How Kayleigh McEnany went from Donald Trump’s biggest defender to a ‘milktoast’ rival

Why did the former president so dismissively insult one of his most loyal White House aides? Oliver O’Connell charts the pair’s path

(Getty)

In a moment that shocked some — but came as no surprise to others — Donald Trump turned on his former White House press secretary Kayleigh McEnany on Tuesday night for allegedly sharing inaccurate poll numbers.

Ms McEnany, who served as the former president’s fourth press secretary, was known as one of his most loyal aides and staunch defenders, something she continued when she joined Fox News as a contributor after he lost the 2020 election and left office.

Nevertheless, the former president pulled no punches in a Truth Social Post, complaining about a segment in which he claims she misreported his lead over Florida Governor Ron DeSantis.

“Kayleigh ‘Milktoast’ McEnany just gave out the wrong poll numbers on Fox News,” Mr Trump wrote, incorrectly spelling the term milquetoast.

“I am 34 points up on DeSanctimonious, not 25 up. While 25 is great, it’s not 34,” he said, using one of his nicknames for his principal GOP primary rival.

“She knew the number was corrected upwards by the group that did the poll. The RINOS & Globalists can have her. FoxNews should only use REAL Stars.”

Ouch.

The former president was referring to a segment on Fox News show Outnumbered, in which Ms McEnany suggested Mr DeSantis was “narrowing the gap” with Mr Trump since he officially launched his 2024 campaign.

Outraged Republicans leapt to Ms McEnany’s defence on Twitter, noting how she had defended the former president during some of the most difficult moments of his presidency to what they see as a hostile press.

How did their professional relationship develop and why would he turn on her now?

Originally from Tampa, Florida, Ms McEnany has been involved in Republican politics since college. She interned for several politicians and wrote media briefings for the White House communications office under President George W Bush, before taking a paid commentator role at CNN.

Early on in candidate Trump’s 2016 run for the White House, Ms McEnany was critical of him, calling Mr Trump a “showman”, saying his comments about Mexicans were “racist”, and that it was “unfortunate” and “inauthentic” to call him a Republican. She later got behind the Trump 2016 campaign that saw him elected.

In mid-August 2017, during the first year of the Trump presidency, Ms McEnany left CNN and was appointed the Republican National Committee’s spokesperson. During this period she spoke on behalf of the RNC, notably defending Mr Trump from bipartisan criticism of his comments about the white supremacist rally in Charlottesville, Virginia.

Kayleigh McEnany at a 2020 White House press briefing (EPA)

In April 2020, during the early days of the Covid-19 pandemic, Mark Meadows replaced Mick Mulvaney as White House chief of staff, and shortly after, hired Ms McEnany as press secretary.

In the run-up to her appointment, she had been particularly effusive in her praise of how she believed Mr Trump had been handling the pandemic, saying: “This president will always put America first, he will always protect American citizens. We will not see diseases like the coronavirus come here, we will not see terrorism, and isn’t that refreshing when contrasting it with the awful presidency of Barack Obama?”

The virus had already been present in the US for a month at that point. She also accused Democrats of trying “to politicise” Covid-19 and claimed they had been “rooting for this outcome”.

Statements such as these set the tone for her tenure at the White House, with the Associated Press saying of her that she “has made clear from her first briefing that she’s willing to defend her boss’s view of himself as well as his most flagrant misstatements”.

In her first press briefing, she pledged to reporters: “I will never lie to you. You have my word on that.”

Over those final nine months of the Trump administration, she steadfastly backed up his every controversial statement and action, whether it related to the pandemic, false accusations of murder, or allegations about fraud in voting by mail.

Ms McEnany defended Mr Trump when he had Lafayette Square forcefully cleared of protesters for a photo-op, and even when a recording surfaced of him saying he was downplaying the severity of the Covid-19 virus, she said he had never done so, despite his repeated public statements to that effect.

Kayleigh McEnany with Donald Trump at the White House in September 2020 (Getty Images)

She was referred to as a “state propagandist” by Clinton administration press secretary Joe Lockhart who said she had “destroyed her own personal credibility and fatally injured her ability to speak for the President, and more importantly, for the United States of America”.

Politifact, the nonprofit fact-checking website, has since said her statements were either “mostly false”, “false” and false accompanied by a “ridiculous claim” about 56 per cent of the time.

She was found to be “mostly” honest only 28 per cent of the times that the organisation had double-checked her claims.

In the 2020 election, Ms McEnany echoed her boss’s incorrect claim of victory and lies about massive voter fraud, and when he refused to concede, she falsely claimed that he had not been given an orderly transition by the preceding Obama administration — which was not true.

Two months after the January 6 Capitol riot and six weeks after the inauguration of President Joe Biden, Ms McEnany joined Fox News as an on-air contributor, rising to be cohost of Outnumbered. 

Former White House colleague Alyssa Farah Griffin, who has publicly denounced Mr Trump and become one of his sharpest critics, described Ms McEnany as a “very smart person” but also as a “liar” who peddled election lies because she knew it would enrich her career post-Trump.

Speaking to the January 6 House select committee, Ms Farah Griffin said: “She knew we lost the election, but she made a calculation that she wanted to have a certain life post-Trump that required staying in his good graces and that was more important to her than telling the truth to the American public.”

Upon Ms McEnany’s appointment at Fox News, an insider at the network told The Daily Beast: “It’s truly disgusting they fired hard-working journalists who did care about facts and news reporting only to turn around and hire a mini-Goebbels whose incessant lies from the White House helped incite an insurrection on our democracy that got five people killed, including a police officer.”

Since her arrival at the network, Ms McEnany has continued to defend her former boss on air and appears to have fit into the role well, even stepping in as a guest host during primetime.

Former President Trump has a slightly more complex relationship with the network than he did while in office, frequently criticising “globalist” coverage while also lauding individual hosts, and still getting their backing over the many investigations into his business and actions while in office.

On 1 June he will take part in a televised town hall from Iowa moderated by Fox News primetime host Sean Hannity as part of his 2024 re-election campaign, but on 31 May he posted on Truth Social: “FoxNews is really pushing De Sanctimonious. He can’t win!”

While his dismissive comments about Ms McEnany have raised the ire of, and even shocked, some conservatives, others including her former colleagues Ms Farah Griffin and Stephanie Grisham — who held the press secretary role before she did — were unsurprised.

Ms Grisham tweeted: “He. WILL. Turn. On. You. There is only loyalty to HIM — not the country, the constitution, his constituents, or anything/anyone else.”

Ms McEnany, and others, perhaps should have known better.