Scott Jennings, the sole conservative voice on CNN who bills himself as “America’s favorite pundit,” has rocketed to the top of prediction markets to replace Karoline Leavitt, who is stepping down from her position as White House press secretary at the end of this month.
As of Sunday morning, Jennings had jumped to a 40% chance of being President Donald Trump’s main spokesperson on the prediction trader Kalshi, followed by White House Principal Deputy Press Secretary Anna Kelly at 15%, White House Communications Director Steven Cheung at just under 8%, and White House communications adviser Margo Martin at 6%.
Jennings also topped the list on Polymarket at 37%, followed by Kelly at 14%, Martin at 9%, former U.S. Attorney Alina Habba at 5%, adviser Natalie Harp at 4% and U.S. Chief of Protocol and former Fox News analyst Monica Crowley at 3%.
Trump discussed some of the possibilities with reporters on Friday, saying: “Scott Jennings is good. That one right there, my friend from Iowa. Maybe Margo? What do you think of Margo? Who do we have in this group?”
“I will tell you this, and Karoline will tell you this,” the president added, “I have never had so many job applications in my life.”
WATCH:
🚨 NOW: President Trump praises SCOTT JENNINGS when asked about the White House press secretary job
“Scott Jennings is good. That one right there, my friend from Iowa. Maybe Margo? What do you think of Margo? Who do we have?”
“I will tell you this…I’ve never had so many job… pic.twitter.com/NAzvqgsi29
— Eric Daugherty (@EricLDaugh) August 21, 2026
As WorldNetDaily previously reported, Trump last week floated the possibility of Fox News reporter Alexis McAdams as the next press secretary, when the journalist asked the president: “Is there somebody you have in mind that you’d like to see up at the podium to take over?”
Trump responded: “You! How about you?”
President Trump tells me @karolineleavitt is NOT replaceable as press secretary. pic.twitter.com/lO3wyxCONs
— Alexis McAdams (@AlexisMcAdamsTV) August 16, 2026
With Leavitt standing off-camera, Trump pointed to McAdams and said, “She could do the job. I think so. What do you think, Karoline? I like it. I’ve always liked you, that’s why I’m doing this.”
“You have done a great job,” the president continued.
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‘Phenomenal’: Karoline Leavitt quitting role as White House press secretary
