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How Kimberly Guilfoyle, the 'human Venus flytrap,' has groomed boyfriend Don Jr. into a political powerhouse and turned herself into a conservative star

Leah Carroll   

How Kimberly Guilfoyle, the 'human Venus flytrap,' has groomed boyfriend Don Jr. into a political powerhouse and turned herself into a conservative star
  • Kimberly Guilfoyle, the former Fox News host, has ingratiated herself with the Trump family and become the female face of MAGA.
  • Thanks in part to Guilfoyle's grooming, her boyfriend, Donald Trump Jr., has gone from just being Ivanka's brother to becoming one of his father's most ferocious right-hand men.
  • A senior campaign advisor said he doesn't know "anybody outside of Hope Hicks or Dan Scavino" who spends more time with the Trumps, or is as trusted.
  • Guilfoyle has been accused of sexual harassment by a former assistant at Fox News, The New Yorker recently reported.
  • A former Fox News colleague told Business Insider that Guilfoyle spoke about sex frequently and "once went through a ranking of Latino men and their capabilities in bed." Guilfoyle declined to comment for the article.

Sometime after Thanksgiving 2008, a Fox News insider remembers her then colleague Kimberly Guilfoyle telling her a story.

According to the insider, Guilfoyle said she had just returned from the office of Fox News' chief executive, Roger Ailes. He was, Guilfoyle said, unhappy with her performance as a contributor and wanted to fire her.

But Guilfoyle quickly came up with a plan to save herself.

Her beloved father had recently died from cancer. Her mother had died of leukemia when Guilfoyle was 11 years old. What Guilfoyle needed in that moment from the Fox executive was something different from what he usually offered: sympathy.

Guilfoyle told the Fox News insider that she burst into tears and cried "But Roger — I'm an orphan!"

Ailes took mercy on the 39-year-old. She would stay at Fox.

Guilfoyle laughed as she recounted the exchange, the Fox News insider said. This source said they were skeptical of Guilfoyle's method but sympathetic about her circumstances.

"When the chips are down, she'll work, she'll fight," the insider said. "And she was really sad during that time. I remember she was very scared. Her second marriage had ended, she was about to get fired, she had a little boy."

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Ailes kept Guilfoyle on as a legal contributor. In 2011 she was given a cohost position on the popular panel show "The Five," which featured a prime leg-cam chair. Once fearful for her career, Guilfoyle had become a bona fide Fox News star.

"She has nine lives," Arthur Aidala, Guilfoyle's friend and Harvey Weinstein defense attorney, told Business Insider. "She knows how to make lemonade out of lemons."

And right now, Guilfoyle, who is 51, has pitchers of it.

After leaving Fox News in June 2018, likely as a result of a sexual-harassment allegations, according to The New Yorker, the newscaster has refashioned herself as a conservative influencer for legions of female Trump supporters.

Guilfoyle, who is dating President Donald Trump's oldest son, Donald Trump Jr., is a lead fund-raiser for the Trump reelection campaign. Her speech at the virtual Republican National Convention, in August, instantly became a meme, drawing comparisons to Mussolini and "The Hunger Games'" Effie Trinket.

Mocked or not, it was the most talked-about speech of the convention, and it put Guilfoyle on a literal podium for Trump-loving conservatives.

As for the 42-year-old Don Jr., in two years he's gone from just being Ivanka's brother to becoming one of his father's most ferocious right-hand men, thanks partly to Guilfoyle's careful grooming, people said.

During his first presidential campaign, President Trump joked: "Don, you can finally do something for me — you can go hunting," calling on Don Jr. to use his controversial hobby to curry favor with middle America. Now Don Jr. is an in-demand Trump surrogate who some are speculating will make his own run for office.

"She's definitely made Don Jr. more serious," R. Couri Hay, a New York publicist, told Business Insider. "She's had years and years on TV. She's helped guide and train and been very influential in Don's increasingly very secure, very formidable, very opinionated television personality.

"She's been able to guide him and lead him in the political waters. And he is basking in it and loving it."

None of this is surprising to those who have followed Guilfoyle's story. They saw how she shaped the career of her first husband, Gavin Newsom, now the governor of California. They saw her remake herself into a New York media personality after leaving her district-attorney job in San Francisco. They've seen her drive and her ability to work a crowd and use her fame as currency, not unlike President Trump.

