The “Real Time” host seemed more interested in praising Trump’s ballroom than pressing tough issues with his former spokesperson.
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 In Real Time with Bill Maher Friday night, and although Maher repeatedly took shots at Trump, 80, in his opening monologue, he struck a noticeably warmer tone once face-to-face with Leavitt.
As Leavitt settled into his chair and began talking about Trump, Maher told him to forget about 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 person to ever do this job, 27 years old.”
Leavitt, now 29, confirmed this and told Maher that she quit her job to be more present for her two young children.
Karoline Leavitt on “Real Time with Bill Maher.”
Maher then turned the conversation back to Trump, about whom he recently began speaking more kindly, telling Leavitt that he didn’t care about the furor over the president’s pet project, the gigantic new White House ballroom.
Get the Best of the Beast
Subscribe to our obsessed newsletter
“I love ballroom. America needs a ballroom, this is the United States of America,” exclaimed Maher. He then praised Trump’s famously gaudy redecoration of the White House.
Donald Trump shows his projects on the construction site of the ballroom planned for the White House, May 19, 2026.
Leavitt told Maher that she didn’t know if Trump would actually follow through on his latest threat to the press: kicking out all the reporters and turning the press briefing room into a swimming pool.
But they both agree that Trump is “a builder,” and Maher went on to observe that in the time he’s spent with Trump at the White House — “about seven hours now” — he’s been struck by the president’s willingness to take criticism and not back down.
Leavitt easily evaded even Maher’s tough questions.
“Is there anything that would cause you – because a lot of Republicans are now saying, ‘We’ve had enough’ – to not be loyal to what he was doing? Maher asked near the end of the interview.
“My relationship with the president, he was obviously my boss, but to me, he was also a friend. And he gave me the opportunity of a lifetime,” Leavitt responded.
Trump speaks to the media before boarding Air Force One on August 21, 2026, with Leavitt at his side.
“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 how he’s always been with me. He’s been just kind and uplifting and encouraging. He actually made me the youngest press secretary ever and a lot of people told him he shouldn’t,” she added.
“He said, ‘Honey, a lot 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 told Trump when he hired her for the White House job.
Maher then asked Leavitt about his short-term replacement, Katie Zacharia, who held the position for less than a full week and gave only one briefing.
Leavitt smiled at the question, but ultimately defended his successor, pointing out that Trump became famous for firing people. The Apprentice.
“He’s known for distancing himself from people; it’s in his nature to do that sort of thing, I guess,” she said.
New White House Press Secretary Katie Zacharia only lasted five days.
“Well, I just hope I’m not next,” Maher replied.
The conversation was a far cry from how Maher had treated Leavitt, whom he once criticized in his monologue for letting the president speak disrespectfully toward female journalists.
In November 2025, after Trump shouted “Quiet, pig” to a reporter on Air Force One, Maher responded to the then-president’s spokesperson by saying, “Well, in that case, ‘Shut up, asshole.’
Obsessed with pop culture and entertainment? Follow us on Substack And YouTube for even more coverage.
Register below to read this article for free or subscribe
to unlock unlimited access to The Daily Beast.
Best value for money
*Substack access provided the next business day, using your subscription email. Choosing the Premium plan constitutes your permission to share your subscription email with Substack and your agreement with Substack. Privacy Policy.
Already have an account? Log in
Looks like you already have a subscription!
You are ready!
Thank you for subscribing.
Subscription$0.00
Total$0.00
Gn headline
