Among Donald Trump’s most loyal campaign surrogates, Kimberly Guilfoyle has been especially eager to throw every name in the book at his rival, Kamala Harris, calling the Democrat presidential candidate a “liar,” a “fraud” and a “failed,” “dangerously liberal” anarchist who’s never rightfully earned any job she’s had.
The former Fox News host and fiancée of Donald Trump Jr. even argued that Trump “brings up a solid point” when he recently told a conference of Black journalists that Harris only recently “happened to turn Black.”
But Guilfoyle’s animosity towards Harris is nothing new and stems from around 2000, when both women were ambitious, up-and-coming prosecutors, and they reportedly clashed over Guilfoyle’s desire to work in the San Francisco District Attorney’s Office. At the time, Harris was a former Alameda County prosecutor who supervised the office’s Career Criminal Unit, while Guilfoyle was trying to return to her hometown of San Francisco as she was dating and would soon marry another rising political star, Gavin Newsom.
In a report Wednesday, the Daily Mail referred to a 2003 column from the San Francisco Chronicle in which Guilfoyle accused the future California attorney general, U.S. senator, vice president and Democratic presidential contender of trying to block her from getting a job in the San Francisco DA’s office.
Guilfoyle first landed a job in the San Francisco DA’s office soon after finishing law school at University of San Francisco in 1994 — having famously modeled lingerie to pay for her education. But her initial stint in the DA’s office was short-lived, when newly elected DA Terrence Hallinan “swept house” in 1996 and chose her as one of the prosecutors to let go.
Guilfoyle moved south and distinguished herself in the Los Angeles District Attorney’s Office but was eager to return to San Francisco after four years. Because of her relationship with Newsom, she probably moved in the same elite political and social circles as Harris, who had dated San Francisco Mayor Willie Brown when he was state Assembly Speaker.
But whatever intrigue erupted when Guilfoyle starting pursuing the San Francisco prosecutor’s job is “open to interpretation,” columnists Andrew Ross and Phillip Matier reported.
Guilfoyle told the columnists that Harris called her in Los Angeles and, for unspecified reasons, told her there was no money to hire her. Guilfoyle said: “She said basically that she was on the hiring committee and in charge of the budget for the DA’s office, and that I should have gone through her if I wanted to return to the DA’s office.”
Guilfoyle said she was told by the DA’s office that there was no such hiring committee and that Harris had no say in the matter. Guilfoyle was flummoxed by Harris’ supposed interference, telling the columnists: “You have to understand, I came with an excellent resume, and talented women should support other talented women.”
Harris acknowledged to the columnists that she called Guilfoyle about returning to San Francisco but remembers the conversation much differently. Harris said she called to offer her help. “I never suggested to her there wasn’t a job for her in the San Francisco DA’s office — of that, I’m very clear,” she said. “We have great rapport and have great respect for each other.”
It turns out that Guilfoyle was offered a job in the San Francisco DA’s office a few months later, and she soon “made quite a name for herself” as one of the two attorneys who prosecuted the infamous dog-mauling death of Diane Whipple, Matier and Ross reported. Harris, meanwhile, had left the DA’s office to work in the San Francisco city attorney’s office.
When this column was written in 2003, Guilfoyle was making a name for herself in other ways. Having married Newsom in 2001, she was helping him with his first run for mayor, though she also was pursuing a budding career as a TV legal analyst — a job that would eventually lead her to Fox News and a growing alliance with conservative politics.
Along with Guilfoyle’s husband, Harris also was campaigning for office in San Francisco. Harris wanted to replace Hallinan as district attorney.
“Exactly whose version of events was true was almost less relevant than the fact that there was a real rivalry and jockeying between them for recognition,” Ross said this week in an interview with the Daily Mail. He also finds it “surreal” that the rivalry of more than 20 years ago continues to play out. Guilfoyle and Newsom divorced in 2006 after she moved to New York to pursue her TV career, but her ex-husband and her old rival became Democratic political allies as they both pursued higher office.
In their 2003 column, Ross and Matier reported that Guilfoyle managed “to summon” some kind words as Harris was running for district attorney. Guilfoyle called Harris “very smart” and “a good speaker” and someone who “will work very hard” if elected.
That’s not how Guilfoyle views Harris now, as she’s become a Trump “firebrand,” a member of his inner circle and his potential future daughter-in-law. Guilfoyle famously yells her way through speeches on his behalf as she hails his MAGA vision of America.
In one recent interview, Guilfoyle derided Harris’ record as a prosecutor. And in another, for Trump Jr.’s “Triggered” podcast, she argued that Harris didn’t legitimately earn the Democratic nomination, saying it was typical of the way she’s been “handed everything her entire career.” Guilfoyle in fact doubled-down on the pro-Trump view that Harris is “a DEI” hire, saying that her former colleague only got the Democratic nomination because she’s “a Black, Asian female.”
