They were young lawyers, rising political stars and social acquaintances in the most exclusive quarters of San Francisco civic life.
But around 2000, Kamala Harris placed a phone call to Kimberly Guilfoyle that would echo, semi-surreally, in the sufficiently semi-surreal presidential campaign of 2024.
Ms. Harris was an assistant district attorney in the city. Ms. Guilfoyle was in discussions to join the office. Ms. Harris was calling, according to Ms. Guilfoyle, to suggest there was no job for her there.
“She pretended to be a member of the hiring committee, which didn’t exist,” Ms. Guilfoyle said in a recent phone interview.
Ms. Harris’s boss at the time, who broadly corroborated Ms. Guilfoyle’s version of events, hired her anyway, describing Ms. Harris years later as fiercely opposed to the move.
Ms. Harris has repeatedly denied snubbing Ms. Guilfoyle since the matter was first raised publicly more than 20 years ago, saying the phone call was merely about offering “help.”
And if that was something of an artful dodge, Ms. Harris’s friends say now, she was prescient to be skeptical of Ms. Guilfoyle from the beginning.
“If she ever did do that,” said Stanlee Gatti, a close friend of Ms. Harris’s and the best man at now-Gov. Gavin Newsom’s wedding to Ms. Guilfoyle in 2001, “she was smart.”
More than two decades later, Ms. Harris is the Democratic nominee for president and Ms. Guilfoyle is a ubiquitous surrogate for her opponent — a memorably zealous speaker at consecutive Republican National Conventions and a de facto Trump relative since her engagement several years ago to Donald Trump Jr.
Her present campaign task: persuading voters that she knows Ms. Harris better than most and imploring them to block her from power.
“I know her for 25 years, and let me tell you something,” Ms. Guilfoyle said recently at a Republican dinner in Florida. “Do whatever it takes to keep her out of the White House.”
The buzzy, hazy tale of Ms. Harris and Ms. Guilfoyle ascending in parallel in San Francisco demands two firm caveats:
Ms. Harris’s supporters say, credibly enough, that this is now something of a one-sided dialogue. The vice president does not seem to have uttered a public word about Ms. Guilfoyle in years.
And modern political history is overstuffed with reductive and often sexist accounts of rivalries between professional women — the province of passing gossip and unfortunate allusions to “cat fights” — as if men were wholly incapable of ambition, conflict and petty grievance.
Yet as Ms. Harris and Ms. Guilfoyle find themselves, a quarter-century later, as political adversaries on the grandest scale, their intersecting early-career arcs reveal something more enduring about these onetime counterparts, their divergent paths and the political parties in which they ultimately rose.
This was the period, in the perpetual tinderbox of San Francisco politics, when Ms. Harris and Ms. Guilfoyle formed the outlines of the public figures they would become.
“Superstar women,” said Willie Brown, the former San Francisco mayor, who once dated Ms. Harris. “They represented the city.”
Relentlessly foresighted and instinctively reserved, Ms. Harris was a respected prosecutor who cast an eye for years toward the office’s top job as she entrenched herself among the city’s elite — an outsider becoming an insider in real time.
And Ms. Guilfoyle, the indefatigable daughter of a Bay Area political fixture, mused about leading the same district attorney’s office one day, friends recalled. (Ms. Guilfoyle said she never seriously considered a run.)
“Everybody was gearing up,” said Phil Matier, who was a longtime political scribe for The San Francisco Chronicle. “We were waiting to see if there was going to be a matchup between Kimberly and Kamala.”
Around San Francisco, where Ms. Guilfoyle has lingered as a distant memory since her divorce from Mr. Newsom, those close to Ms. Harris are generally disinclined to revisit this chapter.
“I might have blocked it out completely,” said Andrea Dew Steele, a Democratic fund-raiser who has known Ms. Harris for decades.
“Say no more!” Mark Leno, a former California legislator and a friend of Ms. Harris’s, pleaded with a laugh when Ms. Guilfoyle was invoked.
“I knew they didn’t get along,” Rebecca Prozan, a top aide on Ms. Harris’s 2003 run for district attorney, said, before moving on quickly. “Kimberly’s been so good at refocusing on other things to remember about her.”
If this era remains more vivid for Ms. Guilfoyle, she has largely spared audiences the details, speaking ominously but vaguely in public appearances about her history with Ms. Harris.
“I watched it firsthand — she left San Francisco worse off,” Ms. Guilfoyle said in Florida this month. “Her only goal is the new job, the next job, the next office.”
Privately, in the years after Ms. Harris became district attorney, Ms. Guilfoyle was sometimes more specific, allowing herself a rueful observation about her hometown, according to a former associate who heard it.
“I should have been D.A.,” Ms. Guilfoyle would say. “I should be D.A.”
