What We Know About Kimberly Guilfoyle's Former Life With The Trumps

If fate — or, let's face it, her fiancé — had been kinder, Kimberly Guilfoyle would probably be planning her White House wedding to Donald Trump Jr. by now. Maybe she would have already changed her last name on official documents too. Alas, Donald Trump Jr. ditched Guilfoyle for his alleged mistress Bettina Anderson in late 2024, leaving her with little more than happy memories. True, her almost-father-in-law, President Donald Trump, did offer Guilfoyle the post of U.S. ambassador to Greece as a sort of consolation prize, but skeptics understandably wondered whether she was asked to avoid giving any juicy tell-all interviews in return.

This new chapter for Guilfoyle follows her former careers as both an attorney and a Fox News host. She also has two other fizzled relationships in her history: Guilfoyle was previously married to Californian Governor Gavin Newsom, and briefly to Eric Villency after that, with whom she shares her only child. Being part of the president's inner circle gave her reputation a boost, not to mention her lifestyle. Here's what Guilfoyle's life was like when she still wore Don Jr.'s ring. 

Kimberly Guilfoyle and Donald Trump Jr. made their home in Florida following the 2020 presidential election, where they entertained friends and raised their six children from previous marriages together. The former Fox News host's son, Ronan Villency, divides his time between her place and his dad's, and Don Jr.'s five kids stay with him when they're not with mom Vanessa Trump (his eldest daughter, Kai Trump, has quickly grown up to be a formidable teen golfer).

Guilfoyle enjoyed showing off her kitchen skills on Instagram, where she posted videos of herself preparing family favorites like chicken Francese and grilled lamb chops. She was clearly sending a message: "I'm just a regular mom who takes the time to feed my loved ones well." But it's worth noting that average mothers don't have huge gourmet kitchens to work in, or the budget for pricey cuts of meat. Nor do they cook while wearing tight minidresses and six-inch heels. 

Even some of her devoted followers raised eyebrows. "Love her, but we could all relate better if she was wearing flip-flops or tennis shoes!" wrote one in response. Now that she doesn't have a fiancé or a houseful of hungry teens to cook for, it's hard not to wonder whether Guilfoyle has put aside her domestic-goddess ambitions in favor of Hungryroot boxes and Chinese food deliveries.

Life within the Trump circle wasn't all rallies and black-tie events for Kimberly Guilfoyle. She was also there for her fiancé and his famous family during difficult times as well. Most notably, she supported Donald Trump Jr. after the heartbreaking death of Ivana Trump, the mother of the oldest three Trump children. Donald Trump's first wife succumbed to injuries following a fall in her Manhattan apartment in July 2022. Guilfoyle posted a touching tribute on her Facebook page at the time, writing, "Ivana Trump was a successful businesswoman, a remarkable athlete, & most notably, a devoted & loving mother to @DonaldJTrumpJr, @IvankaTrump, & @EricTrump. She was the embodiment of the American Dream. It was an honor to know her & to love her. We will all miss her so much."

The entire clan and a few honored guests paid their respects at the funeral mass at St. Vincent Ferrer Catholic Church, which included plenty of touching eulogies alongside a splashy display featuring roses and placard photos of her various magazine appearances over the years. The former Fox News host notably put aside her usual attention-grabbing wardrobe for the occasion in favor of a dignified calf-length black dress with long sleeves and a modest neckline. Two years later, the Trump clan suffered another loss with the death of Amalija Knavs, First Lady Melania Trump's beloved mom, in January 2024. Once again Guilfoyle donned a respectable black dress and stood by her fiancé during the services at the same Episcopal church where Melania and Donald were married. 

Kimberly Guilfoyle's stunning transformation has been widely chronicled on her Instagram account. During her time on Fox News' hit talk show "The Five," she mainly shared promo shots of herself with occasional glimpses of her then-husband, Eric Villency, and their son, Ronan Villency. Once Guilfoyle hooked up with Donald Trump Jr., it was all loved-up couples pics of them. The former attorney also gamely embraced her boyfriend's family and the former president's push for re-election. Scroll up from there, and the images increasingly feature Guilfoyle at GOP rallies, posing with various Trump siblings, and spreading the MAGA word. With Melania, Ivanka, and Tiffany Trump all keeping their distance politically, she quickly became one of the leading female voices of the campaign.

By 2024, the former Fox News star had tossed aside any ounce of neutrality she once had as her page became a never-ending screed against the Biden administration as she pled with voters to put Donald Trump back in office once they got the opportunity. Now that he has achieved that cherished goal, Guilfoyle has switched gears to praise virtually every move he makes and every loyalist he installs in his cabinet. This strategy oddly worked in her favor: By the time she and Don Jr. finally separated, it had been so long since she had posted a date-night selfie that no one even noticed the lack of romance across her social media.

Being one degree of separation away from Donald Trump had plenty of perks for Kimberly Guilfoyle. She appeared at many a glitzy White House event, including the Fourth of July celebrations when she and Donald Trump Jr. were just beginning to date. The former Fox News host dined at Mar-a-Lago multiple times, rubbed elbows with various important friends, and generally enjoyed her proximity to so much power. Perhaps Guilfoyle even dared to dream that her fiancé might one day make a White House run of his own, allowing her to assume the title of first lady.

Any hope of that future was promptly dashed when he began seeing model Bettina Anderson on the side. The two tried to remain discreet, and if Guilfoyle had her suspicions, she kept them private too. But KimDon, as nobody else called them, were already showing signs of strain, which didn't go unnoticed by the tabloids. And once the secret was out, the new couple happily went public while Don Jr. offered assurances that he and his former fiancée were all good with their split. 

The truth may hurt more than Guilfoyle is letting on since insiders claimed that her outspokenness and skimpy dresses didn't fit with the kind of image the president wanted his family to present, and Donald's eldest son notably didn't disagree. Don Jr.'s criticism of her style hasn't fazed Guilfoyle a bit, however. Rather than adopting a more subdued wardrobe in the hopes of winning him back, she continues to appear at fundraisers and girls' lunches in low-cut numbers and towering heels. It's clear she intends to continue doing things her way in her post-Trump life.