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What will Kayleigh McEnany do next?

Kayleigh McEnany says that ‘God had planned’ for her to be the White House press secretary. What has he got in store for her next? Harriet Alexander writes

Wednesday 23 December 2020 10:03 EST
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Kayleigh McEnany has been White House press secretary since April
Kayleigh McEnany has been White House press secretary since April (Getty Images)

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Kayleigh McEnany’s time at the White House podium began with a sunny smile, and a solemn promise.

“I will never lie to you,” she said earnestly. “You have my word on that.”

It ended with angry accusations that she was little more than a state propagandist, as she spun on her heels and marched out the briefing room.

“Isn’t it hypocritical of you to accuse others of disinformation when you spread it every day?” shouted CNN’s chief White House correspondent Jim Acosta, as she stepped down from the podium on 15 December, at the end of a powerpoint presentation attacking those sitting before her.

Ms McEnany kept on walking.

Where the 32-year-old is heading is unclear.

Her predecessors under previous administrations could, on leaving the White House, have their pick of any plum – very highly paid – positions.  

Barack Obama had three press secretaries, who all dabbled in television work on leaving the White House; one then went to head up global communications for McDonald’s, another for Amazon, another for United Airlines.

Ms McEnany might not have that luxury, unless she fancies a job with My Pillow, whose owner Mike Lindell is slavishly devoted to the president.

She is about to find out just how damaging her association with Donald Trump has been.

Kelsey Bolar, senior policy analyst at the Independent Women’s Forum, told The Independent that Ms McEnany should expect to be treated unfairly.

“If American Airlines wanted to hire Kayleigh, there would be a boycott,” she said.

“There is a double standard for conservative women leaving Republican administrations and entering corporate America. It makes finding these positions a lot more difficult. Which is a mistake, as Republicans and Democrats both use these companies.”

Ms McEnany’s qualifications are not in doubt.

Unlike her predecessor Sean Spicer, who rose spectacularly from being the White House Easter bunny to be named Donald Trump’s first press secretary, Ms McEnany, a Harvard law graduate, had long been a figure on cable news networks, in her role as communications director for the Republican National Convention.

People who worked with her praised her skills, and said she is often underestimated.

“People keep taking her lightly, and they keep regretting it,” said Van Jones, a CNN commentator and liberal activist who mentored Ms McEnany when she joined 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.”

Born in Tampa, Florida, Ms McEnany attended a Catholic prep school, where she was senior cheerleader, and chose 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.  

On graduating high school she studied international relations at Georgetown University in Washington DC, interning for George W. Bush and working at the White House communications office.

She also spent a year from September 2008 at St Edmund Hall in Oxford, where her tutors included Nick Thomas-Symonds, appointed as shadow home secretary by fellow “Teddy Hall” alumnus Sir Keir Starmer.  

In a 2014 interview she said she “loved every moment of academia, particularly Oxford.”  

Her only complaint was, according to a tweet, the lack of Taco Bells the city has to offer.

On graduating she began work as a producer on former Arkansas governor Mike Huckabee’s talk show on Fox News, a job she held for three years before leaving to study law.  

Mr Huckabee said that “one of the reasons [McEnany] went on to law school was because she didn’t see she was going to have an on-air opportunity at Fox anytime soon.”

She started law school at the University of Miami, where she earned a scholarship reserved for the top 1 per cent of her class, then finished her degree at Harvard, and cultivated a blossoming career as a TV pundit.

Initially she had been critical of Mr Trump, finding his Twitter habit distasteful and his rhetoric unseemly.

“Donald Trump has shown himself to be a showman,” she said, and it was “unfortunate” and “inauthentic” to call him a Republican. Ms McEnany called his comments about Mexican immigrants “racist”.

Her Damascene convention in the summer of 2015 came over cocktails, at a rooftop bar in Manhattan.

Michael Marcantonio, a Democrat, and fellow summer associate at law firm Kirkland & Ellis, asked her for her favourites in the Republican presidential primary.

Ms McEnany replied that she liked Marco Rubio, Jeb Bush and Ted Cruz, according to The New York Times.

Mr Marcantonio recalled that he interrupted her with some advice.

“Donald Trump is going to be your nominee,” he said.

