Humor laurels for comedian Bill Maher as the Kennedy Center navigates Trump-era upheaval

Previous winners include Conan O’Brien, Dave Chappelle, Julia Louis-Dreyfus, David Letterman, Carol Burnett and Tina Fey. Woody Harrelson, Arianna Huffington and Jay Leno are among the celebrities expected to appear at the Sunday night ceremony.

President Donald Trump, who has spent much of his second term reshaping the performing arts venue, is not expected to attend.

The awards come at an awkward moment for the Kennedy Center, long one of the few relatively nonpartisan institutions in Washington. Shortly after Trump returned to the White House in January 2025, the Republican president fired much of the center's leadership and installed a board largely composed of allies. It named Trump as chairman and his name was added to the building's iconic facade, prompting a legal battle that became a proxy fight over the extent of the president's power.

Trump later said the Kennedy Center would close in July for a two-year renovation. But U.S. District Judge Christopher Cooper upended those plans in May by ruling that Trump's name was illegally added to the building, ordering it removed. The judge also has blocked the closure.

A legal saga that could be fodder for jokes

The legal fight has turned into a saga that could be easy fodder for jokes at the Twain gala.

Trump's name has come down from the building, in compliance with the judge's order. But the part of the building once covered with letters spelling the president's name is now shrouded in a tarp. The full closure is on hold. Lawyers for the Kennedy Center have said they are not planning for now to build out programming.

“The Court’s order did not affirmatively require the Board to reschedule programming that had previously been cancelled or to seek new programming,” the lawyers wrote in a court filing this month.

Cooper has asked for an update next month on how long the tarp will remain on the building. For now, the final event scheduled for the Kennedy Center's well-known Concert Hall is “The Freedom Gathering: A Musical Celebration” on July 3.

Maher and Trump have a fraught relationship

Given Trump's sway over the Kennedy Center, Maher's selection for the award is notable because the two men have long had a fraught relationship.

Before he entered politics, Trump filed a $5 million lawsuit against Maher in 2013 for breach of contract. Appearing on Leno’s “The Tonight Show,” Maher said he would give $5 million to the charity of Trump’s choice if Trump could prove he was not “the spawn of his mother having sex with an orangutan.”

Trump claimed that when he provided his birth certificate, Maher did not pay up, prompting the lawsuit. Trump ended up dropping it.

The Trump-Maher relationship exploded again earlier this year, when the president claimed on social media that he wasted time sitting down for a meal with the comedian last year.

“He came into the famed Oval Office much different than I thought he would be,” Trump wrote online. “He was extremely nervous, had ZERO confidence in himself.” Trump said the comedian admitted he was “scared.”

Maher, during his April 11 episode of “Real Time,” described the dinner. He said Trump was “gracious and measured” and not like the “person who plays a crazy person on TV.” Maher said he was not scared.

He took time in his “New Rules” segment to point out the various Trump policies he liked, including the “mass removal of stone cold criminals” and making NATO members pay “their fair share.”

“I may be the last person from the lunatic left that is still an honest broker when it comes to you,” he said.

Maher hosted Vice President JD Vance on his show heading into the weekend. Vance, who is promoting a book, said he watches the show and laughed at Maher's monologue “even though you were making fun of me.” During the interview, Maher pressed Vance on the Iran war, immigration enforcement and election conspiracy theories.

“You guys have two outcomes that an election can be,” Maher told Vance. “Either we win or they cheated. That s—- has to stop.”

Maher's selection for the award was itself the subject of drama.

After The Atlantic reported in March that Maher would win the award, the White House pushed back hard. White House communications director Steven Cheung said on social media that the story was “literally FAKE NEWS.” Trump's press secretary, Karoline Leavitt, also called the initial report “fake news” and said Maher “will NOT be getting this award.”

The situation evolved after further conversations between the Kennedy Center and event organizers.

Beyond Maher, other celebrities expected to appear on Sunday have had up-and-down relationships with Trump. The president and Huffington, for instance, have feuded at points for more than a decade.

Stephen A. Smith, the sports analyst who is among those expected to appear at the ceremony, recently knocked Trump for attending the NBA Finals earlier this month in New York. Smith, who has signaled political ambitions of his own, called the move “selfish” and “narcissistic.”