GOP strategist turned CNN pundit Scott Jennings is sending clips of his own appearances to members of Donald Trump's inner circle, according to a report from Politico Playbook, as he makes another push to assume the job of White House Press Secretary Karoline Leavitt.

The controversial conservative gadfly — a Kentucky-based strategist who worked in George W. Bush's White House and spent years advising Senate Republican Leader Mitch McConnell before becoming one of CNN's most prominent pro-Trump voices — has ramped up his bid for a new position by rushing to the defense of Trump aide Natalie Harp, and he has not been shy about letting the White House know he has their back as reporting on Trump's constant younger companion has become a media obsession. Harp, a former One America News host, worked on Trump's campaigns before joining his White House staff.

Jennings "pounced on the drama" to turn what some in the White House described as a rapid response team misfire back on Georgia Sen. Jon Ossoff, a potential 2028 Democratic contender. According to Politico, Jennings dedicated radio airtime, fired off rounds of tweets and used his primetime perch on CNN to defend both Harp and the president. His multi-pronged defense labeled Ossoff a "sucker-punching coward" and drew cheers from the pro-Trump crowd.

"I just don't think that's what you sign up for when you're someone like Natalie Harp, who never put her name on a ballot. She's not the White House press secretary. She's not a household name, and I just find it to be appalling," Jennings told Playbook. "Somebody needs to defend her honor."

Some in Trump's circle took notice as focus shifted away from the White House, according to the report. Others viewed Jennings' efforts as a "public audition" for the White House Press Secretary position he has been seeking since the transition.

Jennings sent clips of his appearances to "several senior staffers" at the White House. He also reportedly met privately with Chief of Staff Susie Wiles over the weekend after reaching out to schedule the meeting, with the report adding, "No decision was made and no offer was extended." Wiles, who helped run Trump's 2024 campaign before he named her chief of staff, oversees the White House's day-to-day operations.

Trump reportedly likes Jennings, and the report states the president "has spent recent days calling allies" to ask their opinions of him as a potential replacement for Leavitt, according to sources familiar with the conversations. Leavitt, 27, became the youngest press secretary in White House history when Trump returned to office in January 2025, and the role has seen turnover under Trump before: his first term cycled through four press secretaries in four years.

Sources: Raw Story, Politico Playbook via YouTube