The Temptation of Kayleigh McEnany
How an ardent defender of faith—and Donald Trump—came to think of the press as her enemy
Kayleigh McEnany marched past a graffiti-covered wall and black metal security barriers, her signature cross necklace dangling above her double-breasted navy blazer. She watched as President Donald Trump held a Bible aloft in front of St. John’s Episcopal Church. When he turned to her and pointed, she scooted into the frame, taking her place by his side with her phone clutched behind her back. Stately white corbels framed the plywood-covered windows and door of the building, where a fire had been set in the nursery the night before. McEnany, Trump, and a handful of other administration officials stood silently, sentries ready to defend the church from the next attack. Cameras clicked away.
Later that week, McEnany compared the moment to Winston Churchill inspecting bomb-damaged London during World War II. “For this president, it was powerful and important to send a message that the rioters, the looters, the anarchists—they will not prevail,” McEnany told reporters during a briefing. “Burning churches are not what America’s about.” Trump had reached St. John’s only after police forcibly cleared protesters from Lafayette Square, using horses, smoke, flash-bang grenades, and chemical agents. The gesture, McEnany maintained, showed the American people “that we will get through this through unity and through faith.”
This is the central promise of the Trump administration: Real Americans—especially conservative people of faith—are under siege, and the president will defend them. Trump officials act as a roving band of apostles, evangelizing this message. Attorney General William Barr dedicated a speech at Notre Dame to detailing “the steady erosion of our traditional Judeo-Christian moral system and a comprehensive effort to drive it from the public square.” Vice President Mike Pence told a graduating class at Liberty University to prepare to be “shunned or ridiculed for defending the teachings of the Bible.” Brad Parscale, the 2020 Trump campaign manager, tweeted that “only God could deliver such a savior to our nation,” along with a gauzy black-and-white photo of a Trump rally.
McEnany is a skillful steward of the covenant between the president and his religious supporters, openly suggesting that reporters stand among America’s enemies, no matter how much that may beggar belief. “Boy,” McEnany recently said to reporters who were questioning Trump’s support for reopening churches during the coronavirus pandemic. “It’s interesting to be in a room that desperately wants to see these churches and houses of worship stay closed.” Jeff Mason, a Reuters correspondent, spoke up from behind his face mask. “Kayleigh, I object to that. I mean, I go to church. I’m dying to go back to church,” he said. “The question that we’re asking you … is: Is it safe?”
This kind of press-secretary-versus-the-press tiff is not new. White House briefings have always been a stylized and, at times, sadistic form of theater. Mike McCurry, one of the inspirations for Veep’s Mike McLintock, harangued reporters for sniffing out allegations about Bill Clinton’s sexual misconduct. Jay Carney liked to imply that the press was weaponizing bigoted stereotypes against Barack Obama. Although her pre-Trump predecessors didn’t call the press “fake news” or get asked to defend the president when he uses racist terms such as kung flu, McEnany’s relationship with the media has some of these same symbiotic qualities: Her combativeness makes for spirited prime-time television, and reporters’ relentless questioning tees up dramatic YouTube clips of McEnany defending the president. She is as much a creature of Washington as her opponents: She spent the better part of the past decade mastering the immense D.C. ecosystem of Both Sides debate, and she’s managed to win many grudging admirers and friends in greenrooms up and down the Acela corridor. In the months before the 2016 election, she filled a niche on CNN, speaking on behalf of Trump supporters. Although on-air arguments with her could be fierce, several of her fellow contributors described off-set conversations with McEnany as cordial, like rival players for the Yankees and Red Sox chatting amiably after a game. “You can do a lot worse than Kayleigh McEnany,” Paul Begala, one of the orchestrators of Clinton’s 1992 presidential campaign and himself a cable-news pundit, told me. “She’s terribly smart.”
If press briefings are theater, McEnany’s first couple of months as White House press secretary represent a new height of the form. Since first launching his presidential bid five years ago, Trump has at times aimed his Twitter fire at targets who might otherwise be seen as allies of Christian America, whether calling a prominent Southern Baptist leader “a nasty guy with no heart!” or defending police who violently shoved a 75-year-old supporter of the Catholic Worker Movement to the ground. No matter what her boss says, McEnany is there to explain how he is standing up for his embattled base. She is able to do this job because of the strength of her conviction: Trump, she seems to believe, stands for religious freedom and the open exchange of ideas in a time when those principles are under attack. And she has spent years training for this call.
