Embarrassing Karoline Leavitt Moments That'll Haunt Her For The Rest Of Her Career

While getting her footing as White House press secretary, Karoline Leavitt has had her fair share of ups and downs. Not only has Leavitt suffered some major fashion fails, but her general demeanor seems to be combative and spiteful. Since her job is to be in the media as often as possible — whether that's giving press briefings or simply making the rounds — Leavitt is certainly racking up a reputation for being a difficult personality. There's even a growing list of times Leavitt was undeniably petty with CNN's Kaitlan Collins. In fact, while the feud between Collins and Leavitt begins to simmer, Leavitt herself has been making some blunders.

Of course, having to manage the chaos of President Donald Trump's second administration is surely difficult. For her part, Leavitt appears up for the task. However, among the nonstop executive orders and constant court challenges, Leavitt has been found accidentally embarrassing herself on more than one occasion. While there are several CNN personalities happy to put Leavitt in her place, sometimes she makes her unforced errors. Here are five examples of embarrassing moments that will follow Leavitt into the future.

In March 2025, Karoline Leavitt was mentioning who would be attending President Donald Trump's joint address to Congress when she made an embarrassing faux pas. While discussing the guest list First Lady Melania Trump had put together for the event, the often controversial Leavitt accidentally misspoke, claiming that one of the "every day American heroes in attendance," would be "Corey Comperatore, who lost his life protecting his family in Butler, Pennsylvania." (via The Mirror). Leavitt was referencing the gentleman who lost his life at a campaign rally during an assassination attempt on the now-president. However, her gaffe left her exposed to the online masses.

Leavitt most likely meant to say that Comperatore's family would be in attendance, but the slip-up opened the door for clapbacks. One commenter on X, formerly Twitter, said, "Are they gonna break out the Ouija board mid speech?" Another wondered, "was it a plan to have a seance?" Someone even wondered if "resurrection is on the agenda?" Many, of course, came to her defense, pointing out that accidents happen. One user wrote, "Got to quit making such a big deal about when somebody misspeaks, everybody does it, it is called a mistake." While this is true, it certainly is not the only error Leavitt has made.

In one of the biggest slip-ups of Karoline Leavitt's career so far, the press secretary once again fumbled her words. According to Huffington Post, during a press briefing, Leavitt boldly stated that under President Donald Trump, "We want to restore the Department of Justice to an institution that focuses on fighting law and order." Surely, Leavitt meant to include an extra word in there, such as "for," to indicate the department was on the side of "law and order," not against it. However, this moment was yet another one that Leavitt might never live down.

There were many commenters on X who seemed to agree with Leavitt that yes, the current administration sure does seem to be battling against the rule of law. One commenter said, "She's correct for once. They are fighting law and order." They weren't alone. Others pointed out that President Trump has made the bold step to "pardon 1,500 violent insurrectionists," referencing the many violent offenders Trump pardoned in connection with January 6, 2021. Several others also referenced the fact that Trump, himself, is a convicted felon. One user mentioned that law and order "certainly doesn't happen with a felon running the country." Ultimately, Leavitt was just getting started with her embarrassing moments.

When the uniquely embarrassing fumble of the Signal group chat leak was published by The Atlantic, it was part of Karoline Leavitt's job to pick up the pieces. Notably, the administration of President Donald Trump did its best to blow past the whole incident and desperately wanted to act like it was no big deal. One of the key ways of trying to convince the public that using an open-source app to communicate potentially top-secret military plans is a-okay was by throwing Leavitt to the wolves.

Leavitt's attempt to pivot the blame by saying the hullabaloo around the leak "proves that Democrats and their propagandists ... know how to fabricate, orchestrate and disseminate a misinformation campaign," ultimately backfired. (Per The Daily Wire) However, this left Leavitt on the hook, with many pointing out that what she was doing was, in fact, spreading misinformation. One commenter on X mentioned that Leavitt "doesn't realize that speaking sternly and loudly does not make you right." Another pointed out, "The outrage would be the administration trying to sweep it under the rug."

While Leavitt was able to weather the Signal storm, Mike Waltz, the national security advisor who accidentally added the editor-in-chief of The Atlantic to the group chat, did ultimately lose his position. Luckily, Waltz has an odd Hollywood connection to possibly help him get back on his feet.

With an uptick in all parts of President Donald Trump's administration becoming televised, it sort of made sense when Karoline Leavitt and Deputy Chief of Staff Stephen Miller tried to have a live-streamed press conference. In what became yet another awkward press briefing moment for Leavitt, viewers at home got a glitchy experience. According to a post on X, the audio quality of Leavitt giving initial remarks had some echoing issues.

One X user hit the nail on the head when discussing the debacle by saying, "doublespeak, so on brand." Another made the joke, "Talk about an echo chamber!" Ultimately, this blunder might be hard for Leavitt to live down because it just might have made her boss angry. One commenter pointed out, "You know he's throwing breakfast at the wall because of that," most likely in reference to Trump's assumed displeasure at such a public embarrassment.

This technical blip happened during a time when Trump's White House is trying to welcome what Leavitt has referred to as "new media," according to the Irish Star. Ultimately, what this has shaken out to mean is that more influencer types and YouTubers would gain access to press briefings — although they might have a better time getting the live stream set up properly.

Though it is technically her job, constantly covering for President Donald Trump is beginning to peel at Karoline Leavitt's shellacked exterior. Not only is Leavitt's low energy possibly indicating she can't handle the constantly shifting narrative of the current administration, but it could also be an indicator that all these embarrassing moments are catching up with her. On May 9, 2025, Leavitt posted to X discussing Trump's new trade deal with United Kingdom Prime Minister Keir Starmer.

In her post Leavitt bragged about how "President Trump demonstrated the Art of the Deal and secured a historic trade deal between the United States and the United Kingdom." However, many commenters were quick to point out that this deal was only necessary because Trump himself implemented sky-high tariffs on most of the world, including the UK. One user posted, "Creating a problem and then partially solving it isn't the flex you think it is." Another pointed out in a comment that, "It is comical that this deal has to be touted as historic. The administration is so desperate to show things are happening."

While this might seem par for the course, it does appear as if all the embarrassment is finally catching up with Leavitt. Perhaps that's why Leavitt recently glammed up her look in hopes of catching the president's eye, and possibly keeping her job.