The Brutal Rise & Fall Of Kimberly Guilfoyle

In 2018, Kimberly Guilfoyle was everywhere. Her face was splashed all over posters from Fox News, and her image graced the photo galleries of some of Mar-a-Lago's flashiest parties. She had worked as a co-host on Fox's "The Five" for seven years, and she had sparkled on the arm of her famous boyfriend, Donald Trump Jr., for a couple of months. This was the peak moment of Guilfoyle's career — and it wouldn't last.

Indeed, by the dawn of 2026, the television presenter and political personality found herself firmly on the outs of all things MAGA. Not only had Guilfoyle spectacularly burned her bridges with the world of conservative network television, but she had also lost that spark in her romance with Don Jr. Before she knew it, Guilfoyle had no journalistic career to speak of, no influence on the Trump family inner circle, and no reputation to fall back on. 

Although Guilfoyle began her career as a hard-working law student, she seemingly grew jaded by glamor, luxury, and power. She was accused of abusing her position at Fox to take advantage of at least one lower-ranking employee. And then, she threw herself into the upper echelons of Trumpland — only to receive the boot after Guilfoyle's breakup with Don Jr. Her sudden demise was enough to leave fans wondering what happened to the former prosecutor. Unfortunately, the answer to that question lies in the media personality's most embarrassing errors.

Growing up, Kimberly Guilfoyle knew that she wanted to succeed. Even when she was just a young girl on the soccer pitch, Guilfoyle was hungry for a challenge. She wanted to play on a real soccer team, but no such opportunities existed for girls at the time. With the support of her mother, Guilfoyle requested the opportunity to try out for the boys' team. As she would one day reveal in a 2001 interview with SF Gate, "Well, I made the team, and later we got one other girl, and I was just as happy as can be. And, looking back on it, I think that was exactly the principles my parents tried to teach to me: Everyone should have an equal chance to show their ability."

As she grew older, Guilfoyle carried this sense of fiery determination into the classroom. She earned a spot at the University of San Francisco School of Law, and when it became clear that the cost of a graduate degree was not especially accessible, Guilfoyle turned to modeling. It didn't take long for her to become successful. "I knew I wanted to go to law school, and it ended up being a great way to pay for it," she told People in 2014. "I modeled everything from clothes, swimwear, and lingerie, including Victoria's Secret!" She also posed in a number of more artistic photos that were displayed in European art galleries.

Modeling wasn't the only job that Kimberly Guilfoyle took on during her school days. Because of her tight financial situation, she actually combined the income from several side hustles to make ends meet. "I had three jobs: 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," Guilfoyle told Cosmopolitan in 2014.

Even as she was earning money and attending classes, Guilfoyle never stopped looking for opportunities. She started to expand her network by asking people in her circle what other kinds of jobs were out there. "You can't be shy about it," Guilfoyle revealed in the same interview with Cosmopolitan. "I would say, 'Hey, do you know somebody who is in this field that I may be able to talk to and get some experience?'" She would then volunteer her time in exchange for the chance to bolster her C.V. While this was an incredible amount of work, it paid off in spades. "It was life experience and work that was well worth it," Guilfoyle said. Eventually, her legal dreams came true. She moved to Los Angeles to work as a deputy district attorney before returning to her hometown of San Francisco as an assistant district attorney in 2000. There, she worked alongside big shot lawyers like Gavin Newsom and Kamala Harris.

During her tenure at the San Francisco district attorney's office, Kimberly Guilfoyle got her first glimpse into politics. This dynamic would only intensify in 2001 when she married Gavin Newsom — who, at the time, was at the early stages of a huge political career. Shortly after tying the knot, Guilfoyle would support Newsom in his campaign to become mayor of San Francisco. Once Newsom actually won the elections in 2003, Guilfoyle became the city's first lady. This role entailed a lot of handshaking at glamorous galas and exclusive events. It also meant hosting King Charles III and Queen Camilla just months after their 2005 wedding.