McEnany began her life as an evangelist among the masses. “KMac,” as she was called, stood out as a Protestant at the Academy of the Holy Names, a Catholic girls’ school in Tampa, Florida, choosing to write about Jesus, whom she called “my hero,” for a sixth-grade poetry assignment: “I shout his name,” McEnany wrote, “for he is king.” She grew up in a conservative Republican household in nearby Plant City, and her father operates a roofing business. McEnany was uncommonly interested in politics, and her passion seems to have run in the family: Kayleigh’s younger sister, Ryann, works for the Trump campaign. In school, the elder McEnany adored George W. Bush because he loved Jesus and was a cheerleader just like her, one former classmate told me. She was involved in the school’s debate club and had a streak of what you might call the debate-kid mentality: She was constantly talking about issues such as partial-birth abortion in far more vivid terms than her largely conservative and religious classmates were, former classmates told me. (McEnany declined interview requests for this article.)
McEnany’s friends from her undergraduate years at Georgetown University remember her as focused and studious, with occasional breaks to hype Peyton Manning at Colts watch parties and intern in the White House Office of Media Affairs in the waning days of the Bush administration. By the time McEnany began a study-abroad program at the University of Oxford in the fall of 2008, she was already developing her chops as an amateur newshound. Yuliya Orlova, one of her closest friends from that time, told me McEnany would tote a giant camera around campus, crashing parties and doing short segments for a site that featured student reporting. Occasionally, Orlova said, McEnany might “get a little bit hyper at a party” and start lecturing about Obama’s ascent and the threat of terrorism, but it was more performative fun than anything. In her 2018 book, The New American Revolution, McEnany writes that she supplemented her school curriculum with the work of conservatives such as Laura Ingraham, Sean Hannity, and Mark Levin. According to Orlova, McEnany joked that she often fell asleep listening to Rush Limbaugh.
McEnany has told the story of this time in her life as one of becoming firm in her faith and beliefs. But it was also a taste of being part of an oppositional minority. “When peers challenged the intellectual foundation for my faith” at Oxford, she recently wrote on Twitter, the late Christian pastor Ravi Zacharias “was the usher between the heart & the mind.” Her admiration for Zacharias mirrored her desire to study at elite universities: He was “someone who, from an academic place, as an apologist, could equip you with those arguments where you didn’t have to check your brain at the door when you became a Christian, where there is intellectual foundation for everything we believe,” she said in a recent interview. McEnany wanted to be prepared to defend the hope she found in the story of Christ, no matter how aggressively she was questioned by her peers.
During a visit to Fox News around this time, her potential talent piqued the interest of Alan Colmes, then Sean Hannity’s liberal antagonist on the program Hannity & Colmes. Colmes’s mentorship led McEnany to an internship on his show. The two would have fierce political debates, and he appreciated her for it. Later, he cheered her on from afar as she faced combative panels on CNN. McEnany had discovered the secret to ascending the cable-news ranks in Washington: The most employable people are those who are able to bring a fierce argument without completely alienating everyone around them.
While working as a producer for former Arkansas Governor Mike Huckabee’s Fox News show in the couple of years after her 2010 college graduation, McEnany posted assiduously on her now-defunct blog, which bore the tagline Defending Reagan Conservatism. Her reading recommendations favored those of the business-class lounge—“The Economist is my absolute favorite publication hands down”—and her political commentary was suffused with an air of righteousness: “Being enveloped in sexual controversy speaks volumes to one’s character,” she wrote of former New York Representative Anthony Weiner. Her attempts at hashtag humor occasionally shaded into Trump-style birtherism: “How I Met Your Brother—Never mind, forgot he’s still in that hut in Kenya. #ObamaTVshows,” she wrote in 2012. Many of her fellow politically minded 20-somethings skipped Sunday services, but McEnany remained devout. “I’m heading to church. Need to hear from God today!” she tweeted in 2013, followed by the hashtag #tcot, for “top conservatives on Twitter.”
