6 Rumors About Kimberly Guilfoyle You Can't Ignore

This article includes discussion of sexual misconduct. 

It was the stuff of tabloid dreams: Donald Trump Jr. had been spotted frolicking with another woman in Palm Beach while he was supposed to be a faithful fiancé to Kimberly Guilfoyle. The Daily Mail ran with the story, and other outlets quickly followed suit. It was the kind of rumor (complete with damning photographic evidence) one simply couldn't ignore, no matter how immune you might consider yourself to be against tabloid fodder. Fast-forward to Donald Trump's 2025 inauguration, and it was all over between them but Guilfoyle and Don Jr.'s split wasn't exactly keeping them apart either. Bettina Anderson, his new girlfriend, was by Don Jr.'s side at the festivities, but apparently, Guilfoyle was watching them the whole time. In fact, rumor has it she had a hard time letting go of her fiancé of almost four years, which is understandable. 

"[She] has every intention of maintaining a relationship with [Donald Trump Jr.]," an insider confirmed to Page Six. "Kimberly and Don have known each other for years and have a lot of history together so she feels like they'll always have a connection." Wanting to maintain a close connection with someone who cheated on you publicly might seem odd, but clearly, the former Fox News host is the forgiving type. Still, sources who spoke to People claimed that Guilfoyle and Jr.'s breakup was a mutual decision with no lingering hard feelings. "It's not one that is going to blow up, at least at this point," one said. It's that last bit that had everyone waiting for the other shoe to drop, and there are plenty of signs that Guilfoyle and Don Jr.'s breakup was messier than it seems. It's hardly the only rumor plaguing the new U.S. ambassador to Greece, however.

It would appear that the tabloids were a little late to the punch when it came to discovering Donald Trump Jr.'s supposed infidelity. Sources told People that he was canoodling with Bettina Anderson for a good six months before the press ever got wind of it, disclosing, "He even took her on a trip to Alaska and introduced her around as his girlfriend when he was still very much with Kim." As such, when the Daily Mail broke the news that Don Jr. had been spotted getting cozy with the socialite within full view of passers-by, sources claiming that he and Guilfoyle were headed straight for Splitsville were suddenly abundant. 

"Don and Kimberly haven't been getting along over the past year," one divulged to Page Six. "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." Some insiders claimed that they were simply going through a rough patch; others said the relationship was over. A Daily Mail source posited that, despite Don Jr. reportedly having had an affair with Anderson for months, Guilfoyle was completely taken aback by the news that her fiancé was seeing another woman behind her back. "Kimberly either didn't know about Bettina — or didn't want to know," an insider dished. 

However, they also acknowledged, "Did she hear whispers that Don Jr. was fooling around with someone else? Probably." The former Fox News host must've really wanted that cushy White House job to put up with her fiancé's philandering ways, especially after it became public knowledge. The Daily Mail broke the story in September 2024, but the couple's split was only officially confirmed in December of that year.

Seemingly, if you have a history of sexual misconduct, it secures you a first-class ticket straight to the bowels of the White House — at least, when the Trump administration is running things anyway. President Donald Trump appointed Kimberly Guilfoyle as the new United States ambassador to Greece, and like many of his other questionable cabinet picks, she has a few skeletons in her closet. The staunch Trump loyalist was plagued by past accusations of sexual misconduct, which regrettably seems to be a running theme among Trump's nominees. Guilfoyle left Fox News in 2018, and even though the story at the time was that she resigned, inside sources revealed to HuffPost that the network had actually forced Guilfoyle out after her assistant accused her of sexual harassment. 

The complainant alleged that her boss often insisted she work at her apartment, where the former Fox News host showed her photographs of naked men she'd slept with and regularly walked around nude. Guilfoyle also allegedly divulged details about her sex life and asked her assistant to make assessments of her naked body. Additionally, the former employee professed that Guilfoyle once requested she massage her thighs. It was just the tip of the iceberg, though, since HuffPost's sources claimed Fox's hair and makeup staffers also endured similar mistreatment.

"Any accusations of Kimberly engaging in inappropriate work-place conduct are unequivocally baseless and have been viciously made by disgruntled and self-interested employees," Guilfoyle's lawyer said in a statement. The woman herself, meanwhile, clarified in her own statement to the New Yorker, "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."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Kimberly Guilfoyle faced her fair share of controversy long before Donald Trump Jr. entered the picture, most notably the nightmare that the former Fox News host found itself embroiled in when the network's former CEO, Roger Ailes, was accused of sexual misconduct. Rumor has it that Guilfoyle was his protégé. Many former Fox employees have spoken out about the culture of sexual harassment at the network, with former anchor Alisyn Camerota bravely detailing how Ailes made unwanted advances toward her and demanded sexual favors in exchange for granting promotions.