"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," said Guilfoyle to People. To charm the royal duo, Guilfoyle threw all their strange royal dining rules to the wind and borrowed a bite off of Charles' plate. "During one of the formal dinners, I was sat next to Prince Charles who was kind enough to share the rest of his apple tart dessert with me," she admitted. Ultimately, this experience helped open Guilfoyle's eyes to the fascinating world of politics and diplomacy — a lesson she was sure not to forget.

If Gavin Newsom and Kimberly Guilfoyle had stayed together, she would have become the first lady of California. Alas, that was not to be, and Guilfoyle parted ways with Newsom in 2006. Rather than launch a political career of her own, Guilfoyle developed an interest in journalism. While that may seem like a major career pivot, Guilfoyle tried to take her shifting interests in stride. "Don't be afraid to try different things to see what feels right and what's a good fit," she once told Cosmopolitan. "Then once you're in, if an opportunity presents itself, don't be afraid to go through that door and explore and see if it's something you could become excited about or that you go to bed at night and wake up in the morning and feel good about."

The same year of her divorce, Guilfoyle co-hosted a show on Fox called "The Lineup." This initial foray into the television world did not last, as the show was cancelled after just one season, but Guilfoyle did not give up on her silver screen dreams. She continued to work for Fox as a legal consultant, making a number of commentator appearances over the years. After working very hard to secure a seat at the table, Guilfoyle earned a spot as a co-host for the major political show, "The Five," in 2011.

In the capacity as a co-host for Fox's "The Five," Kimberly Guilfoyle became a big-name political commentator with a significant following. Conservatives, in particular, admired her work and wanted to learn more about what made her so successful. To share her story with her fans, Guilfoyle penned a book titled "Making the Case" and published it in 2015. The tome explained Guilfoyle's unique strategy for achieving her goals — or, as she put it, "just because something isn't already established doesn't mean you can't pursue it, accomplish it, and blaze a path for others while doing it" (via Forbes). Some examples provided in the book include her efforts to pay for law school via modeling, as well as her decision to work as a legal consultant for three separate television networks.

Interestingly, the book was well-received. Writing for Forbes, one political commentator lauded the piece as an excellent tool for women looking to further their professional development. "Kimberly's book is replete with fantastic career advice which everyone should heed, but is especially valuable for women. She knows full well from her own career how important it is for women to be their own advocates when comes to getting jobs, promotions, and leadership positions," he wrote. In many ways, "Making the Case" was the pinnacle of Guilfoyle's career. It represented a moment when people would still turn to her for career advice and professional know-how. That moment would turn out to be rather short-lived.

In 2018, Kimberly Guilfoyle seemed like the woman who had everything. She had a swanky job on network television, a successful book, and a solid overall professional reputation. However, all that took a sudden turn for the worse when Guilfoyle's assistant accused her of sexual harassment. According to a report in the New Yorker, several employees at Fox News anonymously revealed that Guilfoyle had behaved inappropriately in front of a junior worker. The allegations indicate that Guilfoyle would invite her assistant over to her apartment, where she would then walk around naked. Guilfoyle would also allegedly show photographs of nude men to the more novice employee.

Per the same report, the accusations against Guilfoyle were so strong that they resulted in the swift termination of her contract. The assistant reportedly received a $4-million payout from the network, which was reportedly keen to avoid the publicity of a big trial. When confronted with these accusations, Guilfoyle released a statement to the magazine denying the claims: "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. During my career, I have served as a mentor to countless women, with many of whom I remain exceptionally close to this day." Denials aside, the evidence against Guilfoyle was enough to end her career at Fox. 

Kimberly Guilfoyle had a busy year in 2018. Although getting ousted from Fox News may have been a major career blow, the political commentator experienced a boost in her romantic life — linking up with none other than President Donald Trump's son, Donald Trump Jr. Kimberly Guilfoyle and Don Jr. first sparked dating rumors after they were spotted together at a glamorous party in New York. At the time, the budding couple was viewed as scandalous. After all, Don Jr. and his first wife, Vanessa Trump, were in the middle of a divorce. "Don Jr. and Kimberly are seeing each other, and are having a great time," a source told Page Six in 2018. "While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company."

