With White House Press Secretary Karoline Leavitt on maternity leave, her deputy, Anna Kelly, has stepped into the spotlight. Although she is gaining attention, not everyone in the West Wing is convinced she is the right fit.

Anna Kelly, 29, who once held the title of Miss State Fair of Virginia in 2019, has become a familiar face on Trump-supportive media outlets such as Real America’s Voice, One America News, and Fox News.

However, insiders within the administration suggest that Kelly, known for her fiery nature and blunt exchanges with reporters—a characteristic often celebrated in Trump’s administration—still needs to refine her approach before she can truly take over Leavitt’s role.

“Despite her pageant background, she needs more polish,” a former Republican National Committee official candidly expressed to the Daily Mail.

An official from the administration offered a slightly more positive assessment: “She performs well on television, but I wouldn’t say she can fully replace Karoline.”

Leavitt conducted her final press conference on Monday, making an unexpected appearance to discuss the shooting incident at the White House Correspondents’ Dinner on Saturday.

She’s expected to take a couple weeks for maternity leave, but the exact timing of her return is ‘to be determined,’ a White House official told the Daily Mail. 

In the meantime, Kelly will take on a larger role while Leavitt is away, staffing the President on trips and making regular TV appearances.

Deputy Press Secretary Anna Kelly will take on a larger role while Karoline Leavitt is away, staffing the President on trips and making regular TV appearances

Karoline Leavitt and Anna Kelly pose for a picture at a Trump event

And given the ongoing US-Iran conflict, Kelly’s sprawling foreign policy portfolio – spanning the State Department, Pentagon, intelligence community and beyond – has kept her name firmly in the news cycle.

Still, for an administration that prides itself on transparency, the succession plan for the briefing room looks surprisingly thin. 

None of Leavitt’s deputies – including Kelly – have hosted a press briefing or even a gaggle on Air Force One, prompting questions about who will become the point-person for spin-filled soundbites.

This represents a striking departure from prior administrations that have customarily lined up a backup spokesperson waiting in the wings. 

Speaking to the Washington Examiner, Leavitt noted there will be a rotating cast of Cabinet members and advisers who will field questions from the press in her absence, including Marco Rubio and Stephen Miller.

A former White House official noted a replacement is less of an imperative given their roster of camera-ready stars – a point Rubio drove home Wednesday by popping into the briefing room and cheekily volunteering himself for the job. 

At the same time, GOP operatives and allies are raising the stakes for Kelly, whose pageant past helped prime her for her political career – or so she believed long before anyone was paying much attention. 

A 2017 Facebook post revealed a self-proclaimed feminist – ‘I knew my feminist rants would pay off someday!’ she wrote, touting an award for a college paper titled ‘Tween TV and Sexist Oppression in the United States.’ 

From left to right: Assistant Press Secretary Taylor Rogers, Assistant Press Secretary Olivia Wales, Special Assistant to the President and Senior Deputy Press Secretary Abigail Jackson, Associate Director of Press Operations Micah Stopperich, Regional Press Secretary Liz Huston and Deputy Press Secretary Anna Kelly

Before joining the White House’s press team, Anna Kelly competed in pageants in Virginia and Wisconsin 

Kelly won several pageant events and noted how the hobby would be good for her political aspirations

Earlier posts also hint at ambitions stretching well beyond the briefing room.

‘I am a firm believer that pageants are the single best preparation tool for young women who hope to run for office someday like myself,’ she wrote in 2016. 

Though she was raised in Virginia and spent her early adult years in Wisconsin, which state and which office remains an open question.

Kelly did not agree to speak on the record for this story.

She’s swiftly climbed the ladder and made her name by other means: sharp elbows, an acid tongue, and a particular relish for going after the press, saving some of her harshest missives for behind the scenes. 

Like her boss, she’s hurled the ‘fake news’ invective at reporters online and privately lambasted reporters to spike critical stories and tweak embarrassing headlines.

In 2023, when reporters covered her then-boss Congressman Derrick Van Orden’s foul-mouthed tirade at Capitol Hill interns – ‘Get the f*** out of here, you are defiling the space’ – Kelly responded the only way she knows how: by going on the attack, branding the outlet and its reporters as unserious gossip peddlers.

White House press secretary Karoline Leavitt carries her son Niko Riccio, as she walks along the Collonade before U.S. President Donald Trump departs from the White House on April 10, 2026 in Washington, DC. She’s due to deliver a baby girl in mid-May

Leavitt has said that Cabinet members, like Secretary of State Marco Rubio and Vice President JD Vance will take the podium during her absence

Despite her tough-on-media approach, some in the White House press corps privately prefer Kelly to Leavitt. 

‘Karoline has been absolutely dreadful, wrecking the credibility of the press shop by just repeating Trump’s nonsense,’ a White House reporter told the Daily Mail – adding that Kelly, by contrast, ‘has always been pleasant’ and would work to ‘get a quote.’

Kelly’s ascendance may also be a result of a lack of options, as White House reporters don’t see anyone immediately prepared for an outsized role. 

There’s 29-year-old Abigail Jackson, who has done TV hits on conservative outlets like Newsmax and Right Side Broadcasting Network, but evidently far fewer than Kelly.

Some sources told the Daily Mail that Anna Kelly may have what it takes to fill in for Leavitt at the White House briefings. She is pictured with her colleague Taylor Rogers

As White House Press Secretary Karoline Leavitt is expected to take maternity leave next month to welcome a new baby girl questions have swirled about which of her deputies in the White House communications shop could temporarily take her place at the podium

White House Senior Deputy Press Secretary Kush Desai, 30, has also been trotted out to the White House’s TV tents, where he’s done scattered TV hits but is more narrowly focused on economic topics.

White House Communications Director Steven Cheung, 43, has always been more a backroom operator than a camera-ready surrogate.

What’s most likely to happen in the weeks during the Leavitt baby moon is more of the President himself, a prospect Democrats are inviting. 

‘Donald Trump seems very interested in the job of White House Press Secretary himself,’ Andrew Bates, a former communications aide for Joe Biden, told the Daily Mail. ‘And as a Democrat working on midterm races, he’s my top pick.’

Still, for a President with a keen eye for television talent, the coming weeks may still amount to an unofficial audition – a real-life Apprentice, with the briefing room podium in a post-Leavitt era as the prize. 

Doug Heye, a former communications director for the Republican National Committee, had a different prediction about the President’s plan. ‘Whoever looks the part or is the most combative is probably where he will look.’