Why Donald Trump Turned Against His Former Press Secretary Kayleigh McEnany

History shows it doesn't take much to get on former President Donald Trump's bad side, no matter how long you had previously been on his good side. Such was the case for Trump's former press secretary Kayleigh McEnany, who went from "that heavily outnumbered blonde girl fighting for Donald Trump" as a CNN political commentator (via CNN) to being described as "milquetoast" [albeit misspelled] by her former employer. 

McEnany's tenure as press secretary was brief. She joined the Trump administration in April 2020, only seven months before Trump lost his bid for re-election. She quickly moved on from the White House to Fox News' "Outnumbered," where she would later catch flack from her former boss for delivering incorrect polling numbers on air. 

"Kayleigh 'Milktoast' McEnany just gave out the wrong poll numbers on FoxNews. I am 34 points up on DeSanctimonious, not 25 up," Trump said in a May 2023 Truth Social post, referring to his opponent for the 2024 GOP presidential nomination, Ron DeSantis. Trump seems to be referring to the results by his preferred pollster, McLaughlin and Associates (via X, formerly known as Twitter), though exact polling numbers between Trump and DeSantis in May 2023 vary by publication. 

Former President Donald Trump continued in his Truth Social post, "While 25 is great, it's not 34. 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!!!" 

Kayleigh McEnany was a staunch supporter of Trump and his beliefs during her time at the White House. Following the 2020 election, McEnany echoed her boss' statements about election fraud to the point that Fox News cut its feed of the press briefing she was running. Fox host Neil Cavuto warned audiences that, unless McEnany had evidence to back up her divisive claims, he felt it unwise to continue the broadcast, per The Guardian.

The Fox News co-host is still publicly supportive of Trump. Even after being called out by her ex-boss on Truth Social, she lauded his campaigning skills on-air days later. "I don't know if there is anyone in the race that can do it quite like him with a room with voters," McEnany said on "Outnumbered" (via X, formerly known as Twitter).

Kayleigh McEnany was far from "milquetoast" when he worked for Donald Trump. In fact, the former press secretary was a controversial figure during her short tenure in the Trump administration. In her first press conference, McEnany told reporters, "I will never lie to you. You have my word on that" (via X). This, of course, added more speculative fuel to the fire as McEnany navigated major White House scandals like the 2020 "stolen election" conspiracy and the subsequent January 6, 2021, Capitol riot. 

Alyssa Farah Griffin, former communications director to Trump, called McEnany a "liar and an opportunist" while testifying to the House January 6 committee in December 2022. "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" (via The Guardian).

Griffin also claimed that McEnany's end goal was to get a job as a Fox News correspondent, which she did. "It worked out precisely how she'd always planned for it to," Griffin claimed. And indeed, if McEnany's true goal was to stay in Trump's good graces, it's unclear whether she did so after her ex-boss' fiery Truth Social post.