Elie Mystal, a writer at the progressive magazine The Nation, remembers sparring with McEnany over abortion, religious freedom, and the Supreme Court before his appearances on Huckabee. “We disagreed, but we disagreed honorably,” he told me. Several years later, when McEnany was in law school, it was her acquaintance with Mystal that led to her position at Above the Law, a prominent legal blog where Mystal was writing at the time. In his telling, McEnany filled the token conservative slot for the mostly liberal website, which Mystal described in unflattering terms: “You’re looking at what makes clicks. And being crazy is going to get you clicks.” And yet, he added, McEnany came off as a true believer in her arguments. She was not “simply doing it for show or money or power. There is a core belief there that gives her authenticity in what she does.” She was building her career, and benefited from the credential. But the liberals at Above the Law needed her as much as she needed them.
Within a year after McEnany graduated from Georgetown, she was getting booked for television segments as a free-wheeling conservative Millennial voice. Her early hits were lowest-common-denominator television: She went on Fox News’s Red Eye, the only woman on a panel full of dudes, and dutifully explained why men are commitment-phobes. “I can barely find a guy to go on a date with me, much less marry me,” she said. “I’ll have to pay someone to get down on one knee one day.” When it became clear that she wasn’t going to get an on-air job at Fox, as Huckabee recently told The New York Times, McEnany started law school at the University of Miami, where she earned a scholarship reserved for the top 1 percent of her class. In an interview for the school’s website, she described always being ready for calls from bookers, who constantly scour news outlets, blogs, and Twitter for people who speak smoothly and handle themselves well on air: “If being on the show does not interfere with class or studying, I say yes and quickly head to my car to grab a change of clothes,” McEnany said.
By the time she transferred to Harvard for her second year of law school, she was a minor cable-news celebrity, earning slots on big-time shows such as The View. Despite these early successes, though, friends from Harvard described McEnany as down-to-earth. “I think you just met a famous person,” a friend told Alene Anello, a liberal, atheist animal-rights activist, the first time she met McEnany. “I felt shocked because Kayleigh hadn’t acted like a famous person,” Anello wrote me in an email. “She had been warm. She had made me feel important.” When the two would grab meals together, McEnany always chose a vegetarian meal, Anello said, and she never pushed her religious views. McEnany always stuck out at her predominantly Asian church near Harvard’s campus, a friend told me, and often stayed up late reading her Bible when she was going through hard times. She was periodically asked to defend the perspective of conservative Christians on television, including after the Supreme Court legalized same-sex marriage in 2015. “There’s going to be an infringement upon [religious liberty] because of what came out of the Supreme Court,” she said on the HLN show Dr. Drew on Call.
But CNN, with its liberal-tilted panels and dramatic sparring between guests and hosts, was where she thrived. From her earliest days on the network, McEnany excelled at providing a well-argued conservative perspective with a smile. And yet when I texted a former producer for CNN Tonight With Don Lemon, Julie Zann, about how McEnany started getting booked on the show, Zann immediately replied, “Omg. What should I say??” presumably intending to text someone else. In retrospect, a former producer at CNN told me, it doesn't seem likely that the network would make a hire like that again. (Zann declined to comment on the text message.)
When McEnany started making regular appearances on CNN in 2015, she was not yet enamored of Trump. “Hey, I don’t want to claim this guy,” she said during a segment in June of that year. “Donald Trump, if we’re going to be honest, is a progressive.” She condemned his comments about Mexican immigrants being “rapists” and said he was “the last person” who would be able to bring voters into the GOP fold. But within a few months, she had shifted her views and turned to defending him, and by the first primary contests, in early 2016, she was committed. McEnany’s critics, including some fellow conservatives on CNN, point to this change as evidence of hypocrisy and opportunism: “I used to put this pathetic dishonest sycophant in her place every time we were on CNN together in 2016,” tweeted Tara Setmayer, a Never Trumper who served as communications director for the former Republican Representative Dana Rohrabacher. Friends from Harvard, where McEnany was in her third year of law school at the time, remember things differently: Like every other conservative student on campus during the months before the 2016 primaries began, McEnany was deliberating among candidates. One factor in particular drew McEnany to Trump, one of her close friends told me: She believed he was constantly being misrepresented in the media. “It was at Harvard Law School, when I felt attacked as a conservative and as a Christian, that I realized it was that megaphone and that kind of boldness we needed, and that kind of fighter we needed, to represent the Christian community,” McEnany said in a recent interview with the Christian Broadcasting Network, describing the president. Especially as Trump began to court religious conservatives, his air of embattlement was a major part of his appeal.