As one former Fox News colleague said, "It's interesting to me that Donald Trump Jr. ended up with a female version of his father."

'They are like the prom king and queen of MAGA land'

Guilfoyle's affinity for Trump and his family is well documented.

In Brian Stelter's book "Hoax," about Fox News, he recounts Guilfoyle's on-air reaction after Trump declared his 2016 candidacy: "It was like The LEGO Movie, the theme song 'Everything is Awesome.' It really got me excited. I felt richer just listening to him!"

Guilfoyle and the Trumps have run in the same New York City circles for years. Her son, Ronan, and Don Jr.'s oldest daughter, Kai, attended the same Manhattan private school.

Guilfoyle and Don Jr. began dating in 2018, shortly after divorce papers were filed in February by Vanessa, Don Jr.'s wife of 13 years and mother of his five children.

"Don't forget, Don Jr.'s ex-wife, Vanessa, had no interest in politics. She wasn't a political wife. They weren't a power couple," Hay said. "In Don Jr., Kimberly found a real partner."

If anyone understands the buzz a power couple can stir up, it's Guilfoyle.

"Kimberly had gotten an invitation to come to the swearing in," Aidala said of his 2015 inauguration as president of the Brooklyn Bar Association. "And she tells me, 'There is no way you are getting sworn in to be president of the bar without having a first lady by your side.'

"I proposed to Marianne the night before the swearing in," Aidala said, referring to his now wife. "Then Marianne and I planned it out. She didn't wear the ring at the beginning of the ceremony. It was 400 people who were there including Geraldo Rivera and Alan Dershowitz, who both introduced me.

"And so I gave my little speech, and then I said, 'But you know, what is a president without a first lady?' and the whole room went frickin' crazy. It was wonderful. Kimberly deserves a hundred percent of the credit for that."

Within three months of Vanessa's divorce filing, Guilfoyle and Don Jr. made it clear that the president's son had found a new first lady of his own. The two began making appearances on Guilfoyle's Instagram, hunting and fishing in Montana, mugging at a Poison concert with Bret Michaels, and posing for a photo on the White House colonnade, lovingly holding hands.

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"They are like the prom king and queen of MAGA land," a senior Trump advisor said.

(Guilfoyle declined to comment for this article.)

Just a few weeks later, on July 20, Guilfoyle abruptly left Fox News. At the time, she claimed she departed voluntarily to focus on politics. The network issued a short statement on her exit: "Fox News has parted ways with Kimberly Guilfoyle."

In early October, The New Yorker's Jane Mayer reported that Guilfoyle's departure likely occurred after allegations were raised by her assistant of sexual harassment and the threat of a lawsuit.

According to the draft complaint, which The New Yorker said it viewed, the assistant alleged that Guilfoyle showed her lewd pictures of male genitalia that she had on her phone, encouraged her to lie to investigators about sexual-misconduct claims against "The Five" cohost, Eric Bolling, and advised her to sleep with wealthy men to advance her career.

In the draft complaint, the assistant said Guilfoyle asked her to assess her naked body, and that once she'd been asked to give Guilfoyle a massage on her bare thighs. When they traveled together on business, the unfiled suit alleged that Guilfoyle demanded the assistant share a room with her.

"She would torture" the assistant, the former Fox News colleague told Business Insider. When the assistant "would come over to Kimberly's house, she would be naked. She'd just walk out of the bathroom not wearing any clothes."

Regarding whether Guilfoyle showed inappropriate photos to her coworkers, one former Fox News executive told Business Insider that "no one ever, ever, ever came to me with complaints about Kimberly."

Maureen Walsh, Guilfoyle's hairstylist and make-up artist, has worked with Guilfoyle since 2006. She said Guilfoyle was always "100% professional" when they traveled together and that she had her own room on work trips.

Fox News paid Guilfoyle's assistant a multimillion-dollar settlement after seeing a draft of her 42-page complaint, The New Yorker reported. When asked for comment, the assistant said in an email to Business Insider: "I have no comment on my time at Fox. Please do not contact me again — have a nice day."

A source close to Guilfoyle denied that the former news host sexually harassed her assistant.

'She's a human Venus flytrap'

Guilfoyle was already planning her next step before her unceremonious exit from Fox.

