“Where Is My Superstar?”: The Trump-Karoline Leavitt Exchange That Made Headlines

“Where is Karoline? Where is my superstar?” US President Donald Trump had once called White House Press Secretary Karoline Leavitt thus in a ‘packed briefing room’, after which she suggested that was the reason why they needed a ballroom. Trump then jested with the reporters, saying he did not want them to be comfortable. This was back on August 11, 2025.

Leavitt, the youngest Press Secretary ever, announced her departure earlier this month. The undertone of her relationship with the press was imminent in the conversation. The GenZ member of Trump 2.0 administration is expected to remain in its orbit even after departure as she will be a top Trump Advisor and said she will soon be working for President Donald Trump’s MAGA Inc., USA Today reported.

From Ice Cream To White House

Karoline Leavitt was raised in Rockingham County, New Hampshire. She attended a Catholic high school in Massachusetts and spent her summer holidays working at her family's ice-cream shop.

She later enrolled at St Anselm College in New Hampshire on a softball scholarship, where she was among a relatively small group of conservative students. During her time there, she contributed to the student newspaper and wrote letters to the editor.

In those letters, she accused professors of introducing liberal bias into the classroom and criticised the media for what she considered unfair coverage of Donald Trump during his 2016 presidential campaign.

She joined the Trump administration as a White House intern after graduating in 2019. She subsequently rose to the position of assistant press secretary, where she sought to challenge what she described as “the biased mainstream media”.

Following the 2020 election, Leavitt became communications director for Representative Elise Stefanik of New York. She worked with Stefanik during her campaign to succeed Representative Liz Cheney of Wyoming as chair of the House Republican Conference.

Leavitt then launched her own campaign at 23, seeking to represent her home state’s 1st Congressional District in New Hampshire. Her vocal support for Donald Trump in a state he had lost twice prompted the two highest-ranking House Republicans to back her rival, hoping a more moderate candidate would prevail.

Leavitt nevertheless exceeded expectations, defeating her opponent by 10 points in the primary. Her victory attracted a wave of prominent endorsements, including one from Trump. She eventually lost the general election to Democratic incumbent Representative Chris Pappas.

The 27-Year-Old Behind The Podium

Vanity Fair describes Trump’s media team as an “extension of his own id”.

Leavitt was hardly a traditional peacemaker. She helped transform the White House briefing room into another battleground in Trump's confrontation with the media, mocking journalists while defending limits placed on their access.

“Let me just set the record straight- it is a privilege to cover this White House. It's a privilege to be the White House Press Secretary and nobody has the right to go into the Oval Office and ask the president of the United States questions... We reserve the right to decide who gets to go into the Oval Office and you all have credentials to be here,” she had said during a press briefing.

At the same time, she became a crucial link between the administration and the reporters covering it. Her proximity to Trump gave her insight into what was happening inside the White House, while the confidence she had earned from journalists and officials allowed her to keep ordinary tensions from spiralling into disorder.

In her first press briefing, Leavitt said that the US Department of Government Efficiency (DOGE) and Office of Management and Budget (OMB) found that about USD 50 million was used to fund 'condoms in Gaza', describing it ‘preposterous’.

Last year, she attracted attention after responding to a reporter seeking her comment with a “your mom” joke. She also developed a tendency to dismiss reporters she dislikes as “left-wing hacks” and has consistently defended Trump when he personally attacks members of the press.

Leavitt famously has exchanged barbs with several reporters in the briefing room. But, a White House reporter told Vanity Fair, “I’m just being completely honest with you, I like Karoline,” adding, “I think she’s charming and funny and gossipy, and her behind-the-scenes persona is totally different from the Baghdad Bob rants at the podium.”

She was not merely Trump's spokesperson, but she helped redesign how the White House communicates with the public. But behind the podium, the White House officials were ‘super professional’, Vanity Fair stated.

“They take reporters’ calls, they interact with reporters, even if they’re from outlets that might not write the best thing about them. They understand the need to talk with the press, to spin the press, and they understand that just shutting down reporters results in worse coverage rather than better coverage,” the report stated, adding that the White House receives over 200 inquiries daily and the President reads everything daily.

Leaving The Podium, Not The Trump Movement

On August 24, Trump said, at a Rose Garden Event, “Our Press Secretary and mother of two, decided she loved her children more than she loved Donald Trump. I'm very upset about this. She has to go home and spend time with her children. That does happen on occasion with some people when they love their children. And she does.”

Leavitt, who turned 29 on Monday (local time), said she will be working with MAGA Inc., the pro-Trump political action committee. She will be accompanying Trump with the new title to Dallas in September for the GOP midterm convention, New York Times reported.

The administration has yet to decide who will succeed Leavitt, with the search still described as an “open book”, a senior administration official told The New York Post this week. According to the report, Conservative CNN Commentator Scott Jennings and Trump Aide Margo Martin are also being considered for the job.