If “a smart, young, blonde Harvard graduate” wanted “to get on television and have a career as a political pundit, you would be wise to be an early backer.”

She took his advice and became one of Mr Trump’s most dogged defenders, mixing fierce loyalty with a megawatt smile and immaculately waved hair, in a look straight from the Trumpworld catalogue.

A month before securing the press secretary job, Ms McEnany insisted on Fox News that Mr Trump would keep the coronavirus from American shores.

“We will not see diseases like the coronavirus come here. We will not see terrorism come here,” Ms McEnany said. “And isn’t it refreshing when contrasting it with the awful presidency of President Obama.”

She and her husband, the Tampa Bay Rays pitcher Sean Gilmartin, had a baby girl, Blake, in November 2019 – just a few months before Ms McEnany, in April, took the press secretary job.

Her appointment came initially as a relief.  

Her predecessor, Stephanie Grisham, had not done a single briefing in her eight months in the role.

Sarah Huckabee Sanders, who held the position before her, was fierce, but more or less respected.

Then there was Mr Trump’s first press secretary, the much-parodied Mr Spicer, whose ignominious start bellowing about crowd sizes set the tone.

He has struggled on leaving the White House, which must concern Ms McEnany: his plans for a TV show in 2018 fizzled, and he ended up as a comedy contestant on Dancing With the Stars.  

In March he launched Spicer & Co on Newsmax, a small conservative television station, owned by Mr Trump’s friend Chris Ruddy. Initially the ratings were poor, with only 24,000 people tuning in on the first week.

He has been given a boost by Mr Trump’s turning on Fox News after the election, enraged at their calling Arizona for his rival Joe Biden: by December, Mr Spicer had 513,000 viewers, and was the second-most watched show on the network.

Maybe that will encourage Ms McEnany to look for a job there?

Anthony Rizzo, a spokesperson for Newsmax, told The Independent: “Newsmax is not commenting on any of its hiring options or plans.”

One America Network, another niche conservative outlet, did not return requests for comment.

Dana Perino, now a Fox News anchor, was George W. Bush’s press secretary, and has charted a course for Ms McEnany to follow.

Yet maybe she won’t have to worry about the whims of Fox or OAN or Newsmax’s bosses. Strong rumours suggest Mr Trump may set up his own network, to rival them all – Ms McEnany could well play a starring role, perhaps alongside Kellyanne Conway, who according to author Michael Wolff took the role of Mr Trump’s 2016 campaign manager with an eye not on the White House but on a cable TV job.

“As one of the highest-ranking women in the Trump administration, I’d hope that she wouldn’t have any trouble finding work,” said Ms Bolar, of the conservative think tank.

“Trump still has a massive voter base, which is being silenced. And that’s a loss not just for CNN, but for the whole country.”

Asked whether she would still work for Mr Trump is he makes a 2024 run to retake the White House, Ms McEnany refused to reply.

Could she, like Mr Trump’s son Don Jr and daughter-in-law Lara Trump, be considering entering politics herself? 

Kayleigh McEnany denies any discussion of pardons for Trump's family

She has shown no signs of wanting to, unlike Ms Huckabee Sanders, who is said to have her eye on following in her father’s footsteps and making a run for governor of Arkansas. But is that a possibility?

“If she chooses to pursue a career in politics, I think she’ll be wildly popular,” said Ms Bolar.

“She is brilliant and highly-successful, and a new mum. She deserves so much credit for juggling so much at the same time. The world is her oyster.”

Meghan Milloy, from GOP Women for Progress, agreed with Ms Bolar that Ms McEnany was a force to be reckoned with.

“She’s great at what she does,” she told The Independent. “She spins facts into not facts. She can defend anyone – even the absolutely worst humans.

“So maybe for CNN she could go back and be their right-wing person again, but the problem is that there is some semblance of truth in the networks, so she may no longer fit in.”

Ms Milloy, who knows Ms McEnany personally, said she expected her to negotiate a book deal, and agreed that working for a new Trump TV network would appeal.

“These Republican sycophants have turned their entire careers into being this hype team for the president,” she said.

“I do wish she hadn’t got stuck into this defence of racism, and bigotry, and lies: she’s great, she’s smart, she’s fun.

“If you didn’t realise what she was doing for a day job, you wouldn’t think she was a horrible person.”

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