"Right before she got axed, when she was still on 'The Five,' she personally reached out to the New York Post trying to plant an item about the fact that she was a contender for the White House press secretary job," a former New York Post staffer said.

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"She wanted in," a colleague from Guilfoyle's early days in television who still socializes with her said. "Somehow, she was going to get on the president's staff. And that didn't happen, but she got into the family."

Hay added, "She's a human Venus flytrap."

In 2018 Guilfoyle became vice chairwoman for America First Action, a pro-Trump super PAC. In April 2019, Brad Parscale, Trump's now disgraced campaign manager, hired Guilfoyle to be a senior advisor to the Trump 2020 reelection campaign.

"I have been present on numerous occasions where the president turns to Kimberly and seeks her counsel on issues of policy like the judiciary and tax reform," a family friend and senior campaign advisor said.

Guilfoyle so impressed the president in her advisory role that he personally asked her to lead the fund-raising effort of Trump Victory, a fundraising organization focused on mid-tier donors, a group Trump has had difficulty marshaling.

"A lot of the professional fundraisers thought she was just being given a title and were very skeptical, and she's been an animal," former White House press secretary Sean Spicer said. "She is tenacious when she comes to raising money."

Gary Rabine, the CEO of a construction company in Schaumburg, Illinois, was one of the donors Guilfoyle was tasked with courting.

This month, Rabine hosted an event in Woodstock, Illinois, with Guilfoyle and Don. Jr headlining. An hour before it was set to start, Rabine was informed that the Secret Service and members of the campaign team had nixed the rally portion because of inadequate security.

"I knew I needed to talk to Kimberly and Don," Rabine said. "Kimberly showed up and right away said 'We gotta figure this out.' She said to Don, 'We got a problem! Bad communication here! We can't let these people down!' And right away Don agreed."

Against the protestations of the Secret Service and grumblings from the campaign team, the couple delivered their signature fiery stump speech and Rabine delivered nearly $450,000 for the Trump campaign.

"She's a character. She is tough and outspoken," Rabine said. "I have daughters, and I hope they can be like her. Maybe not exactly like her. But she's definitely not afraid to challenge Don Jr. in public."

As long as the challenge is accepted, Hay said. "She has to be careful. She can't outshine the Trump men," he added. "Don Jr. likes to be front and center too. She goes as far as they are comfortable — and maybe a little farther."

'She was the only assistant DA who showed up at trial with a publicist'

At the end of Guilfoyle's speech at the RNC, she shouted with almost religious fervor, "The best is yet to come!" The speech was about America, but she might as well have been talking about her own life.

Guilfoyle was born and raised in San Francisco. Her mother, Mercedes, originally from Puerto Rico, was a special-education teacher. Her father, Anthony, emigrated to America from Ireland in his early 20s. In San Francisco, he worked in construction, eventually becoming a real-estate developer and trusted advisor to the man who would become his daughter's first husband, Gavin Newsom.

Guilfoyle attended San Francisco's Mercy High School, a large all-girls Catholic school. A classmate recalls that Guilfoyle was bright, played softball, and participated in student government and the school's Irish Club.

After graduating from Mercy, in 1987, Guilfoyle attended UC Davis where she majored in rhetoric and communications. She went on to attend the University of San Francisco's law school, which she paid for in part through her work as a catalog model for Macy's and Victoria's Secret and a teaching job at the same school where her mother once worked.

In 1998, Guilfoyle was hired at the San Francisco District Attorney's office. She began dating Newsom, then a city supervisor.

Guilfoyle gained national attention not long after January 26, 2001 when Diane Whipple, a beloved 33-year-old women's-lacrosse coach, was mauled to death in the hallway of her San Francisco apartment building by a pair of dogs. By then Guilfoyle was an assistant DA, and one of two prosecutors assigned to the case. The trial became a media sensation.

A colleague from Guilfoyle's time as a prosecutor told Business Insider that while Guilfoyle was focused on her prosecutorial duties, "she placed a lot of emphasis on cultivating television relationships."

She became the face of the case, conducting a majority of the interviews while coprosecutor Jim Hammer handled the opening and closing arguments and cross examination of the defendants, according to the prosecutorial colleague. "Good Morning America," CNN, and Court TV began to regularly seek Guilfoyle out as a legal analyst.

