Kayleigh McEnany's Transformation Is A Staggering Sight To See

Kayleigh McEnany's story in politics is somewhat inspiring, yet ultimately fraught. At just 31 years old, she was appointed to be the White House press secretary under the Donald Trump administration, making history as one of the youngest in U.S. history to hold the position. At the time, McEnany pledged her allegiance to the country, assuring Americans of her commitment to the truth.

"I will never lie to you. You have my word on that," she said in her first official briefing as press secretary. However, McEnany's nine-month tenure was riddled with skepticism, with critics constantly questioning her truthfulness. Even worse, amid the January 6 insurrection investigation, Alyssa Farah Griffin, former communications director further cast doubts on McEnany's integrity, telling the committee: "I am a Christian woman, so I will say this. Kayleigh is a liar and an opportunist."

While serving as press secretary is the highest point of her career so far, McEnany's success in media and politics had been a long time coming. Before her appointment, McEnany made a name for herself as a conservative political pundit, later going on to fearlessly defend Trump amid his many controversies. But even before her association with the former president, McEnany was accomplished in her own right.

Kayleigh McEnany's grew up in a faith-driven household

On April 18, 1988, Kayleigh McEnany was born into the family of roofing company owners Michael and Leanne McEnany, becoming the oldest of three children. Raised in a Protestant home, Kayleigh received her high school education at the Academy of the Holy Names, an all-girls preparatory Catholic school in Tampa, Florida. But despite the differences between the Catholic and Protestant faiths, a young Kayleigh stayed true to her doctrines and beliefs in high school.

"From the moment of my first recollection, my parents taught me that Jesus Christ is at the center of your life," she recounted in a 2022 Mother's Day special for Fox Nation. "I was given a very good foundation from my grandmother and grandfather and my mom and dad."

Kayleigh has also merged her faith with her political career. In April 2021, the commentator explained that she became a Republican because it aligned with her religious beliefs. "For me, I find my home in the Republican party because I'm someone who's pro-life and believes in religious freedom," she told Fox 13. While politics might be a tad too cutthroat for a Christian, Kayleigh looks at her career and engages with people only "through the lens of Christ."

McEnany had an interesting college education

In high school, Kayleigh McEnany kick-started her interest in a career in politics, serving as a volunteer and intern for the 2004 George Bush/Richard Cheney campaign team. After her high school graduation, McEnany followed through on her political dreams, moving on to study international politics at Georgetown University.

"I have always been fascinated by politics and political commentary. Interestingly, besides me, no one in my family has a specific interest in politics or comes from a political background," she explained of her interest in the subject, per Miami Law. During her time at Georgetown, McEnany studied politics abroad for a year at the University of Oxford's St Edmund Hall. Notably, while at Oxford, McEnany studied under Nick Thomas-Symonds — a British politician who was later appointed shadow home secretary in the U.K.

It wasn't until she was at Georgetown that McEnany's political career really took off, though. As a college student, Kayleigh landed internships with prominent political figures in the United States, including Congressman Adam Putnam. She also briefly worked as an intern in the White House Office of Media Affairs. "To this day, I still find this surreal," McEnany recalled to Fox News. "I vividly recall standing in the Brady Press Briefing Room as a young college student, watching Dana Perino give a briefing as she fielded questions ... 12 years later, I was standing behind the podium taking questions."

She was a star student at law school

Following her graduation, Kayleigh McEnany proceeded to the University of Miami Law School, where she once again showed off her academic prowess. In no time, she was named in the top 1% of her class, earning herself the Bruce J. Winick Award scholarship. While at the school, McEnany left a lasting impression on her professors, including Professor Peter Nemerovski. "Kayleigh is a creative thinker and a talented writer whose performance in my LComm class was excellent... I expect great things from Kayleigh in the future," Nemerovski complimented, per Miami Law.

McEnany's time at Miami Law was short-lived, as she transferred to Harvard Law after her first year. At Harvard, McEnany wore her political commentator hat, appearing on several shows as a guest opinionator. She openly criticized the 2014 Harvard protests following two instances of the non-indictment of white policemen who killed unarmed black men. As a show of solidarity, students sent a letter to the school's dean, asking to have exams postponed. "It was a coalition of about 10 of them that sent the letter. Because they're 'traumatized,' they can't handle this. It's ludicrous," she argued during an appearance on "The O'Reilly Factor" (via Vanity Fair) at the time.

But while McEnany might not have been too keen on her peers' activism, she stuck it out, eventually bagging her JD in 2016. "At 12 years old, I visited Harvard Law School and vowed to graduate from this institution. Today, my dream came true!" she gushed in a Facebook post.

Her early days as a Trump supporter

Hard to believe, but once upon a time, Kayleigh McEnany was one of Donald Trump's biggest critics. In 2015, McEnany was unsure of Trump's legitimacy as a presidential candidate. "Donald Trump has shown himself to be a showman, I don't think he is a serious candidate. I think it is a sideshow. It's not within the mainstream of the candidates," McEnany said of the businessman during a 2015 appearance on CNN.

