Trump calls Scott Jennings 'good' as White House hunts for Karoline Leavitt's replacement

 August 22, 2026 
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President Trump says he has been flooded with applications to replace outgoing White House Press Secretary Karoline Leavitt, and singled out conservative commentator Scott Jennings as a strong contender for the job.

Trump made the remarks before boarding Air Force One this week, fielding questions from reporters about who would take over the podium after Leavitt announced her departure last week. When a reporter floated Jennings's name, Trump didn't hesitate. Trump told reporters, "Scott Jennings is good." He then turned to the broader field of candidates and offered a blunter assessment of the demand.

"I will tell you this. I have never had so many job applications in my life."

Leavitt, who became the youngest White House press secretary in history when she took the role at 27, is set to leave at the end of August. She announced her decision last week, citing the demands of raising two young children, a two-year-old son and a daughter born in May, while holding one of the most visible and grueling positions in government.

Leavitt struggled with the balance after returning from maternity leave

Leavitt returned from maternity leave on July 16, walking back into the White House briefing room with a three-word declaration: "Let's get back to work." But sources close to her told the Daily Mail the energy didn't last. One source said she recognized almost immediately that the job no longer fit her life.

"First week back she realized she wasn't feeling it anymore."

That realization, according to two sources, had been building for months. Over the past two months, Leavitt had been confiding in people close to her that she was ready to step down. The challenge wasn't the work itself, it was the math of trying to be fully present for two small children while running a press operation that never sleeps.

In her formal departure announcement, Leavitt laid out the conflict plainly: "The truth is since returning to the White House after the birth of my daughter, I have felt in my heart that I cannot be the best mom my two young children deserve while devoting the constant time, energy, and attention required of the White House Press Secretary."

A source close to Leavitt described the decision as "no doubt one of the hardest decisions of her life so far." Another source indicated Trump himself was reluctant to let her go, noting that the president "actually trusts her and doesn't like having to deal with new people in his circle when he wants to focus on getting stuff done in his time left in office."

By the time Leavitt made the announcement public, she had been working for weeks to secure Trump's blessing. One source said she "was just trying to figure out how to politely step down" with his approval.

Trump praised Leavitt as one of the best press secretaries ever

Trump responded publicly on Truth Social, calling Leavitt "one of the best White House press secretaries in the history of the office" and describing her departure as "a decision I totally understand and respect." He said she would remain a "top outside adviser" and an "influential voice" in the Republican Party heading into this November's midterm elections.

Leavitt's trajectory through the Trump orbit has been unusually fast. She first entered his political world in 2018, served as an assistant press secretary during his first term in 2020, and ran communications for his 2024 presidential campaign before stepping into the top role. Along the way, she sat in on classified Situation Room meetings and helped steer crisis strategy around the Jeffrey Epstein scandal.

Her departure is the latest in a string of senior White House exits as the administration moves into the second half of Trump's term. Legislative director James Braid recently announced his own departure weeks before the midterms, adding to the sense of transition inside the West Wing.

On her final day, Leavitt accompanied Trump aboard Air Force One to a midterm campaign rally in South Carolina. Trump, standing near the plane, kept it simple. "I'm gonna miss her," he told reporters. Leavitt, for her part, struck a lighter tone: "I'm gonna miss her White House job, but I love my kids even more."

Leavitt heads to MAGA Inc. as the replacement search widens

Leavitt won't be stepping away from politics entirely. She plans to join MAGA Inc., the pro-Trump super PAC that has reportedly accumulated more than $350 million in campaign funds ahead of the midterms. "You guys will still see me all the time," she told reporters.

The move keeps her inside the MAGA political infrastructure at a moment when the party needs every effective communicator it can field. With midterms approaching, the press secretary vacancy is more than an HR problem, it's a strategic one.

And the list of potential replacements is growing. Beyond Jennings, the conservative CNN commentator Trump praised publicly, the Washington Examiner identified four other names in the mix: Anna Kelly, Leavitt's 29-year-old deputy who has been filling in on television and radio; Kingsley Wilson, the 26-year-old Pentagon press secretary and daughter of former Trump adviser Steve Cortes; Sean Parnell, a War Department public affairs adviser; and Alina Habba, Trump's former acting U.S. attorney for New Jersey. Habba ranks among the top bets on the Kalshi prediction market.

Margo Martin has also been floated as a possibility. Analysts tracking the transition note that Trump may not rush to fill the slot, the position went unfilled during Leavitt's maternity leave, and the White House managed to function without a named press secretary for weeks.

Trump himself seemed to enjoy the attention the vacancy has generated. Standing before reporters, he gestured toward the press pool and joked, "Maybe you, maybe you." Leavitt, standing nearby, nodded and responded, "Yes, sir."

Trump added: "They all want that job, they love that job. She's made that job very glamorous."

That assessment is hard to argue with. Leavitt brought a combative, media-savvy presence to the briefing room that earned her both admirers and critics. She turned the podium into a platform, and now whoever steps behind it will be measured against her performance.

The broader pattern of departures, including White House counsel Samuel Adkisson's move to the federal bench, is not unusual for a second-term administration heading into midterms. Staff turnover accelerates as officials burn out, cash in, or reposition for the next phase of their careers.

But the volume of exits does raise a practical question: can the White House maintain its operational tempo through November with this many senior roles turning over simultaneously? Deputy national security adviser Andy Baker's departure for the private sector adds another gap on the national security side, compounding the challenge.

Jennings would bring a different skill set to the podium

Scott Jennings, the name Trump endorsed most directly, is a familiar face to cable news viewers. A conservative commentator who appears frequently on CNN, Jennings has built a reputation for defending Republican positions in hostile media territory, precisely the kind of skill set the press secretary role demands.

Whether Jennings has been formally approached remains unclear. Trump's public praise, "Scott Jennings is good", stopped short of an offer, and the White House has described the search as still an "open book." But in Trump's orbit, a public compliment of that specificity often signals more than casual admiration.

The next press secretary will inherit a podium shaped by Leavitt's tenure and a media environment that grows more adversarial by the week. With midterms weeks away and ongoing policy disputes inside the administration demanding clear public messaging, the pick will matter beyond optics.

Leavitt chose her family over the briefing room. That's a decision any working parent can understand. The harder question now is whether Trump can find someone who matches what she brought to the job, and whether he can do it before the midterm sprint is already underway.

About Craig Barlow

Craig is a conservative observer of American political life. Their writing covers elections, governance, cultural conflict, and foreign affairs. The focus is on how decisions made in Washington and beyond shape the country in real terms.
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