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"She was the only assistant DA who showed up at trial with a publicist," the coworker from Guilfoyle's early days in TV said. The prosecutorial colleague added that while there are public information officers who work in the DA's office to answer press inquiries, the fact that Guilfoyle had a personal publicist pitching TV appearances was "from another f--king planet."

(A person familiar with the situation told Business Insider that Guilfoyle "never once hired a publicist.")

In addition to her rising national profile, Guilfoyle's local celebrity rose to new heights when she married Gavin Newsom, in December 2001. The wedding was the society and political event of the year.

Guilfoyle, who once dated oil heir Bill Getty, had remained close with his mother, Ann Getty. The reception was held at the Getty Villa and had "a marble gazebo turned into an exotic tent made from yards of aqua-colored velvet with a gold-leaf pattern selected by Ann," according to an article in the San Francisco Chronicle.

So coveted was an invitation to the affair that Guilfoyle told the prosecutorial colleague that up-and-coming assistant district attorney Kamala Harris had called Newsom begging for an invite. The colleague said Guilfoyle refused, despite her fiancé's pleas.

According to the source, Guilfoyle said Harris had slighted her the year before, telling her there were no jobs available in the San Francisco prosecutor's office when there apparently were. A representative for Senator Harris did not respond to a request for comment.

In September 2004, Harper's Bazaar christened the couple the "New Kennedys." But while Newsom's liberal bona fides are well established — as mayor he made national news when he legalized same-sex marriage in San Francisco — Guilfoyle's political views have skewed right.

In 2017 she told The Washington Post that though she'd been a registered Republican since she was 18, she aligned with Newsom's "pro-business mentality." Regarding their marriage the same article said, "The couple seemed to treat each step of their careers, and each other, as a means to an end."

'It was truly like a scene out of "Anchorman"'

After winning the Whipple-mauling case, in 2004, Guilfoyle left San Francisco to host a show on Court TV in New York. In January 2005, three years after marrying Newsom, the couple filed for divorce, citing "difficulties due to their careers on opposite coasts."

It wasn't long before Guilfoyle attracted the attention of Fox News executives. In 2006 she left Court TV to host Fox's crime-and-justice program "The Lineup."

Guilfoyle's divorce from Newsom was finalized in late February 2006; in May of that same year she married Eric Villency and gave birth to their son, Ronan, in October. The two divorced in 2009. (Villency would go on to design bikes for SoulCycle and Peloton.)

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At Fox News, Guilfoyle quickly ingratiated herself with the network's inner circle, hanging out in Geraldo Rivera's office for postshow drinks and attending baseball games with Roger Ailes and Bill O'Reilly.

Following the cancellation of "The Lineup," in 2008, she became cohost of "The Five" when it debuted, in 2011.

The show was popular, and Guilfoyle's gift for playfully sparring with her cohosts became a highlight for many viewers. She offered unfiltered opinions and a touch of glamour, Fox News style — big hair, lots of makeup, and dresses that fit like shrink wrap.

But while Guilfoyle was popular with viewers, two sources said she wasn't always as personable off-camera, and she sometimes took her frustrations out on the staff.

"Once, the sign-off in the prompter didn't say 'I'm Kimberly Guilfoyle,'" the Fox News insider said. "It said something like 'Thanks for watching "The Lineup." Goodnight.' And when it wrapped, she freaked out on the staff.

"She was like, 'Why the fuck wasn't my name in there?! You're lucky I remembered to say it! I'm a professional!' It was truly like a scene out of 'Anchorman.'"

"She was a diva," the Fox News insider added. "She'd be snapping her fingers to get her papers delivered to her, screaming at the staff if they didn't find exactly the right yogurt for her to eat before she went on air."

A person familiar with the situation denied this. "High standards? Yes. Wrong yogurt drama? No," the person said. "Another fabrication from someone who might not know she does not eat yogurt."

Three people told Business Insider that Guilfoyle crossed professional boundaries at Fox when she talked about her sex life.

"All she talked about was sex," said the former Fox News colleague, adding that Guilfoyle "once went through a ranking of Latino men and their capabilities in bed."

In addition to allegations that Guilfoyle behaved inappropriately, there have been allegations that Guilfoyle herself was a victim of sexual harassment at Fox.

In August 2017, the Huffington Post reported that Bolling had been sending lewd photos and messages to female coworkers at Fox News. As women came forward, the Fox News insider and former Fox News colleague said Guilfoyle added photos that Bolling had sent her, claiming she too had been harassed.

