Steve August 25, 2020
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Kimberly Guilfoyle’s spirited slam of California during her Republican National Convention address may have seemed like garden-variety Golden State bashing, a long-practiced routine for GOP personalities.

But those watching in the Bay Area heard a far more nervy attack than the average put-down of San Francisco liberals.

“She was part of the political culture that she has now turned against,” said Nathan Ballard, who worked as an aide to then-San Francisco Mayor Gavin Newsom. “It’s like she joined a cult. She seemed completely unhinged.”

Guilfolye, a former San Franciscan, was, for a time, deeply enmeshed in her hometown’s political power circle, married to one rising star (Newsom, now governor) and legal contemporary of another (Kamala Harris, California’s junior senator and Democratic vice presidential hopeful).

Her paean to American greatness under Tweety McTreason on Monday evening got immediate notice, largely negative, both for her thundering delivery and her lacerating description of her home state, which is currently engulfed by hundreds of wildfires.

While her detractors say her disparaging take smacks of hypocrisy, supporters say her long history in California is exactly what makes her critiques credible.

“The way she portrayed it, as somebody from the epicenter of San Francisco and who knows what’s happening in California because she knows the players — personally, I think that was incredibly effective,” said Harmeet Dhillon, a San Francisco lawyer and national co-chair of Women for Trump.

After Guilfolye, the Fox News personality-turned-Trump surrogate (and girlfriend of Tweety McTreason Jr.) roasted California as littered with heroin needles and ravaged by chaos and blackouts, she was immediately a trending topic on Twitter; so was Newsom, as the Internet discovered, or rediscovered, her now-incongruous marriage to California’s governor.

San Franciscans have long been familiar with Guilfoyle, whose relationship with Newsom put her on the map in the city’s most exclusive circles.

“I would see her and have little superficial chats. She was all sparkly and happy, very beautiful at that point,” Susie Tompkins Buell, a philanthropist and influential Democratic donor, said. “It was appealing, in a way. But there was always an edge.”

Guilfoyle’s upbringing was more working-class than high-society. She was born in San Francisco to a Puerto Rican mother and an Irish father. On Monday, she spoke of her mother’s Latino heritage and self-identified as a “first-generation American,” raising eyebrows given that Puerto Rico is an American territory.

After attending UC Davis and University of San Francisco Law School, she did stints as a prosecutor in San Francisco and Los Angeles.

Along the way she met Newsom, whose father, a retired judge, introduced them, she said in a 2004 interview with Charlie Rose. As their courtship progressed, she moved back to the Bay Area and resumed working as a prosecutor under Dist. Atty. Terence Hallinan, who was known for his progressive approach to criminal justice, opposition to the death penalty and low conviction rate. (In a sign of the insularity of the San Francisco political world, Hallinan is also known for losing his 2003 reelection bid to an upstart Harris, which launched her career in elected office.)

Gavin Newsom and his then-wife, Kimberly Guilfoyle Newsom

Gavin Newsom and his then-wife, Kimberly Guilfoyle Newsom, celebrate his victory over Matt Gonzalez for the post of San Francisco mayor in 2003.

(Marcio Jose Sanchez / Associated Press)

Newsom and Guilfoyle wed in 2001. As the city’s first lady, she carved out her own professional reputation as a prosecutor in a high-profile dog-mauling case.

She was actively involved in Newsom’s ascendant political career, attending campaign events and strategy meetings for his 2003 mayoral bid, said Jim Ross, Newsom’s campaign manager. Her convention speech reminded Ross of one planning session late on a Friday afternoon, when Guilfoyle launched into an uninterrupted 20-minute monologue about homelessness and quality-of-life issues.

“There’s nothing you can do,” he said. “It’s the candidate’s spouse.”

While Ross described Guilfoyle as a burden to Newsom’s campaign, he painted her father, Anthony Guilfoyle, as the opposite — a helpful political operator who would use his sway with Irish laborers to raise money for the campaign at the city’s lumberyards.

On Tuesday, the Trump campaign emphasized her father’s migrant background.

“She is a proud daughter of an immigrant, and is the epitome of the American Dream,” said Sergio Gor, chief of staff for the Trump Victory Finance Committee. The campaign did not make Guilfoyle available for an interview.

During the 2003 mayoral race, Ross said, Guilfoyle voiced political opinions well within the “mainstream of moderate San Francisco politics” — which would firmly be considered liberal elsewhere in the country.

She was unabashedly enthusiastic over Newsom’s decision to issue marriage licenses to gay couples in 2004, a provocative act that predated the Supreme Court decision legalizing same-sex marriage by 11 years.

“I told him he was like Robert Kennedy,” she told the San Francisco Chronicle at the time. “He will be remembered for his work in civil rights.”

Still, Newsom acknowledged Guilfoyle was more politically conservative than he was on matters of law and order. Newsom opposed the death penalty, while his then-wife publicly criticized Harris, who had just became San Francisco D.A., for not pursuing capital punishment against a man convicted of shooting and killing a police officer.

Harris and Guilfoyle overlapped in the district attorney’s office for just a few years, but were rumored to have had a chilly relationship. A San Francisco Chronicle article dished that when Guilfoyle was seeking to return to San Francisco as a prosecutor, she felt Harris threw cold water on the prospects. Harris denied any discouragement. A spokesperson for Harris declined to comment.

Guilfoyle left the law for a broadcast gig with Court TV — a New-York based job that put her and her husband on different coasts. Still, the couple built a flashy reputation, dubbed by Harper’s Bazaar as “the new Kennedys.” She made headlines in 2005 for sexually suggestive jokes about her husband at a gay right’s dinner, although she denied reports she coupled the comments with a suggestive gesture. (Fourteen years later, Guilfoyle departed Fox News amid allegations of inappropriate behavior and misconduct.)

In 2006, the pair divorced, citing the strain of the bicoastal relationship.

Guilfoyle, who remarried and later divorced, joined Fox News in 2006, placing her in a conservative orbit that eventually brought her to Trump Jr., whom she began dating two years ago. She has become an integral part of the Trump team.

“What we know her for at the Trump campaign is heading the most successful fundraising operation ever of a Republican candidate,” said Dhillon, the San Francisco lawyer. “She’s a real behind-the-scenes, substantive person in the campaign.”

Newsom has been married to Jennifer Siebel Newsom for 12 years, and they have four children. He has built a national figure as a progressive foil to the president. A spokesman for Newsom did not respond to requests for comment.

He and Guilfoyle maintain a cordial relationship, Ballard said.

But her sharp-tongued sentiments about her home state — and the unspoken knock on the man who leads it — garnered strong reactions from those who knew her in her San Francisco days.

Ross said her remarks showed a lack of empathy for a state contending with raging wildfires in the midst of a pandemic.

“That speech was clearly an indication she’s cut all ties with California and San Francisco,” Ross said.

Buell said she was inundated with text messages Monday night from acquaintances marveling at Guilfoyle’s turn at the podium. But it was Newsom who occupied Buell’s thoughts.

“I am a big fan of Gavin’s,” she said. “I am so sorry that on top of everything else that he has to carry on his shoulders, he has to be reminded he was once married to her.”

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