The Shady Side Of Kimberly Guilfoyle

Kimberly Guilfoyle has become a familiar face in Republican circles, first as a Fox News host and then as the fiancée of Donald Trump Jr. But her first introduction to the world of politics was through her father, the so-called "Godfather" of San Francisco elections. As SFGATE noted in his obituary, Anthony Guilfoyle closely advised his daughter's first husband, Democrat Gavin Newsom, and helped him become mayor in 2003.

Kimberly married Newsom in 2001 and the pair were branded "The New Kennedys" at the time, although they would later divorce in 2005 and embark on remarkably divergent political careers. In 2017, she told the Mercury News that they were still friends. "I respectfully disagree with some of his positions that I don't believe in," she admitted. "However, I think he's authentic in terms of what he believes and what he's willing to fight for and I think that's really the most you can ask for of our politicians."

Keep reading to find out more about how Kimberly went from the political world of her dad and first husband to being one of Donald Trump's closest supporters.

The messy allegations involving co-host Eric Bolling

During Kimberly Guilfoyle's time at Fox News, she worked alongside Eric Bolling. Per HuffPost, he was let go following an investigation into allegations he had sent sexually explicit pictures to female colleagues. According to Business Insider, Guilfoyle reportedly claimed that she had also been sent lewd images from Bolling, but others have alleged that she was in a secret consensual relationship with him at the time and was using the photos tactically. "The minute [Bolling] became expendable to her, she did this. She felt betrayed by him and pushed him out," one source told Business Insider, insisting that their relationship was spoiled by Bolling getting his own show, "Fox News Specialists." Bolling's attorney and Fox News denied the allegations.

According to legal papers obtained by The New Yorker, it was alleged that she also tried to bribe young women to cover up Bolling's behavior in 2017. Guilfoyle allegedly promised one of her assistants, who also worked for Eric Bolling, that she would "would work out a payment to take care of her" if she lied to a law firm about sexually inappropriate behaviour at Fox News. The host reportedly promised private plane trips to Rome, the opportunity to appear on TV, and payments up to a million dollars, implying that Bolling would also compensate the assistant for her "loyalty." Guilfoyle denied the accusations.

The remarks she made about young female voters

As a host on the Fox News talk show "The Five," Kimberly Guilfoyle wasn't afraid to speak her mind. And some of her comments got her in trouble, like in 2014 when she suggested young women don't understand politics.

"When you're young like that, you think — same reason why young women on juries are not a good idea, they don't get it," Guilfoyle argued during a charged debate. "They're not in that same life experience of paying the bills, doing the mortgage, kids, community, crime, education, healthcare. They're like healthy and hot and running around without a care in the world." The Fox presenter, who previously worked as a prosecutor and a deputy district attorney, then assured her co-hosts that she wouldn't rule out the idea of young women serving on juries altogether. "I just thank and excuse them so they can go back on Tinder and," she joked.

Her remarks sparked outrage from many online critics, including Leonard Nimoy. The "Star Trek" icon tweeted, "Kimberly Guilfoyle on Fox telling young people not to vote? Unbelievable !!" Guilfoyle denied that she told young women not to vote or be politically involved, however. "My point is you've been given a powerful blessing in life in this country to be able to vote and to be able to sit on the jury so come equipped," Guilfoyle said, per Cosmopolitan. "Come prepared because you don't want to dilute the votes out there because you are uninformed... this goes for everyone."

When did she jockey for her Trump administration job?

Before Kimberly Guilfoyle could become Donald Trump's next daughter-in-law, she apparently had her sights set on a position in his administration. Publications like Politico first started reporting that she was being considered for a role soon after Trump's election in 2016, but the story might have been slightly exaggerated. "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 source at the New York Post claimed to Business Insider.

