CNN conservative commentator Scott Jennings, 48, has been holding secret dinner meetings with White House Chief of Staff Susie Wiles to discuss replacing Karoline Leavitt as White House press secretary — with sources now insisting the coveted position is essentially his for the taking, new reporting published Aug. 19, 2026, reveals.
Three sources familiar with the selection process say he and Wiles sat down for dinner over the weekend at Morton’s steakhouse in Washington, D.C., just a short walk from the White House. The meeting was the most recent in a series of encounters between the two, with sources saying they “speak often.” Jennings serves as a columnist for the Daily Mail. The White House has officially denied that any meetings between Jennings and Wiles took place.
Secret Meetings Before Leavitt’s Announcement
Sources say Jennings first met with Wiles to discuss the press secretary role before Leavitt, 28, had even publicly confirmed she was stepping down. Leavitt announced on Aug. 12 that she would be departing the White House at the end of the month to spend more time with her family. After taking eight weeks off work following the birth of her daughter Viviana, Leavitt said balancing her role with motherhood had become untenable.
According to sources, Wiles has since met with Jennings on at least one additional occasion after that initial conversation, and the chief of staff considers him her preferred candidate for the role. A source close to Jennings said the job is his if he wants it, and that he does want it.
Jennings himself has played it cool publicly. Despite being put on the spot in multiple television appearances since the story first broke, he has declined to say whether he is interested in the position, repeatedly dodging the question on-air.
The Bedminster Scramble
While Jennings and Wiles were dining quietly in the capital, a very different scene was playing out at President Donald Trump’s golf club in Bedminster, N.J. Multiple other candidates for the press secretary role descended on the venue over the same weekend, all angling to catch the president’s eye. One person familiar with the situation compared the chaotic atmosphere to “The Apprentice” and said it reeked of desperation.
The field of hopefuls is crowded. Reported contenders include Natalie Harp, 35, a senior White House aide whose close relationship with the president has drawn increasing scrutiny in recent months and who has formally thrown her hat into the ring. Former Trump attorney Alina Habba, current Department of Homeland Security press secretary Katie Zacharia, her predecessor Tricia McLaughlin, Republican National Committee spokesperson Elizabeth Pipko, and former Kennedy Center spokesperson Roma Davari have also been mentioned. Federal Housing Finance Agency Director Bill Pulte, Breitbart’s Washington bureau chief Matthew Boyle, and White House Communications Director Steven Cheung round out the list.
Trump’s Preference — and the Jennings Complication
There is a significant wrinkle in the Jennings narrative: President Trump has made clear internally that he would prefer to see a woman take the podium after Leavitt’s departure, according to insiders. That preference puts Jennings — a 48-year-old Kentucky native and longtime Republican operative — at an apparent disadvantage despite his reported support from Wiles.
Who Is Scott Jennings?
Jennings brings a substantial Republican résumé to the table. He served as a special assistant and deputy director of political affairs under President George W. Bush, and later worked as an adviser to Sen. Mitch McConnell of Kentucky, whose campaigns he also assisted. He obtained his political science degree from the University of Louisville and completed the program at the McConnell Center for Political Leadership at the same institution. In addition to his CNN role and his Daily Mail column, Jennings writes for the Los Angeles Times. He lives in Kentucky with his wife, four boys, and three dogs.
Leavitt welcomed her second child, a daughter named Viviana, with her husband, Nicholas Riccio, in May. Her departure is expected by the end of August, and as of Aug. 19, no successor had been officially named. Whether Trump ultimately follows Wiles’s lead — or overrules his own chief of staff in favor of a woman — remains the central question hanging over one of the most publicly contested job searches in recent White House history.
