Bill Maher Feuded With Trump. Did He Get the Last Laugh?

The Mark Twain Prize would go a long way toward rectifying those injustices. Maher would be the prize’s 27th recipient, joining the ranks of Richard Pryor, Steve Martin, Tina Fey and last year’s winner, Conan O’Brien. Emmys, schmemmys. But Maher still wasn’t entirely sure it would happen. He has spent years locked in a public feud with President Trump — and, in one final surprise, Trump installed himself as chairman of the John F. Kennedy Center for the Performing Arts, which administers the award in conjunction with Netflix, where the ceremony streams each year. Would Trump intervene, turning Maher’s long-awaited honor into another chapter in their public psychodrama?
Their fraught history predates the last decade of political surrealism. In 2013, after Trump spent years demanding that Barack Obama prove where he was born, Maher offered $5 million to a charity of Trump’s choosing if he could prove he wasn’t “the spawn of his mother having sex with an orangutan.” Trump’s lawyer sent over a copy of his birth certificate, “demonstrating that he is the son of Fred Trump, not an orangutan,” then unsuccessfully sued when no check arrived. Maher spent the next decade as one of Trump’s loudest Cassandras, routinely insulting him — “conscienceless scumbag,” “syphilitic monkey” — and warning, correctly, that he wouldn’t concede an electoral loss.
Then came the plot twist that scrambled everyone: The antagonists shared a steak dinner. In March 2025, Kid Rock brokered a sit-down at the White House that Maher saw as a practical attempt to puncture the bubble around the president. “It’s an administration of ‘people are saying,’” he told me. “If that’s how the president gets his information … then be one of the people saying things.”
But when he recounted the meeting 12 days later on “Real Time,” many viewers thought he had too many nice things to say. He called Trump “gracious and measured” and far more self-aware in private than the “crazy person” he plays on television. Though Maher added that “it doesn’t matter who he is in a private dinner with a comedian — it matters who he is on the world stage,” many people, including Maher’s friend Sean Penn, questioned the emphasis on Trump’s likability. “I didn’t understand that,” Penn told me.
Others couldn’t get past Maher’s accepting the dinner invitation at all. Among them was another friend, Larry David, who was so outraged that he wrote a New York Times guest essay titled “My Dinner With Adolf.” Their relationship hasn’t recovered. Seinfeld, who remains friends with the two men, told me that “they both got kind of bugged out.” (In a line worthy of “Seinfeld,” he added that the rift didn’t keep him up at night: “Their friendship doesn’t really do anything for me.”)