Awkward Kayleigh McEnany Moments That Were Caught On Camera

It's no secret that Donald Trump's public relations were fraught with tension, drama, and insults throughout his presidency. Not only did the former president use his personal Twitter account to communicate with the public, but his rotating door of press secretaries made it difficult to determine the messaging coming from his administration.

By the time November 2020 rolled around, Trump had gotten through four press secretaries — Sean Spicer, Sarah Huckabee Sanders, Stephanie Grisham, and Kayleigh McEnany — each one bringing a personal style and messaging practice all their own.

If it felt as though 45's public messaging was intertwined with personal strife, you're not far off. Spicer went on to compete on "Dancing With the Stars" in an attempt to rehabilitate his personal image, Huckabee Sanders left her turbulent tenure to run for political office herself, Grisham went on to write a tell-all book about Donald and Melania Trump, and McEnany made headlines when she claimed to have never lied to the press during her time at the podium. The press secretaries, as it turns out, became integral aspects of Trump's White House coverage, and there were some pretty cringeworthy moments captured on camera as a result. When it comes to McEnany, specifically — well, let's just say her spars with journalists and on-air fumbles will go on to live in infamy.

The aftermath of January 6 was beyond awkward for Kayleigh McEnany

The violence that took place on January 6, 2021 was an unprecedented sight to behold, and Donald Trump became a central player in the investigation turning over every stone to get to the truth regarding his involvement. In the immediate aftermath of January 6, however, press secretary Kayleigh McEnany took to the podium for about two minutes, addressing the violence at the hands of Trump's supporters and the siege that almost was.

"Let me be clear," McEnany began while at the podium. "The violence we saw yesterday at our nation's Capitol was appalling, reprehensible and antithetical to the American way. We condemn it, the president, and this administration, in the strongest possible terms. It is unacceptable, and those who broke the law should be prosecuted to the fullest extent of the law."

While her words were poignant, McEnany then awkwardly pivoted to the Black Lives Matter protestors who took to the streets in the summer of 2020, comparing — on equal footing — the alleged fire that was set in a church. After a very brief statement, McEnany stepped away from the podium, amidst many journalists shouting, "Where is the president?" 

Kayleigh Mcenany blamed CNN for her anti-Trump sentiments

Before she made it to the White House as press secretary, Kayleigh McEnany had already made a name for herself as a vocal defender of Republican politics as the Republican National Committee's spokesperson. Jumping on the chance to defend Donald Trump — even before she worked in his White House – McEnany even stood by Trump's side in 2017 when he was criticized for his response to the racist, violent attack in Charlottesville, Virginia. However, her support wasn't always so cut and dry. Back in 2015, McEnany found fault with Trump's message on immigration — or so she said at the time.

During a segment on CNN back when Trump was a candidate, McEnany did not mince her words when it came to the "Celebrity Apprentice" host turned politician. "Donald Trump has shown himself to be a showman, I don't think he is a serious candidate," she said, adding, "I think it is a sideshow. It's not within the mainstream of the candidates." However, McEnany walked back her words once press secretary and stated that she was led to such an opinion due to "watching CNN" and "naively believing some of the headlines."

"I very quickly came around and supported the president," McEnany continued in 2020. "I was on [many panels] where I proudly supported this president who I believe is one of the best presidents, if not the best president this country will ever have."

The briefing following the 2020 election was cringeworthy

Not only did Kayleigh McEnany establish a reputation as a fierce defender of Donald Trump, but she also made it clear that addressing White House reporters daily was not her priority. When she finally took to the podium after Trump lost the 2020 election, McEnany answered journalists' questions for the first time since October 1 of that year, breaking a seven-week streak of zero briefings from the press secretary (via CNN). And McEnany's return to the briefing room was nothing short of awkward.

For example, McEnany brought up the Mueller investigation into Trump's ongoings with Russia, accompanying the old throughline with "falsehoods" about voting irregularities and the response to the pandemic. In an extremely tense moment, McEnany then claimed that Trump "was never given an orderly transition of power" from Barack Obama and his administration in 2016.

CNN was quick to point out that McEnany's statement from the podium was simply not true. While Trump did block Joe Biden's transition team from an orderly transfer of power, Obama's White House "never denied Trump's victory and transitioned power to the incoming administration."

Things got awkward when the press secretary had to address Trump's TikTok criticisms

As noted by PBS, the Trump administration launched "sweeping" orders against the social media app, TikTok, claiming that it posed a threat to personal data and national security. However, some suspected he was simply retaliating for a large prank he fell victim to (via Forbes). K-pop stans and other TikTok users sold out his June 2020 Tulsa rally — only to leave the event largely unattended.

