nside the British oak-paneled library at Mar-a-Lago, on a humid spring day in 2022, Karoline Leavitt found herself in the middle of the most important meeting of her still nascent political career.She had come to Palm Beach on a fundraising swing for her longest-of-longshots congressional campaign. With only five months left before the September primary, she was still trailing badly. So she had made a calculated political gamble. She had asked for a meeting with the man who had inspired her to enter politics: Donald Trump. She didn’t expect to get his endorsement. All she needed was to ensure that he didn’t endorse her Republican opponent in the race for New Hampshire’s 1st Congressional District. As Leavitt walked into the library, Trump was already seated at a table, before him a series of printed out polls. As is his custom, Trump did most of the talking.

“These don’t look good,” Trump told her.“Sir, I know they don’t,” Leavitt responded. “But I’m working very hard every day, and I’m telling you, the energy on the ground is different and it hasn’t translated to the polls.” She would do whatever it took to eke this out, she told him. “I’m just asking,” Leavitt told Trump, “that you let me prove myself and watch.”

Karoline Leavitt at an event for her congressional campaign. | Courtesy of Karoline LeavittAt just 23, Leavitt had only graduated from St. Anselm College a few years earlier. But she had already managed to parlay a White House internship in the Eisenhower Executive Office Building mailroom into the role of assistant press secretary in the first Trump administration, a job in which she said she fought “against the biased mainstream media,” according to an archived version of her campaign website. After the 2020 election, she briefly worked as New York Rep. Elise Stefanik’s communications director.

She had launched her congressional campaign in July 2021 from her father’s Plaistow, New Hampshire used truck dealership. She was one of the nation’s first Gen Z congressional candidates. But she was running against a crowded field of nine others, and trailed badly from the earliest primary poll. She was at 7 percent when she met with Trump. What distinguished Leavitt from her rivals, however, was the fervor of her MAGA platform. In particular, she was an ardent amplifier of the false belief that the 2020 presidential election had been stolen from Trump, at a moment when the former president’s embrace of election denialism had gotten him exiled from polite society and mainstream social media.

The family car dealership in Plaistow, New Hampshire, served as Leavitt’s campaign center during her New Hampshire congressional campaign. | Jason Grow for POLITICO“We’ll keep watching,” Trump told her at the Mar-a-Lago meeting, “and maybe we’ll be in touch.”Her gambit bought her time and paid off. Despite her long odds at the outset, she ended up winning the primary. And while she may have lost the general, the campaign would launch her eventual rise in Trump’s inner circle.

How she managed to dispatch her older GOP opponents offers a window into how the youngest White House press secretary in history operates, according to interviews with more than two dozen former advisers, allies and rivals in the race who spoke with me for this story, many of whom were granted anonymity to speak freely about someone close to the president. She exhibited a confidence beyond her years, including in that first meeting with Trump, described to POLITICO Magazine by three people familiar with the interaction and reported here for the first time. She also spoke MAGA as her native political language.

THE MEDIA ISSUE

Trump’s Most Important Relationship Is Ending. And the Break-Up Isn’t Pretty. | By Michael Kruse

The 7 Most Shameless Attention-Seekers in Congress | By POLITICO Magazine

‘We’re the Rising Power’: The MAGA Media Stars Taking Over the White House Briefing | By Ian Ward

How Gen Z Became the Most Gullible Generation | By Catherine Kim

How Donald Trump Revealed Jeff Bezos’ True Self | By Michael Schaffer

How Karoline Leavitt Used a Failed Congressional Campaign to Join Trump’s Inner Circle | By Adam Wren

Maddow’s Back! The Resistance Is Rising! So Why Is MSNBC’s Future Uncertain? | By Lachlan Cartwright

“Tough as boot leather,” Steve Bannon, who was an early booster, hosting her on his War Room show nearly a dozen times throughout the primary, told me. “I used to call her a flinty Yankee.” Leavitt had learned how to cultivate Bannon and his audience from Stefanik, as her boss challenged Rep. Liz Cheney for House Republican conference chair in May of 2021.

These same traits now are serving Leavitt well as she displays an unusually steady, unblinking devotion to Trump’s messaging early in her tenure. Unlike Trump’s five prior White House press secretaries, Leavitt is the only one who had previously been through the crucible of a campaign as a candidate, and the only one whose political life so thoroughly depended on, and was saturated by, Trump himself. (Leavitt and the White House declined to comment for this article.)If some of her predecessors at times seemed uncomfortable with selling the logical leaps that are necessary when tasked with defending Trump — Sean Spicer’s furrowed-brow-scolding, Sarah Huckabee Sanders’ Southern sternness, Stephanie Grisham’s aloofness, Kayleigh McEnany’s Oxford-hewn sunny cerebralism — Leavitt has always seemed to be as inside his head as possible. She relishes dispatching mainstream reporters’ hardballs with dismissive quips and, increasingly, welcomes right-leaning influencers’ softballs. She has amped up Trump’s anti-media tirades while playing loose with the facts, breaking longstanding precedents for how the White House interacts with the press. Reporters in the briefing room, while friendly with Leavitt interpersonally behind the scenes, are worried about what norms will be shattered next in the administration’s assault on the media.

Top: Leavitt arrives with Donald Trump at a Manhattan criminal court hearing in April 2024. Bottom: Leavitt calls on members of the media during a news conference in the James S. Brady Press Briefing Room at the White House, on April 8, 2025. | Pool photo by Jabin Botsford; Al Drago/Bloomberg via Getty ImagesPeter Baker, the New York Times’ chief White House correspondent, is chronicling his 17th press secretary and is used to navigating what has always been an adversarial relationship. He told me that the current tension “goes beyond anything that is traditional to the point of open hostility, and mockery and disparagement in a way that’s meant for the larger audience, not for the people in the room.”

“They don’t view the briefing room as a way to impart information,” Baker continued. “They don’t even view the briefing room as a way to shape reporters’ stories. They view the briefing room as a theater for the MAGA audience.”But Leavitt seems unbothered by any such concerns, seeming to relish her tussles with the press. After all, she is also as much a product of the Trump era as she is one of its shapers.

Throughout the 15 months of her congressional campaign, Leavitt’s opponents criticized her youth and inexperience, but missed that it was, in some ways, also a kind of superpower. She came of age politically as Trump was rising to power. No one in the primary could channel MAGA better. She might not have won a seat to the House in the end, but she is now the most prominent figure channeling the president’s views to the public. Better than any slice of the 27-year-old White House press secretary’s still-young career, her 477-day campaign for Congress both explains and foreshadowed her tenure as Trump’s foot soldier in his war on the press.