A CNN conservative panelist is now considered the leading candidate to take over as White House press secretary following Karoline Leavitt’s exit, according to new reporting that surfaced on Aug. 19, 2026. Scott Jennings, 48, who also writes columns for the Daily Mail, has been conducting private discussions with White House Chief of Staff Susie Wiles about accepting the position, with insiders claiming the job is now his to accept or decline.
The most recent dinner between Jennings and Wiles occurred over the weekend at Morton’s steakhouse in Washington, D.C., located a short distance from the White House, according to three individuals with knowledge of the hiring deliberations. The pair “speak often,” sources indicated, and this latest encounter marked another in an ongoing series of conversations.
Officially, the White House has denied any such meetings took place between Wiles and Jennings.
Leavitt’s Departure and Family Priorities
Karoline Leavitt, 28, announced on Aug. 12 that she would leave the White House by the end of the month in order to prioritize her family. Following an eight-week absence after giving birth to her daughter, Leavitt concluded that juggling the press secretary responsibilities with being a mother was no longer sustainable. She and her husband welcomed their second child, a daughter, in May.
According to sources, initial talks between Jennings and Wiles regarding the press secretary vacancy began before Leavitt had even made her departure public. Since that first discussion, Wiles has convened with Jennings at least once more, and the chief of staff now views him as her top pick for the role, sources said. An individual close to Jennings confirmed he is interested in the position and that it is available to him if he chooses to pursue it.
Despite having been questioned repeatedly on television since news of the discussions emerged, Jennings has publicly dodged inquiries about his interest in the job, declining to confirm or deny his intentions during on-air appearances.
Competing Candidates and a Chaotic Weekend
As Jennings quietly dined with Wiles in the capital, a starkly different scene unfolded at President Donald Trump’s Bedminster, N.J., golf club. Over the same weekend, numerous other aspirants for the press secretary job converged on the venue, each seeking to gain the president’s favor. One source described the environment as resembling “The Apprentice” and characterized it as desperate.
The list of potential candidates vying for the role is extensive. Natalie Harp, 35, a senior White House aide whose proximity to the president has attracted growing attention in recent months, has formally entered the race. Other names in the mix include Alina Habba, who previously served as Trump’s attorney, Katie Zacharia, the current press secretary at the Department of Homeland Security, along with Tricia McLaughlin who held that role before her, Elizabeth Pipko from the Republican National Committee’s communications team, and Roma Davari, formerly with the Kennedy Center. Federal Housing Finance Agency Director Bill Pulte, Matthew Boyle who heads Breitbart’s Washington operations, and Steven Cheung, the White House communications director, have also been mentioned as contenders.
Trump’s Gender Preference Creates Hurdle
A major complication for Jennings’ candidacy has emerged: President Trump has privately expressed a desire to have a woman assume the podium following Leavitt’s departure, insiders say. That stated preference creates an obstacle for the 48-year-old Kentucky native and veteran Republican strategist, despite his apparent backing from Wiles.
Jennings’ Background and Credentials
A political science graduate of the University of Louisville who also completed his studies at the McConnell Center for Political Leadership there, Jennings has deep ties to Republican politics. His experience includes working in the George W. Bush administration where he held the position of special assistant and deputy director of political affairs, and he later became an adviser to Sen. Mitch McConnell of Kentucky, assisting with his campaigns as well. Beyond his CNN appearances, Jennings contributes columns to both the Daily Mail and the Los Angeles Times. He lives in Kentucky where he and his wife are raising four sons and caring for three dogs.
As of Aug. 19, no official replacement for Leavitt had been announced, with her departure anticipated by the end of August. The unresolved question is whether President Trump will defer to Wiles’ recommendation or exercise his stated preference for a female successor, a decision that will conclude one of the most visibly competitive personnel searches in recent White House memory.