How could these snowflakes be capable of such cruelty, you wonder.
In reality, McEnany wasn’t exactly a pariah on campus. Talking to some of her classmates, one gets a picture of a right-wing version of Elle Woods, a would-be TV star bouncing into class in full makeup while everyone else was in sweats. “Whenever she spoke it was like, Are we on TV? Are there cameras here?” says a student from her American Jury class. “It felt like Fox News was happening.””
“There’s an air of likability about her, of sociability,” says Charles Nesson, who teaches the class, which encourages, as he puts it, “civil discourse” among students. While McEnany’s views were definitely conservative, “I found her to be quite open-minded,” he went on, recalling a surprisingly sensitive paper she wrote about Ras Iyah V, the Rastafarian ganja advocate and human rights defender. “She started out very unfamiliar and opposed and then finally came around.”
“She’s an incredibly sweet person,” says one friend from her summer-associate program at the New York law firm Kirkland & Ellis. “You would never know that she’s a Republican firebrand.”
But McEnany didn’t make a lot of friends in the program, the friend says, probably due to her politics.“At lunch she would be like, reading Scalia’s dissent on DACA and like highlighting passages.” Kirkland & Ellis isn’t exactly liberal—one of its partners is former Bush administration official Jay Lefkowitz. But McEnany’s peers found her particular brand of conservatism difficult to swallow.
“It was kind of like, you hold morally abhorrent beliefs. You think gay marriage is like a sin. You think women should be back in the closet. You’re not really going to be hanging out with someone like that if you are from New Jersey or New York and a normal person.” Although McEnany was studious and focussed, few expected McEnany to stick with law once she landed a steady gig moonlighting as a conservative commentator on CNN.
McEnany had been on the fence about Trump. “I don’t think he’s a serious candidate,” she said in 2015.
As time went on and it became clearer that Trump was going to be the nominee, McEnany came around. “I find him very distasteful,” another friend from Harvard said, “and I remember her being like, ‘Why?’ She would ask what my parents thought.”
“Let’s talk about something else,” the friend would say eventually. “Let’s talk about The Bachelor.”
In the summer of 2015, the Kirkland & Ellis associate class went on a field trip to one of the partner’s mansions in the Hamptons. “[Kayleigh] wasn’t there. She had to go on CNN that day,” recalls the friend from the program, who pulled out their phone to watch the segment on the bus. “All of a sudden she’s full MAGA.”
It was a visit home and to Bell Shoals Church that seemed to convince her, according to McEnany’s book. In a sermon, the pastor had urged the congregation to vote “based on policies, not personalities.” For Christian voters, he counseled, two things mattered most: “The sanctity of human life and religious liberty.”
While some of the things McEnany said on air were head-spinning (“He was on the cutting edge of civil rights when at Mar-a-Lago,” she informed two Black panelists, of Trump), she kept her personability on air, and occasionally, reasonable discussions were had. “A racist statement is a racist statement,” she agreed, of Trump’s comments about Mexican immigrants. “She’s a good person with a wonderful heart of gold,” one of her sparring partners told me back then. They no longer speak.
McEnany’s book devotes a sizable amount of space to election night 2016, her delight in the results, and the stupefaction of her panelist peers. While she is kind to her colleagues, it’s clear she sees the network that helped elevate her as yet another venue for her unfair persecution at the hands of snowflake liberals. A place, she writes, where she was “continually rebuked” and condescended to, perhaps even brainwashed: “For about the first four weeks of the election, I was watching CNN, and I was naively believing some of the headlines that I saw on CNN,” she told reporters when asked about her early criticism of Trump, whom she has since compared to Abraham Lincoln and Winston Churchill. She also recently took back a 2015 description of Joe Biden as “a man of the people,” alleging that he has since become “an empty vessel for the liberal elites and far left.”
In the days leading up to the election, McEnany’s Twitter feed had grown more spiritual, Bible verse alternating with attacks on critics, and the comment oddly echoed a verse from Christian music group Hillsong she’d posted days before: “Make me Your vessel / Make me an offering / Make me whatever You want me to be.” If there were any doubt about whose vessel she was, that was made clear on November 4, when she preemptively tweeted that Trump had claimed “VICTORY” in Pennsylvania. The social media platform flagged it, but this time it didn’t block her. Kayleigh McEnany would live to tweet again.
More Great Stories From Vanity Fair
— Progressives Are Going Rogue to Flip Pennsylvania for Biden
— Cover Story: AOC’s Next Four Years
— Why Anti–Trump Attack Ads Might Actually Be Helping Him
— Tax Mess Aside, Can Trump Pay Off His $1 Billion in Debt?
— News Media Begins to Contemplate a Post–Trump White House
— The Kimberly Guilfoyle Sexual Harassment Allegations Get Even Darker
— As Trump Falters, Democrats See an Expanding 2020 Senate Map
— From the Archive: Inside Trump’s Twisted, Epic Battle for Mar-a-Lago
— Not a subscriber? Join Vanity Fair to receive full access to VF.com and the complete online archive now.