Around the same time that Guilfoyle embarked on her new romantic relationship with Don Jr., she also began to seek out new career opportunities — this time in politics. She became the vice-chair of a pro-Trump super PAC called America First Action. And, she began to give Don Jr. a couple of pointers about how to work the media. Before long, Guilfoyle and Don Jr. were known as that political power couple. "They are like the prom king and queen of MAGA land," gushed a senior Trump aide in a 2020 conversation with Business Insider. For a second, the duo seemed unstoppable.

In the weeks leading up to the 2024 presidential elections, Kimberly Guilfoyle should have been getting ready to take her MAGA career to the next level. Instead, she was nursing a broken heart. "Don and Kimberly broke up before the election and started to divide assets around the end of September," a source close to the former couple told Us Weekly. They reportedly refrained from announcing their split at the time so as not to stir up drama right before election day.

The same source went on to allege that Don Jr. was the one to break up with Guilfoyle. The president's son was indeed spotted hanging out with socialite and former model Bettina Anderson before it was even announced that Guilfoyle was out of the picture, according to Don Jr. and Anderson's official relationship timeline. That said, Don Jr. has only expressed kind things about his former flame. "Since the very beginning, no one on Team Trump has worked harder than Kimberly to help elect and reelect my father," he told Page Six at the time.

Despite Guilfoyle's efforts to support President Donald Trump, her split from Don Jr. was not great for her MAGA career. It became awkward for her to spend too much time among members of Trump's inner circle. As one well-placed source told Rob Schuter for his #SchuterScoop substack, "The second Don moved on, so did the family. Kimberly was discarded like yesterday's news."

In March 2025, Kimberly Guilfoyle's ex-partner, Don Jr., announced his engagement to Bettina Andersen. The proposal marked a shift in social dynamics that pushed Guilfoyle firmly out of MAGAland. Once known as Don Jr.'s eternal plus one, Guilfoyle suddenly stopped receiving invitations to major political events. The Mar-a-Lago galas, golf tournaments, and Trump family birthday parties that once stood at the center of Guilfoyle's social life were suddenly ripped away. Anderson, of course, quickly stepped in and took her place.

Adding insult to injury, a source close to the Trump family told Rob Schuter's #SchuterScoop substack that Anderson has been much more popular with the MAGA crew than Guilfoyle ever was. "They never embraced Kimberly like this. Bettina fits their polished image. Kimberly never quite made the cut," dished the insider. Chatting with Schuter for the same report, another source revealed that Guilfoyle has been losing Trump friends left and right: "Kimberly's putting on a brave face. But behind the scenes, it hurts. She went from nearly being a Trump to being totally iced out."

Apparently, the women of the Trump universe have taken a step back from their friendships with Guilfoyle. Alina Habba and Lara Trump seemingly kicked Kimberly Guilfoyle to the curb following the breakup. What's more, Guilfoyle's initial interest in maintaining a friendship with Don Jr. has not exactly come to fruition, with the two attending almost none of the same events since their split.

By the time 2025 came to a close, Kimberly Guilfoyle's fall from grace was made complete in the form of a good old-fashioned Trojan horse. Indeed, the former television presenter was appointed the American ambassadorship to Greece — a punishment disguised as a gift. The aforementioned professional opportunity may have given Guilfoyle the chance to travel the world, but it also came with a serious drawback. The newly-minted ambassador would be forced to spend a lot of time overseas — far away from President Donald Trump and his political universe. In essence, this would mean that Guilfoyle would be going into a sort of political exile, and it didn't take fans long to realize that Guilfoyle was ousted from Trumpland in a major way.

Additionally, Guilfoyle reportedly had been hoping to be made chair of the Republican National Committee (RNC) after everything she did to support the reelection of President Donald Trump. It seems that when Lara Trump, Eric Trump's wife, was selected for the role in her place, there were some hard feelings. "Kimberly speaks very badly about Lara Trump. She told me that she was p*ssed Lara got RNC co-chair over her. So yeah, she doesn't like her," a former Trump administration official told the outlet. "Guilfoyle believed that she was the more natural fit to be selected for the role of RNC co-chair over Lara."