As a crowded field of would-be contenders worked to get Donald Trump’s attention at his Bedminster golf club over the weekend, the person with real influence over the next White House press secretary pick was notably elsewhere.
Chief of Staff Susie Wiles was back in Washington, dining at Mastro’s steakhouse just blocks from the White House with the candidate she appears to be lining up for the high-profile role.
CNN political commentator and Daily Mail columnist Scott Jennings, 48, is being actively pursued by Wiles, Our News Outlet can exclusively reveal, following Karoline Leavitt’s unexpected resignation last week.
“It’s his if he wants it,” a source close to Jennings said of the White House press secretary position. “And he does.”
Still, people familiar with the discussions say Trump has repeatedly signaled that he would rather see a woman succeed 28-year-old Leavitt behind the briefing room podium, even as he remains an admirer of Jennings, a former George W. Bush aide known for forcefully defending the president during his CNN appearances.
According to three White House sources briefed on the selection process, Jennings sat down with Wiles even before Leavitt officially confirmed her departure last Wednesday.
The two met again over the weekend at Morton’s and have been in regular contact, with one source telling Our News Outlet that they “speak often.”
But as Jennings and Wiles continued their conversations over dinner, Trump spent Saturday at his Bedminster golf club fielding attention from other hopefuls, including his polished and combative former attorney, Alina Habba.
The Daily Mail can exclusively reveal that White House Chief of Staff Susie Wiles has been secretly wining and dining CNN political commentator Scott Jennings (pictured at the White House Correspondents’ Association Dinner in April, 2025) for the top communications job
Wiles speaks to Leavitt before a speech by Trump at the Kennedy Center in January
But while Jennings and Wiles were meeting at Morton’s, Trump (right) spent his Saturday at his Bedminster golf club being wooed by rival contenders – including his telegenic and tenacious former attorney, Alina Habba (left)
Habba, 42, was vying for Trump’s attention alongside real estate mogul and close confidante Bill Pulte, 38, as well as his aide Natalie Harp, 35.
Dinner at the president’s New Jersey golf club was a scene of fierce competition.
‘They were all trying to get in front of him this weekend. It was like The Apprentice,’ one source who was informed about the weekend said. ‘It reeks of desperation.’
Other candidates include former Department of Homeland Security press secretary Katie Zacharia, ex-DHS spokeswoman Tricia McLaughlin, Breitbart Washington bureau chief Matthew Boyle, RNC spokeswoman Elizabeth Pipko, White House communications chief Steven Cheung and ex-Kennedy Center spokeswoman Roma Daravi.
But it is understood that the pick will likely come from outside the White House.
Jennings remains the man to beat.
He has often served as the sole conservative voice on hostile cable news panels and has built a reputation for holding his own against a barrage of liberal co-panelists.
Jennings’ emergence as a top contender comes despite having broken ranks with the president on national television at times.
Habba was vying for Trump’s attention alongside real estate mogul and close confidante Bill Pulte, as well as his aide Natalie Harp (seen arriving back to Washington with the president on Sunday)
Trump and Leavitt outside the White House on July 15
Former Department of Homeland Security press secretary Katie Zacharia, above with Donald Trump, is seen as a possible replacement for Leavitt
On the controversial topic of a third term, Jennings once publicly rejected speculation about Trump extending his presidency beyond 2028, declaring on CNN that Republicans know it won’t happen.
‘I am on the record of opposing violating the 22nd amendment of the constitution,’ he said.
Despite those past on-screen statements, Trump’s team view Jennings as a combat-ready media personality who will be able to ‘hold his ground’ against hostile reporters.
In the past, Trump has publicly praised Jennings, who is an occasional Daily Mail columnist.
In one recent example, at a campaign rally in Warren, Michigan, Trump praised Jennings’ ability to defend the current administration.
‘We have a man here that I don’t know, but he’s defending me all the time on CNN. And he defends me really well – but he can’t go too far, because if he goes too far, he’ll get fired… don’t worry we will take care of you Scott,’ Trump said to the crowd.
Jennings lives in Prospect, Kentucky, with his wife, Autumn Stiff, and their four sons.
Because of his work as a political commentator, he also travels frequently to New York and Washington for TV appearances.
Besides the role of White House press secretary, Jennings was also reportedly encouraged to run for Kentucky Senator Mitch McConnell’s open Senate seat earlier this year.
The White House officially denies any meetings taking place. Jennings and Wiles have been contacted for comment.
Leavitt’s shock departure sparked a scramble inside the White House last week, with her exit with less than three months to go before crucial midterm elections in November.
Leavitt said in a statement that returning to work soon after the birth of her second child had been ‘the most rewarding yet challenging season of my life.’
Insiders told Our News Outlet she had suffered ‘burnout’ after being rushed back to work by the president.
‘It was a constant stream of messages from him [during maternity leave] and it was overwhelming,’ one insider explained.
‘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.’