Kayleigh McEnany addressed the awkward situation during a press briefing in August, telling reporters that the Chinese government would not get away with stealing information about TikTok users. "The administration is committed to protecting the American people from all cyber threats and these apps collect significant amounts of private data on users," McEnany said. "Such information can be accessed and used by the PRC, and TikTok has a documented history of censoring free speech to conform to CCP propaganda."

But in response, creators on the app made it clear that Trump's attack on the platform was uncalled for, with technical program manager Patrick Ryan telling PBS, "This is unprecedented, and it's frankly really uncool."

This moment between Kayleigh McEnany and CNN's Kaitlan Collins was beyond awkward

You'd have to be living under a rock not to know of Donald Trump's well-documented distaste for CNN, and such resentment made its way to the briefing room. During a briefing in which Kayleigh McEnany spoke to the then-president's attempts to question the results of the 2020 election, CNN's Kaitlan Collins applied pressure on the press secretary to further answer questions. Snapping back at the White House reporter, McEnany snarked, "I don't call on activists."

As the official briefing came to an end, Deadline noted that Collins fired back at the remark, highlighting the fact that McEnany hadn't held a press briefing in over a month. "I am not an activist, and you didn't take questions since October 1st and just took about five, Kayleigh. That's not doing your job. Your taxpayer-funded job," Collins retorted, by which point the then-press secretary had left the podium.

Of the briefing itself, Deadline further reported at the time that of the big cable news networks, only Fox News aired the briefing. Both CNN and MSNBC chose not to, with CNN's Dana Bash explaining that the decision was made due to the high risk of McEnany promoting falsehoods while at the podium. You truly can't make this stuff up.

When the topic of white supremacy came up in the briefing room, things got very awkward

According to African American studies professor Keeanga-Yamahtta Taylor, "Trump's election clearly activated the white-racist fringe, sparking record numbers of hate crimes." With such a clear association, Kayleigh McEnany had to address the close-knitted relationship on more than one occasion, but one particular briefing left much to be desired for White House reporters. C-SPAN noted that McEnany's October 1, 2020 briefing was of highlighted influence, as "several reporters pushed back" on her comments surrounding Trump's weak-filled denouncement of white supremacy.

"I'd like to ask you for a definitive and declarative statement, without ambiguity or deflection: As the person who speaks for the president, does the president denounce white supremacism and groups that espouse it in all their forms?" a reporter asked. McEnany replied, "This has been answered." When probed yet again to "make a declarative statement" about Trump's denouncement of white supremacy, McEnany fired back, "The president was asked this. You're making — you're contriving — a storyline and a narrative." Journalists countered her yet again, making it clear that they wanted to "put this to rest," but McEnany tried to move on to the next issue. She may not have been prepared for such a follow-up, when another White House reporter put it bluntly, "[Trump] has not been consistent on the issue of white supremacy."

The press secretary caught flack online after an eyebrow-raising comment on Fox News

Perhaps Kayleigh McEnany's greatest strength as press secretary — and now as a contributor to Fox News — is her unwavering dedication. This could be seen as a positive or negative trait depending on the person, and while McEnany is sure to have supporters among Donald Trump's base, she caught a lot of flack online when she pushed theories about the COVID-19 pandemic.

As seen on Twitter in August 2021, McEnany appeared on Fox News and claimed, amid President Joe Biden's faltering approval ratings, that voters didn't experience back-to-back crises when Trump was in office. "We are eight months into a Biden presidency. Wrap your head around that. We still have three years and four months left," McEnany said. "When President Trump was president, you didn't see crisis after crisis. You just didn't see it. I shudder to think about what COVID would have been like under Joe Biden."

People on Twitter quickly came after McEnany for her comments, with many users unabashedly telling her that she didn't know what she was talking about. "What's amazing about Kayleigh McEnany is her constant ability to lie with such ease and conviction," one user wrote, while another commented, "Well, to be fair — it really was more of one continuous, rolling, never ending crisis." Talk about awkward.

The feud between the press secretary and CNN continued in a really cringey way

As the COVID-19 pandemic continued to escalate in an alarming way, people looked to the White House — and journalists looked to Kayleigh McEnany — for answers. During her September 9, 2020 briefing, however, McEnany's feud with CNN went from bad to worse. McEnany was asked how then-president Donald Trump was reckoning with his statement of bearing "no responsibility" to the lives lost to the virus. Without missing a beat, McEnany responded. "The president never downplayed the virus," she said. "The president expressed calm."

Before she could continue, CNN cut away from the briefing, with host Brianna Keilar telling viewers that she would not allow the briefing to air when such falsehoods were being stated. "That was the press secretary at the White House lying. She said the president never downplayed the coronavirus," Keilar said.

As for the rest of her briefing, McEnany stated that Trump "was serious about [COVID-19] when Democrats were pursuing a sham impeachment." "This president embodied the American spirit," the then-press secretary touted.

