Kimberly Guilfoyle's Transformation Over The Years Is A Sight To See

Kimberly Guilfoyle is most famous for being a proud Republican, TV anchor, and Donald Trump ally who's not afraid to speak her mind. But this former prosecutor lived quite the life before she fell in love (and then out of it) with Donald's namesake son, Donald Trump Jr.

In fact, Kimberly had a successful stint as a model before her foray into politics and TV news. "I modeled everything from clothes, swimwear and lingerie, including Victoria's Secret!" she told People in 2014. "I met an incredible number of interesting people through modeling and really learned a lot about self-confidence and self-worth," she added. 

Kimberly's come a long way since then, but her journey wasn't without its ups and downs. Along the way, she went through multiple divorces, became a mother, and even landed a high-profile job as the U.S. ambassador to Greece. All of it culminated in one stunning transformation.

Kimberly Guilfoyle was born in San Francisco in 1969. Her mom, Mercedes, hailed from Puerto Rico, while her dad Anthony immigrated from Ireland. Much of Kimberly's childhood was spent with her paternal family in Ireland, as she visited the country every summer after she turned 5. 

"I lived in Ennis where my Guilfoyle relatives had businesses," she told The Times, adding that having a job at her family's store at a young age taught her the importance of hard work.

Kimberly was close with her parents, who had a big influence on her upbringing. "I've tried to live my life in a way that respects the beliefs of my mother and father. They sacrificed a tremendous amount for me to be able to do what I do today," she told Mediaite. To The Times, she said, "My parents worked hard to ensure we had a better life. They supported us and gave us the courage to pursue our dreams. I appreciate that greatly."

As a child, Kimberly Guilfoyle was desperate to play soccer. "I remember being in the second grade and all I wanted to do was play soccer. Soccer, soccer, soccer — I was driving everyone crazy," she told SFGate in 2001. There wasn't a girl's team at the time, so Mercedes Guilfoyle demanded her daughter be given a shot on a team made up exclusively of young boys. "My mother said to the coach, 'Give her a try out. If she's good enough, she should be on the team. If she's not, then she shouldn't,'" Kimberly recalled. Not only did she land a spot on the squad, but another girl later joined too.

Kimberly's mom had a profound impact on her life outlook. "I learned that just because something hasn't been done before, it doesn't mean it can't be done now," she told Cosmopolitan. "You have to speak up and you've got to assert yourself because it takes somebody to be the first one to make it happen." Kimberly's sportiness didn't end with her childhood soccer playing. Being active still has a special place in her heart, she told People, saying, "I love to watch sports, but play them even more."

Kimberly Guilfoyle was dealt a devastating blow at age 11 when her mother died of leukaemia. "My mother was just everything to me, I loved her so much," she told Mediaite. "I had to go through a lot to be able to heal," After her mother died, Kimberly began caring for her younger brother, Anthony Guilfoyle Jr., who was 8 years old. She spoke to Harper's Bazaar in 2004 about how she dealt with grief, explaining, "Time ... does not heal all wounds; [it] just makes it easier to function on a daily basis. I'd cut my own life in half to have my mother back."

The death of Kimberly's mom also had an impact on her decision to become a prosecutor, she said, explaining that she felt a special connection to cases involving violent crime victims. "I understood that profound sense of loss, and I could relate to it, and I wanted to do anything to help them heal by seeking justice," Kimberly said. "It's so hard when you have a family member pass away, like cancer, it's debilitating."

To kick-start her career, Kimberly enrolled at University of California, Davis and worked hard to pay her way. "I was working at the district attorney's office as an intern, I worked at the clothing store Clothestime, and I was modeling and doing different jobs in and around San Francisco and Sacramento," she told Cosmopolitan. The money she earned also helped her pay her tuition for the University of San Francisco's law school and studying at Trinity College Dublin.

