Bill Maher sat down with former White House Press Secretary Karoline Leavitt for a one-on-one interview on Friday’s episode of HBO’s “Real Time” — and the whole thing played out against the awkward backdrop of Maher’s increasingly cozy relationship with Trumpworld. It was Leavitt’s first-ever late-night interview, and Variety did not mince words about how it went down.
Bill Maher and Karoline Leavitt on Real Time (Credits: Variety)
The timing could not have been more loaded. Just days earlier, the 70-year-old HBO host had joined Kid Rock and Stephen A. Smith as President Trump’s White House dinner guests — his second such dinner, following a first sit-down brokered by Kid Rock in 2025. In his opening monologue Friday night, Maher addressed it head-on: “Yeah, I did it again, bitches,” he said of the four-hour dinner, adding, “You know what? Fuck you. I like these dinners.”
Trump, for his part, told reporters after the dinner that Maher’s on-air criticisms of him are mostly bluster and that the comedian “likes me a lot more than people understand.” Maher did not exactly dispute that on Friday night.
Bill Maher Karoline Leavitt Interview: The Swimming Pool Scoop
The interview’s biggest news moment came when Maher pressed Leavitt on reports that Trump wants to convert the James S. Brady Press Briefing Room back into a swimming pool. “So, I see now he wants to get rid of the press pool in the White House and make it into an actual swimming pool,” Maher grilled her. “Did you see that?”
“Yes, I have seen it,” Leavitt responded. “Look, it was a swimming pool at one time. In fact, if you go down the stairs, underneath where the briefing room is, you can actually see the tile from where the pool used to be.” She added that Trump has been “flirting with” the idea of restoring it — confirming a New York Times report from three days earlier that the White House pointedly did not deny, with Communications Director Steven Cheung saying only that “all options remain on the table.”
Leavitt also came bearing a message for the host. “The president sends his regards,” she told Maher. “I told him I was coming on the show, and he said, ‘Tell him he loved that dinner, and he knows it.'”
From Punchline to Guest: Leavitt’s Late-Night Role Reversal
For Leavitt, the appearance marked a genuine role reversal. During her 19 months as Trump’s press secretary — she stepped down in late August — she was a fixture of late-night television mostly as the target of the joke, with hosts regularly mining her White House briefings for material. Maher himself took shots at her on the show, including a November monologue mocking her defense of Trump telling a reporter “Quiet, piggy.”
Friday’s panel discussion rounded out the episode with Steve Hilton, the 2026 Republican candidate for Governor of California, and Gov. Andy Beshear, the Democratic Governor of Kentucky — keeping the night’s political crosscurrents flowing well past the Leavitt interview.
Also Read: Trump Buries The Hatchet With Bill Maher: “He Likes Me A Lot More Than People Understand” | Iron Maiden’s Nicko McBrain Rejected Trump’s Golf Invite: “He and His Cronies Should Be Put in Jail”
Source: Variety — read the full story there.