If the speculation is true and Scott Jennings does replace Karoline Leavitt as the White House press secretary, he’d be another controversial cable news figure in Donald Trump’s administration. Jennings, a political strategist who went from special assistant to George W. Bush to advisor Mitch McConnell advisor to fiery TV commentator, has been in the middle of many imbroglios over the last 20 years.
As chatter about a possible White House job circles Jennings, here’s a timeline of what we’d consider to be his biggest PR issues, most of which come from his time on CNN.
His General Services Administration presentation
Jennings, then a White House aide, came under scrutiny from then-House Oversight and Government Reform Chairman Henry A. Waxman in 2007 after it was revealed Jennings had delivered a presentation about Republicans’ election targets to political appointees at the General Services Administration.
“At this event, Mr. Jennings presented a 28-page PowerPoint briefing that reviewed the 2006 election results and identified the Republican party’s top electoral targets in upcoming federal and state elections,” Waxman wrote in a letter to the Republican National Committee’s leadership, per Politico.
Waxman also mentioned “serious questions” about “the legality and propriety of Mr. Jennings’s presentation and the discussion that followed it.”
His involvement in the firing of a U.S. attorney
Later that year, Jennings was subpoenaed as the Senate Judiciary Committee investigated the George W. Bush administration’s 2006 firings of nine U.S. attorneys, per Politico. During the hearing, Jennings repeatedly declined to answer questions, citing executive privilege.
But documents released in 2009 revealed that Jennings emailed another White House aide to urge “getting rid” of David Iglesias, then a U.S. Attorney in New Mexico, for not pursuing the prosecution of a Democratic congressional candidate aggressively enough, according to ABC News.
His defense of Elon Musk’s salute
After Elon Musk made a hand gesture that looked to some observers like a Nazi salute at a 2025 post-Trump inauguration rally, Jennings had the Tesla CEO’s back. “Anybody who is asserting this thing he did on the stage the other day was a Sieg Heil, which I just heard you say, lawyer up maybe,” he told Washington Post columnist Catherine Rampell on CNN NewsNight With Abby Phillip, per Mediaite.
“Do [the gesture] right now on TV,” Rampell told Jennings later in the conversation. “If you think it’s normal, if you think it’s a normal way to greet people, do it right now on TV! Why won’t you?” (Jennings did not.)
His reputation with CNN staffers
This January, the Status newsletter reported (per The Daily Beast) that CNN staff at an all-hands meeting complained about Jennings’ behavior — and, specifically, about him using the term “illegal aliens,” counter to CNN’s editorial standards.
“Jennings has cultivated a reputation — not just among viewers, but among female guests — for being rude, dismissive, and antagonistic in ways that feel personal rather than substantive,” Democratic political consultant and fellow CNN contributor Julie Roginsky wrote on her Substack. “His dynamic is familiar: interrupt, sneer, accuse, repeat. If challenged successfully, escalate the aggression. … CNN should ask itself a simple question: What is Scott Jennings adding that could not be accomplished by any number of conservative analysts who are capable of making arguments without bad faith theatrics?”
His alleged inauthenticity
In March, former Homeland Security official Miles Taylor wrote on X that Jennings is “a pundit who mocks Trump with us during commercial breaks — but fawns over Trump when the camera is rolling” and “brave enough to speak out… in the green room.”
The following day, in an interview on Tommy Christopher’s Substack, former U.S. Representative Joe Walsh said Jennings was “a fraud” and “an actor playing a role” who “doesn’t believe what he says.”
And in an X post that same day, Roginsky corroborated Taylor and Walsh’s statements. “Scott Jennings trashed Trump in the green room repeatedly in front of me,” she wrote. “Also have my suspicions that he has a say in getting people banned from the show who stick it to him and make him look like a fool.”
His blow-up with Adam Mockler
Scott Jennings snaps at Adam Mockler:
“Get your f*cking hand out of my face!” pic.twitter.com/kS3bmBsMdw
— Leading Report (@LeadingReport) May 1, 2026
Jennings lost his temper with Adam Mockler as they debated the Iran War on CNN NewsNight this April, telling the MeidasTouch commentator, “Get your f***ing hand out of my face.” That outburst was an outrage to journalists like former CNN anchor Jim Acosta, who wrote on his Substack (via The Independent), “At any other network, in any other era of television news, uttering an impromptu F-bomb would be a fireable offense.”
Poynter.org senior media writer Tom Jones, meanwhile, wrote, “Jennings’ aggressive, foul-mouthed remark is unacceptable on a national network news program. Heck, it’s unacceptable in any workplace.”