But those two people, in addition to another Fox employee who was there at the time, told Business Insider that Guilfoyle was engaged in a consensual relationship with her "The Five" cohost.

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The Fox News insider and former Fox News colleague said they believed Guilfoyle's handing over the photos was a tactical move. They claimed she kept the photos as an insurance policy for her own bad behavior and felt slighted after Bolling got a new show of his own, "Fox News Specialists."

"The minute [Bolling] became expendable to her, she did this. She felt betrayed by him and pushed him out," the former Fox News colleague said.

Bolling's lawyer told Business Insider that Bolling "denies all these claims." The former Fox News executive said allegations of Guilfoyle and Bolling's relationship are "stupid and they're rumors — [the rumors] have been following Kimberly for years, and it's time to move on."

On September 8, 2017, about a month after the investigation into Bolling commenced, Bolling and Fox News parted ways in what the network described as an "amicable" agreement. Execs cancelled "Fox News Specialists."

"Have you read that book 'Gone Girl'?" the former Fox News colleague asked. In the novel, the protagonist, Amy, frames her husband for her own fictitious murder. "She's that person. I read that book and I was like, Oh, my God. This is Kimberly Guilfoyle."

'If Trump wins, there will be a White House wedding'

No matter what the outcome of this election, Guilfoyle is sticking by the Trumps, sources say.

"Donald Trump wants to leave behind a legacy of Trumps, and Kimberly Guilfoyle is part of that picture," a Guilfoyle friend said. "She's tall, she's beautiful, she's busty — of course the president loves her."

"I have spent hundreds of hours with that family, and I know the difference between someone who is staff and someone who is family, and she is in a very unique position to be both," the senior campaign advisor said.

"I don't know anybody outside of Hope Hicks or Dan Scavino who spends more time with them, or is as trusted."

Guilfoyle recent listed her Upper West Side apartment for $5 million. She and Don Jr. purchased a $4.4 million home in Bridgehampton, New York in July 2019. Guilfoyle's best friend said Guilfoyle personally furnished each kid's room to make them feel at home.

"She sent me a photo of a pretty pink pouf for Kai's room, asking if I thought Kai would like it or purple better. She had a lot of fun pulling it all together," the best friend said.

The couple have created a familial unit, everyone vacationing together at Mar-a-Lago, in Florida, where Guilfoyle had a lavish $50,000 51st birthday celebration on March 7. The tab, according to The New York Times, was picked up largely by campaign donors.

There seems no doubt that Guilfoyle is comfortable in the role of Trump matriarch.

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A longtime friend of Guilfoyle's said that when Don Jr.'s longtime head of security had stage-four cancer, it was Guilfoyle who sprang into action.

"Kimberly personally went and moved him to one of the top hospitals in the city," the longtime friend said. "She said, 'He's going to die with dignity.' She even paid for part of the funeral cost. She's a fiercely loyal person."

Hay, the publicist, said he believed marriage was in Guilfoyle and Don Jr.'s immediate future.

"If Trump wins, there will be a White House wedding. That's a plan I've heard repeated a number of times," Hay said.

(A source close to the couple said that while Guilfoyle and Don Jr. are "very happy together, there is absolutely no planning of any White House wedding.")

Despite people saying Don Jr. is happiest hunting and fishing, he welcomes the popularity he's been able to bring to the campaign with Guilfoyle's help.

"Kimberly and Don Jr. are a very powerful couple together," the senior campaign advisor said. "They have perfected the 'Make America Great Again' messaging.

"They complement each other on the campaign trail, and her extensive television experience has been evident in the way that Don has been able to hone his messaging points to support his father."

The longtime friend said Don Jr. never wanted the attention that came with politics. "But with Kimberly, he went from zero to 10. It was like a light switch," she said.

A number of people who spoke with Business Insider, from within and beyond the Trump campaign, are less certain of the romance.

Associates throughout Guilfoyle's prosecutorial, television, and fundraising days said Guilfoyle often tried to collect personal details that she could use against potential adversaries.

And some Trump allies are on edge in the event Guilfoyle and Don Jr.'s love affair combusts.

"People are worried that the breakup would be really bad," a former Trump campaign advisor told Business Insider.

"She's going to have receipts."

Additional reporting by Anna Peele and Dana Schuster.


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