Kimberly Guilfoyle's Rise And Fall In Trump Land

Many who have managed to land themselves within the inner circle of Donald Trump and his family have discovered that association doesn't always stand the test of time. Just ask former New Jersey governor Chris Christie, ex-attorney general William Barr, and onetime national security adviser John Bolton — just a few of the numerous folks who were once trusted allies before being on the outs, trashed by Trump as, respectively, "a bum," "a gutless pig," and a "sick puppy." Then, of course, there's the sad downfall of beleaguered and embarrassment-prone Rudy Giuliani, once lauded as "America's Mayor" and now forced into bankruptcy after a court ordered him to pay $146 million to a mother and daughter whom he falsely accused of election fraud — at Trump's behest, no less.

Suffice it to say, being a MAGA insider can bring perks galore, yet can also be fraught with peril. The latest to wind up on the outside looking in is Kimberly Guilfoyle, the twice-divorced lawyer and former Fox News personality who has been at the epicenter of Trump's 2024 presidential campaign — in no small part due to her role as fiancée of Donald Trump Jr. 

Once a fixture of Trump's ever-evolving group of insiders, her circumstances have seemingly changed radically and rapidly. So, how did it all go so wrong? To find out, read on to experience the rollercoaster ride that led to Kimberly Guilfoyle's rise and fall in Trump Land.

Given her history, Kimberly Guilfoyle would seem an unlikely candidate to become a leading right-wing figure. After all, she was once married to California governor Gavin Newsom (then liberal mayor of San Francisco), one of the shining stars in the Democratic party. That union didn't last, and after their four-year marriage ended in divorce, she married businessman Eric Villency in 2006. 

That marriage was also doomed to fail. However, during her brief three-year stint as Villency's wife (Guilfoyle and her second spouse divorced in 2009), she and her future ex crossed paths repeatedly with Donald Trump Jr. and his then-wife, Vanessa Trump. During her marriage to Villency, Guilfoyle's politics shifted to the right, moving her from a non-partisan TV gig at Court TV to Fox News, the deeply conservative cable news channel owned by controversial media mogul Rupert Murdoch. 

It was during her early years at Fox News that she first began encountering members of the Trump family at various society functions in New York City. She was first introduced to Donald Trump Jr. at a party while both were married to other people. They got to know each other because her son with Villency, Ronan, attended the same school as Kai, the daughter Trump shares with then-wife Vanessa. They were friendly but would become even better acquainted about a decade later.

After Donald Trump's victory in the 2016 presidential election, Kimberly Guilfoyle put both her Fox News cred and her Trump family connections into action when, in 2017, she made a play to become White House press secretary. At the time, Trump reportedly looked to shake up the White House communications strategy, having grown unhappy with then-press secretary Sean Spicer. According to a New York Times report about the then-president's plans, Trump floated Guilfoyle's name for the position. 

Guilfoyle confirmed that report when she told the Mercury News she was in serious discussions to take on a role within the Trump administration, potentially replacing Spicer as White House press secretary. "I'm a patriot, and it would be an honor to serve the country," she said. "I think it'd be a fascinating job, it's a challenging job, and you need someone really determined and focused, a great communicator in there with deep knowledge to be able to handle that position."

Speaking on Fox News, in what seemed to be an on-air job interview, Guilfoyle shared her philosophy of how a press secretary could succeed when working with the freewheeling Trump. "If you want to be successful and do communications with President Trump, you have to be someone who he actually wants to spend a little bit of time with," she said, explaining how face time with the president was crucial in conveying his message. She did not get the job, however, which ultimately went to Sarah Huckabee Sanders.

It wasn't long after Kimberly Guilfoyle's name was floated as a potential White House press secretary that she began popping up in gossip columns. It started in March 2018, when Vanessa Trump announced that she'd split from husband, Donald Trump Jr., and had begun divorce proceedings. In May, Page Six reported that Donald Trump's eldest son had already moved on, and was dating Guilfoyle. "Don Jr. and Kimberly are seeing each other, and are having a great time," a source told the outlet, which claimed the two had been seen together in public on more than one occasion. "While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company," that source added. 

While neither confirmed it, Guilfoyle and Trump weren't exactly keeping their budding romance under wraps. In June, the two went Instagram official, pictured with Poison frontman Brett Michaels in a post.

Years later, Guilfoyle recalled how the two went from acquaintances to lovers. "Don and I knew each other for years but when we went on one date years later, that was it. Sparks," she told Metropolitan Palm Beach magazine in 2022. "In fact, we have been together from that night on, happily ever after!" 

