It had taken months of practice, but McEnany had perfected her act as one of the original pro-Trump pundits on CNN. She described herself as “that blond girl passionately advocating for then candidate Donald Trump proudly wearing my gold cross” in her 2018 book.
Now, her rise to President Trump’s next press secretary — at 31, among the youngest to ever to hold the position — turns her Trump defender role on cable news into an official White House position. She is replacing a camera-shy Stephanie Grisham, who did not hold a single press briefing during her nine-month tenure. McEnany, by contrast, loves a camera, and vice versa — with the glossy looks of a cable host, an appealing quality for a boss known to assess the telegenics of his appointees.
But it was a network the president purports to hate that made McEnany everything he would want in a press secretary. For over two years, CNN paid her to come to fight with other commentators over Trump, opportunities she took night after night. Before then, she was a virtual unknown.
“She auditioned on our air for this gig,” said an executive at the network who was not authorized to comment publicly and spoke on the condition of anonymity.
Many of her appearances devolved into shouting matches captured and monetized in countless videos described by the network’s YouTube page as “CNN commentators clash.” She clashed with other commentators over Trump’s support from white supremacists: “He’s not going to be baited into these traps you are trying to lay for him,” she said. She clashed over Stephen K. Bannon’s appointment as his chief strategist. Over polling data.
When Trump retweeted a doctored video that showed him body-slamming a WWE fighter with the CNN logo superimposed on it, McEnany defended him again: “It was just a joke.”
McEnany never apologized or conceded a point, a sensibility that she shared with Trump — and that put her on his radar.
“Outnumbered 8-to-1, or if she was lucky, 7-to-2, Kayleigh never backed down in fighting for the conservative movement supporting Donald Trump,” Sean Hannity wrote in his forward to her book, “The New American Revolution: The Making of a Populist Movement.”
“The thing that is amazing about her is that she manages to defend incredibly gross and disgusting behavior without seeming gross and disgusting,” said Sally Kohn, a liberal pundit and frequent Trump critic who appeared alongside McEnany as a CNN contributor.
McEnany was one of CNN President Jeff Zucker’s early experiments in assembling crowded panels with a mix of political views. They created the model for a pro-Trump cable news pundit, which has become a well-worn path to the White House.
Zucker, who has been pilloried for his role in airing live campaign rallies and promoting other political spectacles that some say helped Trump become president, saw McEnany and the other pundits on his channel as characters in a drama.
“Everybody says, ‘Oh, I can’t believe you have Jeffrey Lord or Kayleigh McEnany,’ but you know what?” Zucker told the New York Times in 2017. “They know who Jeffrey Lord and Kayleigh McEnany are.”
Liberal commentator Van Jones snapped at McEnany on election night in 2016 as images of anti-Trump protesters filled the CNN broadcast, telling her: “You need to back off. You need to have a little bit of empathy and understanding for people who are afraid because your candidate has been one of the most explosively, provocative candidates in the history of our country, and there is a price to be paid for that.”
But she and Jones often praise each other and their friendship.
“She was an extraordinarily bright and effective co-panelist during the 2016 election when it was frankly very hard to find super-talented people in the media who wanted to be on Team Trump,” Jones said in an interview.
A Tampa native, McEnany has often played up her roots, saying she grew up “in the world’s strawberry capital” listening to Rush Limbaugh in her dad’s truck.
McEnany began her journey through politics and punditry as a high school student when she volunteered for the 2004 Bush-Cheney campaign, followed by an internship in the Bush White House while attending Georgetown University. Later, she transferred from University of Miami School of Law to Harvard Law — all the while pursuing a television role, making appearances between classes.
As a young conservative woman, she was a coveted figure for television bookers. One appearance led to the next. An internship for “Hannity & Colmes” turned into a job at Fox News as a booker with “The Mike Huckabee Show.”
One of her first gigs at CNN was as a panelist on the short-lived political panel show “(Get To) The Point,” where she argued against teachers unions and gun control.
Before McEnany was a known Trump booster on CNN, she was, along with most of the Republican Party, dismissing him. In a June 2015 appearance on Don Lemon’s CNN show, McEnany said that Trump’s comments about Mexicans were “unartful and inappropriate,” and she praised NBC’s decision to cut ties with him.
“He has shown himself to be a showman. I don’t think he’s a serious candidate,” she said, adding: “He’s not going to be anywhere near the top five. He’s not a serious contender within the Republican primary.”
But as Trump gained political momentum in 2015, McEnany became a strident defender.
While her pro-Trump appearances often drew eye rolls inside CNN, McEnany made her own decision to leave the network in August 2017 for what she billed as a “new role.” Soon after, she briefly hosted a video streaming program recorded at Trump Tower and airing on Trump’s Facebook page called “Real News Update.”
Critics called it pure propaganda.
“Wow. Feels eerily like so many state-owned channels I’ve watched in other countries,” Michael McFaul, the former U.S. ambassador to Russia, tweeted at the time.
Days later, she became the Republican National Committee’s national spokeswoman. Soon, she joined Trump’s reelection campaign. She has earned roughly $324,000 between the two roles, according to filings.
After news broke of her new White House job, CNN’s Andrew Kaczynski — a political reporter with a knack for digging up old social media posts and other damning material — divulged screen shots of McEnany’s tweets from 2012 in which she espoused Trump’s birther conspiracy about President Barack Obama. He also recirculated a clip of McEnany in a Feb. 25 appearance on Fox Business Network asserting that Trump’s border-closing initiatives would keep the coronavirus from entering the United States.
As if on cue, McEnany went to battle with her former network colleague, a posture she will settle into officially when she starts her new role. “Context matters,” she tweeted in response to Kaczynski, arguing that he had missed the nuance of her statement. “Ridiculous spin.”