Kimberly Guilfoyle

After law school, Guilfoyle taught in a public school district[7] and briefly worked as a prosecutor in San Francisco. She lost her job in 1996 when Terence Hallinan was elected district attorney and fired 14 of the city's prosecutors.[15]

Guilfoyle worked for four years in Los Angeles as a deputy district attorney, serving on adult and juvenile cases. She received several awards at the Los Angeles District Attorney's Office, including Prosecutor of the Month.[14]

In 2000, Guilfoyle was rehired by Hallinan in the San Francisco District Attorney's Office, where she was an assistant district attorney from 2000 to 2004. During this time she obtained a conviction while co-prosecuting with James Hammer in the 2002 case People v. Noel and Knoller, a second-degree murder trial involving a dog mauling; it received international attention.[16][17]

In January 2004, Guilfoyle moved to New York to host the program Both Sides on Court TV. In addition, she worked as a legal analyst on Anderson Cooper 360°.[18]

She joined Fox News in February 2006 as host of the weekend show The Lineup. This was eventually canceled. Guilfoyle remained a regular contributor for the network, and in 2011 was picked as co-host of The Five. She worked as a host on the show until 2018.[19]

In 2014, she began hosting and then co-hosting Outnumbered for nearly fifty episodes, plus a few more appearances until June 2018.[20] Guilfoyle also appeared weekly on the recurring segment "Is It Legal?" on The O'Reilly Factor until that show was cancelled in 2017, and as a weekly Thursday guest on Brian Kilmeade's Kilmeade and Friends radio show.[14] Guilfoyle guest-hosted Hannity, On the Record, Justice with Judge Jeanine, and Fox & Friends.[21]

In mid-2017, Guilfoyle signed a long-term contract extension with Fox.[22] A year later, in July 2018, Guilfoyle abruptly left Fox News;[23] she began working for a pro-Donald Trump super PAC.[24][25] HuffPost reported that, at the time of her departure, the network had been in the midst of a year-long investigation of a sexual harassment accusation against Guilfoyle. Network officials had given Guilfoyle an ultimatum: Resign by the end of July or be fired.[24] The New Yorker subsequently corroborated reports that Guilfoyle had been forced to resign rather than leaving by choice.[26]

After Guilfoyle left, Fox News agreed to an out-of-court settlement with an assistant who had accused Guilfoyle of sexual harassment. Terms were not disclosed. The New Yorker reported that the settlement was at least $4 million.[26] The assistant alleged that Guilfoyle frequently displayed herself naked, showed photographs of the genitalia of men she had sex with, and required her to sleep over at Guilfoyle's apartment.[26] The New Yorker independently verified several of the assistant's allegations.[26]

In 2015, Guilfoyle published a semi-autobiographical advice book, titled Making the Case: How to Be Your Own Best Advocate, on her experiences growing up, working as a prosecutor, and encouraging people to advocate for themselves.[27]

Guilfoyle speaking at a campaign rally in Sun City, Arizona, in November 2018

In December 2016, it was reported that Guilfoyle was being considered for the position of press secretary for President Donald Trump. Sean Spicer was considered the front-runner for the position[28] and was ultimately selected. On the May 12, 2017, edition of The Five, co-host Bob Beckel hinted that Guilfoyle turned the job down. However, in an interview with Bay Area News Group on May 15, 2017,[29] Guilfoyle confirmed she was in contact with the White House about the position following Spicer's resignation.[30] "I'm a patriot, and it would be an honor to serve the country", Guilfoyle said. "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." However, on May 19, Guilfoyle said she was under contract with Fox, indicating she turned the White House down. One month later, she extended her contract with Fox.[31]

In 2018, The Washington Post described Guilfoyle as a "conservative cheerleader for President Trump".[32]

Charlie Kirk, Guilfoyle, and Donald Trump Jr., pictured at the Palm Beach County Convention Center, 2019

In 2019 with Donald Jr. she jointly toured school campuses, invited by venues such as the University of Florida, where they were paid $50,000 for their appearance from student activity fees, which led to complaints by anti-Trump students. At the event, two people were arrested and five were injured. Two years earlier, white nationalist Richard B. Spencer had preceded them as an invited speaker, generating similar controversy.[33][34]

In 2020, Guilfoyle was reported to be the chair of the finance committee of the Trump Victory Committee.[35] As of early 2020, the Trump campaign was secretly paying Guilfoyle $15,000 per month through the campaign manager's private company, Parscale Strategy. Guilfoyle served as a surrogate on the stump and took on broad advisory roles.[36][37] In the Trump 2020 campaign, Guilfoyle managed a fund-raising division. This division paid socialite Somers Farkas to raise money.[38] The fundraising division managed by Guilfoyle was in internal turmoil amid departures of experienced staff and accusations of irresponsible spending.[39]

In August 2020, at the Republican National Convention, Guilfoyle gave a speech endorsing Trump that was widely described by some observers as unnecessarily loud[40] or unhinged.[41][42] Others in media described it as passionate.[43] She was criticized for describing herself as a first-generation American when her mother was from Puerto Rico and thus an American citizen.[44] She is a first generation American on her father's side, as he immigrated here from Ireland.[9]

On January 6, 2021, Guilfoyle joined President Trump, Donald Jr., Rudy Giuliani, Eric Trump, and others on the Ellipse in Washington, D.C. to address the "Save America March". This resulted in the attack on the Capitol.[45] Having raised millions of dollars to support the rally, Guilfoyle was also involved in organizing the protest at the Capitol.[46] She was paid $60,000 for her 2.5 minute rally speech.[47]

Guilfoyle was featured in a video screened at the rally by Donald Jr., "break[ing] into the hip-shaking dance she's been showcasing at other recent pro-Trump rallies" and "tell[ing] Trump fans: 'Have the courage to do the right thing! Fight!'".[48]