A high-stakes game of political musical chairs is playing out inside Trump world, and insiders say the music may already be stopping in favor of one man.
Karoline Leavitt‘s surprise announcement that she will step away from her post as White House press secretary has ignited a fierce, largely private competition to determine who speaks for the president next.
Leavitt informed the public last week that she intends to leave her position by the end of August, explaining her decision as a choice to prioritize time with her two young children.
That leaves the administration barely two weeks to settle on a successor, and multiple sources now point to CNN commentator Scott Jennings as the man positioned to win the job.
Rather than entertaining hopefuls at Trump’s Bedminster golf club this past weekend, Chief of Staff Susie Wiles chose a different venue for her real business: a Washington, D.C., steakhouse, where she sat down with Jennings to discuss the communications role directly, according to sources who spoke to the Daily Mail.
The message from Jennings’ camp was unambiguous. “It’s his if he wants it,” a source close to him said. “And he does.”
Jennings brings a resume built for combat.
At 48, he served as an aide during the George W. Bush administration and now writes as a columnist for the Daily Mail, but he is best known for holding his ground on CNN panels stacked against him, defending the president in territory hostile to conservative viewpoints.
The courtship between Wiles and Jennings did not begin this weekend.
Three White House sources confirmed the two met before Leavitt’s departure was even made public last Wednesday.
They met again over the weekend at Morton’s, and a source described the pair as staying in frequent contact.
Complicating matters, Trump has signaled he would like to see a woman take over the role once held by 28-year-old Leavitt. Even so, sources say his regard for Jennings remains undiminished.
Time pressure looms over the entire process.
Leavitt’s exit arrives less than three months ahead of the November midterms, a stretch when the White House cannot afford a communications operation caught flat-footed.
While Wiles and Jennings dined privately, a separate cast of characters made the trip to Bedminster in hopes of catching the president’s eye.
Alina Habba, 42, Trump’s former personal attorney, was among them.
Bill Pulte, the 38-year-old real estate executive and Trump ally, also appeared at the golf club over the weekend. White House aide Natalie Harp, 35, rounded out the group of hopefuls.
One source who was briefed on the weekend’s activity did not mince words about the scene.
“They were all trying to get in front of him this weekend,” the source said. “It was like The Apprentice.” The source went further, adding, “It reeks of desperation.”
Amid the jockeying, Jennings has emerged as the candidate to beat, with his history of unflinching media appearances cited as proof he can handle the briefing room’s toughest questioning.
Not everyone is confirming the storyline, however.
The White House formally denied to the Daily Mail that any meetings between Jennings and Wiles ever occurred, and both were contacted for comment.
The circumstances surrounding Leavitt’s departure add another layer to the story.
In her own words, she called her return to work after the birth of her second child “the most rewarding yet challenging season of my life.”
Those close to Leavitt point to the collision between new motherhood and an unrelenting job as the driving force behind her exit.
“It was a constant stream of messages from him [during maternity leave] and it was overwhelming,” one insider said.
The insider offered additional detail on what Leavitt endured.
“It was a very stressful job to do with her children. She never got any sleep, and she didn’t want her performance to slip either, so she decided to stay as long as she could and do the job well. The president did everything he could to keep her,” the source added.
With the clock ticking toward September, the administration now faces mounting pressure to settle the question of who will stand behind the podium when the midterm fight begins in earnest.
