Karoline Leavitt spent the better part of two years as a fixture of late-night television—usually as the target of the joke. On Friday, she’ll finally be a guest.
The former White House press secretary is set to join Bill Maher on HBO’s Real Time for her first-ever late-night interview, on the same night Maher is expected to address his second White House dinner with Donald Trump.
Maher returned to the White House last Thursday for dinner with Trump, Stephen A. Smith, and Kid Rock, who brokered Maher’s first sit-down with the president in 2025.
For Leavitt, the Real Time appearance marks something of a role reversal. During her 19 months as Trump’s press secretary, she was a regular presence on late-night shows in clip form, with hosts frequently mining her White House briefings for material.
Maher himself has taken several shots at Leavitt.
Last November, after Leavitt defended Trump telling a female reporter “Quiet, piggy” as an example of the president being “frank” and “open,” Maher turned the logic back on her.
“Well, in that case, shut up, b*tch,” he said during his Real Time monologue.
In February, Maher again singled out Leavitt while blasting the White House response to Trump sharing—and later deleting—a video that depicted Barack and Michelle Obama as apes. Leavitt had dismissed the controversy by saying the post was an internet meme depicting Trump as “the King of the Jungle” and Democrats as characters from The Lion King.
“[Leavitt] said the president was just reposting a meme of him as the king of the jungle with Democrats as characters from The Lion King, as world leaders do,” Maher joked.
The two also found themselves on opposite sides of an odd dispute in March, after reports emerged that Maher had been selected to receive the Kennedy Center’s Mark Twain Prize for American Humor. Leavitt publicly called the report “fake news” and insisted Maher “will NOT be getting this award.” Days later, the Kennedy Center officially announced that he would.
Leavitt left the White House in August, saying she wanted to spend more time with her two young children. She subsequently returned to the Trump-aligned MAGA Inc. super PAC and is set to begin a new job as a Fox News contributor Nov. 1.
The timing of her Real Time appearance also gives Maher another obvious topic to explore: what happened after she left.
Leavitt’s successor, Katie Zacharia, lasted just five days as press secretary before leaving the job last Friday following a rocky debut briefing and questions about her professional credentials.
Leavitt reportedly offered Zacharia advice before she took the job, warning her about the difficulty of balancing the famously demanding position with family life.
Now, a week after Zacharia’s abrupt exit—and a week after Maher once again broke bread with her former boss—Leavitt will get her own turn in the late-night hot seat.
Friday’s episode will also feature Kentucky Gov. Andy Beshear, a Democrat, and Republican California gubernatorial candidate Steve Hilton.
How very apropos!