Meanwhile, national television networks were struggling with a dearth of pro-Trump voices, Mary Katharine Ham, a conservative CNN contributor (and occasional Atlantic writer), told me. McEnany was adept at providing CNN producers with that ideological voice, which was in the minority even among conservative commentators at the network. “Trump is a figure who can make it hard to defend him. If you are good at doing that, and you give voice to a bunch of voters who deserve a voice, your value goes up,” Ham said. As Trump’s campaign gained momentum, self-declared Never-Trump conservatives started getting less time on air. Some of the network’s seasoned conservatives were incensed by McEnany’s inexperience and willingness to defend Trump. “She just popped up on CNN and we were informed she speaks for conservatives there,” Ben Howe, a former Tea Party activist who has appeared on CNN, told me in a text. Some of McEnany’s best allies were also her political opponents. Van Jones, a former Obama-administration official, made common cause the first time they met, according to her book: “I love your cross,” he called out from across the greenroom.
McEnany became a regular fixture on CNN’s top prime-time shows, including CNN Tonight, Anderson Cooper 360, and The Lead With Jake Tapper. “I find her to be a useful counter to all of our intellectual bubble,” Ham told me. While McEnany always stayed polite, several contributors and past producers told me, she was able to deliver tension and conflict; the phrase good television came up in several of my conversations. McEnany’s segments became “kind of like political Jerry Springer,” said one contributor, who asked not to be named out of fear of professional repercussions. Ratings soared.
As 2016 wore on, however, some at CNN lost patience with McEnany’s commitment to defending Trump regardless of what he said or did. A month before the election, after The Washington Post reported on comments Trump had made while filming an episode of Access Hollywood about grabbing women “by the pussy” without their consent, McEnany joined a panel hosted by Tapper ahead of the second presidential debate. “On Friday, a tape was revealed with Donald Trump saying—boasting—about sexually assaulting women. Fact,” Tapper said. “It’s been denounced by Mike Pence and Melania Trump, to name two people. Is your passion for the victims of sexual assault—does it extend to whomever Donald Trump grabbed by the P-word?” McEnany pushed back. “We don’t have proof that Donald Trump acted in that way. There’s one person out of both of these families who has been accused of sexual assault in a court of law. One. And that is Bill Clinton.” The conversation devolved into chaos: Other panelists tried to jump in, and Tapper attempted to intervene. “Talking over me doesn’t make what you’re saying true,” he said to McEnany, prompting loud oohs from the audience. A producer from Tapper’s show said the program is committed to booking ideologically diverse voices, including Trump supporters. But when they start lying or “defending the indefensible,” people stop getting booked. This exchange was the moment, the producer said, when McEnany crossed a line.
It also may have been the best possible audition tape for her next job. McEnany stuck around CNN through Trump’s inauguration and into the first summer of his presidency before formally joining Trump’s team. She started hosting a “real news” update on social media, touting Trump’s accomplishments. She quickly climbed the ranks of Trumpworld, serving as spokesperson for the Republican National Committee, then for the Trump campaign, where she led weekly Bible studies. On April 7, 2020, she received her official post at the White House. Now when she appeared on CNN, she was cast as a bête noire: no longer part of the family of contributors, but fully available for pillorying.
Last summer, Chris Cuomo brought McEnany on his show for a segment with Jennifer Granholm, the former governor of Michigan, after Trump said that a group of progressive congresswomen should “go back” to the “totally broken and crime infested places from which they came.” As the women yelled over each other, Cuomo wore a satisfied smirk. “Continue the banter,” he said, gesturing like an orchestra conductor. A month later, as Cuomo repeatedly demanded in a different segment that McEnany admit Trump has lied to the American people, she looked defeated.“The fake-news media lies,” she said, over and over. “I don’t need any prizes from the fake-news media.”
