appeared aware the crowd had soured. He questioned aloud whether anyone grasped his material, then complained his unnamed writers had given him inferior content. He asserted that he alone keeps the media industry afloat, cautioning reporters they face bankruptcy when he departs because nobody else generates interest. He proceeded to tally the number of New York Times front-page articles focused on himself.
Familiar complaints dominated the address: disputes over the 2020 election, antagonism toward the media, plans for a White House ballroom, his habit of branding buildings and ventures with his surname, and attacks on Biden’s mental fitness. The audience remained mostly quiet throughout material that seemed better suited for a political rally than a celebration of the First Amendment.
Named Attacks and a Constitutional Limit
Individual journalists became targets, including CNN anchor Kaitlan Collins, whose award Trump dismissed as fraudulent and undeserved. Boos erupted as he launched the assault, then the room went silent. California Gov. Gavin Newsom numbered among the Democratic officials who received similar treatment.
An odd scene unfolded as the president shook hands with and honored reporters from organizations he routinely sues and denounces. A Wall Street Journal team received recognition for its reporting on his ties to disgraced financier Jeffrey Epstein. Trump claimed to respect “most of them,” yet accused many attendees of Trump Derangement Syndrome, calling the dinner the biggest concentration of such individuals ever gathered.
The red hat moment generated the strongest response. Donning the “Trump 2028” headwear, he framed it as breaking news — declaring his plans for a fourth campaign, seemingly referring to a fourth run rather than a fourth term. He had earlier quipped that his presidency, like the dinner itself, improved with the second iteration and that a third would surpass it, before claiming he was merely joking. The 22nd Amendment, ratified in 1951 following Franklin D. Roosevelt’s four consecutive terms, bars presidents from serving more than two.
Harsh Reviews From Critics
Newsom’s official X account fired back aggressively, branding the president a pig while resharing video of the Collins segment. CNN political commentator and former Obama adviser Van Jones delivered one of the most scathing assessments, suggesting the opportunity for connection had been wasted. “It just wasn’t funny,” Jones said, characterizing Trump as a “rabid grizzly” lashing out at everything nearby who failed to mention a single American beyond himself and his adversaries.
Similar judgments followed. Washington Post writer Maura Judkis termed the occasion crass, surreal and deeply cringeworthy, observing that consistent laughter originated only from a section seemingly filled with administration officials. Social media users compared the content to a barrage of internet troll posts, with one commenter expressing disbelief that anyone felt pride in the display.
Friday night included calmer passages. Trump commended the Secret Service and condemned political violence, reminding attendees that Americans resolve disagreements through debate, not bullets. He honored Secret Service officer Victor Gonzales, who sustained a gunshot wound to his protective vest during the April disruption.
Jiang, who told the crowd she would not allow violence to have the last word, announced the dinner’s return next year to the Washington Hilton, where that attack occurred.