By June 2018, Donald Trump Jr. and Kimberly Guilfoyle (who'd exited Fox News a year earlier amid allegations of sexual harassment) were a full-fledged couple; if the Make America Great Again movement were a wedding cake, tiny plastic versions of them would adorn its top. That was apparent when Trump took her on every woman's dream date: as his plus-one to the 2018 Montana Republican Convention, where he delivered a speech before the two went on a fishing and hunting expedition that he joked was a compatibility test. "Just as everyone else thanks their significant others, I got to thank Kimberly for coming out here," Trump told the crowd, as reported by Vanity Fair. "We're going to take her fishing tomorrow, then shooting. This is a miniature test to see if she really likes it, or if she's going to pretend to like it, but either way we're going to have a good time — or at least I will."

Not long after that, Page Six reported on their sickeningly sweet alleged pet names for each other. "She called out her boo and called him Junior Mints," a "friend" told the outlet, which also reported that Trump's term of endearment for her was Pooh Bear. 

As the official girlfriend of Donald Trump Jr., Kimberly Guilfoyle entered the Trump family's inner sanctum. Guilfoyle, however, was far more than just arm candy. She put herself into service of the president and his MAGA movement, becoming a Trump surrogate and delivering fiery speeches at his rallies. 

Meanwhile, her influence on Don Jr. had increased his MAGA cachet, with sources claiming that she'd groomed and molded him in a manner that increased his popularity with his notoriously fickle father — and, by extension, his political base. "She's definitely made Don Jr. more serious," NYC publicist and former gossip columnist R. Couri Hay told Business Insider. "She's had years and years on TV. She's helped guide and train and been very influential in Don's increasingly very secure, very formidable, very opinionated television personality." Added Hay: "She's been able to guide him and lead him in the political waters. And he is basking in it and loving it." Meanwhile, Hay also pointed out that his ex-wife, Vanessa Trump, had no interest in politics, while Guilfoyle was all in. "In Don Jr., Kimberly found a real partner," he added.

Meanwhile, another insider pointed out Guilfoyle's similarities to her beau's father, implying his attraction to her was due to his daddy issues. "It's interesting to me that Donald Trump Jr. ended up with a female version of his father," said the source. 

Kimberly Guilfoyle's rise within the ranks of Trump Land was evident during the 2020 Republican National Convention when she was chosen to deliver a keynote speech. That speech was ... well, it was something. Not only did she describe Donald Trump's opponent, Joe Biden, as a raving socialist, but she also made a few eyebrow-raising claims about the Democrats. "They want to destroy this country," she said, her voice growing louder with each word. "They want to steal your liberty, your freedom, they want to control what you see, and think, and believe so that they can control how you live. They want to enslave you to the weak, dependent, liberal victim ideology to the point that you will not recognize this country or yourself."

While her strident speech appeared to go over well at the convention, that certainly wasn't the case elsewhere. There were some, for example, who compared her histrionic speaking style and shouting style to that of Dwight Schrute's Mussolini-like rant in an episode of "The Office." 

Among the many to weigh in were "Late Show" host Stephen Colbert, who described Guilfoyle as a "vengeful banshee who will haunt your dreams," and New York Times TV critic James Poniewozik, who wrote that she was on a mission to "Make America Deaf Again." "Daily Show" host Trevor Noah may have put it best when he quipped, "I want to wish a speedy recovery to anyone who was listening on headphones."

Kimberly Guilfoyle and Donald Trump Jr. had been the pre-eminent MAGA power couple for years when they made a 2019 appearance on "The View." They were asked about whether they'd be walking down the aisle anytime soon. "Oh my God!" Guilfoyle responded (via People), insisting that any wedding plans were in second position to their primary goal. "We need to get the president re-elected!" she declared.

That did not happen. With Donald Trump exiting the White House and returning to Mar-a-Lago, the rest of the Trump family followed suit and made Florida their home base. In 2021, The Palm Beach Post reported that Guilfoyle and Trump had been scoping out a waterfront home in Admiral's Cove, a chi-chi gated community in Jupiter, Florida.

As it happened, those who already lived there weren't exactly welcoming to their prospective new neighbors. "About half have concerns about safety," said Peter Moore, general manager of the property owners association. "The others have political concerns with what's happened in the last couple of weeks." Despite their new neighbors' misgivings, the couple pulled the trigger on the $9.7 million purchase of an 11,300-square-foot mansion, situated 20 minutes from Mar-a-Lago.

