The Untold Truth Of Kayleigh McEnany

In April 2020, Kayleigh McEnany was named President Donald Trump's new White House press secretary, replacing Stephanie Grisham (who replaced Sarah Huckabee Sanders, who replaced Sean Spicer), per The New York Times. It's the biggest stop yet in McEnany's meteoric career, and one that seems like a foregone conclusion and a logical next step for the rising conservative star.

In August 2017, McEnany was named spokesperson for the Republican National Committee, per The Hill. The following year, she published her political philosophies in the form of the book, The New American Revolution: The Making of a Populist Movement (with a forward by Fox News big shot Sean Hannity). In 2019, McEnany joined Trump's re-election campaign as its press secretary, before making the jump to Trump's administration in the same capacity.

According to Business Insider, McEnany is an "outspoken, combative defender of the president," who made a name for herself in the 2016 election season as a Trump surrogate on cable news shows. Here's a look at the early life and career achievements of Kayleigh McEnany.

Kayleigh McEnany grew up rich

Kayleigh McEnany is well-off and famous, but only the second part of that came from working hard and making connections. Raised in a wealthy family, McEnany's parents — Michael and LeAnne McEnany — run McEnany Roofing, a lucrative commercial roofing company in the booming Tampa, Fla. area, so large that it employs more than 140 people and received at least $1 million in the Paycheck Protection Program issued as a form of coronavirus economic relief. 

The future pundit and communications specialist's family life was also religious, and Kayleigh attended the elite and expensive Academy of the Holy Names, a private Catholic school in Tampa. As one of the few Protestant students, she was heavily involved in the debate club (arguing conservative viewpoints at even a young age) and participated on the cheerleading squad.

Kayleigh McEnany has since made a name for herself in Washington, D.C., but she never fully left The Big Guava. Per the Tampa Bay Times, she owns a home in the city's fancy Davis Islands neighborhood.

Kayleigh McEnany is extremely educated

Politicians and journalists are often highly and thoroughly educated, boasting multiple degrees from some of the world's most prestigious learning institutions. Kayleigh McEnany has worked in both politics and journalism, and as such entered the workforce with an impressive "education" section on her resume. 

After graduating from the Academy of Holy Names, she attended Georgetown University, majoring in international politics in the college's School of Foreign Service, per The New York Times. During her undergrad years, McEnany studied abroad for a year at St Edmund's Hall, a constituent of Oxford University, studying under prominent U.K. politician Nick Thomas-Symonds.

Upon earning her degree from Georgetown in 2010, McEnany found work in the media, serving as a production assistant for three years on Huckabee, the Fox News show hosted by former Arkansas governor and presidential candidate Mike Huckabee. According to Huckabee, McEnany was frustrated that she couldn't get an on-air job at the network, which prompted her to go back to school. She enrolled in law school at the University of Miami, earning a merit-based scholarship for landing among the top 1 percent of her class. Nevertheless, McEnany later transferred to Harvard Law School.

Kayleigh McEnany started a family

If real life is like high school, then Kayleigh McEnany and Sean Gilmartin are exactly the kind of couple that wind up together: The former cheerleader, successful student, and overachiever eventually married the hotshot baseball player. 

According to the Tampa Bay Times, McEnany and Gilmartin first got together in 2015, when the seasoned minor league relief pitcher was spending his first season in the big leagues with the New York Mets. He was later traded to the Baltimore Orioles and then the Tampa Bay Rays by 2020, which just so happens to be McEnany's hometown. In November 2017, McEnany and Gilmartin were married in a lavish ceremony, according to the New York Daily News. 

The wedding was just a few months after she was named spokesperson for the Republican National Committee — but McEnany tends to group big professional milestones with big personal ones. Not long before she took the job of White House press secretary, McEnany gave birth to their first child, a daughter named Blake.

Kayleigh McEnany interned a lot

Long before it became her nine-to-five job to support the administrative aims of President Donald Trump — by explaining and defending its actions to the media as White House press secretary — Kayleigh McEnany served in a similar capacity for a number of other influential and powerful conservative men. 

The self-proclaimed Ronald Reagan acolyte (she carried a book of that president's quotes around at age 16) once held the email handle "RealReaganConservative," according to The New York Times. In 2004, she worked as a volunteer for George W. Bush's campaign in Florida, making such an impression that it won her an internship with the president's successful re-election operation (via Cosmopolitan). When veteran Florida politician Tom Gallagher ran for governor for a fourth time in 2006, McEnany served as an intern in that campaign, too. (Unlike Bush, however, Gallagher didn't win.) Similarly, when Florida Commissioner of Agriculture Adam Putnam was serving in Congress in Washington, D.C., McEnany also interned for him, per the University of Miami School of Law

While still in college, McEnany even came very close to the job she currently holds. During the George W. Bush administration, she wrote media briefings as an intern in the White House's Office of Media Affairs.

