Bill Maher appears to be firmly carving out a space where he is on surprisingly good terms with Trumpworld, much to the amusement of his critics and the fascination of his late-night audience. The 70-year-old HBO host, known for decades of sharp political satire and contrarian viewpoints, recently found himself rubbing shoulders with President Trump at a high-profile White House dinner earlier this month.
The exclusive gathering also featured high-profile figures such as musician Kid Rock and sports commentator Stephen A. Smith. Following the dinner, the dynamic between the unconventional comedian and the commander-in-chief shifted into public view when Trump intimated to reporters that Maher’s sharp, often caustic criticisms of him on his weekly program are mostly bluster. According to the president, the late-night host actually "likes me a lot more than people understand."
Maher did little to quiet those rumors during his return to the airwaves. Addressing the four-hour dinner during his opening monologue on HBO’s "Real Time" on a Friday night, Maher leaned right into the controversy with his trademark defiance.
"Yeah, I did it again, bitches," Maher told his studio audience, addressing the backlash head-on. "You know what? Fuck you. I like these dinners."
This newfound warmth toward the administration’s inner circle did not stop at the White House dining room doors. Shortly after the dinner, Maher managed to land Karoline Leavitt as an interview guest on his program. Leavitt, who served as Trump’s press secretary before stepping down from the demanding post in August, made for a particularly curious pairing given their recent public history.
Only weeks prior, Maher had fiercely attacked Leavitt on his program following her ardent defense of a controversial moment aboard Air Force One. During the flight, Trump had publicly shouted, "Quiet, piggy!" to Bloomberg News reporter Catherine Lucey when she attempted to question him about Jeffrey Epstein. Rather than distancing the administration from the remark, Leavitt had spun the incident publicly, claiming on television that it was actually "admirable" and represented the president being "frank, open, and honest." That defense prompted Maher to fire back on his show with a scathing, sarcastic retort, jokingly telling Leavitt through the camera, "Well, in that case: Shut up, bitch."
Despite that sharp exchange, water appeared to be entirely under the bridge by Friday night. Maher welcomed Leavitt to the "Real Time" stage, where he largely treated her with kid gloves, avoiding aggressive questioning and instead pivoting early in the interview to lighthearted banter. At one point, Maher even poked fun at Leavitt’s brief-tenured successor, Katie Zacharia, highlighting the fact that Zacharia had infamously only lasted five days on the job before departing her role as press secretary.
The interview quickly turned conversational and chummy, with Leavitt bringing warm greetings straight from the Oval Office.
"The president sends his regards," Leavitt told Maher during their segment. "I told him I was coming on the show and he said, ‘Tell him he loved that dinner and he knows it.’"
"I do like it," Maher admitted openly, before steering the conversation back to Leavitt’s personal and professional trajectory. Noting her rapid ascent in political communications, Maher asked, "You were the youngest one to do this job… So what are you going to do now?"
Leavitt explained that she chose to step away from the grueling White House press secretary position primarily to focus on caring for her two young children, who are currently two years old and six months old. She then shared her next professional step, announcing that she would be transitioning directly into a role as a Fox News pundit starting November 1. Maher offered no journalistic follow-up regarding the well-worn revolving door and political pipeline between the Trump administration and Fox News. Instead, he opted for a much lighter, albeit eccentric, rejoinder, bringing up a whimsical idea about how Trump reportedly wants to transform the historic White House press pool into an actual swimming pool.
Cue Maher launching into a defense of some of the president’s more debated aesthetic desires: "You know what? This is the one thing that people get mad at me [about]… I don’t give a shit about any of this. I like the ballroom! America does need a ballroom. It’s the United States of America."
The softball questions, gentle humor, and mutual flattery continued unabated throughout the rest of the interview segment. Maher prompted Leavitt to discuss her penchant for being "sarcastic" in the public eye, and he offered virtually no pushback or follow-up questions when she enthusiastically touted Trump’s aggressive posture and war with Iran.
As the conversation flowed, Maher delivered a litany of glowing compliments about the president, asserting at various points that Trump simply "gets it." The exchange reached a notable peak when Leavitt claimed that Trump was "far more sane than the last [president]," whom she characterized disparagingly as "a mental patient." Rather than challenging the hyperbole, Maher offered a mild pivot, replying, "He’s far more energetic."
The entire sequence served as yet another vivid reminder to media observers and loyal viewers alike that Maher is, at his core, a comedian and commentator rather than a traditional hard-news journalist. True to form, he consistently refuses to adopt an adversarial posture toward conservative guests on his show, appearing far more interested in cultivating personal access, sharing a laugh, and enjoying the company than holding political figures to a rigorous standard of accountability.
