Sad Details About Kimberly Guilfoyle

Chronicling Kimberly Guilfoyle's ascent to the top of the U.S. social elite is like conjoining the realization of the American Dream with a Grimm's fairy tale. But in the case of the latter, "grim" might be a more appropriate adjective. It's been a journey pockmarked by family tragedy, workplace dismissals, tanked marriages, partisan hysteria, and even death threats. She could attribute some of those roadblocks to sheer circumstance, but in other cases, she likely brought them on herself.

Guilfoyle's done well accumulating a bank account estimated to be around $25 million and achieving arm candy status as the girlfriend of Donald Trump Jr. She's worked hard, starting as a model and had a brief stint as a teacher, then as a District Attorney Deputy who prosecuted a bizarre murder case that first threw her name in the headlines. But she's been dogged by controversy in later years, starting at Fox News where she became embroiled in a scandal, followed by working for the Trump Republicans where her current romance began.

Today, Guilfoyle stands to be a formidable force, being in one of Washington, D.C.'s most popular power couples; an influence that stands to greatly expand should a Trump occupies the Oval Office in 2024. If it happens and given the sad events dotting her backstory, the jury's out on whether she'll be responsible for any dark clouds that might hover over 1600 Pennsylvania Avenue. 

Religious values ruled the Guilfoyle homestead in San Francisco where Kimberly was born March 9, 1969. Much of that was due to her mother Mercedes, a Puerto Rican special education teacher, and her construction worker father Anthony, who were both staunch Catholics and hard-working individuals (via The Mercury News).

Kimberly Guilfoyle quickly picked up on how those ethics garnered respectability. She said she noticed how people looked up to her mother, determined to ensure her handicapped students received the best education possible. Understandably, at the age of 11, she was particularly devastated when Mercedes died after a lengthy battle with leukemia in 1980. But even back then, Kimberly felt if she could get through such a personal tragedy, she might eventually be able to help other suffering people do the same. "Don't make this life about you, it's about other people," she said to Mediaite. "I've tried to live my life in a way that respects the beliefs of my mother and father. They sacrificed a tremendous amount for me to be able to do what I do today." 

Relying on support and guidance from her father, Guilfoyle finished her basic schooling, got her degree from the University of San Francisco School of Law while modelling on the side, and continuing her studies in Ireland. Per SFGate, She returned home and chose teaching as a career briefly, just like her mother, until her professional path suddenly changed.

In 1996, Kimberly Guilfoyle hadn't been teaching long before she was hired to become a deputy district attorney in San Francisco. Per SFGate, she had interned at the same office a few years early while studying for her law degree, but this time, she'd get a taste of what it would be like as a professional in the legal system. At best, it was bittersweet.

Guilfoyle was only on the job for a few months when she and 13 other deputies were fired in the wake of an ugly district attorney election pitting their current boss against an aggressive rival. The incumbent lost and the new D.A. in charge cleaned house, ignoring a grievance filed by some of the dismissed deputies. Meanwhile, Guilfoyle eventually found a similar position in Los Angeles, where she worked for four years.

But she hinted at that experience when she weighed in on a similar incident in San Francisco 14 years later. "As a former San Francisco assistant district attorney, I know this isn't just a typical case of administrative shake-up," she wrote in the San Francisco Chronicle's opinion section. "Criminal organizations and their operations are often very complex, especially in a metropolitan area such as San Francisco. Without prosecutors who have a deep understanding of the various syndicates and the players within them, lawful prosecution of crimes becomes tremendously more difficult, allowing real criminals to walk free."

After Kimberly Guilfoyle worked for four years in Los Angeles, the San Francisco District Attorney's Office hired her back in 2000. The following year, her profile escalated nationally when she was handed a case involving a woman mauled to death by two vicious Presa Canario dogs, per Mel magazine.

Details over the homicide were grisly, which made for compelling media attention across the country, especially when the perpetrators included two lawyers and an Aryan Brotherhood member already serving time with two life sentences. Adding to the drama was a contract put out on Kimberly's life by the convict, resulting in around-the-clock protection for the prosecutor. "I stayed on the case, bulletproof vest, locked plates, the whole deal," she told Tucker Carlson on Fox News years later. "I had security sleeping with me, you know, in the room and managed to survive and convict and persevere." In the end, the judge handed out a second-degree murder verdict to one lawyer and involuntary manslaughter to the other. The convicted white supremacist received another life sentence. 

