The many faces and scandals of Kimberly Guilfoyle: From her ‘fertile’ years with Gavin Newsom to buying her own engagement ring when Don Jr wouldn’t… what friends are saying comes next for ‘cockroach’ Kim

Kimberly Guilfoyle’s fall from grace has come not with a whimper, but with a decidedly on brand bang.

Last week, Guilfoyle, 57, resigned as Donald Trump’s ambassador to Greece, crashing out of a position she held for only 11 months, after it was revealed that she was the subject of an Inspector General investigation into her lifestyle and spending habits in Athens.

Donald Trump Jr’s former fiancée called the allegations against her ‘false’ in a statement on X and vowed to ‘vigorously defend’ her name and reputation.

Insiders confirmed to the Daily Mail that she is now holed up inside the official diplomatic residence in Athens, gripped by mounting paranoia over what her future holds.

Yet don’t count her out just yet – after all, retreat isn’t really Guilfoyle’s style. ‘Kimberly will now have time to do what she does best: make money,’ a Republican political operative told the Daily Mail. ‘She could start businesses, hopefully ethically. She could be MAGA.’

Truth be told, like a phoenix or a cockroach, the former Fox News host always seems to find a way of surviving whatever the world throws at her, whether it’s a professional set-back or a romantic rug-pull.

Don Jr called time on their four-year engagement in December 2024 and within a year and a half had wooed and married Palm Beach socialite, Bettina Anderson, 39.

But Guilfoyle has always been a shapeshifter. She parlayed that heartbreak into the high life she enjoyed, albeit briefly, in Greece. It was just the latest in a long line of transformations that have seen her overhaul everything from her appearance to her political identity. Because there is only one constant when it comes to Guilfoyle – ambition.

That drive was one of the things her ex-husband California Governor Gavin Newsom said he admired most about her during their marriage, which lasted from 2001 to 2005.

‘She has a prosecutor’s mind,’ the then-mayor of San Francisco said during a 2004 joint appearance with Guilfoyle on Charlie Rose’s namesake talk show. ‘Accordingly, she is tough. She is tenacious, but she is fair and she has remarkable compassion.’

Newsom, 59, also admitted that his then-wife, who he first met in 1994 at a Democratic fundraiser, was ‘probably a little more conservative than I am’ – the understatement of the century knowing where she is today politically.

Guilfoyle, a former model and San Francisco assistant district attorney, was notably a registered Republican when she married Newsom, then a young city supervisor and millionaire restaurant owner.

Yet despite their political differences – or perhaps because of them – the fresh-faced couple were a political operative’s dream.

In 2004, Harper’s Bazaar crowned the pair ‘The New Kennedys’ in a lavish fashion spread that featured the now infamous photo of the Ralph Lauren-clad rising political star spooning his cable-news analyst wife on an intricately patterned rug inside the Getty mansion. This was Guilfoyle 1.0.

Thanks to the internet, neither has been able to escape the decades-old photo, which often pops up at the most inopportune times. Like, say, when one of them is in the news for losing an ambassadorship.

But at the time, the couple were focused on tamping down the Kennedy comparisons.

The magazine wrote that the couple ‘promises to be one of the most glamorous political unions since Jack and Jackie.’ Newsom’s hair did much of the heavy lifting, described by the magazine as a ‘Kennedy-esque mop.’

When talking to SFGate shortly after the issue dropped, Guilfoyle bristled at the Kennedy comparison. ‘Oh my God,’ she said. ‘We made no suggestion of any similarity. Public service, that’s it. It’s not a comparison we make.’

Though, she did tell Harper’s Bazaar that she thought Newsom would make for a good president. ‘Absolutely,’ she said. ‘I’d gladly vote for him.’ But not before telling the magazine that they wanted to be parents. ‘Maybe six, maybe one; who knows?’ she said. ‘I’m a very fertile Puerto Rican.’

The shoot took place in August 2004. In January 2005, the three-year marriage ended in divorce.

In a joint public statement they shared: ‘It is with great sadness that we announce today that we have decided to end our marriage. Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple.’

Days after Newsom was sworn into office, Guilfoyle moved to New York City to host her own Court TV show. For the tail end of their marriage, she was flying back to San Francisco most weekends to attend events with him.

But while the couple blamed schedules, whispers abounded that Guilfoyle – never as time would prove one of life’s diplomats – had ruffled feathers with her less than First Lady-like behavior.

Months before they announced their divorce, Guilfoyle loosened up the audience at a gay-rights gala in New York by praising her absent husband’s anatomy in graphic terms. She also suggested that her own talents in the bedroom had kept the then-mayor firmly in the heterosexual camp. At the time, her antics raised some eyebrows with the political bloggers, who nicknamed her ‘Potty Mouth.’

A year after her split from Newsom, Guilfoyle began working at Fox News, becoming a host for the now defunct show The Lineup in 2006. And with a new job, came a new look.

Guilfoyle’s makeup got heavier, her hair got bigger and her clothes got tighter. The former prosecutor swapped out her more court friendly attire for the bodycon dresses that would become her wardrobe staple.

That same year, she married Eric Villency, the CEO of a design firm and the entrepreneur behind Peloton bikes. The two had a son, Ronan, before splitting in 2009 after three years of marriage.

In 2011, she joined Fox’s primetime panel show The Five. Washington Post later reported that she was assigned ‘the leg chair’ on the end of the row because it would allow the audience a full view of her lower half.