In 2017, she teased the idea of becoming the new White House press secretary, claiming that "a number of people" had suggested it. "I'm a patriot, and it would be an honor to serve the country," she told the Mercury News. "I think it'd be a fascinating job, it's a challenging job, and you need someone really determined and focused, a great communicator in there with deep knowledge to be able to handle that position." In the end, of course, Sean Spicer was chosen for the role and Guilfoyle signed a long-term deal at Fox News instead, claiming that she was "excited" to remain a commentator.

Kimberly Guilfoyle's support for Roger Ailes

After many allegations of sexual harassment led to the downfall of Fox News CEO Roger Ailes in 2016, Kimberly Guilfoyle was quick to defend her former boss. Although figures like Megyn Kelly and Gretchen Carlson spoke up about their experiences, Guilfoyle tried to debunk their accusations of sexually predatory behavior at the network.

"Total disbelief. I've known Roger Ailes for 15 years and I have been treated with the utmost professionalism and respect," she told TVNewser, declaring that Ailes had been "a fantastic mentor in television" for her. "This is a man who champions women," Guilfoyle added. She also suggested that Carlson might have been "disgruntled" after her contract wasn't renewed and filed her sexual harassment suit after that disappointment.

"Nobody believed this," Guilfoyle continued, insisting that "more than 30" women at Fox agreed with her. "Nobody that I've spoken to said that this was their experience." She even claimed that Fox News was "by far, the best, most professional supportive environment" she had ever worked in. According to Brian Stelter's book "Hoax," Guilfoyle was trying to threaten her female colleagues into backing Ailes at the time; per The New Yorker, she warned them that she was "taking notes."

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).

She was accused of sexual harassment

Although Kimberley Guilfoyle signed a long-term contract with Fox News, she ended up leaving the network unceremoniously in 2018, as CNN reported. Their statement at the time simply announced that Fox had "parted ways" with the host, who was already dating Donald Trump Jr. and soon began working for a pro-Trump super PAC.

Soon after her representative assured HuffPost that the split was "mutual and amicable," however, multiple sources divulged that Guilfoyle had not left on her own terms. Instead, as HuffPost reported, she had been forced to leave after months of investigation from HR. The host was facing accusations of sexual misconduct and inappropriate workplace behavior, particularly towards support staff like hair and makeup artists.

Guilfoyle allegedly showed pictures of male genitalia to and constantly discussed her own sex life in detail with these staff members, who described her as "emotionally abusive." Despite trying to pull strings with Rupert Murdoch to save herself, the host was told to find a new position so that she could leave quietly, rather than face a public firing. Her attorney John Singer told HuffPost that these claims were "unequivocally baseless and have been viciously made by disgruntled and self-interested employees."

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).

Kimberly Guilfoyle's assistant was reportedly paid off

Kimberly Guilfoyle dismissed any allegations of sexual misconduct in 2018 after HuffPost reported that Fox News had forced her to leave over her behavior. But in 2020, The New Yorker uncovered claims that she showed photographs of genitalia to colleagues and was frequently naked around her assistant, who was pressured to sleep over at Guilfoyle's apartment. The host also allegedly asked her assistant to give her legs a massage and insisted that the younger woman should sleep with powerful men at Fox.

The network reportedly gave Guilfoyle's assistant $4 million to keep the allegations of sexual harassment against the host out of court. Two "well-informed" sources confirmed the payoff, which means that the assistant won't be able to take Guilfoyle to court over her claims of "degrading, abusive, and sexually inappropriate behavior." Guilfoyle completely denied any inappropriate behavior, emphasizing her significance as a role model to other female professionals. "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 stated in response to The New Yorker. "During my career, I have served as a mentor to countless women, with many of whom I remain exceptionally close to this day." 

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).

She took in a lot of cash from the Trump campaign

Kimberly Guilfoyle may have been forced to leave her job as a TV host, but she hasn't struggled for money. The former news commentator, who is reportedly worth $25 million, joined the Trump camp. Word eventually got out that she was apparently raking in $180,000 per year.