After graduating, Kimberly Guilfoyle worked as a teacher and a prosecutor, but soon left San Francisco for Los Angeles, where she landed a job as an assistant district attorney. San Francisco pulled her back in, though, with the promise of love. After she began dating politician Gavin Newsom in 1994, she returned to the San Francisco District Attorney's Office. The two first met at a political fundraiser, she told Harper's Bazaar. "I looked across the room and saw Gavin — tall, elegant, handsome, charismatic." 

Newsom and Kimberly married in 2001, and Kimberly's political profile grew when Newsom become the Mayor of San Francisco in 2004. Kimberly's spotlight also intensified outside her marriage due to her involvement in the high-profile case of Diane Whipple, who was mauled to death by a dog. "I got a lot of media requests and offers. Six offers to work in television, [including] ABC News, CNN, MSNBC, Court TV, Fox News," she told The Daily Signal. The promise of big TV gigs saw her uproot and make a solo move to New York.

But as her TV career grew, Kimberly was also rubbing shoulders with royalty as the wife of the mayor. "I did the first official visit of Prince Charles and Camilla when they came to San Francisco; it was one of the three main cities they traveled to in the United States. I spent three days with them and it was a wonderful experience," she told People.

In 2004, Kimberly Guilfoyle's career ambitions saw her spend more time in the Big Apple while Gavin Newsom remained in San Francisco. She'd landed a regular gig on the Court TV series "Both Sides" and made appearances on CNN shows, as well as ABC's "Good Morning America." But not all the attention she was getting was good. Many questioned her decision to move across the country without her husband and speculated that a break-up was imminent.

Kimberly said relocating alone was hard on her marriage, but she hit back at the haters, too. "I miss [Newsom], but he's doing great. He's kicking butt and I'm so proud of him," she told SFGate in 2004. "Why can't a couple have two major careers?" she continued. "To these people who question our marriage, I want to ask: How is your marriage doing? Mine is just fine. If you have respect and love for each other, there's no reason this can't work out great for everyone." 

Despite Kimberly Guilfoyle's insistence that all was well between her and Gavin Newsom, their bi-coastal marriage didn't last long. The two announced their separation in early 2005, blaming busy schedules. "Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple. Over the past 10 years, we have developed a tremendous bond of love and respect for each other. That will never change," they said in a statement obtained by SFGate.

The exes didn't finalize things until March 2006, by which time Kimberly had gotten back into dating, despite her divorce. She'd struck up a romance with businessman Eric Villency, and the two confirmed they were expecting their first child together that May, the same month they married. The newlyweds became parents to Ronan Anthony Villency the following October. Kimberly opened up about motherhood in a sweet Instagram post for Ronan on Mother's Day 2024, writing, "I have loved every moment of being your mom. You always make me so proud. Being a mother is truly the best job on the planet." Sadly, things between Ronan's parents didn't work out, and Kimberly and Villency split in 2009.

The split came the year after Kimberly experienced more tragedy when her dad, Anthony Guilfoyle, died. She paid tribute to him in a touching Facebook post in 2021. "Thank you for the incredible job you did as a single father raising Anthony and I after our sweet mother Mercedes passed away," Kimberly wrote. "Thank you for fighting so hard to live and be with us and your sweet grandson Ronan. He reminds me of you everyday."

By 2011, Kimberly Guilfoyle was becoming increasingly well-known nationwide thanks to her thriving TV career. The author was the co-host of Fox News show "The Five," and also began appearing on "Outnumbered" in 2014. She also made appearances on the likes of "America Live," "Red Eye," and "The O'Reilly Factor." In 2016, she confirmed her new career meant she could no longer work as a prosecutor. "I work full-time as a journalist for the Fox News channel so I'm not allowed to practice law or give opinion," she told Premiere Collectibles, sharing she was still a California bar member.

In 2017, Fox News confirmed plans for Kimberly to remain on the channel for the foreseeable future. But their working relationship ended abruptly in 2018 when Kimberly left the network amid sexual misconduct allegations – which she later denied to The New Yorker. "In my 30-year career working for the SF District Attorney's Office, the LA District Attorney's Office, in media and in politics, I have never engaged in any workplace misconduct of any kind," she wrote in a statement. "During my career, I have served as a mentor to countless women, with many of whom I remain exceptionally close to this day."

