Reports: CNN Commentator Scott Jennings Courted as Potential Replacement for Press Secretary Karoline Leavitt

White House Press Secretary Karoline Leavitt is preparing to step down at the end of August to spend more time with her family, and multiple reports indicate that CNN political commentator Scott Jennings has emerged as a leading candidate to succeed her.

Leavitt, who has served as the administration’s primary spokesperson since the start of President Donald Trump’s second term, announced her departure earlier this month. She cited the desire to focus on her young children after recently welcoming a second child and plans to continue supporting the president as an outside senior adviser. The move has set off a search for her replacement less than three months before the midterm elections.

According to reporting that first circulated widely this week, Jennings has held private discussions with White House Chief of Staff Susie Wiles about the position. Sources familiar with the conversations told the Daily Mail that the meetings began even before Leavitt’s exit became public and have continued since. One source described the role as “his if he wants it… and he does,” while another noted that Jennings and Wiles speak frequently. The most recent reported discussion occurred over the weekend at a Washington steakhouse near the White House.

Jennings, 48, is a veteran Republican strategist who served as a special assistant to President George W. Bush and later became a prominent conservative voice on CNN, where he frequently defends Trump administration policies. He has also written a book on Trump’s political approach and maintains a radio presence. When asked on air about the speculation, Jennings has avoided a direct answer, instead praising Leavitt as perhaps “the greatest White House press secretary in the last 30 years” and deflecting with humor.

Several other names have circulated as potential candidates, including former Trump attorney Alina Habba, principal deputy press secretary Anna Kelly, and various communications veterans from the administration and outside media. Trump has met informally with multiple contenders, including at his Bedminster golf club, but no decision has been announced. Some accounts suggest the president has weighed preferences for the public face of the administration, though officials have downplayed the existence of a formal shortlist.

The timing of the transition places added importance on the choice, as the new press secretary will handle daily briefings during a high-stakes political period. Jennings’ combination of prior White House experience, television combat readiness, and established relationship with Trump’s circle has positioned him prominently in the ongoing discussions, even as the administration continues to evaluate options. No official offer or acceptance has been confirmed.