But of course, it didn't take too long for McEnany to change her mind, as she soon became a staunch supporter of Trump. This decision was reportedly inspired by Michael Marcantonio, one of McEnany's fellow law associates. "Donald Trump is going to be your nominee ... To get on television and have a career as a political pundit, you would be wise to be an early backer," Marcantonio told The New York Times of his advice to McEnany.

During her earliest days as a Trump supporter, McEnany fiercely defended him, even in situations that seemed less than ideal. In September 2016, McEnany addressed Trump's feud with former Miss Universe Alicia Machado, who accused him of hurling racist comments while also body shaming her. In her defense, McEnany called out Machado's past history, while comparing her to a terror suspect.

McEnany had a stint as a political commentator at CNN

As a recent graduate of Harvard Law School, McEnany pursued her passion for being an on-air news personality, eventually landing a role as a political commentator on CNN. The position was reportedly a part of the network's attempt at having impartial political debates ahead of the 2016 presidential election.

"They brought her on board when it became pretty clear that there were few people who were willing to defend Donald Trump that were somewhat sane," a source claimed to The Guardian of McEnany's contributor role. "Most people who were credible and experienced were not willing to put their names or reputations on the line to defend Donald Trump's crazy during 2016."

At CNN, McEnany's passion for politics and media shone bright, earning her praise from both Republican and Democratic commentators. Van Jones — a liberal lawyer, civil rights activist, and her fellow commentator at CNN — commended McEnany's competence and doggedness. "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 told The New York Times. In 2017, McEnany announced she was leaving CNN for a new role.

She was a big critic of the Obama administration

Kayleigh McEnany's past social media posts criticizing President Barack Obama and poking fun at his ancestry resurfaced following her appointment as press secretary. "How I Met Your Brother — Never mind, forgot he's still in that hut in Kenya. #ObamaTVShows," a tweet from 2012 read. "Obama filling out his 'presidential bracket' now on ESPN. Don't you have better things to do son? Like.. oh, I don't know ... govern," another tweet read.

In 2017, McEnany also faced backlash for accusing Obama of going golfing after announcing the murder of American journalist Daniel Pearl by Al Qaeda terrorists. "When President Bush took time off from the golf course in honor of the Iraq War, you had President Obama who after the — I believe it was the beheading of Daniel Pearl — spoke to how upset he was about that, then rushed off to a golf game," McEnany said during an appearance on CNN.

Her comments were not well-received by the public, as she had, in fact, mixed Pearl (who died in 2002) up with James Foley, another American journalist who was murdered by ISIS in 2014. At the time, Obama was criticized for going golfing shortly after announcing Foley's gruesome murder. Viewers wasted no time in calling McEnany out for her errors. "McEnany is an utter disgrace trying to use a tragedy like Daniel Pearl to push a cheap political lie," one user wrote.

McEnany became an RNC spokesperson

In August 2017, Kayleigh McEnany was announced as the new spokesperson of the Republican National Committee (RNC). "Kayleigh will be an integral part of our Party's ongoing commitment to promoting the Republican message to Americans across the country," the chairwoman Ronna McDaniel said in the press release. In her statement, McEnany shared her excitement, adding that she was "eager to talk about Republican ideas and values and have important discussions about issues affecting Americans across this country."

In her role as RNC spokesperson, McEnany continued to champion Donald Trump's political ambitions, often defending him against backlash from the public. For instance, in 2017, Trump was subject to backlash after refusing to denounce white supremacists and their role in a violent attack that broke out in Charlottesville. Instead, Trump asked that anti-racist counterprotesters also share in the blame. Expectedly, many were not impressed.

McEnany, however, soon jumped to the president's defense, alleging that his comment was aimed at promoting inclusion and not division. "President @realDonaldTrump once again denounced hate today. The GOP stands behind his message of love and inclusiveness!" she wrote in a tweet shared at the time. 

She married Sean Gilmartin

In 2017, after two years of dating, Kayleigh McEnany married baseball player Sean Gilmartin in a lavish ceremony. "Married the love of my life @GilmartinSean on Saturday, and @rodrigorvphoto captured it beautifully!! What an amazing photographer. Couldn't be happier with how these turned out," McEnany wrote on X, formerly known as Twitter, alongside two pictures from the couple's big day. 

While McEnany found a home in media and politics, Gilmartin enjoyed a career in the MLB, during which he played for some of the league's biggest teams, including the New York Mets and Minnesota Twins. Notably, in 2020, Gilmartin signed a contract with the Tampa Bay Rays, bringing him closer to his family in Tampa, Florida. "Having Sean with the Tampa Bay Rays is what we've been hoping and praying for. We always dreamed of this happening but never knew it would become a reality," McEnany shared with the Tampa Bay Times at the time.

Gilmartin retired from baseball during the 2021/2022 off-season, leaving behind a legacy that would be remembered by those he worked with. "Gilly, it was a complete honor training you. Thank you so much for your trust in me over the years ... It was amazing to watch all of your success on and off the field. Congrats on retirement," Nicole Gabriel, a personal trainer wrote in an Instagram tribute to Gilmartin.

