Keith Olbermann launches scathing attack on 'aggressively stupid' Karoline Leavitt on podcast

Keith Olbermann mocked Karoline Leavitt’s mispronunciations, calling Hitler 'Hilter', pundits 'pundints' and repeatedly referring to Trump as 'chump'
PUBLISHED AUG 22, 2025
Former MSNBC host Keith Olbermann slammed White House press secretary Karoline Leavitt on his 'Countdown' podcast (Getty Images)
Former MSNBC host Keith Olbermann slammed White House press secretary Karoline Leavitt on his 'Countdown' podcast (Getty Images)

WASHINGTON, DC: Former MSNBC host Keith Olbermann ripped White House Press Secretary Karoline Leavitt on Thursday, August 22, and argued that she’s exceptionally awful compared to several of her predecessors.

In a recent episode of his 'Countdown' podcast, Olbermann said that Leavitt’s background as a softball player serves her well, considering the "softball questions from right-wing plants" in the press briefing room.

Listen to what Olbermann said about Leavitt in the YouTube video above at 29:07.

Keith Olbermann calls Karoline Leavitt 'aggressively stupid'

Former MSNBC host Keith Olbermann said, "We may have achieved perfection!" and added that the word "lie" can be spelled using letters in either her first or last name.

Olbermann, who is a frequent critic of President Donald Trump and his administration, declared, "She is also belligerent, condescending and aggressively stupid." 

Moreover, he pointed to Leavitt’s history of mispronunciations. She once referred to Adolf Hitler as “Adolf Hilter”, pundits as “pundints”, and repeatedly mistakenly called her boss “chump”.

Keith Olbermann arrives for the 'Late Show with David Letterman' at Ed Sullivan Theater on March 10, 2015, in New York City (Donna Ward/Getty Images)
Keith Olbermann arrives for the 'Late Show with David Letterman' at Ed Sullivan Theater on March 10, 2015, in New York City (Donna Ward/Getty Images)

Furthermore, Olbermann also slammed her suggestion that the POTUS deserves a Nobel Peace Prize for mediating "one peace deal or cease-fire per month". It is a figure that Trump continues to add to despite fact-checkers calling it into question.

During the podcast, Olbermann also took a jab at Leavitt for accusing reporters of rooting against Trump's attempts to broker peace between Russia and Ukraine and noted that nothing has happened other than the President burning "another week off the clock".

He said, "So all you Hilter chump pundints, just remember, you may try to get it. Karoline is way ahead of you in the running — the Nobel Peace Prize."

WASHINGTON, DC - APRIL 15: White House press secretary Karoline Leavitt speaks during a daily press briefing in the Brady Press Briefing Room at the White House on April 15, 2025 in Washington, DC. Leavitt took questions on the Trump administration's plan to block federal grants and contracts from Harvard University, deportations, a Russia peace deal with Ukraine and other topics. (Photo by Win McNamee/Getty Images)
White House press secretary Karoline Leavitt speaks during a daily press briefing in the Brady Press Briefing Room at the White House on April 15, 2025, in Washington, DC (Win McNamee/Getty Images)

Interestingly, on Tuesday, August 19, Karoline Leavitt went on a tear against the "left-wing media" during the White House press briefing for negatively covering Trump’s Russia-Ukraine war peace talks.

She claimed that the meeting's outcome was a success for the US, despite Trump walking away empty-handed, as "Russia and all countries around this world actually respect the United States again."

"We’ve seen that not just lead to progress with Russia and Ukraine, but also we’ve seen it in the closing of seven global conflicts around the world as well," Leavitt added.

Karoline Leavitt’s recent job struggles

Karoline Leavitt started her tenure as the White House Press Secretary confidently as she famously declared on 'Fox & Friends', "I might bring some notes with me, but my binder is in my brain because I know President Trump's policies, and we have truth on our side at this White House."

However, recently, certain incidents have cast doubt on her preparedness.

During a press briefing on June 3, she stumbled while trying to respond to a question about the South Korean election.

"Yes, we do, in fact. Let me find it here for you," she said, as she flipped through her binder as she admitted, "Hmm. We do not. But I will get you one."

WASHINGTON, DC - MARCH 17: White House Press Secretary Karoline Leavitt calls on reporters during a news conference in the Brady Press Briefing Room at the White House on March 17, 2025 in Washington, DC. Leavitt talked about U.S. airstrikes on Houthi rebels in Yemin, the deportation of Venezuelans to El Salvador and whether the Trump administration will conform with federal judges' orders. (Photo by Chip Somodevilla/Getty Images)
White House Press Secretary Karoline Leavitt calls on reporters during a news conference in the Brady Press Briefing Room at the White House on March 17, 2025, in Washington, DC (Chip Somodevilla/Getty Images)

Moreover, her patience seemed to be wearing thin as she engaged in a tense exchange with journalist Andrew Feinberg while defending agents investigating the transnational criminal organization Tren de Aragua.

Leavitt said, "You are questioning the credibility of these agents who are putting their life on the line to protect your life and the life of everybody in this group?" She added, "Shame on you and shame on the mainstream media for trying to cover for these individuals."

Similarly, she abruptly left a press briefing after clashing with reporter Jasmine Wright, as she dismissed a question about peaceful protests, saying, "What a stupid question."

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