On a recent Tuesday afternoon, McEnany, in a blazer of bubblegum pink, took a stroll near the White House with David Brody, the chief political analyst for the Christian Broadcasting Network. The two stood bracingly close for pandemic times, neither wearing a mask, smiling and chatting. “You’ve been called a lot of names out there,” Brody said to McEnany during their sit-down interview. “They’re calling you a liar already; they’re calling you other names: racist and birther and all that type of stuff.” McEnany didn’t hesitate, the debate kid ready with her answer. “I stand as a Christian woman, someone who believes in equality and truth and loyalty and honesty,” she said. “It’s the values that I’ve lived by my whole life. It’s the values I’ll continue to live by.”
This is the role in which Christians are cast in the Trump administration: that of victim and fighter, of the steadfast believer in a city of cynics. Every modern president, along with the large majority of Supreme Court justices and members of Congress, has identified as Christian. And yet in polls, white evangelicals say that Christians face more discrimination than Muslims, who compose just 1 percent of the population and tend to be ethnic minorities. McEnany, like Mike Pence and Sarah Huckabee Sanders before her, is an emissary to the evangelical world at a time when the president seems to need its backing more than ever: A recent poll showed that just 27 percent of registered voters believe Trump is religious. Like other vocal Christians in the Trump administration, McEnany is eager to show her battle wounds and vouch for Trump’s Christian bona fides. “This country needed someone to fight for life, to fight for religious liberty,” McEnany told Brody. “And I believe that President Trump was that person, and he’s done that. There’s just so much that he’s done to fight for the Christian community.” Although she’s been in the press-secretary job for only a couple of months, McEnany is well on her way to a coveted spot in the Trumpworld pantheon. The president has retweeted several memes celebrating his newest champion: McEnany wearing sunglasses and smoking something that looks suspiciously like a joint at the briefing-room lectern; McEnany, arms akimbo in a Superwoman suit, as she calls on members of the press. “Doing a GREAT job!” the president wrote.
McEnany’s role in the Trump administration played differently on the Facebook page of her alma mater, the Academy of the Holy Names. When the school announced her promotion to press secretary, a debate broke out in the comments over whether the academy should be congratulating her at all. Some classmates expressed confusion about how their Christian education aligns with the vision of politics she promotes. While several of her peers defended her achievement in becoming press secretary, even one of McEnany’s former teachers conveyed disappointment in how she has done so: “We taught that truth was not expediency but was the touchstone of relationships,” the teacher wrote. “Much of the rhetoric I have read and interviews I have seen when she was a commentator on television show how far from [the academy’s] values she now espouses. This saddens me.”
Of all the criticism McEnany has received, accusations that she has betrayed Christian teachings seem to be the only ones that bother her, perhaps because her faith is so personal. She and her husband, the Tampa Bay Rays pitcher Sean Gilmartin, had a baby girl, Blake, just a few months before McEnany took the press-secretary job. Between bringing Blake to visit the White House and posing her in a bright-red “KEEP NH GREAT” Trump cap, McEnany is intent on raising her daughter as a Christian: “If I give Blake the same faith upbringing and relationship with Jesus Christ that my parents gave me, she will be an unstoppable woman of faith in whatever she decides to do,” she recently told CBN. McEnany wrote in her book that she was upset when a CNN viewer suggested she should tuck in her cross necklace “when showing support for someone who goes against so many things that the Bible teaches.” She knows that no one is perfect, including politicians, she wrote. She bears her cross because she believes that it represents how “humanity might have a chance at a salvation that we do not deserve.”
And the Trump administration has given the press a crusade of its own. Trump has never stood for all Christians, but the media has also never been that curious about why Christians might support him. By now, the only story most of the media want to tell about the 81 percent of white evangelicals who voted for Trump in 2016 is one of betrayal and bad faith. As Mystal, the Nation writer, put it, “The Christian values that [McEnany] claimed to stand for and fight for were worth nothing to her when power and victory were on the table.” When McEnany takes the podium, or poses with the president before a boarded-up church, or defends Americans’ right to pray, she knows the press will go on the attack. She is peaceful in her faith. Their derision is her strength.
But even fighters get to rest every once in a while. As McEnany sat with Brody and spoke to Christian viewers, she let herself be just a little vulnerable about her sacrifices for her boss. “People will malign you. It comes with the job,” McEnany said. “But I know who I’m ultimately working for, and it’s the big guy upstairs.” Her cross necklace glittered just above her collar, and she pointed up.