The case also provided a bigger spotlight for Guilfoyle, who was able to hit the city's party circuit in complete safety once again. Only this time, the gossip surrounded a romance between the prosecutor and a political hopeful.

Long before the infamous dog-mauling homicide case, Guilfoyle was already generating additional media scrutiny in San Francisco by her frequent public appearances with city supervisor Gavin Newsom. The coupling seemed serious, at least enough to warrant her marrying him in a high-society wedding in 2001. Two years later, when Newsom threw his hat into the mayoral ring, Guilfoyle dutifully quit her district attorney job to support his campaign that put him into office in 2003. But while Newsom ran City Hall, Guilfoyle grew restless and after being seduced by the media in recent years, took a broadcasting job at Court TV in New York. The geographic distance proved too great to sustain a marriage and by 2005, the couple amicably split.

While Newsom, now California's Governor, wouldn't remarry for another three years, Guilfoyle leapt into the nuptial ring in 2006 by marrying designer Eric Villency. Three years later, the couple filed for divorce. Guilfoyle and Villency remain friends and share a son, Ronan.

To this day, Guilfoyle bears no animosity over those experiences. "With marriages, people can take the easy way out and grow apart," she said to Mediaite. "Or you can show respect and loyalty and that's what I've tried to do in all my relationships. I leave no friend behind."

In 2006, Kimberly Guilfoyle left Court TV for politically right-leaning Fox News, ironic for someone who once married a Democrat mayor. She originally hosted a crime-based series called "The Lineup," before joining a table of established pundits on the more highly-rated show "The Five." Her presence seemed to be for more than her political insight. "If those legs of yours were a foot shorter, do you think you'd be here?" asked co-host Bob Beckel in one segment reprinted in Mediaite.

Perhaps she bought into that objectification or let success get to her head. Regardless, rumors of inappropriate behavior on her behalf started circulating to the point where a Fox internal investigation resulted in her departure in 2018. Two years later, The New Yorker published a piece about those allegations from sources speaking on condition of anonymity. One of them was an assistant who recalled working with Guilfoyle in her apartment where her boss sometimes stripped naked, showed off graphic pictures of former lovers and requested thigh massages. She added that Guilfoyle threatened her job should any word of those incidents leak out.

"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 in a statement to The New Yorker. By then, she was already on another career path destined for the White House.

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).

While still married to Eric Villancy, Kimberly Guilfoyle suffered another tragedy when her father, Anthony, died from cancer in 2008 at the age of 72. Forced to raise Kimberly and her kid brother Anthony Jr. on his own after the death of his wife Mercedes nearly 30 years earlier, Anthony left an indelible stamp on his children, including a fierce determination to make their marks on the world. 

The incubation of that influence started when Anthony emigrated to the U.S. from Ireland to work in construction before he served in the U.S. Army. In 1968, he married Mercedes and Kimberly was born shortly after. He later went into real estate, although politics was a passion for him. To that end, he supported Gavin Newsom's successful bid to become San Francisco city supervisor. A few years later, after Newsom married Kimberly, Anthony acted as the candidate's political advisor during his victorious run for the mayor's chair.

Through it all, even during Kimberly's job shifts and failing marriages, Anthony remained a heartfelt and motivational force in his daughter's life. "I was blessed to be raised by a truly amazing father," wrote Kimberly in an Instagram post. "He was deeply compassionate and inspired me to always reach higher."

While details of Kimberly Guilfoyle's departure from Fox are foggy at best, her arrival into the Trump world was more like an open buffet for the media. In 2018, she fell for the Commander-in-Chief's oldest son, Donald Trump Jr., before quitting her job to work on Donald Trump's re-election campaign (via Politico). The pairing was puzzling, considering Don Jr. was brash, impulsive and sometimes as vulgar as his father, a huge contrast from the more genteel men she had in her life. It wasn't long before media wags like The Washington Post reported the two were dating, even though Don Jr was still separated from his wife Vanessa at the time.

"We're having a great time," said Don Jr. to the Daily Mail, which dubbed the couple a political dynamic duo. "She's brilliant, exciting, fun."

