Kimberly Guilfoyle's Most Cringeworthy Moments

Owner of a million-watt grin, an entire color palette of dresses, and an inherent comfort before still photo lens or winking tally light, ex-prosecutor, ex-district attorney, ex-San Francisco First Lady, ex-Fox News media personality, and newly-minted MAGA mouthpiece Kimberly Guilfoyle has always made it her business to include her business in the business of being Kimberly Guilfoyle.

Once part of a Democratic power couple with California politician (and current governor) Gavin Newsom — in 2004, Harper's Bazaar dubbed them "The New Kennedys" (via SF Gate) — Guilfoyle later upped her national profile as the paramour of Donald Trump, Jr. Since confirming the relationship, the duo has become omnipresent in Trumpian circles, acting as a sort of two-headed pep squad for the president's election effort in the media and on the campaign trail. But with a bigger platform, more exposure, and more microphones comes more scrutiny — and Guilfoyle's brash, free-speaking style has created its share of cringeworthy moments. Let's go to the tape.

Kimberly Guilfoyle joined Fox News in 2006, and by 2011 was a co-host on the panel gabfest The Five. (And yes, she was regularly seated in the "the leg chair.") In October 2014, during a debate over the political value of the Democrats' accusations that Republicans were waging war on women, Guilfoyle's take seemed to disparage "young women" who might sit on a jury or wish to vote. "They don't get it. 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."

Guilfoyle wasn't done. "I didn't say they shouldn't be," she told her fellow panelists, referring to women being selected for juries. "I just thank and excuse them so they can go back on Tinder and Match.com." The comment drew ire across the Twitter landscape and at progressive outlets like Salon, where it was suggested that Guilfoyle and her Five crew might feel differently if the young women in question were "more likely to vote conservatively." Unapologetic, Guilfoyle doubled down with a tweet of her own the following day, teasing the topic of whether any young people "who haven't studied the issues" should vote.

In another yikes moment on The Five in 2014, Kimberly Guilfoyle spoke mirthfully of her desire for a strongman to rule the United States. With then-President Barack Obama under fire from the panel for what they viewed as a wishy-washy response to terrorism, Guilfoyle dreamed out loud a fanfic scenario of a brief, shining period of profound American toughness. "Can I just make a special request in the magic lamp? Can we get like Netanyahu, or like Putin in for 48 hours, you know, head of the United States?" she proposed (via Media Matters For America). Guilfoyle continued on in her her broad distaste for Obama Administration policymaking, saying, "I just want somebody to get in here and get it done right so that Americans don't have to worry and wake up in the morning fearful of a group that's murderous and horrific like ISIS."

Misguided adoration for the autocratic figures like Vladimir Putin is a longstanding conservative tack, particularly in the context of Democratic leadership they view as weak. And while nobody's saying ISIS isn't objectively terrible, Steve Benen of MaddowBlog countered with: "It's not like a US president could wake up, decide to eliminate ISIS, make an order, and watch it happen." Essentially, Benen's takedown of Guilfoyle explained how her oversimplification of the foreign policy issues at stake as a wimpy vs. strong binary revealed the wincing lack of subtlety in her ham-fisted grousing for a dictatorial tough guy ruler. 

Appearing on Fox in August 2016, Kimberly Guilfoyle attempted to deny agency to former NFL quarterback and social activist Colin Kaepernick's right to peaceful protest with a teeth-clenching moment of enterprise-class whataboutism. "I think Dr. King, if he were alive today, he wouldn't disrespect the flag or the anthem. He would use his words and his voice to send a message for positive change," Guilfoyle said (via Raw Story), using her words and her voice. Raw Story then pointed out the holes in Guilfoyle's theorizing, offering as a counterpoint quotes from King that did acknowledge large scale protest as a tactic for societal change. Amazingly, this did not become the last time Guilfoyle would channel Dr. Martin Luther King Jr.

During a speaking engagement at the University of Florida in October 2019, the former Fox host caused an uproar when she once again referenced the legendary civil rights advocate. "I have a dream ... to continue to give back and fight for this country," Guilfoyle said during her speech, which triggered immediate blowback in the room, according to WUFT, not to mention outside the contentious event, and online in the days that followed. 

"I feel like I play for the Yankees," Kimberly Guilfoyle told a student group during a 2016 appearance at Cornell University. "We have a great team, a great lineup." She was reveling in the media limelight as a panelist on The Five at the time, proud of burnishing the Guilfoyle brand with a glossy Fox sheen. But just as her romance with Donald Trump Jr. blossomed, things went south between the network and its rising star. In July 2018, Vanity Fair reported that Guilfoyle's departure from Fox was imminent, and revealed that an internal Fox investigation had explored whether she had pressured her female colleagues to offer support for Fox News CEO Roger Ailes, who had been "fired for sexual harassment."

As rumors of her relationship with Trump swirled, it was further revealed that Guilfoyle's ouster from Fox came after her alleged toxic presence at the network could no longer be tolerated. Guilfoyle is said to have openly discussed her sex life in the workplace, displayed personal pictures and identities of male co-wokers, and regularly berated makeup artists and other support staff. With the bad blood publicly flowing and her ethically murky connections to the Trump Universe strengthening, the network made a terse announcement: "Fox News has parted ways with Kimberly Guilfoyle."

