First posted on Instagram
Former White House press secretary Karoline Leavitt has recalled the encouragement President Donald Trump gave her when critics said she was too young for the job, telling Bill Maher on Friday's edition of HBO's Real Time that Trump brushed aside the doubters by comparing her age to his own early career.
According to Leavitt, Trump told her that people had called him to argue against giving her the job because of her age, and that he answered them: "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."
Maher had pressed Leavitt on her loyalty to Trump, asking whether anything could make her break with him. Leavitt said Trump was her boss but also a friend who gave her the opportunity of a lifetime, and that she would not be sitting on Maher's show if Trump had not given her the chance.
Leavitt, 28, was 27 when Trump named her press secretary in January 2025, making her the youngest person ever to hold the job. She served until the end of August 2026, when she stepped down to spend more time with her two young children, and she is due to start as a Fox News on-air contributor on November 1.
The Maher appearance also took up the short tenure of her successor, Katie Zacharia, who lasted less than a week after a debut briefing that ran about 14 minutes. Leavitt said the pressure in the briefing room is enormous and the press are vicious, wished Zacharia well, and said that, as Trump put it, it was not a good fit. She joked that Trump, who hosted The Apprentice, is known for moving on from people.
Leavitt has told the Manhattan-buildings story before, including in a March 2025 interview; she retold it on Maher's show on Friday, October 23, 2026, in the same conversation in which she discussed Zacharia's exit.