Inside Kayleigh McEnany's Relationship With Trump

Kayleigh McEnany made headlines in April 2020 when she stepped in and took over the role as President Donald Trump's fourth White House press secretary, all while in the midst of a global pandemic and economic crisis. As reported by CNN, McEnany's new position came on the heels of press secretary No. 3 Stephanie Grisham's abrupt retreat back to the East Wing as chief of staff to First Lady Melania Trump. 

Luckily for McEnany, who previously served as press secretary for Donald Trump's re-election campaign, it appears her White House gig isn't much different from her last: her mission is simply to defend POTUS. In an article by Business Insider, the Harvard Law graduate was described as an "outspoken, combative defender of the president." And well ... that tracks. It's reported that McEnany first gained traction and notoriety as an avid Donald Trump supporter in 2016 while working as a CNN commentator. During that time, the author of The New American Revolution: The Making of a Populist Movement worked tirelessly to justify the future president's controversial antics, often times at her own ridicule and detriment. 

But what's the real story behind Kayleigh McEnany and Donald Trump's relationship, along with her sudden rise to the West Wing of the White House? Keep reading to find out!

Kayleigh McEnany minced no words in 2015 when she first spoke out about then-candidate Donald Trump's campaign. "I don't want to claim this guy. Donald Trump, if we're going to be honest, is a progressive," she said during an appearance on CNN, calling his controversial comments on Mexican immigrants "racist." She later described it as "unfortunate" and "inauthentic" to refer to Trump as a republican. Ouch ... them's fighting words!

It wasn't until a chance encounter with a colleague, who reportedly delivered some strategic advice, that the conservative commentator had a change of heart. The story, per The New York Times, goes that it was Michael Marcantonio who predicted that Trump would be the party's nominee, and if the "smart, young, blond Harvard graduate" hoped "to get on television and have a career as a political pundit," she'd be quick to pledge her early support. 

By 2016, McEnany was suddenly singing Trump's praises, a 180-degree move that was openly criticized by many. When asked about her past criticism of Trump during a May 2020 briefing, the president's then-new press secretary seemingly engaged in the time-old tradition of backpedaling ... or maybe she really did come to an epiphany of sorts. Who's to say, really? According to McEnany, it was her "naively believing some of the headlines" in the early weeks of Trump's campaign that fueled her premature judgement. "I very quickly came around and supported the President," McEnany explained. And that she did!

It's no secret that Kayleigh McEnany had tough shoes to fill when she signed on as President Donald Trump's fourth press secretary. But it appears — so far, at least — that POTUS is pleased with the work she's doing. He also seems to hold no ill will for her past grievances of him securing the GOP nomination. In May 2020, Trump retweeted of a photoshopped meme of McEnany sporting a Superwoman costume, writing, "Doing a GREAT job!"

In the wake of ongoing criticism, McEnany has also garnered some respect from others across the aisle, such as CNN commentator Van Jones. "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," he said (via The New York Times), before warning, "People keep taking her lightly, and they keep regretting it." It's worth noting that Jones served as McEnany's mentor during her time at CNN.

While it remains to be seen whether or not the law graduate-turned-White House press secretary will prove to put an end to what some might refer to as a revolving door of press secretaries, it appears she's happy to defend President Trump for as long as he will allow it. Good luck, McEnany!