Every year since its inception, the WHCA has invited the sitting president to its annual celebration of press freedom.
Except for Trump, all have attended at some point during their presidencies.
After Trump boycotted the black-tie event in his first term and in 2025, his participation in 2026 has become both the subject of high anticipation in Washington, particularly given the president's combative, complicated relationship with the media.
He has filed lawsuits against media outlets, dismissed coverage as "fake news" and personally attacked journalists.
His administration banned The Associated Press from the White House press pool and restricted reporters' access at the Pentagon, among other moves.
Yet, he also provides reporters with far more access than his recent predecessors, regularly speaking to journalists on his mobile phone and answering their questions during frequent media appearances.
Some within Washington's press corps object to Trump's presence at the Washington Hilton on Saturday.
"Trump's entire presidency is, of course, an affront to a free press," HuffPost editor-in-chief Whitney Snyder wrote in a column explaining the outlet's decision to skip the dinner.
More than 350 individual former and current journalists, including former network news anchor Dan Rather, signed a letter calling for the WHCA to use the dinner as an opportunity to "forcefully demonstrate opposition to President Trump's efforts to trample freedom of the press".
The WHCA says the dinner reinforces the importance of press freedom.
"As we mark America's 250th birthday, our choice to gather as journalists, newsmakers and the president in the same room is a reminder of what a free press means to this country and why it must endure," WHCA president Weijia Jiang said in a statement.
A White House spokesperson referred Reuters to Trump's March 2 Truth Social post, in which the president said that he previously skipped the event because the press was "extraordinarily bad" to him, but accepted in 2026.
"In honor of our Nation's 250th Birthday," he wrote, "and the fact that these "Correspondents" now admit that I am truly one of the Greatest Presidents in the History of our Country, the G.O.A.T., according to many, it will be my Honor to accept their invitation, and work to make it the GREATEST, HOTTEST, and MOST SPECTACULAR DINNER, OF ANY KIND, EVER!"
For many Trump chroniclers, the dinner holds a fabled place in his story.
As a private citizen in 2011, Trump attended the dinner when Democratic president Barack Obama roasted him from the stage.
Trump appeared not to take the jokes well, giving rise to a storyline that the event helped crystallise Trump's decision to run in 2016, a theory Trump has denied.