Guilfoyle's legal team denied the claims, and the Daily Beast reported of an apparently hostile "whisper campaign" waged against Guilfoyle in the Fox newsroom. The Yankees couldn't be reached for comment.

With the spectacle of her fall from grace at Fox News still fresh, Kimberly Guilfoyle wasted no time taking her next trick public. She was soon installed in a finance role at a Trumpworld political action committee and began publicly swooning over her romance with Donald Trump Jr. (Town & Country laid out a helpful timeline of her professional and personal narrative.) "I love him so much," she told The Washington Post in August 2018, adding, "I love spending time with him. I have no apologies."

Always outspoken, it wasn't a stretch for Guilfoyle to lay it on thick, no matter the audience. As the Post reported, the Trump team's newest star made an appearance before a Washington, D.C.-based group of "mostly male" conservative high school students. "Some of you may have heard I recently started dating the president's son. I mean, what can I tell you? Mama's a closer, you know what I mean?" 

In 2018, Kimberly Guilfoyle and Donald Trump Jr. hit the campaign trail for the midterm elections. Re-christened as, um, DONBERLY, the duo traveled the country, appeared at rallies, gave speeches and in general fed the MAGA messaging machine. They were also fully, shamelessly committed to becoming the GOP's highest profile power couple, with plenty of schmoopy arm-in-arm shots on Instagram seamlessly blended into campaign material.

This sense of Kimberly and Don Jr. living their best life in the Trumpworld ideal seeped easily into their talking points out on the trail, presenting their lifestyle as aspirational. However, some of Guilfoyle's questionable stumping revealed possibly sinister undertones. Fearing a Democrat congressional sweep, she warned, "You will not recognize America," and pleaded for "every fearless patriot out there to get out and get your friends involved... Otherwise you are going to get the Star Wars bar scene." Daily Kos responded in its own unsubtle way, posting guidelines for 'How to deal with racist people.' 

Violent imagery wasn't a bridge too far for Guilfoyle, either, when she equated midterm races as a swamp-draining by any means necessary. CT Post reported that a rally in Kentucky, Guilfoyle said she had a "hit list" of Democrats and called out a few of the party's stars. Perhaps it was a flippant choice of words, perhaps not, but a few of the Dem political players Guilfoyle mentioned, including Representative Maxine Waters and Senator Cory Booker, had been recent targets of very real pipe bombs.

Now firmly a cog in the Trump hype machine, Kimberly Guilfoyle was deployed on the first night of the 2020 Republican National Convention to give a speech hitting the marks she'd honed out on the campaign trail with Donald Trump Jr. The resulting screed, delivered at max volume and with an excruciating lack of subtlety, rampaged through the Twitter and pundit-sphere. CNN's Ana Navarro called it "somewhat unhinged, crazy, incredibly loud," noting that it drove her dog to dive under her bed. Communications expert and presidential speechwriter Michael Sheehan told The Hill that Guilfoyle appeared "like the crazy lady yelling at you on the Metro," and actor Bette Midler tweeted, "Guilfoyle knows her future father-in-law loves all caps, that's how she did her speech. 'DO YOU LIKE ME NEW DADDY???'"

Beyond the hysterics and even more hysterical reaction memes, one of the speech's most wincing takeaways was Guilfoyle's proclamation of her Latina bonafides as the daughter of a Puerto Rican mother and a father who she described as "also an immigrant." The problem there, of course, is that Puerto Rico is a U.S. territory, meaning its residents are born citizens.

"The woman the GOP picked as their 'proud' Latina to tout 'the immigrant experience' didn't seem to know that Puerto Rico is already part of the United States," US Representative and frequent target of Guilfoyle Alexandria Ocasio-Cortez later tweeted, adding, "It's quite on message, bc it reflects their belief that Latinos aren't real citizens, even when we are native descendants."

In the wake of the RNC, Kimberly Guilfoyle appeared on America First, the syndicated radio program hosted by Trumpworld mouthpiece Seb Gorka. With the internet still crowing over her bombast at the convention, Guilfoyle sailed into Gorka's safe harbor with an even harder edge on her election messaging, casually conflating the ongoing protests over racial justice and police reform with what she considers the views of Republican voters concerned for the soul of their country. "They're tired of seeing the American Dream burn down," she told Gorka, adding, "Rioters, you know, and looters tearing down and burning down buildings and stealing..."

Guilfoyle went on to dismiss the chatter and hubbub over her RNC appearance, and seized the opportunity to belittle a favorite foe who also happens to be a sitting member of the United States House of Representatives. "They tried to criticize me, you know, and AOC tried to attack me, which was, like, pathetic, it was like a little gnat on the edge, I didn't even notice it." Not noticing something and referencing it specifically are two different things, but Guilfoyle was by now onto more pressing matters, like consciously tweaking the biggest gaffe in her speech's messaging. "My mother was a proud Puerto-Rican American," she told Gorka, "and my father a proud Irish immigrant." Problem fixed! The Best! Is Yet! To Come!