According to several insiders, when Ailes was ousted from the network, Guilfoyle didn't quite catch on to the fact that the culture at the company was changing. HuffPost's sources explained that her close association to Ailes made her powerful, and despite (reluctantly) taking his leave, Guilfoyle continued her questionable behavior unabashedly, which included harshly criticizing some of her fellow hosts. Jeanine Pirro typically got the brunt of it, with Guilfoyle reportedly telling anyone who would listen that, at 67 years old, the TV personality was well past her expiry date.

When news about Ailes' sexual harassment of his employees broke, his wife knew who to call first: Guilfoyle. Her instincts were sound; the former "Fox & Friends" co-host reportedly did everything in her power to convince her co-workers to sing Ailes' praises. In a film made about the whole scandalous saga, Guilfoyle is portrayed as going all out to ensure her female colleagues didn't speak negatively about their boss and instead showcased their support by wearing T-shirts to show solidarity with the disgraced CEO. The actor portraying Guilfoyle is even seen handing the shirts out around the office, instructing her co-workers to wear them that instant.

When former Fox News CEO Roger Ailes found himself in hot water for allegedly sexually harassing his female employees, those working both for and closely with him were forced to choose a side. Either they believed former news anchor Gretchen Carlson's very serious allegations or they supported Ailes' vehement denials. As it turns out, Kimberly Guilfoyle took this decision away from some of her colleagues, pledging their support to Ailes before they even had a chance to assess the situation for themselves, according to sources who spoke to HuffPost. Some couldn't be convinced, however, because they'd experienced Ailes' harassment first hand. Megyn Kelly, in particular, reportedly didn't get along with Guilfoyle after she refused to defend Ailes. 

According to insiders, things got increasingly nasty between the two colleagues after Ailes was ousted for his shocking crimes, with Guilfoyle reportedly launching an outright smear campaign against her fellow Fox host in retribution. Kelly, meanwhile, detailed her experiences in her book, "Settle for More," writing, "I would be called into Roger's office, he would shut the door. He would engage in a kind of cat-and-mouse game with me [...] veering between obviously inappropriate sexually charged comments...and legitimate professional advice." She also recalled a horrifying instance when the CEO tried to kiss her repeatedly. Kelly explained that she didn't speak up out of fear that she would lose her job at the network. In the end, she left Fox for NBC News.

If you're finding yourself questioning whether the sexual harassment allegations against Kimberly Guilfoyle had any merit, her 2020 shenanigans may convince you, after she reportedly exhibited similar behavior while managing the financial side of Donald Trump's 2020 re-election campaign. Members of the Republican Party were incredibly offended by Guilfoyle's behavior, which included discussing her sex life with Donald Trump Jr. in much more detail than anyone should ever have to hear. Some members of the GOP went as far as to dub Guilfoyle an "HR nightmare," (via SFGATE).

Under her guidance, Trump's 2020 finance team failed to achieve anything notable, and donors were apparently so put off by Guilfoyle's wildly unprofessional conduct that they summarily closed their wallets and walked out the door. To offer some additional context, she reportedly once offered to reward the most generous donor with a lap dance. Michael C. Bender, who was the Wall Street Journal's White House correspondent during Trump's first term, dished a little about Guilfoyle's shocking behavior in his book, "Frankly, We Did Win This Election: The Inside Story of How Trump Lost." 

Among other things, Bender claims that she reportedly once told gathered donors how Don Jr. was a "naughty boy [when she] let him out of his cage" and that he loved it when Guilfoyle dressed up as a cheerleader. One can't help but wonder whether Trump has realized (albeit too late) that Guilfoyle might be the real reason he lost the 2020 election.

Believe it or not, the Trump family might actually be just a little bit afraid of Kimberly Guilfoyle and all the dirty secrets she could spill should they ever get on her bad side. The fact that the former Fox News host has been so forthcoming about her sex life with Donald Trump Jr., with complete strangers, should serve as a major red flag to the controversial clan since, clearly, Guilfoyle isn't shy about discussing, well, anything. "The Trump family does not want to create an enemy in Kimberly," an insider informed RadarOnline. "They are concerned about what damage she could do."

Likewise, several insiders who spoke to People echoed these sentiments, pointing out that Don Jr. tried his best to handle their breakup as carefully as possible since, "They didn't want the split to get in the way of anything to hurt Donald in the election." His new girlfriend, Bettina Anderson, can hardly wait for Guilfoyle to get out of the picture, though, suggesting that her appointment as the U.S. ambassador to Greece was a calculated move. 

"They are trying to send Kim abroad," the source disclosed. Apparently, Guilfoyle loves the idea of being a Trump, but she no longer loves Don Jr. nearly as much, and rumor has it many of his family members weren't exactly fans of hers to begin with. "Despite what the Trumps might say in public, they were never fully behind Kimberly. Some of them were even turned off by her, though they'll never admit it," an insider confessed to RadarOnline.