Karoline Leavitt, the 27-year-old White House press secretary, is used to being the one on offense. Snapping at journalists, shutting down tough questions, and defending Donald Trump at every turn. But this week, the tables turned when a well-known media voice set his sights on her.
On his podcast Countdown, former MSNBC host Keith Olbermann gave a blistering takedown of Leavitt. He talked about her repeated habit of mangling words and names from the lectern. He described her as “belligerent, condescending, and aggressively stupid,” before adding, “Her chief achievement is she doesn’t actually speak English.”
I might be able to take more seriously the criticisms of this amazingly stupid, self-satisfied clown @PressSec if she spoke English
Add it to the “Hilter,” “Noble,” “President Chump” list. Today she called pundits “pun-dints.”
She probably meant “fondant.”🎂 https://t.co/OGZA18wMPE
— Keith Olbermann (@KeithOlbermann) August 19, 2025
Olbermann pointed to several of her verbal missteps. She once referred to Adolf Hitler as “Hilter,” stumbled over Trump’s own name more than once, and most recently declared that he deserved the “Noble Peace Prize.” To state his point, Olbermann played a montage of her bloopers, calling it “the Hall of Fame of Karoline Leavitt.”
According to him, her mistakes are more than just slips of the tongue. “Leavitt clearly stopped learning around the sixth or seventh grade because she became convinced that at that point she knew everything,” he jabbed.
Earlier in the week, while scolding TV journalists for not giving the president enough credit in negotiations with Vladimir Putin, Leavitt pronounced “pundit” as “pundint.” Back in May, during an appearance on Hannity, she also fumbled “apprenticeships,” telling the host America needs more “apprentinships.”
In an embarrassing example of ignorance, Karoline Leavitt says
America needs more “Apprentinships” – botching the word, and says we need fewer LGBTQ graduate majors from Harvard University. Is the Trump Administration the dumbest group of people ever?— CALL TO ACTIVISM (@CalltoActivism) May 28, 2025
Olbermann’s criticisms went beyond her vocabulary. He accused her of being hostile toward the press while also benefiting from a friendlier environment created by the Trump White House. He noted the administration’s preference for outlets like Real America’s Voice and The Daily Caller over traditional outlets such as AP and CNN.
“As I’ve pointed out several times, there is the word ‘lie’ in both her first and last names,” he quipped. Then he reminded listeners that Leavitt herself once played softball at Saint Anselm College. “In a room full of softball questions from right-wing plants, like the Pizzagate guy who was there the other day, she was literally a softball player who got a scholarship to play softball at an obscure college.”
Leavitt’s rise has been fast. She joined Trump’s first White House in 2019 straight out of college, and by mid-2020, she was already serving as assistant press secretary. Between Trump’s terms, she launched a congressional run in New Hampshire in 2022. She lost the race but walked away with $300,000 in campaign debt, something she only recently disclosed to federal regulators.
Despite the mockery, Trump has stood firmly behind her. He once praised her, saying she has “lips that move like a machine gun” and calling her a “superstar.”
Olbermann, clearly, doesn’t share the same admiration.
The White House, for its part, had no comment so far.
