Scott Jennings has been meeting privately with Susie Wiles about possibly replacing Karoline Leavitt as White House press secretary, even before Leavitt said she would step down to spend more time with her young family. The talks have put Jennings, 48, at the center of an increasingly active search for the next face of the White House briefing room.
That search matters now because Leavitt, 28, has already announced her departure, and the White House role is no longer just a future opening. It is being treated like a live contest, with names circulating and allies testing where Donald Trump may want the podium to go next.
Three sources familiar with the selection process said Jennings met with Wiles on at least one more occasion, and that the two speak often. One source said the job is his if he wants it. Another put it more bluntly: he does. Jennings and Wiles also had dinner at Morton’s over the weekend, while other hopefuls were trying to get in front of Trump at an event at his golf club in Bedminster, New Jersey. One source described the scene this way: “They were all trying to get in front of him this weekend. It was like The Apprentice.”
The White House denied that any meetings took place between Jennings and Wiles, even as the selection chatter kept building around him. That denial sits uneasily beside the account from people familiar with the process, and it leaves the central question less about whether the vetting is happening than how far along it has already gone. Insiders also said Trump would prefer to see another woman take the podium after Leavitt leaves.
The bench is crowded. Natalie Harp, Alina Habba, Katie Zacharia, Tricia McLaughlin, Elizabeth Pipko and Roma Davari have thrown their hats into the ring, while Bill Pulte, Matthew Boyle and Steven Cheung have put themselves forward as well. Jennings is a familiar Republican voice with a long record in politics, including work in the George W. Bush administration and as an adviser to Mitch McConnell, and he has recently been visible as a conservative commentator and a columnist at the Daily Mail.
What comes next is not whether the White House has started thinking about Leavitt’s replacement. It has. The real question is whether Trump wants Jennings, whether he wants a woman in the role instead, or whether the chatter around a secret meeting is simply the first sign of a contest that is still being shaped behind closed doors.
