Kentucky GOP Strategist and CNN Commentator Scott Jennings Next Trump Press Secretary Odds - Now Favored

OAKLAND PARK, Fla (Gambling911.com) - A popular CNN pundit, Scott Jennings, is now favored to be named U.S. President Donald Trump's next Press Secretary, according to the prediction markets.

Karoline Leavitt, the youngest White House press secretary in history, announced her departure from the role effective at the end of August, citing her desire to spend more time with her two young children. No successor has been named, with her exit coming less than three months before the 2026 midterm elections.

The president has indicated that a group of rotating individuals will take to the podium for the time being. 

Jennings had opened as a 16-1 long shot following the news that Leavitt would be leaving.  The payout would be $1600 for every $100 bet.

Love him or hate him, the conservative commentator has become one of CNN's most recognizable—and deliberately combative—political personalities and is a regular fixture on NewsNight With Abby Phillip. 

The Wall Street Journal profile of Scott Jennings specifically discussed CNN's strategy of using Jennings to attract and represent conservative viewers. It noted that NewsNight averaged about 485,000 viewers in June 2024, immediately before its shift toward the roundtable/debate format. The audience increased to 669,000 in July and 717,000 in October. Jennings became one of the central personalities in that format.  

Jennings, 48, is a Kentucky Republican strategist who worked for President George W. Bush and has been a longtime political adviser and confidant of Mitch McConnell. He joined CNN as an on-air political contributor in 2017.

Prediction markets now give Jennings a 38% chance of being named the new Trump Press Secretary. 

Next White House Press Secretary

Alina Habba 3/1

Anna Kelly 4/1

Jenn Pellegrino 6/1

Roma Haravi 7/1

Steven Cheung 10/1

Emerald Robinson 10/1

Chanel Rion 10/1

Scott Jennings 16/1

Natalie Harp 16/1

Jason Miller 16/1

Scottie Nell Hughes 22/1

Lara Trump 33/1

Kari Lake 33/1

Spencer Pratt 50/1

Erika Kirk 66/1

Tucker Carlson 100/1

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