Guilfoyle was successful at Fox but her reputation started to crumble in the summer of 2016 when she rallied women to defend disgraced Fox chairman Roger Ailes’s reputation after he was accused of sexual harassment.

It was a stance that landed Guilfoyle very much on the wrong side of history. Unperturbed, she pivoted, planting her seeds of loyalty firmly in the Trump camp when Donald Trump declared his candidacy for the election that same year.

Her affinity for the soon to be president apparently caught the attention of Don Jr, who told the Washington Post in 2018: ‘When everyone else said that Hillary was unstoppable, Kimberly stood firmly with my father.’

Guilfoyle was introduced to Don Jr by mutual friends at a Manhattan party. Her son went to the same school as Don Jr’s daughter Kai and the two parents grew close.

In 2018, Don Jr and Guilfoyle officially announced they were a couple. That same year she abruptly left her role as the host of The Five.

At the time, in July 2018, not much was said of her sudden departure. Fox News had released a blunt and concise statement that she was no longer working for the network. ‘Fox News has parted ways with Kimberly Guilfoyle,’ the spokesperson said.

Guilfoyle maintained that she had chosen to leave Fox on her own terms to begin a new job at America First, a Trump super PAC. However, in 2020, the New Yorker reported that there were more serious allegations at play.

Namely, a ‘$4 million’ sexual harassment settlement with her female assistant, who claimed the host had exposed herself to her and showed her nude photos of men.

Guilfoyle denied the allegations in a statement to the magazine. ‘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,’ she said.

‘During my career, I have served as a mentor to countless women, with many of whom I remain exceptionally close to this day.’

But Guilfoyle was already gliding into her next incarnation – Don Jr’s persistent plus one.

Trump’s eldest son began dating Guilfoyle two months after his wife of 12 years, Vanessa Trump, filed for divorce. The couple became a fixture at Trump events, becoming the first couple of MAGA.

Guilfoyle once again transformed her look, becoming one of the earliest adopters of the now ubiquitous Trumpian makeover ‘Mar-a-Lago face,’ a look built on the apparent belief that more is more: heavier make-up, plumper lips, longer lashes, darker tans and cavernous contouring.

The former news personality has been hit with plastic surgery allegations on multiple occasions but has not commented as to whether they are true.

For six years, Guilfoyle was on the podium at every opportunity, espousing her loyalty to Trump and, in the process, presumably attempting to cement her relationship with his son. When Don Jr failed to put a ring on it, sources told the Daily Mail, she bought one herself and announced their engagement.

But while Guilfoyle may have looked the part of Trump devotee, Don Jr no longer thought she could play the part of his wife. Ironically, for someone who had made such an effort to become the very image of a MAGA woman, part of the problem, sources told People magazine, was Guilfoyle’s fondness for those bodycon dresses. According to the source: ‘The tight dresses need to go, and she has been told that.’

After six years together, Guilfoyle was out – dumped by Don Jr for his new wife, Palm Beach socialite Bettina Anderson.

As a consolation prize for her heartbreak, Trump made Guilfoyle the ambassador to Greece days after the Daily Mail published exclusive photos of Don Jr and Anderson, 39, walking hand-in-hand after dinner at a swanky Palm Beach eatery – serving as incontrovertible proof that they were an item.

But mastering the subtle art of diplomacy always seemed a stretch for Guilfoyle who, as the Daily Mail exclusively reported, elicited complaints for her ‘tyrannical’ leadership style as well as raising eyebrows with her fondness for lavish perks and a champagne lifestyle.

Asked why Guilfoyle had been removed from her position, Trump said quite bluntly: ‘We didn’t like what we were hearing.’ And perhaps he didn’t like that everyone else was hearing it too as allegations came tumbling out in the most public and humiliating fashion.

Kentucky attorney and GOP donor Eric Deters, who Guilfoyle reportedly asked for a six-figure payment, told the Daily Mail that she recruited his wife and her friend to secretly sneak alcohol to her during a political festival, acting ‘like a high schooler’ hiding booze from her parents.

When the event ended, Guilfoyle insisted on packing up all the leftover catered VIP food to take home, Deters said.

Guilfoyle’s affinity for champagne and parties have widely been documented. According to one former colleague at Fox News, the lawyer-turned-activist was once known as ‘the Margarita girl’ thanks to her love of the popular cocktail.

That fondness for a cocktail certainly put her at odds with avowed teetotaler Trump who on Tuesday referred to her dismissively as someone who: ‘I guess, dated my son a long time ago.’

Yet Guilfoyle may still have a card to play.

Insiders claim that she has kept a secret ‘burn book’ documenting the Trumps and is ready to burn her bridges with the family following her dramatic fall from grace.

She is now threatening to release contents of the diary insiders are dubbing ‘The Devil Wears MAGA.’

As for her trademark look – that, like her fortunes, can always be reversed. ‘Anti Mar-a-Lago face’ is, according to some plastic surgeons, now all the rage.

Dr Melinda Lacerna Kimbrell, a double board-certified plastic surgeon and owner of LA Plastic Surgery, told the Daily Mail this week that the ‘anti-Mar-a-Lago’ has seen a ‘definite pendulum swing’ in popularity in recent months as clients move away from ‘obvious filler and conspicuous cosmetic work.’

Fillers can be removed, and Botox treatments paused and who, given Guilfoyle’s chameleon-like shapeshifting, would bet against her putting her best – and maybe her new – face forward as she embarks on her next chapter?