Rumors Surrounding Kimberly Guilfoyle We Can No Longer Ignore

Kimberly Guilfoyle and Donald Trump Jr. are no more. Their great love affair ended in heartbreak amid rumors of infidelity. In December 2024, PDA pics of Don Jr. and his purported mistress emerged, sucker-punching Guilfoyle and hammering the final nail in the #Donberly coffin. Still, Guilfoyle may well be gone from Don Jr.’s side, but she most definitely will not be forgotten or squirreled away in hiding.

Quite the opposite, in fact. As Don Jr.’s affair continued to heat up, Guilfoyle ramped up her scandalous revenge style. And Guilfoyle continues to thrill us all with her arsenal of inappropriate outfits and saucy style.

Guilfoyle’s rise and fall in Trump land was pretty epic. She rapidly ascended the GOP ranks to become a key figure in the MAGA movement before being unceremoniously dispatched to Greece by Donald Trump. Living in the lap of luxury in Athens is none too shabby, but still, it’s a long way from home — which, let’s face it, could be the very reason she was appointed to the role in the first place. However, out of sight is unlikely to mean out of mind when it comes to Guilfoyle. Her seeming lack of diplomatic skills and fiery rhetoric will inevitably ensure she’ll continue hogging the headlines for a long time to come. Plus, there are all the rumors surrounding Guilfoyle, which, true or not, are definitely worthy of entertaining. We’re taking a look at some of the ones we just can’t ignore.

Everybody’s appearance changes with time, for better or for worse. However, Kimberly Guilfoyle appears to have transformed into an entirely different person, and it’s pretty impossible to ignore the rumors that she’s had more than a few “tweaks.” Guilfoyle’s old modeling pictures prove how far her fantastic plastic transformation has gone. She posted a stunning black and white throwback pic on Instagram in June 2015. And how she looked then compared to now is like night and day. Guilfoyle still had her trademark puffy pout, but back then, it looked natural and not like it’d been stuffed to bursting with a gallon of filler.

Following Guilfoyle’s memorable 2024 RNC shenanigans, Hollywood plastic surgeon Dr. Gary Motykie was inundated with questions about Guilfoyle’s appearance. He speculated in an Instagram video that much of her physical evolution is likely due to shedding some serious pounds, possibly thanks to what many celebs rely on, good old Ozempic (there’s even been speculation that Guilfoyle’s ex-father-in-law-to-be, Donald Trump, has tried it). Motykie explained that following up with filler and/or fat grafting after the sometimes extreme weight loss that occurs is common to compensate for the inevitable sunken Ozempic face. He concluded Guilfoyle had likely undergone both.

Motykie then addressed the elephant in the room: “We notice her lips have gotten bigger, more plump. And as I’ve always said, that doesn’t happen naturally,” he continued, noting that he detected some slight pulling to her mid and lower face, indicating Guilfoyle had possibly also undergone a facelift.

Kimberly Guilfoyle and her now ex-fiancé, Donald Trump Jr., weren’t exactly champions of the #MeToo movement. Don Jr. told Daily Mail TV in October 2018 that he feared for his sons in a climate where bad behavior is no longer tolerated. But then, his father Donald Trump’s “grab ’em by the p***y” boasts were just written off as “locker room” talk by Donald and his supporters. And, no real consequences (just a financial blow) arose from a civil court jury determining Donald sexually assaulted writer E. Jean Carroll in 1996.

Meanwhile, Guilfoyle stressed the importance of thoroughly investigating claims of sexual misconduct but suggested accusations can often be politically motivated, citing the case of Brett Kavanaugh, who was appointed to the Supreme Court in October 2018 despite compelling testimony by three women who claimed he assaulted them — accusations Kavanaugh denied. “People need to be careful to understand the politics involved as well and what motivations people may have,” Guilfoyle warned.

So, it’s surprising (not) that she didn’t insist on a rigorous and transparent investigation into rumors of her problematic workplace behavior, sexual misconduct, and penchant for sharing dirty pics with long-suffering co-workers. Guilfoyle’s behavior is rumored to have been so abhorrent that an assistant filed a complaint against her in November 2018. Two sources told The New Yorker that Fox paid the plaintiff an estimated $4 million to buy their silence. Oh, and Guilfoyle, who denied any wrongdoing, was axed years before her contract was due to expire.

