Kimberly Guilfoyle is known for her relationships with politicians like Gavin Newson, a lengthy career as a lawyer and television personality, her brief stint as a lingerie and fashion model, and her 2017 scandal on Fox News.
Guilfoyle has been deeply involved with the Trump campaign and family since 2016, becoming Donald Trump Jr.’s fiancée in 2020.
But years later, the stability of that relationship is called into question.
Don Jr. was caught kissing a Republican socialite from Palm Beach, DailyMail.com revealed on Sunday.
The former president’s son was spotted dining with “it girl” Bettina Anderson, 37, during an intimate brunch last month.
Exclusive images from DailyMail.com showed Don Jr. meeting the model, influencer and philanthropist at The Honor Bar, located inside the Royal Poinciana Plaza shopping center in Palm Beach on August 17.
Guilfoyle has been deeply intertwined with the Trump campaign and family since 2016, becoming Donald Trump Jr.’s fiancée in 2020.
Pictured: Donald Trump Jr. (left) and Kimberly Guilfoyle (right)
The former president’s son was spotted dining with “it girl” Bettina Anderson, 37, during an intimate brunch last month, DailyMail.com revealed today. PICTURED: Don Jr (left) and Bettina Anderson (right)
Witnesses said it was clear it was a date and one said Anderson was seen moving in to kiss Don Jr. three times.
But her fiancé Guilfoyle was nowhere to be seen.
Kimberly Guilfoyle is a prolific attorney who received her J.D. from the University of San Francisco School of Law in 1994.
Guilfoyle told Cosmopolitan that she paid for her law studies by working three jobs: as an intern at a district attorney’s office, at a clothing store, and as a lingerie and fashion model in the San Francisco and Sacramento area.
Modeling campaigns appeared in local department stores such as Macy’s and she modeled Victoria’s Secret lingerie for a bridal magazine.
He also had an interest in politics.
In 1995, she worked on District Attorney Arlo Smith’s re-election campaign. Guilfoyle frequented political fundraisers hosted by oil billionaire Gordon Getty, who was dating her son William.
Following their breakup, Guilfoyle rose up the political ladder after she began dating politician Gavin Newsom, who was the San Francisco city supervisor at the time.
Guilfoyle told Cosmopolitan that she paid for her law school by working three jobs: as an intern at a district attorney’s office, at a clothing store, and as a lingerie and fashion model in the San Francisco and Sacramento area.
Guilfoyle broke into the broadcast world in 2004 when she worked as a legal analyst at Anderson Cooper 360 and joined Fox News in February 2006 as host of The Lineup; she later joined The Five as a co-host in 2011. Pictured: Guilfoyle and Don Jr. with their family.
Pictured: Gavin Newsom at home with his then wife, Kimberly Guilfoyle
She married him in 2004 before divorcing in 2006 after it was revealed in 2008 that Newsom had an affair with Ruby Rippey-Tourk, the wife of his then-campaign manager and former staff deputy, Alex Tourk.
While working as a prosecutor in San Francisco, Guilfoyle clashed with Kamala Harris, who served as the former Alameda County prosecutor and oversaw the office’s Career Criminal Unit.
Guilfoyle said, “She called me and basically told me that she was on the hiring committee and in charge of the budget for the DA’s office, and that I should have contacted her if I wanted to come back to the DA’s office, and that there was no money to hire me.”
Harris recalled that conversation differently: She said she never told Guilfoyle there was no job or discouraged her from joining the office.
Guilfoyle broke into the broadcast media world in 2004 when she worked as a legal analyst at Anderson Cooper 360 and joined Fox News in February 2006 as host of The Lineup; she then joined The Five as a co-host in 2011.
She would land a long-term contract with Fox in mid-2017, before abruptly leaving in July 2018 after a year-long investigation into sexual harassment against officials at her left network, giving Guilfoyle the option of firing or resigning.
Fox News has reportedly agreed to a settlement against Guilfoyle’s accuser, who was an assistant, for at least $4 million, The New Yorker reported.
This did not leave Guilfoyle out of work or feeling the repercussions of the #MeToo movement that was in full swing.
Pictured: Guilfoyle and Trump Jr. in Morning View, Kentucky, just hours before photos surfaced of him with another woman.
She had already been considered for former President Donald Trump’s press secretary position in 2016, so the decision to work for the pro-Donald Trump super PAC was a no-brainer.
She had also been dating Donald Trump Jr. since mid-2018, confirmed by Vanessa Trump, who had filed for divorce from Donald Trump Jr. three months earlier.
The couple got engaged on December 31, 2020, but did not go public until January 2022.
Guilfoyle has been criticized for being “loud and annoying” and for airing her bedroom affairs.
Though Don Jr. was spotted kissing a Palm Beach socialite, the two are displaying an air of normality: They were photographed together Saturday at a Rumble Creators event in Morning View, Kentucky.