McEnany underwent a double mastectomy

In her early 20s, Kayleigh McEnany received a scary diagnosis — she had tested positive for the BRCA2 genetic mutation, a gene proven to increase the risk of breast and ovarian cancer. Given her family's history of breast cancer, Kayleigh decided to get a preventive double mastectomy, a procedure posed to reduce her chances of getting diagnosed with breast cancer.

Her mother, Leanne McEnany, had also undergone a preventive double mastectomy back in 2009, which prompted Kayleigh to test for the gene herself. "I wanted to do it fairly quickly. Within the year, I had hoped. But I was single at the time. I wasn't sure what dating post-mastectomy would be like, and the unknown worried me," Kayleigh wrote in her 2021 memoir "For Such a Time as This: My Faith Journey through the White House and Beyond" (via Fox News).

In May 2018, Kayleigh underwent the surgery, waking up to the faces of her loved ones. "After the six-hour surgery, I woke up and saw my mom. My first words were: 'That was easier than a CNN panel!' We still laugh at that," she recounted. In the years since, Kayleigh has been open about her surgery, noting it as one of her best decisions yet. "My post-mastectomy life is not one embattled but emboldened. I live free of fear and full of hope," she declared in her 2019 op-ed for Fox News.

Her journey into motherhood

Kayleigh McEnany and her husband, Sean Gilmartin, welcomed their first child, a daughter named Blake in November 2019. "@GilmartinSean and I are so blessed to welcome our first baby — Blake Avery Gilmartin — into the world!" McEnany wrote on X. "What a blessing from God she is to our family!"

In June 2022, the political commentator announced she was expecting her second child during an appearance on Fox News' "Outnumbered." "My husband, Sean Gilmartin, and I are about four months pregnant. We will reveal the gender in the coming weeks," she shared. Less than six months later, McEnany and Gilmartin welcomed their second child, a son. "@Gilmartinsean & I are thrilled to announce the birth of our son, Nash! What a truly joyful time. God has blessed us immensely!" McEnany announced on X.

Over the years, McEnany has opened up about motherhood, often describing Blake and Nash as God's gift to her. "You start to feel your baby kick, and it's just hard to believe that there is a child living within you that God has woven together," she explained in a special episode of Fox Nation's "Mothers and Daughters of the Bible Speak." "And that's what the Bible tells us, that you're knitted together in your mother's womb."

She was appointed the White House's press secretary in 2020

In April 2020, Kayleigh McEnany was officially dubbed the new White House press secretary. "She has been one of the strongest assets to the president's reelection campaign with her keen mind, positive attitude, strong faith, and tireless work ethic," Brad Parscale, Donald Trump's campaign manager, said in a statement, per Fox News

As expected, McEnany's role as press secretary further propelled her fierce defense of the Trump administration, even in the face of alleged misinformation. According to an article by CNN, McEnany's first official press briefing, during which she promised to "never lie," was filled with many untrue statements. For instance, while speaking about former national security adviser Michael Flynn — who, in 2017, admitted to lying to the FBI about having Russian contacts — McEnany shared that special counsel Robert Mueller's spent $40 million on his investigation, among other inconsistencies. A report from the Justice Department capped the investigation's cost at $32 million.

Similarly, in June 2020, McEnany supported Trump's decision to forcefully disperse peaceful George Floyd protesters in Washington D.C. for a photo op at St. John's Church. "For this president it was powerful and important to send a message that the, rioters, the looters, the anarchists — they will not prevail — that burning churches are not what America is about," she stated in a press briefing (per CBS News). Despite her growing unpopularity, McEnany served as Trump's press secretary for nine months until President Joe Biden was sworn in on January 20, 2021.

McEnany has been a frequent guest on Fox News

Following Tucker Carlson's exit from Fox News in April 2023, Kayleigh McEnany was named an interim host of "Fox News Tonight." Announcing the news, McEnany took to X, writing: "I am honored to share that I will be hosting Fox News Tonight on @FoxNews at 8pm ET all next week (5/8-5/12)! Set your DVR. Please join me next week as we dig into the state of politics, media, culture, and faith in America!" Though temporary, this was not McEnany's first rodeo with the television network.

In 2021, McEnany was announced as co-host of Fox News's "Outnumbered" show, joining Harris Faulkner and Emily Compagno to discuss national issues. "Kayleigh's unique background in politics and law coupled with her experiences confronting women's health challenges and life as a new mom will add robust insight to 'Outnumbered,'" Fox News Media CEO Suzanne Scott shared in a statement

Plus, following her college graduation, McEnany worked as a production assistant on the "Mike Huckabee Show" for three years before moving on to the University of Miami Law School. "I think one of the reasons that Kayleigh went on to law school was because she didn't see she was going to have an on-air opportunity at Fox anytime soon," Huckabee explained in an interview with The New York Times. Past her time as a Carlson replacement, McEnany has continued to appear on the network, even guest-hosting on "Fox & Friends" in January 2024 and "Hannity" in February 2024.