Back in her pre-MAGA days, Kimberly Guilfoyle was proud to be Mrs. Gavin Newsom. She was so proud, in fact, that it’s rumored she sang his praises and boasted about his sizable assets at every opportunity that arose. One such occasion was when she appeared at the Empire State Pride Agenda fundraiser in October 2004.

Guilfoyle was a last-minute stand-in for Newsom at the event, but she ensured the crowd of 1,000 or so didn’t feel like they’d missed out. Instead, she’s rumored to have more than made up for his absence by spilling the tea on his penis (figuratively, not literally, thankfully). “I know that many of you wanted to see my husband, and some of you had questions out there. Is he hot? Yeah. Is he hung? Yeah,” she told the crowd, per SF Gate. “Is he [gesticulating to indicate swinging both ways]? Not unless you can give a better [mimicking stuffing a banana down her throat] than me.” Kimberly Guilfoyle, keeping it classy since the early aughts.

Guilfoyle’s risque stage act didn’t play well with Newsom’s camp or rival factions. In fact, it’s rumored to have caused more than a few headaches for the sitting Mayor of San Francisco. Still, not to be deterred, Guilfoyle simply wrote the whole thing off as fake news. “I may have made some arm gesticulation,” she told SF Gate, “but no gesturing in terms of his manhood.”

Kimberly Guilfoyle continued to keep it classy following her split from Gavin Newsom and then from her second husband and baby daddy, Eric Villency. You would think it’d be near on impossible to cause shock and controversy at any Trump-related events, given Donald Trump’s bizarre penchant for endlessly debating the benefits of death by shark or electrocution and Elon Musk’s propensity for leaping around on stage wielding a giant chainsaw like a MAGA-hatted Leatherface.

Still, Guilfoyle has always been an overachiever, and she matched Donald and Elon’s antics just fine and even raised them a considerable stake. According to Politico, when the going got tough on the 2020 presidential campaign trail, Guilfoyle got going and started pulling out the big guns. Two separate eyewitnesses at a Washington D.C. fundraising event told the site Guilfoyle offered to give a lapdance to whoever donated the most money. Presumably, the commiseration prize for the second highest was two lapdances.

But that’s not all. Guilfoyle, flanked by her beloved then-fiancé Donald Trump Jr., apparently boasted to a Jackson Hole, Wyoming, crowd that they did their best (fundraising) work in a hot tub. One attendee claimed the couple also offered one lucky donor the chance to join Guilfoyle for a soak if they made it rain with the right amount of Benjamins.

Were they, or weren’t they? That’s what enquiring minds demanded to know about Kimberly Guilfoyle and Anthony Scaramucci in July 2017. The consensus was: You betcha! According to them, though? Oh no! Oh, no, sirree!

Scaramucci was single — kind of — as his wife, Diedre Ball, had filed for divorce days after he joined the Trump administration, a tad prematurely perhaps, given he only lasted 10 days. However, Scaramucci went into meltdown when New York Magazine writer Olivia Nuzzi reported “The Mooch” was spotted wining and dining Guilfoyle on July 26. Scaramucci furiously denied, denied, denied, little surprise perhaps, given Ball was heavily pregnant. To hammer the point home, a friend told HuffPost that Guilfoyle and Scaramucci are “very close friends but nothing more.” Then, rubbing salt into the wound, they added, “He is way too short for Kimberly.”

Still, all’s well that ends well. Ball and Scaramucci reunited in November, and he continued publicly humiliating himself. This time by appearing on Season 2 of “Celebrity Big Brother,” where he lasted even less time than the White House. “First off, from this moment on, I’m out of the house,” Scaramucci announced in a video message following his six-day stint. “That means you’re all one step closer to the quarter-million-dollar prize. You know, the Big Brother house was just like my experience in Washington. You get judged quickly before people really know who you are, and you never get a second chance.”