According to HuffPost, Guilfoyle received $15,000 per month through a private company owned by Donald Trump's campaign manager Bradley Parscale, allegedly to get around Federal Election Commission rules. If she was paid directly by the president or his campaign, they would have to reveal the financial details to the public.

"A lot of people close to Donald Trump are getting rich off of his campaign," said Paul Ryan, a campaign finance legal expert at the watchdog group Common Cause. "They don't want donors to know that they're getting rich. Because, at the end of the day, it's donor money." Lara Trump, wife of Eric Trump, apparently has a similar set-up and has also been receiving $15,000 every month. "I can pay them however I want to pay them," Parscale dismissively told HuffPost in response to the revelations.

Donors accused her of inappropriate behavior

After leaving Fox, Kimberly Guilfoyle became a dedicated campaigner for Donald Trump. According to The New York Times, the president was so impressed by her work as a senior adviser to his campaign that he personally put Guilfoyle in charge of his main fundraising committee. But as Politico reported, she may have done more damage in that role than the Trump camp ever anticipated.

Not only was her disorganized team failing to meet their targets, Guilfoyle herself was accused of inappropriate behavior. Her comments reportedly made some of the major donors extremely uncomfortable. According to Politico's findings, there was one event, for example, where she suggested that whoever contributed the most money could receive a lap dance from her. Guilfoyle also apparently alluded to earning big donations while in hot tubs and told attendees that Donald Trump Jr. enjoyed her dressing up like a Dallas Cowboys cheerleader.

"Kimberly Guilfoyle is an excellent fundraiser and was a highly valued asset to the President's team," a Trump campaign spokesman stated in response to the report. "There was nothing offensive about her presentations in context."

Her viral speech raised some eyebrows

At the 2020 Republican National Convention, Kimberly Guilfoyle became a subject of national ridicule after she delivered her loud, grandiose speech to an empty theater. During the six-minute address, she disparaged the "socialist Biden-Harris future," called California "a land of discarded heroin needles in parks," and warned viewers that Democrats "want to enslave you to the weak dependent liberal victim." At the end, Guilfoyle yelled that "the best is yet to come." As well as being mocked online, Guilfoyle's speech became the target of late-night hosts like Stephen Colbert, who joked that she was a "vengeful banshee."

Guilfoyle had her defenders, however, including her future father-in-law himself. According to the Daily Beast, Trump rang her up afterward with a series of effusive compliments, drawing comparisons between her distinctive speech-making style and Eva Peron. "That was fantastic ... so amazing," the Republican reportedly told the TV personality, referring to her as "My Kimberly." He went on to praise the "energy" and "passion" Guilfoyle had displayed during one of the "greatest" speeches he had ever witnessed. "Nobody could have done that but you," Trump concluded.

She raised millions for Save America rally

Kimberly Guilfoyle came under scrutiny for her role in the rally that preceded the deadly Capitol building riots that took place on January 6, 2021. Text messages published by ProPublica reportedly showed Guilfoyle boasting about her fundraising efforts ahead of the "Save America" event, as she convinced donors to give millions.

In a conversation with White House aide Katrina Pierson, Guilfoyle expressed frustration that she might not be allowed to speak at the event, given that she had "raised so much money for this" and only wanted to introduce her boyfriend Donald Trump Jr. "Literally one of my donors Julie at 3 million," she continued, referring to the Publix heir and Trump supporter Julie Jenkins Fancelli. Her phone records have since been obtained by the House committee investigating the insurrection, according to CNN.

According to ProPublica, Guilfoyle also apparently attempted to influence the event during a phone call, in which she argued in favor of including more controversial speakers like "Stop the Steal" organizer Ali Alexander and conspiracy theorist Alex Jones. Alexander also claimed that he spoke to Guilfoyle on January 6, confirming that the former TV host was directly involved with far-right personalities who were trying to overturn the election. And on the day, Guilfoyle wasn't alarmed by the massive crowd that gathered at the event. "They're just reflecting the will of the people," she told Trump, according to the Washington Post. "This is the will of the people."