As a college student, McEnany interned for several politicians, including
Tom Gallagher,
Adam Putnam and
George W. Bush, and later worked in the
White House Office of Communications, where she wrote media briefings. In early 2015, before becoming a Trump supporter, McEnany was highly critical of him, declaring on CNN and
Fox Business that "Donald Trump has shown himself to be a showman" and it was "unfortunate" and "inauthentic" to call him a Republican. McEnany called his comments about Mexican immigrants "racist". According to Michael Marcantonio, a fellow summer associate at a law firm, she began supporting Trump after accepting Marcantonio's advice, which he gave to her over cocktails. In an interview with the New York Times, Marcantonio recalled telling McEnany, "Donald Trump is going to be your nominee," and that if "a smart, young, blond Harvard graduate" wanted "to get on television and have a career as a political pundit, you would be wise to be an early backer." On August 5, 2017, McEnany left her position at CNN. The following day, she hosted a 90-second webcast,
Real News Update on Trump's personal
Facebook page. She praised Trump throughout the segment, saying she had brought the "real news" to the American people. Former employer
Mike Huckabee has called her a "meticulous researcher" and "extraordinarily prepared." Her rapid occupational success was noted by
Van Jones, who worked with her at CNN: "I'm not trying to defend the messaging, but what I hope people can acknowledge is there's very few people in either party who can accomplish what Kayleigh has accomplished in such a short time... People keep taking her lightly, and they keep regretting it." In 2012, McEnany tweeted about Obama's half-brother
Malik Obama, who lives in
Kenya: "How I Met Your Brother – Never mind, forgot he's still in that hut in Kenya". On August 7, 2017, the
Republican National Committee (RNC) appointed McEnany as its national spokesperson. In 2017, as RNC spokeswoman, McEnany supported Trump amid a bipartisan backlash in response to his comments about a
white supremacist rally in
Charlottesville, Virginia, in which he suggested that
white supremacists and
anti-racist counterprotesters shared blame for violence; in a tweet, McEnany wrote that the Republican Party supported Trump's "message of love and inclusiveness." In August 2019, after
The Washington Post reported that Trump had made 16,241 false or misleading statements in his first three years in office, McEnany told CNN's
Chris Cuomo: "I don't believe the president has lied." In the weeks before her appointment as White House press secretary, McEnany praised Trump's handling of the
COVID-19 pandemic, saying, "This president will always put America first, he will always protect American citizens. We will not see diseases like the coronavirus come here, we will not see terrorism, and isn't that refreshing when contrasting it with the awful presidency of Barack Obama?" The disease had been present in the United States for at least a month prior to McEnany's claim that the virus would not "come here"; in December 2020
Politico named McEnany's prediction one of "the most audacious, confident and spectacularly incorrect prognostications about the year". In March 2020, McEnany said Democrats were trying "to politicize" the coronavirus and that Democrats were almost "rooting for this outcome."
Stephanie Grisham, who had served in the role and as
White House communications director since June 2019, became
First Lady Melania Trump's chief of staff and spokesperson. Two months into her tenure, the
Associated Press wrote of McEnany, she "has made clear from her first briefing that she's willing to defend her boss's view of himself as well as his most flagrant misstatements." In April 2020, McEnany defended Trump's assertion that the
World Health Organization had shown a "clear bias towards China" and said that the WHO put Americans at risk by "repeating
inaccurate claims peddled by China during the coronavirus pandemic" and "opposing the United States' life-saving travel restrictions."