Spiky Politics
All politics can be strange; San Francisco’s is stranger, spikier, more claustrophobic.
The roughly seven-by-seven-mile city of Nancy Pelosi, Dianne Feinstein and Mr. Newsom has long punched above its proverbial weight — and has occasionally tested the bounds of that metaphor, with reported fistfights among politicos and a former district attorney, Terence Hallinan, known as “Kayo” (as in “KO,” for knockout) because of his boxing background.
Ms. Harris, as she takes care to point out, was not from San Francisco. She was born in Oakland and began her career as a prosecutor in Alameda County. She joined Mr. Hallinan’s office across the bay in 1998, after which the district attorney sometimes congratulated himself openly on his good judgment.
“Great hire,” Mr. Hallinan would say of Ms. Harris. (“Reflecting some glory back on him,” Fred Gardner, a former Hallinan aide, remembered.)
By this time, Ms. Harris had already enshrined herself as a regular on the San Francisco society circuit, with its galas and Gettys and opera after-parties. Ms. Guilfoyle — whose father, Anthony Guilfoyle, was a political adviser known as “The Godfather” — had her own early experience in some of the city’s esteemed spaces.
“Kamala eventually got in the same political circles — she didn’t start there,” Mr. Brown said. “They were still trying to find out exactly what made sense for them beyond all of the social activities and being part of the ‘first group’ in the city, so to speak.”
Ms. Guilfoyle, a few years Ms. Harris’s junior, briefly worked for Mr. Hallinan’s predecessor in San Francisco before joining the prosecutor’s office in Los Angeles.
Around 2000, she spoke to Mr. Hallinan’s team about returning.
This is where accounts begin to collide. Ms. Guilfoyle has said she received a call from Ms. Harris a short time later claiming she had budgetary authority in the office and no spot for her.
“She was threatened,” Ms. Guilfoyle said in the interview. “Most things in life make sense — jealousy, envy.” (Ms. Harris’s presidential campaign declined to comment.)
Ms. Guilfoyle said she immediately told others in the office what Ms. Harris had said. “They’re furious,” she recalled.
Ms. Harris has said she never discouraged Ms. Guilfoyle from joining the office or suggested she could not have a job.
Mr. Hallinan, who died in 2020, said that Ms. Harris “forbade” him from hiring Ms. Guilfoyle even though he was her boss. He brought Ms. Guilfoyle aboard, anyway.
“Timing is everything!” Mr. Hallinan wrote in a note explaining the hire to Mr. Gardner, who recently shared it.
What no one has supplied is a compelling explanation of what transpired between Ms. Guilfoyle and Ms. Harris in the first place.
People who spoke to both women at the time said the fraught dynamic seemed to grow out of a personal conflict in their social circles, not any professional clash. (Ms. Guilfoyle’s diagnosis is more straightforward — and, perhaps conveniently, fit for an attack ad: “She wasn’t supportive about lifting women up.”)
Whatever the origins, they would not be colleagues for long. By late 2000, Ms. Harris had left the office, frustrated by what she would later describe as an unruly and dysfunctional culture under Mr. Hallinan.
In short order, Ms. Harris was consulting with friends about a run for his job, forming a fund-raising network drawn from a hulking Filofax full of estimable social contacts.
“Determined and ambitious,” said Denise Hale, a friend of Ms. Harris’s and a grande dame of San Francisco high society. “Thank God.”
Ms. Harris’s farewell party was a study in political maneuvering. Some lawyers feared that their attendance might register as disloyalty to Mr. Hallinan, who had already grown suspicious of Ms. Harris’s campaign intentions.
But Ms. Harris was also popular with much of the office and might well return to run it someday.
The send-off, it was determined, would be planned while Mr. Hallinan was on vacation.
“The sign-up list for the party got so long,” Mr. Gardner recalled years later, “that even Kimberly Guilfoyle decided to come.”
A Dog Attack
Within months, though, something unexpected happened: Ms. Guilfoyle was everywhere.
A 33-year-old woman named Diane Whipple had been fatally mauled by a 120-pound Presa Canario dog in her Pacific Heights apartment building, and Ms. Guilfoyle was helping to prosecute the married couple responsible for the animal.
In a case that would attract international attention, with true-crime elements that felt culled from a network procedural — a hyper-sympathetic victim, a ritzy neighborhood, a dog owner with ties to the Aryan Brotherhood prison gang — Ms. Guilfoyle’s duties included representing the office in the news media.
She was good. Television executives noticed. So, it seemed, did some unsavory actors who wished her harm: Ms. Guilfoyle’s legend grew after she was placed under police protection amid reports that a murder contract had been put on her head.
“She wore a bulletproof vest over her evening gowns,” Mr. Gatti remembered.
“Kamala,” Mr. Brown noted, “did not have, in San Francisco, a case of that visibility.”
