‘Stopped Learning In Sixth Grade’: Karoline Leavitt Roasted in Viral Takedown as Clip Exposes Her Repeatedly Mispronouncing Trump’s Name

Former MSNBC host Keith Olbermann has had enough of White House Press Secretary Karoline Leavitt, especially after she managed to repeatedly mispronounce her own boss Donald Trump’s name.

On Wednesday’s episode of his podcast “Countdown with Keith Olbermann,” the veteran broadcaster tore into her as “aggressively stupid,” mocking the blunders in a takedown he blasted out to his more than 200,000 followers on social media.

President Donald Trump is seen on a monitor watching footage of military strikes on Yemen’s Houthi rebels, as Karoline Leavitt, White House press secretary, conducts a press briefing on Monday, March 17, 2025. (Tom Williams/CQ Roll Call)

“We may have achieved perfection!” Olbermann said sarcastically, adding that the word “lie” can be spelled with letters in both her first name and surname.

“She is also belligerent, condescending and aggressively stupid,” the frequent critic of the Trump administration stated.

He highlighted Leavitt’s frequent mispronunciations, including repeatedly calling her boss President Donald Trump “chump.” She’s referred to Hitler as “Adolf Hilter” and called pundits “pundints.”

“Her chief achievement is she doesn’t actually speak English,” he said. “She has repeatedly mispronounced Trump’s name.”

“Last week she insisted Trump — or as she often calls him, Chump — deserves the Noble Peace Prize,” Olbermann continued.

He had a field day with that one, swatting down the suggestion that Trump deserves a Nobel Peace Prize for “one peace deal or cease-fire per month,” something that just doesn’t pass muster, according to multiple fact-checkers.

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Olbermann called into question Trump’s attempts at brokering a peace deal between Russia and Ukraine, pointing out he’s gotten nowhere and that he’s just burning “another week off the clock.”

The podcast host played a hilarious clip of Leavitt’s slip-ups, which he called “the Hall of Fame of Karoline Leavitt.”

“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,” he said.

“P D I N Ts. No. Dumber than a box of 200 lb of rocks. Now, I know a lot of people make this exact mistake and say, ‘Pundant, so what?,” he added. “A lot of people get drunk and drive into telephone polls, too. Does that make it any more okay to do that?” This person speaks on TV every day. Does she have any pride?

Leavitt also had trouble with the word “apprenticeships,” during an interview in May on Fox’s “Hannity,” saying that the US needs more “apprentinships.”

Leavitt’s short tenure as press secretary so far has been marked by repeatedly reprimanding reporters over their questions. Olbermann suggested Leavitt’s experience playing softball in college set her up perfectly for the “softball questions from right-wing plants” at the daily White House briefings.

“Leavitt clearly stopped learning around the sixth or seventh grade because she became convinced that at that point she knew everything,” he continued.

Leavitt is the youngest press secretary ever at 27. She turned a stint as an intern in the first Trump administration in 2019 into the role of assistant press secretary by 2020.

After Trump’s failed presidential bid in 2020, Leavitt ran for office herself in 2022 at the age of 23 in New Hampshire’s 1st Congressional District, just a few years after graduating from St. Anselm College. As one of the first Gen Z congressional candidates, the MAGA Republican lost that election amid a crowded field of more veteran politicians.

And Leavitt’s congressional campaign committee still hasn’t repaid most of the more than  $300,000 it owes to creditors and donors, according to a disclosure filed with the Federal Election Commission.

Her committee did not take in any money this spring and hasn’t made any payments on the huge debt, a majority of which was raised through illegal campaign contributions that surpassed federal limits, according to the website OpenSecrets.

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