Status-wise, it's one thing to be the girlfriend of Donald Trump Jr., but quite another to be his fiancée. In 2022, Guilfoyle took to Instagram to share a photo of herself and Don Jr. posing in front of a festive Christmas tree at the White House. His hand on her hip, the ring finger on her left hand sported a large engagement ring. "Tonight was extra special celebrating @donaldjtrumpjr's birthday," she wrote in the caption, confirming they were engaged. "Don, you are strong, smart, courageous, funny and the love of my life. I can't wait to spend the rest of our lives together."

Their engagement, however, may not have been as recent as most people had assumed. As a source told Page Six, they'd actually been engaged for well over a year but had made the mutual decision to keep things hush-hush. "They've kept it private for the past year as they settled into life in Florida after moving from New York," the source said, pointing out that "both are focused on their children — they have six between them — and their work."

After Donald Trump won the 2024 presidential election, the obvious assumption was that Donald Trump Jr. and fiancée Kimberly Guilfoyle would tie the knot at some point in the not-too-distant future. Those assumptions, however, hit the skids when reports emerged that Don Jr. had been seen enthusiastically kissing a woman who was decidedly not his fiancée.

According to the Daily Mail, eyewitnesses saw Don Jr. "canoodling" in a bar with Palm Beach socialite Bettina Anderson — with Guilfoyle nowhere in sight. Those sources told the outlet that the two kissed each other no less than three times. "She seemed totally smitten with Don — and he with her," the source said. "They looked totally relaxed, she wearing a white shirt tied off to show her midriff and wide-leg pants, he in shorts and a t-shirt." That source added, "They were definitely on a date. They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other."

Another source indicated that this new romance was not a secret, and had become the talk of the Palm Beach social scene. "I guess they're not trying to hide it," that insider claimed. "They've been seen together all over Palm Beach."

That Daily Mail report about Donald Trump Jr.'s shenanigans with Bettina Anderson reportedly hit Kimberly Guilfoyle like the proverbial ton of bricks. However, insiders claimed that Don Jr. had hardly been low-key about his cheating and that Guilfoyle had possibly even been turning a blind eye to her fiancé's dalliances. "Kimberly either didn't know about Bettina — or didn't want to know," an insider told the Daily Mail. "Did she hear whispers that Don Jr. was fooling around with someone else? Probably."

According to that source, discretion has never been Don Jr.'s strong suit. "He's pretty bold and, as smart as she is, Kimberly looked the other way," the insider added. 

Despite the lack of shame with which her fiancé approached his new romantic relationship, Guilfoyle's future with Don Jr. remained an open question. "What happens now is anyone's guess. Will she stick? Will he dump her?" said the "friend," who pointed out that it was clear during the 2024 Republican National Convention that Guilfoyle's position within Trump World had been marginalized. "She seemed odd woman out," the source said.

Speculation about the state of the engagement between Donald Trump Jr. and Kimberly Guilfoyle hit a fever pitch when President-elect Donald Trump took to social media to tweet some news. "Today, I am very pleased to announce the appointment of Kimberly Guilfoyle as the United States Ambassador to Greece," Trump wrote.

Given the rumors about Don Jr. and Bettina Anderson — and the simple fact that Guilfoyle had neither any connection to the country nor any experience whatsoever in international diplomacy — one key question arose immediately: was Guilfoyle's appointment to Greece a way of getting her out of the way so that Don Jr. could pursue his new romance?

If the ambassadorship was indeed a form of exile from Trump Land, Guilfoyle was savvy enough to put a different spin on it. "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 wrote via Instagram.

Rumors that Kimberly Guilfoyle and Donald Trump Jr. had booked one-way tickets to Splitsville seemed to solidify into fact when numerous sources came forward to confirm that they had ended their engagement and gone their separate ways. As one source told Page Six, the writing had been on the wall for some time. "Don and Kimberly haven't been getting along over the past year," that source told the outlet. "They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public."

There may have been even more to the couple's breakup than that. "Don Jr. has always wanted to look good in his father's eyes," a source told People, claiming that Guilfoyle's stock within MAGA's inner circle had fallen significantly in recent months and that Don Jr. was anxious to prevent her from dragging him down with her. As the source claimed, Don Jr. was on the hunt for another romantic partner who would help to elevate him in the eyes of his dad. "Someone like Bettina," said the source, "who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him."

Meanwhile, Don Jr.'s family is reportedly happy to see him put Guilfoyle in the rearview mirror — with the President-elect offering the ambassadorship as a smooth exit from Trump Land. "Kim is not a nice person and always wants the limelight," a source told People. "Don and Kim are over but they are going to offer her some kind of an administrative position so she will be happy."