Though reports suggested leaving Fox News wasn't her decision, Kimberly maintained she was in control of the career move. "I've decided to leave Fox News Channel and dedicate myself full time to joining America First as Vice Chairwoman, campaigning across the country and firmly standing with President Trump," she tweeted in 2018. "I will miss my Fox family. I thank Fox for the opportunities it has provided me." But Donald Trump wasn't the only member of the famous family she was getting close with.

Kimberly Guilfoyle's political work with Donald Trump came as her romantic relationship with his son, Donald Trump Jr., hit the headlines. Page Six confirmed the two were an item in May 2018, two months after Don Jr. announced his divorce from ex-wife Vanessa Trump. "Don Jr. and Kimberly are seeing each other, and are having a great time," a source said.

Though Kimberly was already well-known in the political, legal, and media world, her relationship with Don Jr. brought her even more attention. The outspoken Republican began working closely with her new boyfriend's family and accepted a job as Trump's senior advisor in 2019 as he prepared to run for re-election. The Atlantic reported she had wanted a White House press secretary job, but an insider claimed, "Even [Trump] can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads." Ouch.

That didn't stop Kimberly — who fit right in with the Trump women (and their embarrassing makeup mistakes) – from publicly backing her boyfriend and his dad, though. She and Don Jr. made a joint appearance on "The View" in 2018, where Kimberly shared, "I know the measure of the man. I know his character ... Both of them, the entire family. I stand for them because I do believe their commitment."

2020 saw Kimberly Guilfoyle land two even more prominent positions in the Trump world ... in very different ways. Early in the year, the confident political figure became chair of the Trump Victory finance committee. But Kimberly's extra responsibility didn't slow down her and Donald Trump Jr.'s romance. Don Jr. popped the question on New Year's Eve 2020, which was also his birthday. The two kept the news quiet for a while, with their plans to wed only becoming public in early 2022. 

"They've been together for almost four years now and have been friends for 15 years," a source told Daily Mail. The insider claimed they kept things on the down low because they were focused on relocating from New York to Florida and supporting their blended family. The happy couple had settled on a $9.7 million mansion, 20 minutes away from Trump's Mar-a-Lago resort, realtor Rob Thomson told People. "They loved the house both inside and out. They are doing a few things to the inside but are anxious to move in," Thomson shared.

In 2023, the former "The Five" star landed her own online Rumble show, the eponymous "The Kimberly Guilfoyle Show." "You can trust that nothing will be off limits and that I will always speak my mind without fear," she said in a press release (via Global Newswire). And speak her mind, she did.

2024 was a transformational year for Kimberly Guilfoyle, and not only because she landed a spot on our worst dressed celebs list. As Don Jr. was spotted with another woman, fans started noticing major warning signs Kimberly and Donald Trump Jr. wouldn't last. Don Jr. spent time with Bettina Anderson on multiple occasions and shared he was no longer in a relationship with Kimberly in December 2024. "Kimberly and I will never stop caring for each other and will always keep a special bond," he told Page Six.

That same month, President-elect Trump announced Kimberly would be the next U.S. ambassador to Greece. She seemed thrilled with her unexpected new role, which would see her relocate to Europe. "I'm honored to accept President Trump's nomination to serve as the next Ambassador to Greece and I look forward to earning the support of the U.S. Senate," she wrote on X, formerly known as Twitter. "As ambassador, I look forward to delivering on the Trump agenda, supporting our Greek allies, and ushering in a new era of peace and prosperity," she added.

Kimberly wore some questionable looks to Trump's inauguration in early 2025, but confirmed she was still on good terms with her ex's family as she supported the 45th and 47th President of the United States at various events. And she seemed very optimistic about her future in a November 2024 Instagram post. "So blessed to be part of the greatest campaign and political comeback of all time. Now it's finally time to get this country back on track!" she wrote. "THE BEST IS YET TO COME!"