Even Fox News cut away from Kayleigh McEnany during a briefing over factual errors

As far as media outlets are concerned, if CNN was Donald Trump's archrival during his presidency, then Fox News was his No. 1 fan. The right-leaning network that was the brainchild of Rupert Murdoch regularly supported the then-president's rhetoric and had him as a guest on its programming on a number of occasions. With that in mind, then, you'd think that Fox News would be the last outlet to cast judgment on Kayleigh McEnany, who served as Trump's talking head for the last stretch of his presidency. However, that was not always the case.

In a very awkward caught-on-camera moment, McEnany was addressing the 2020 election, claiming while behind the podium that illegal voting and rigged voting machines were to blame for Trump losing to Joe Biden. And in an incredibly surprising move, Fox News' Neil Cavuto cut her off mid-sentence, taking viewers back to split screen and muting McEnany's ongoing briefing. "Whoa, whoa, whoa," Cavuto started, the video of which can be seen on Twitter. "I just think we have to be very clear ... She's charging the other side as welcoming fraud and illegal voting. Unless she has more details to back that up, I can't in good countenance continue showing you this."

The Fox News host made it clear that if McEnany did "have something to back that up," he'd gladly welcome the information on-air — until then, however, he didn't feel comfortable sharing such a briefing. "That's an explosive charge to make, that the other side is effectively rigging and cheating," Cavuto concluded.

Kayleigh's comments in her first interview since leaving the White House turned heads

Recounting the horrific images and footage that emerged from the January 6 attack on the United State Capitol is just as skin-crawling today as it was on that historic morning. And while many would argue that Donald Trump's rhetoric surrounding the legitimacy of the 2020 election and his undeniable support of false claims unwittingly led to the day in question, Kayleigh McEnany claimed in an incredibly awkward interview that she did not see such an event coming.

During an appearance on Fox News' "The Faulkner Focus," which marked her first interview since leaving the White House, McEnany said, "I think at the beginning of the day before everyone went to the rally, everyone was expecting peace. We had been to hundreds of rallies — I've probably been to hundreds at this point, certainly many dozens — and they were nothing but peaceful events, and we expected that day to be the same."

Going on to say that she was in "shock" and "disbelief" over the events that unfolded, McEnany's eyebrow-raising comments shook Twitter to its core, with many taking to the platform to call out her description. One wrote, "They're all guilty of lying and provoking the mob to action. If any of them had any decency they would admit it. But of course none of them do so none of them will." Clearly, McEnany's words were not taken well.

Trump's poorly attended Tulsa rally proved awkward for the press secretary

After the poorly attended Tulsa rally, Kayleigh McEnany had to address the remarks Donald Trump made during the event as well as TikTok's involvement with it. And the result was a fumbled mess of awkwardness. In part, Trump said during his Tulsa event that if the United States simply stopped testing for COVID-19, there would be fewer cases and therefore better numbers — of course, that's not how it works. But nevertheless, McEnany had to address the comments the following Monday and said, in part, that Trump was trying to bate the media during his off-the-cuff remarks.

"The president was trying to expose what the media oftentimes does is they ignore the fact that the United States has more cases because we have more testing. We are leading the world in testing, and he was pointing that out that it's a fact that the media readily ignores," McEnany said. "Any suggestion that testing has been curtailed is not rooted in fact [and] it was a comment that he made in jest," the then-press secretary also told the press.

As The Washington Post pointed out, McEnany's use of "Trump was just joking" was a tactic that her predecessor, Sarah Huckabee Sanders, also used as an attempt to explain her boss' comments. 

Kayleigh McEnany's text message to Sean Hannity came to light

While former press secretary Kayleigh McEnany has made a consistent presence on Fox News as an on-air contributor, it was her on-camera appearance amid the January 6 House select committee hearings in 2022 that has made more of a splash. A letter sent to McEnany by the committee in November — informing her that she had been subpoenaed and would be required to testify and provide records — noted that she made "multiple public statements from the White House and elsewhere about purported fraud," thus requiring her testimony in front of the panel.

"You were with former president Trump when he traveled to the Ellipse and spoke at the Stop the Steal rally, and popped in and out to join Mr. Trump as he watched the attack on the U.S. Capitol later that afternoon," the committee wrote, concluding that her involvement on the day was "within the scope" of the committee's investigation.

McEnany did cooperate with the subpoena and appeared before the panel, and awkward truths were laid bare. It was revealed that Fox News' Sean Hannity texted McEnany the day after the riot, saying, "Key now, no more crazy people ... No more stolen election talk ... Yes, impeachment and 25th amendment are real, and many people will quit" (via New York Magazine). McEnany's reply? In part, she wrote, "Love that. That's the playbook."