Bill Maher’s newfound affection for Donald Trump was on full display Friday night as he rolled out the red carpet for the president’s former press secretary, Karoline Leavitt.
Leavitt was the featured guest on Real Time with Bill Maher Friday night, and although Maher took a number of shots at Trump, 80, in his opening monologue, he struck a decidedly cozier tone once he was face-to-face with Leavitt.
As Leavitt settled into her chair and began to talk about Trump, Maher told her to forget the president for a minute.
“Let’s talk about you first. It’s not always about him,” Maher began the interview. “You were the youngest one ever to do this job, 27.”
Leavitt, now 29, confirmed as much, and explained to Maher that she left the job to be more present for her two young children.
Maher then steered the conversation back to Trump, whom he has recently begun speaking more kindly about, telling Leavitt he didn’t care about the furor over the president’s pet project, the gigantic new White House ballroom.
“I like the ballroom. America does need a ballroom—it’s the United States of America,” Maher exclaimed. He then praised Trump’s famously gaudy redecoration of the White House.
Leavitt told Maher she didn’t know if Trump would really follow through on his latest threat to the press: to kick out all the journalists and turn the press briefing room back into a swimming pool.
But they both agreed that Trump is “a builder,” and Maher then observed that during the time he’s spent with Trump in the White House—“around seven hours now”—he was struck by the president’s willingness to take criticism and not pull rank.
Leavitt easily sidestepped even Maher’s difficult questions.
“Is there anything that could make you—because a lot of Republicans now say, ‘We’ve had enough’—make you not be loyal to whatever he was doing?” Maher asked toward the end of the interview.
“My relationship with the president, obviously he was my boss, but to me he was also a friend. And he gave me the opportunity of a lifetime,” Leavitt replied.
“I know his heart, and I know he loves this country. He wants to do what’s right,” she continued.
“Yeah,” Maher agreed.
“And that’s who he’s always been to me. He’s been nothing but kind, uplifting, encouraging—he did name me the youngest press secretary ever and a lot of people told him he shouldn’t,” she added.
“He said, ‘Honey, lots of people said you were too young and I told them I was building buildings in Manhattan when I was your age and you can do it,’” Leavitt said Trump told her when he hired her for the White House job.
Maher then asked Leavitt about her short-lived replacement, Katie Zacharia, who lasted less than a full week in the job and gave only one briefing.
Leavitt grinned at the question, but ultimately defended her successor, pointing out that Trump became famous for firing people on The Apprentice.
“He’s known for moving on from people; it’s in his nature to do that type of thing, I guess,” she said.
“Oh well, I just hope I’m not next,” Maher replied.
The conversation was a far cry from Maher’s previous handling of Leavitt, whom he once called out in his monologue for letting the president talk disrespectfully about female journalists.
In November 2025, after Trump snapped “Quiet, piggy,” at a reporter on Air Force One, Maher clapped back at the president’s then-mouthpiece, saying, “Well, in that case, ‘Shut up, b----.’”
