CNN pundit Scott Jennings has emerged as a leading contender to replace Karoline Leavitt as White House press secretary, but some of President Trump's closest allies are attempting to block his potential appointment. These objections stem from Jennings' long-standing relationship with Senate Minority Leader Mitch McConnell, whom Trump has often criticized.

One individual close to the administration stated that Jennings' selection is unlikely. Weeks before Leavitt announced her departure, Jennings, 48, spoke publicly about his decades-long connection with McConnell, a figure whose legislative priorities often diverge from Trump's second-term agenda. Jennings described McConnell as his "mentor" and credited him with changing the trajectory of his life.

Jennings' background includes managing McConnell's successful 2002 re-election campaign and studying at the McConnell Center at the University of Louisville. Allies of Trump have pointed to Jennings' commentary following the January 6, 2021, Capitol riot, which echoed McConnell's assessment that Trump bore "practically and morally responsible" for the violence. Jennings wrote an op-ed for CNN stating that Trump "caused this insurrection with his lies and conspiracy theories about the election process being rigged against him." He also referred to the participants as "domestic terrorists" who "ought to be treated like any other terrorist uprising with the full force and fury of the US government."

When asked for comment, Jennings responded by texting a GIF with the caption: "Opinions vary."

Despite Trump's emphasis on loyalty, he has previously appointed individuals who have criticized him. For example, he selected J.D. Vance as his running mate in 2024, even after Vance had mused in 2016 that Trump could become "America’s Hitler."

According to a senior administration official, the search for the next press secretary is ongoing with no clear frontrunner. "It's an open book. There are no favorites or preconceived ideas," the official said. However, some suggest Trump has not fully accepted Leavitt's departure and is delaying the selection process as he contemplates the desired qualities for the role.

The press secretary position is a highly visible role, requiring comfort with public appearances and the ability to respond effectively to critical questions about the president.

White House Chief of Staff Susie Wiles has met with Jennings and several other individuals regarding the position. Potential alternatives favored by Trump loyalists include deputy press secretary Anna Kelly, Chief of Protocol Monica Crowley, and Breitbart Washington bureau chief Matt Boyle.

Former Counselor to the President Alina Habba fueled speculation after being seen at Trump's Bedminster golf club, but a source clarified that she was using her membership privileges and not involved in a secret meeting about the press secretary job. Habba later posted on social media that she was not a candidate for any position.

Trump has had five press secretaries during his presidencies. He is reportedly open to appointing a man to the role, following a recent succession of four female press secretaries.

Jennings has recently used his social media and CNN appearances to defend Trump and his aide Natalie Harp against criticism.

Until a new press secretary is appointed, the White House is expected to continue using a rotating group of fill-in briefers, a practice implemented during Leavitt's maternity leave. Trump himself is also expected to continue engaging with the press on an impromptu basis.