A conservative CNN political commentator is reportedly the leading choice of White House Chief of Staff Susie Wiles to take over from outgoing Press Secretary Karoline Leavitt, according to new reporting published Aug. 19, 2026. Scott Jennings, 48, has participated in confidential discussions with Wiles about assuming the role, including at least one dinner over the weekend at a Washington, D.C. steakhouse.
Leavitt, 28, revealed Aug. 12 that she would leave the position by month’s end to focus on raising her family. Following an eight-week absence after giving birth to daughter Viviana, she determined that continuing in the demanding post while caring for a newborn was impossible.
According to three individuals with knowledge of the process, Jennings and Wiles dined together over the weekend at Morton’s steakhouse, located a brief distance from the White House. The two have held multiple conversations, with sources characterizing their contact as frequent. The White House officially denies any such encounters occurred.
Discussions Began Before Departure Became Public
The initial conversation between Wiles and Jennings regarding the press secretary position took place before Leavitt had made any public statement about stepping down, sources say. Since that first discussion, the chief of staff has spoken with Jennings on at least one more occasion and views him as her top pick. An individual close to Jennings indicated the position is available to him should he choose to accept it, and that he is interested.
When asked directly about the role during several recent television appearances, Jennings has repeatedly refused to confirm his interest, consistently avoiding the question on air.
President Trump Favors Female Candidate
A major obstacle stands in the way of Jennings landing the job: President Donald Trump has communicated internally that he wants a woman to succeed Leavitt at the podium, insiders say. This creates tension between the president’s stated preference and the apparent backing Jennings enjoys from Wiles.
Competing Candidates Descend on Bedminster
While Jennings met quietly with Wiles in the nation’s capital, numerous other contenders converged on President Donald Trump’s Bedminster, N.J., golf resort during the same weekend, hoping to secure face time with the commander-in-chief. A person familiar with the scene described the frenzied environment as reminiscent of “The Apprentice” and characterized the mood as desperate.
The pool of potential replacements is extensive. Senior White House aide Natalie Harp, 35, whose proximity to the president has attracted growing attention lately, has formally entered the competition. Also mentioned are former Trump attorney Alina Habba, Katie Zacharia who serves as press secretary for the Department of Homeland Security, Tricia McLaughlin who held that post before Zacharia, Elizabeth Pipko who handles spokesperson duties for the Republican National Committee, and Roma Davari who previously worked as a spokesperson at the Kennedy Center. Additional names floated include Federal Housing Finance Agency Director Bill Pulte, Matthew Boyle who leads Breitbart’s Washington bureau, and Steven Cheung who directs communications for the White House.
Jennings’ Background and Credentials
A Kentucky native, Jennings earned his undergraduate degree in political science at the University of Louisville and received instruction at the McConnell Center for Political Leadership at that same school. His government experience includes serving as special assistant and deputy director of political affairs during the George W. Bush administration. He subsequently advised Sen. Mitch McConnell of Kentucky and worked on the senator’s reelection efforts. Beyond his CNN appearances, Jennings also writes columns for the Los Angeles Times and the Daily Mail. He resides in Kentucky with his wife, four sons, and three dogs.
Leavitt gave birth to Viviana, her second child with husband Nicholas Riccio, in May. As of Aug. 19, no official announcement regarding her replacement had been made. The question now is whether Trump will defer to his chief of staff’s judgment or stand firm on his preference for a female successor in what has become one of the most publicly visible hiring processes in recent White House memory.