Ms. Guilfoyle’s celebrity turn only enhanced the spectacle of her wedding to Mr. Newsom in December 2001, a union instantly held up as a kind of West Coast Camelot.
“Forget ‘Kennedyesque.’ I think we need a new word — Newsomly,” The Chronicle wrote. “And Julia Roberts only wishes she was played by Kimberly in a wedding flick.”
As the city approached its next major election cycle, the three up-and-comers seemed committed to their respective routes. Ms. Harris was gathering momentum in her bid to unseat Mr. Hallinan. Mr. Newsom was poised to become mayor. And Ms. Guilfoyle had positioned herself for a future in television, eventually landing an anchor’s chair on Court TV.
It was striking, then, when an explosive headline landed in The Chronicle weeks before the 2003 election: “Brains, brio, beauty — and wounded feelings.”
The accompanying cartoon portrayed Ms. Harris pressing her body against a door, struggling to keep a perspiring Ms. Guilfoyle from entering.
“Talented women should support other talented women,” Ms. Guilfoyle told the newspaper. She was going public with long-simmering criticisms of her former colleague just as Ms. Harris and Mr. Newsom were about to take power, antagonizing the next district attorney from her husband’s own party.
The reasons were more cathartic than strategic, people who know her said. (Ms. Guilfoyle suggested recently that she had been reluctant to speak and obliged only after being pestered by The Chronicle.)
“That’s Kimberly,” Mr. Matier, a co-author of the article, said. “She felt compelled to speak about it because she wasn’t thrilled about Kamala becoming district attorney.”
The allegation that Ms. Harris had been less than collegial was hardly a major factor in the late stages of the district attorney’s race.
But during a break at a final debate with Mr. Hallinan, the candidates were apparently so piqued by the subject that they seemed to be sniping in private about it.
“Getting some serious contentiousness here off the air,” the moderator told listeners when the discussion resumed. “Let’s at least air this.”
The next question was about Ms. Guilfoyle.
“I have a great deal of respect for Kimberly Newsom and her work as an attorney,” Ms. Harris said calmly, “and I look forward to working with her.”
“She absolutely told me not to hire her,” Mr. Hallinan objected, saying he found Ms. Harris’s opposition so confounding at the time that he immediately told his wife about it.
Ms. Harris got the last word, at least with the voters, dismissing Mr. Hallinan as a desperate incumbent ”throwing a lot of things out there to muddy the waters.”
She was elected the next week.
Becoming a Right-Wing Star
Their faces were splashed across opposite sides of a heart sculpture outside City Hall, part of an unmissable public art project in 2004 that elevated the two women who seemed to augur a new San Francisco order: Ms. Harris, rendered to evoke Billie Holiday with gardenias in her hair, and Ms. Guilfoyle, styled as Frida Kahlo.
“They’re both strong women who care a lot about justice,” the artist, Tim Gaskin, said at the time, explaining his vision in highlighting the pair.
But by then, friends said, the two had little to do with each other.
Soon after Ms. Harris and Mr. Newsom took office, Ms. Guilfoyle was spending much of her time in New York for her television roles — one half of a bicoastal marriage that would end after just a few years.
Her own political campaign would never come.
“She had bigger items, and the bigger items were television,” Mr. Brown said. “That would be Kimberly. She had that kind of chutzpah.”
Long considered a relative moderate — certainly by San Francisco standards — with a law-and-order bearing, Ms. Guilfoyle found her place in due time within the star system of right-wing media, becoming a Fox News stalwart before leaving in 2018 amid allegations of sexual harassment against her. (According to The New Yorker, Fox paid a settlement to a former assistant to Ms. Guilfoyle. Ms. Guilfoyle has previously denied wrongdoing.)
In recent years, she has been an unyielding advocate for Donald J. Trump, who considered hiring Ms. Guilfoyle as White House press secretary and was said to have approvingly compared her to Eva Perón after a viral, speaker-jangling 2020 convention address in which she insisted, “The best is yet to come!”
“I swear that the telephone circuitry in San Francisco had to have been on overload,” Mr. Gatti said of that night. “The first person I called was Gavin, of course.”
After Mr. Trump’s defeat, Ms. Guilfoyle suggested darkly in 2021 that Ms. Harris was already running the White House as vice president.
“Very customary for her career,” Ms. Guilfoyle said more recently on a livestream, after President Biden dropped out of the 2024 race. “Everything’s been handed to her.”
She now hosts a program on Rumble, a video platform embraced by the right, where she regularly thrashes Ms. Harris and plugs her dog-themed children’s book. (A “Joe Bite’em Chew Toy” is also available as part of a bundle “for conservative canines and their owners.”)
This time, Ms. Harris has let others do any rebutting for her.
“She’s not someone who really talks about other people,” Mr. Gatti said, “unless they mean something to her.”
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