Donald Trump in September 2020|alt=A 74-year-old man to the left and a 33-year-old woman to the right, both walking towards something to the left of the camera. On May 1, 2020, as part of her first public press briefing and the first one by a White House press secretary in 417 days, McEnany was asked by an Associated Press reporter: "Will you pledge to never lie to us from that podium?" McEnany replied: "I will never lie to you. You have my word on that." McEnany falsely claimed that the
Mueller Report as part of the larger investigation into
Russian meddling in the 2016 Presidential election had resulted in a "complete and total exoneration of President Trump," despite the report reading "Accordingly, while this report does not conclude that the President committed a crime, it also does not exonerate him." Amid reports on May 8, 2020, that the White House was "shelving" the release of COVID-19 re-opening guidelines, McEnany said that the guidelines had not been approved by
Robert Redfield, the director of the
Centers for Disease Control and Prevention (CDC). Following Associated Press reports that Redfield had previously cleared the release of the guidance, Redfield addressed the issue personally, saying that the documents were still in "draft form" and had been released for "interagency review", not for public dissemination. That same week, Obama, in a private phone call with members of his former administration, described the Trump administration's response to the coronavirus crisis as "an absolute chaotic disaster". McEnany responded the next day by providing a statement to CNN claiming that, to the contrary, the "response has been unprecedented and saved American lives." In May 2020, McEnany defended Trump's false accusation that
Joe Scarborough had a person murdered, offering no evidence in support of the accusation. The same month, McEnany defended claims that Trump made about the dangers of
vote by mail, repeating his inaccurate claims that vote by mail has a "high propensity for voter fraud." McEnany herself has voted by mail 11 times in 10 years. In June 2020, she defended the
Trump administration's decision to forcibly remove peaceful protestors using smoke canisters, pepper balls, riot shields, batons, officers on horseback and
rubber bullets so that Trump could stage a photo op in front of
St. John's Episcopal Church in Washington. She likened Trump's action to that of
Winston Churchill walking the streets to survey bomb damage during World War II. When General
Jim Mattis, former
secretary of defense in the Trump administration, condemned Trump's action, McEnany described Mattis' comments as "little more than a self-promotional stunt to appease the DC elite." On September 9, 2020, news agencies released the audio recordings of interviews with Trump that former
Washington Post journalist
Bob Woodward had conducted in February and March 2020 for his book
Rage, in which Trump acknowledged to Woodward that he was intentionally downplaying the severity of the
SARS-CoV-2 coronavirus, which CNN had obtained ahead of the book's September 15, 2020 release. In the wake of this development, McEnany falsely asserted, "The president never downplayed the virus." In fact, Trump repeatedly and publicly downplayed the risk of the virus and the severity of the pandemic, and in a recorded March 19, 2020 interview with Woodward said, "I wanted to always play it down. I still like playing it down, because I don't want to create a panic." while
Joe Lockhart, who served as White House Press Secretary during the Clinton administration, wrote her answers confirmed her as a "state propagandist". On October 5, 2020, McEnany tested positive for
COVID-19. Even though she had interacted with individuals who had been diagnosed with coronavirus days prior, McEnany on several occasions spoke with the press while not wearing a mask before she ultimately tested positive for the coronavirus. the cousin of McEnany's husband.
2020 presidential election and aftermath While ballots were still being counted on election day, McEnany made an early false declaration of victory for Trump. After
Joe Biden won the election and Trump refused to concede, McEnany spread
false claims of fraud in the 2020 election. On November 20, 2020, McEnany falsely claimed Trump was not given an "
orderly transition of power". Previously in 2016, within two days of Trump's victory, his opponent
Hillary Clinton conceded to Trump, while then-President
Barack Obama had recognized Trump as president-elect and hosted him at the White House. Trump himself thanked Obama and his wife
Michelle "for their gracious aid throughout this transition". Trump fired the leader of his transition team (
Chris Christie), threw out months of transition planning, and rejected help from the
Obama administration. McEnany's comment was stated while Trump himself was refusing to recognize Biden's victory as legitimate; Trump was also actively delaying the start of a transfer of power to president-elect Biden for two weeks. Following the
2021 storming of the United States Capitol,
Randall Lane, writing for
Forbes, warned corporations against hiring McEnany or other people "who lied for Trump", stating that "
Forbes will assume that everything your company or firm talks about is a lie. We're going to scrutinize, double-check, investigate with the same skepticism we'd approach a Trump tweet. Want to ensure the world's biggest business media brand approaches you as a potential funnel of disinformation? Then hire away."
Later career On March 2, 2021, McEnany joined Fox News as an on-air contributor. She was later named co-host of
Outnumbered, alongside
Harris Faulkner and
Emily Compagno. In May and June 2023, she served as an interim host of
Fox News Tonight following the firing of
Tucker Carlson. In May, in response to McEnany claiming that Trump's then primary rival Florida Governor
Ron DeSantis was gaining on Trump in the polls for the Iowa primary, Trump called her “Kayleigh Milktoast McEnany”, an insult likely a misspelling of the word
milquetoast. In September 2025, Fox News announced that McEnany was named host of a new Saturday morning program called
Saturday in America with Kayleigh McEnany airing from 10am-12pm every Saturday morning beginning on September 20. ==Personal life==