Kayleigh McEnany faced down breast cancer

According to an editorial she wrote for Fox News in May 2019, Kayleigh McEnany faced concerning health news nine years earlier. She'd tested positive for the BRCA 2 genetic mutation, which indicated an extremely strong likelihood that McEnany would one day develop breast cancer — women with that particular genetic issue carry an 84 percent chance of a future diagnosis for the potentially fatal disease. (As McEnany mentioned at the 2020 Republication National Convention, per CNN, "In my family, 8 women were diagnosed with breast cancer — several in their 20s.") 

However, there's a medical procedure that cuts those odds down to what McEnany said in her Fox News op-ed are "virtually zero": a preventative double mastectomy, or the voluntary surgical removal of the breasts. In May 2018, the then-30-year-old pundit checked into the Moffitt Cancer Center in Tampa, Fla. for her pre-scheduled surgery, similar to one her mother had undergone years earlier. 

McEnany got through the operation just fine and she remains cancer-free, writing, "My post-mastectomy life is not one embattled but emboldened. I live free of fear and full of hope."

Kayleigh McEnany is no fan of Barack Obama

In an April 2020 appearance on Fox Business' Trish Regan Primetime, Kayleigh McEnany mentioned what she believed to be the "awful presidency of President Obama," which is not exactly a new sentiment for this White House press secretary. McEnany's college years coalesced with that of the Barack Obama presidency. Already a staunch conservative, McEnany didn't care for the progressive, democratic commander-in-chief. 

According to USA Today, 2012 saw McEnany post several tweets supporting the "birther" movement, the alleged idea that the African-American president was not a natural-born U.S. citizen, and thus not qualified to occupy the Oval Office. One such tweet, which carried the hashtag, "#ObamaTVShows," McEnany suggested, "How I Met Your Brother — Never mind, forgot he's still in that hut in Kenya." Yikes.

Late that same year, in a series of old tweets dug up by Yahoo! News correspondent Alexander Nazaryan, McEnany participated in another hashtag game. Tagging them with the hashtag, "#ThingsThatOffendObama," McEnany quipped, "Work outside of the golf course," "logic," "when people accidentally call him Osama," and "THE FACTS."

Kayleigh McEnany also wasn't always a Trump supporter

These days, Kayleigh McEnany is all-in on Donald Trump ... but she's a relative latecomer to the bandwagon. Not only did she support different Republican candidates, she also spoke out against Trump when he was a primary candidate during the 2016 election. 

"I don't think he is a serious candidate," McEnany told CNN in 2015. "I think it is a sideshow. It's not within the mainstream of the candidates." She also called out the future POTUS' comments about Mexico "not sending their best" people, who he alleged were "bringing drugs" and "bringing crime" into the United States. McEnany labeled those remarks "derogatory" and "hateful," adding that to her, "A racist statement is a racist statement." She doubled down on her assessments in an appearance on Fox Business' Kennedy a few weeks later, saying (via CNN): "Look, the GOP doesn't need to be turning away voters and isolating them. We need to be bringing them into the tent. Donald Trump is the last person who's going to do that."

According to The New York Times, McEnany got on board after a conversation with a Kirkland & Ellis law firm colleague. After mentioning that her preferred picks for the GOP nomination were Marco Rubio, Jeb Bush, and Ted Cruz, Michael Marcantonio predicted that Trump would win out, adding that "if a smart, young, blond Harvard graduate" is interested in pursuing a career as a pundit and cable news talking head, she "would be wise to be an early backer."

Kayleigh McEnany vigorously performs the job she was hired to do

While being on Donald Trump's side often means answering hard-hitting questions from persistent reporters, Kayleigh McEnany has never had a problem showing her support for the president — controversial as some of his positions may be. As the official White House mouthpiece, McEnany rarely minces words or speaks vaguely, but promised in her first briefing (via Vanity Fair), "I will never lie to you, you have my word on that."

In February 2020 (while still serving as campaign press secretary), McEnany told Fox Business' Trish Regan Primetime, "We will not see diseases like the coronavirus come here." Among other claims during her first White House briefing that May, she responded to accusations that Trump mishandled the pandemic response by dismissing scientific reports, alleging, "This president has always sided on the side of data." For his part, late-night host (and longtime Trump critic) Seth Meyers quipped of that same briefing, "She seamlessly transitioned from Fox News liar to White House liar."

During nationwide anti-police brutality protests the following month, the Trump administration faced major backlash after employing tear gas and non-deadly ordnance to disperse non-violent protesters so POTUS could have a photo-op in front of a Washington, D.C. church. McEnany defended the action, likening Trump's decision to U.K. Prime Minister Winston Churchill's leadership during World War II (via CBS News): "We've seen presidents and leaders across the world who have had leadership moments and very powerful symbols that were important for a nation to see at any given time to show a message of resilience and determination."