CNN Personalities Who Didn't Hesitate To Put Karoline Leavitt In Her Place

Karoline Leavitt's role as the White House press secretary and woman responsible for answering the impossible questions about why President Donald Trump made yet another controversial remark or divisive political decision has proved challenging. She's had to come up with a lot of looping answers and ask for quite a bit of mental gymnastics from reporters — and when said reporters have failed to fall for tricks, she's often outright ignored them or had them barred from the White House.

Whether it's been trying (and failing) to spin Elon Musk's infighting with Trump staffers, taking random Trump-esque jabs at political opponents, or dodging questions about her own controversial moments that have tarnished her reputation, Leavitt's relationship with the mainstream press has been anything but amicable. While she's often played tough with journalists, there are quite a few who haven't given her the chance to walk all over them.

It seems CNN has been a particularly challenging opponent for Leavitt — even before Trump's election victory when she was simply his campaign spokesperson. The network's many respected journalists have been pushing back against the narratives being presented, and there have been more than a few CNN anchors who wasted no time when it came to correcting, fact-checking, and putting Leavitt in her place.

When it comes to verbally duking it out with Karoline Leavitt, few have gone toe-to-toe with the press secretary more times than CNN's Kaitlan Collins. The White House correspondent has experienced several heated exchanges with Leavitt during Donald Trump's second term and has not shied away from asking the tough questions and demanding real answers.

Given the slew of controversies and scandals that have boiled over into the public eye during just the first few months of Trump's second term, there's been no shortage of drama for Leavitt to spin. While she's largely tried to shut down or ignore questions about said scandals, Collins has given no quarter. Collins has sparred with Leavitt over the Signal Chat scandal, in which sensitive military plans were communicated over an unsecured text chain that inexplicably also included a reporter, as well as Trump's claims that many of the pardons issued by former president Joe Biden were invalid because he used an autopen machine.

In March 2025, Leavitt threw a bit of a tantrum when she was answering questions about the infamous war plans text chat and refused to address Collins' questions regarding how Trump felt about the information being exposed. "Kaitlan, I am not taking your follow-up," Leavitt said, before repeating the sentiment again as Collins pressed on, undeterred (via Daily Mail).

Before Donald Trump was reelected, Karoline Leavitt served as his campaign spokesperson and often found herself having to answer for some of the things her boss said and alleged at various times. This came to a head when she spoke with CNN's Kate Bolduan in October 2024, and Leavitt was asked about misinformation Trump had been spreading about FEMA spending money on housing migrants instead of paying to help people dealing with the aftermath of Hurricane Helene.

When asked if Trump would stop sharing fake news stories once they had been debunked, Leavitt tried to double down and incorrectly argue that the stories Trump had shared weren't fake at all. As the debate got more contentious, Bolduan's own temper flared, and the newswoman demanded respect. "I'm talking! Let me finish," Bolduan declared, the way an exasperated parent would snap at an argumentative child (via Daily Mail).

As the conversation continued, Leavitt repeatedly sidestepped questions about FEMA using money for migrants during Trump's first term in office, and eventually, Bolduan got tired of the evasiveness and cut off the interview. "We're going to leave it there because I offered you three times to give me the answer, and I'm not getting it!" Bolduan exclaimed after getting a prescient glimpse of what dealing with Leavitt would look like in the future when she became the official White House press secretary.

When Karoline Leavitt decided to take swings at other CNN anchors, Kasie Hunt decided to push back and defend her hard-working colleagues. In June 2024, when Donald Trump agreed to debate Joe Biden on CNN, the network chose Dana Bash and Jake Tapper to serve as moderators. During an interview with Hunt on "This Morning," Leavitt slammed the anchors when asked about Trump's strategy for the debate and said that Tapper and Bash were "biased" against Trump and that they'd "made their opinions about him very well known" (via The Guardian).

Hunt wasn't going to let this stand, and she quickly stood up for the venerated journalists, shutting down Leavitt's accusations. "My colleagues, Jake Tapper and Dana Bash, have acquitted themselves as professionals as they have covered campaigns and interviewed candidates from all sides of the aisle," Hunt said, adding, "If you're attacking the moderators, you're usually losing."

Despite Hunt's best efforts to get Leavitt to answer even one question about Trump, the acerbic spokesperson refused to stop slamming Tapper and Bash's alleged bias. Hunt finally decided the interview was going nowhere and just cut things off entirely, ending Leavitt's time on the air for that segment.