An extensive piece in The Atlantic, however, revealed that a few Trumps weren't excited by the romance, especially Donald Trump himself. As someone suspicious of outsiders trying to boost their own fortunes using his name, Don Jr.'s father thought the pairing distracted from his self-promotion with re-election less than two years away. Also reportedly less than thrilled was the then-President's daughter Ivanka, long touted as his favorite successor who felt her status being upstaged by Guilfoyle and Don Jr.'s presence at public gatherings. It didn't help that a McClatchy dispatch declared Don Jr. was already eclipsing Ivanka's work in getting their famous father re-elected.

By 2020, Kimberly Guilfoyle had positioned herself well into the Trump administration's corridors of power. She was already chairing the finance part of the Trump Victory Committee and frequently accompanied boyfriend Donald Trump Jr. to Make America Great Again rallies across the U.S. Although the country was still in the grips of a COVID-19 pandemic, Guilfoyle was rarely seen in public at these events wearing her mask or physically distancing herself from colleagues. Ignoring those safeguards came to a head In July 2020, when Guilfoyle caught the coronavirus, which at that point had already infected nearly three million Americans and killed more than 130,000 others.

Inexplicably, after two uncomfortable weeks in quarantine fighting the infection, she credited fellow Republicans for her recovery. "When I tested positive for COVID, I too was able to see just how loving and supportive this MAGA movement is, and your prayers lifted me up," she said during a campaign broadcast (via The Hill).

His girlfriend's bout with the coronavirus did little to dissuade Don Jr. from downplaying the effects of the pandemic. "These people are truly morons," said Don Jr. on Fox News about his opposition to the death toll. "The numbers are almost nothing." Months later, both Don Jr. and President Trump tested positive for COVID-19, but remained unrepentant that the pandemic's effects on the U.S. was minimal.

Kimberly Guilfoyle's climb to the top of the social ladder via sinking her hooks into one of Donald Trump's progeny hit a crescendo at the Republican National Congress, held in August 2020 in Washington, D.C. On the night of August 24, she made sure her six-minute speech would be heard. It was a bombastic performance more befitting a death metal vocalist as she belted out her talking points, taking aim at the Democrat Party's plans to destroy the country, and treating President Trump more as a god than a national leader.

Her dramatic closing, shrieking "The best is yet to come!" impressed the President. Comparing Guilfoyle to Eva Peron, he reportedly told her "Nobody could have done that but you" (via Daily Beast). However, several advisors to the President were less than impressed, with one person allegedly saying "Kimberly shouting is weird," per SFGate.

Elsewhere, results were mixed. The New York Post called Guilfoyle's speech passionate and that it was "[making] waves on social media." Meanwhile, Intelligencer called the cameo "six terrifying minutes." "The View" co-host Sunny Hostin felt compelled to correct the celebrity speaker, who declared herself a first-generation Puerto Rican. "Puerto Ricans are American last I checked," tweeted Hostin. "I'm horrified. And embarrassed as a fellow Latina." CNN political commentator Alice Stewart said Guilfoyle's goal was obvious. "The reality is she's speaking to an audience of one, President Trump," Stewart said on CNN. "I'm sure she got two thumbs up for that."

In November 2020, Kimberly Guilfoyle's ascent to the top of the political heap was put on hold when Donald Trump lost the federal election to Joe Biden. Presumably in denial over the results and buying into the defeated President's declaration that the election was hijacked, Kimberly went to work campaigning to raise funds for a January 6 Trump rally in Washington D.C., apparently raising as much as $3 million. 

The rally at the Ellipse took place the same day former Vice President Mike Pence was to approve the certification of the election result in front of Congress on Capitol Hill a few blocks away. Before Trump spoke to the masses gathering to dissuade Pence, Guilfoyle was captured on Don Jr.'s phone dancing and urging the vice president to "have the courage and do the right thing! Fight!" A few hours later after Trump's "fight like hell" speech, the angry multitudes invaded Capitol Hill in an insurrection that killed five people and injured dozens more, although it didn't stop the political process. 

Guilfoyle supported an initiative that turned deadly for the sake of her boyfriend and his father, a defiance of the pledge she took when her mother died.