Kimberly Guilfoyle was first lady of San Francisco. Now she is dating Donald Trump Jr. and vice chair of a pro-Trump super PAC. (Washington Post Staff Illustration; Getty Images)

In the summer of 2004, the new mayor and first lady of San Francisco were photographed for an eight-page spread in Harper’s Bazaar. Gavin Newsom wore a thousand-dollar tuxedo, and Kimberly Guilfoyle Newsom had on a black dress that was twice the price. The magazine thought their young marriage would be “one of the most glamorous political unions since Jack and Jackie.”

Earlier that year, just five weeks into his tenure, the charismatic mayor had flouted California law by instructing San Francisco to issue marriage licenses to same-sex couples, drawing condemnation from President George W. Bush and adoration from progressives nationwide. The first lady, a prosecutor by trade, had left the San Francisco district attorney’s office to campaign for her husband and was now introducing herself to the rest of America on television, as a legal analyst for CNN and ABC News.

“The New Kennedys” was the headline across the Harper’s Bazaar spread. “Do I think he could be president of the United States?” Guilfoyle Newsom said then of her husband. “Absolutely. I’d gladly vote for him.”

Fourteen years later, after an amicable divorce from Gavin Newsom and long run at Fox News, Guilfoyle has made it to the doorstep of the White House — as a conservative cheerleader for President Trump, the new romantic interest of his eldest son, and an opening act for Vice President Pence on a promotional “Make America Great Again” tour that ends, at every stop, with a prayer.

“Isn’t it fascinating?” says Guilfoyle, 49, about her journey from belle of the Bay Area to princess of MAGAland. She’s waiting to introduce Pence in a hotel ballroom in downtown Cincinnati and just finished taking selfies with fans who are still mourning her sudden departure from Fox last month.

Her trajectory might appear baffling, but it aligns with the mind-bending physics of the Trump era, in which ideology is second to notoriety, allowing peripheral performers proximity to the presidency.

In a previous life, Guilfoyle hobnobbed with the Pelosi family and was a trusted adviser to Newsom. Now, Newsom is running for California governor on a platform that includes gun control and universal health care, and Guilfoyle is trying to stop politicians like him.

She is the new vice chair of America First Action, a pro-Trump super PAC that supports candidates in the mold of Trump and Pence. She is also dating Donald Trump Jr., gleeful troller of liberals, which brings her into the president’s cutthroat inner circle — and opens her to the ethical and legal perils that have come to define this administration.

Guilfoyle sees no true conflict between the phases of her life.

She was on the phone with Newsom recently — the two divorced in 2006 but stayed friends — and playfully threatened to bring Don Jr. to the West Coast to campaign against him. Then she put the two men on the phone with each other, because how funny would that be?

They made a joke about their mutual reliance on hair product, she says. “Gav’s hair is slicked back,” she explains helpfully, “and Don’s hair is slicked back.”

But, Guilfoyle does want to make one thing clear as she prepares to take the stage to introduce Pence: “I have fully recovered from San Francisco,” she says.


San Francisco Mayor Gavin Newsom takes the oath of office with wife, Kimberly Guilfoyle Newsom, during his inauguration in 2004. (Jeff Chiu/AP)

As a child in San Francisco, she routinely wore a red T-shirt that said "PLAN AHEAD." Her Puerto Rican mother, a teacher, died of leukemia when Guilfoyle was 11. Her father, a contractor who emigrated from Ireland, was nicknamed "the godfather" because of his strong relationships with local officials and the city's Irish construction "mafia."

Her father was a guiding light who didn’t want his children “to live with the regret that we didn’t go after something,” Guilfoyle wrote in her 2015 book, “Making the Case,” which converted her legal experience into life advice about “how to be your own best advocate.”

“Kim was always in charge,” says her younger brother Tony, especially after their mom died. After attending a private all-girls Catholic school in San Francisco, Guilfoyle helped pay for college and law school by modeling (for soap, for clothing, for lingerie). She worked in the district attorney’s offices in Los Angeles and then San Francisco starting in 2000, when she got serious with Newsom, who was on the city’s board of supervisors.

She had the “utmost integrity” and was a “warrior for the prosecution,” according to Paul Cummins, who headed the criminal division at the DA’s office.


Gavin Newsom, left, and his wife, Kimberly Guilfoyle Newsom, drink wine and talk with staff during a visit at the PlumpJack winery in Oakville, Calif. in 2002. (Eric Risberg/AP)

“She never took advantage of the fact that she was dating this ridiculously handsome, talented guy who looked like he was going to become the mayor,” says Cummins. “She was a down-to-earth, classy prosecutor.”

The media at the time referred to her as “the babe of the San Francisco bar” and a part of “the city’s glitterati” via her romances with Billy Getty, a grandson of the oil tycoon J. Paul Getty, and then Newsom (who could not be reached for comment).

Her work at the DA’s office was much edgier than society gossip: robberies, domestic violence, arson. In the fall of 2001, weeks before marrying Newsom, Guilfoyle was given 24-hour police protection because a prison inmate put a bounty on her head, related to her aggressive prosecution of a dog-mauling case. A bulletproof vest became part of her ensemble. Police inspected the church before her wedding, which the San Francisco Chronicle called “the social event of the year.”

After Newsom announced his campaign for mayor, Guilfoyle left the DA’s office to campaign with him: “Six hundred house parties, group community meetings and fundraisers with him in one year,” she recalls now.

Guilfoyle says she’s always been a Republican, having registered with the party at 18, and that she aligned with Newsom’s pro-business mentality. But in San Francisco, she never talked much about her conservative leanings, even in private; the couple seemed to treat each step of their careers, and each other, as a means to an end, according to some friends and colleagues from that era.

The pair “felt like they were passing through,” says longtime city official Aaron Peskin, who served on the San Francisco board of supervisors with Newsom.

Three days after she held the Bible for his swearing-in as mayor, Guilfoyle started a new job in New York hosting a show for Court TV. A year later, Gavin and Kimberly Newsom filed for divorce.

Passing through, in Guilfoyle's view, is not a shortcoming.

“I am always changing and doing stuff,” she says. “Grass doesn’t grow too long under my feet. I’m on the move.”

Guilfoyle joined Fox News in early 2006 as the host of a crime show that featured murders, rapes and missing young women. About that time, she met the Trump family at charity events in New York. She and Don Jr. were introduced by mutual friends at a Manhattan party; the two grew closer because her son, Ronan — with second husband Eric Villency, a businessman and designer — went to the same school as his daughter Kai.

In 2011, she joined Fox’s popular prime-time panel show “The Five.” On set, Guilfoyle was always seated in “the leg chair,” because the position allows viewers a full view of the host’s bottom half. During a meeting with the show’s co-hosts, Fox chairman Roger Ailes presented an image of the set. Guilfoyle was seated on the end, legs on display.

“There’s Kimberly, doing her job,” Ailes told the group, according to two people familiar with the meeting. (Guilfoyle says she doesn’t remember this).

She became a reliable supporter of Trump after he declared his candidacy, and Don Jr. took notice. “When everyone else said that Hillary was unstoppable,” he says, “Kimberly stood firmly with my father.”

Guilfoyle was well-liked by her colleagues for much of her Fox career, but her reputation began to slide in the summer of 2016. When Gretchen Carlson publicly accused Ailes of sexual harassment, Ailes’s wife, Beth, enlisted Guilfoyle to rally women to his defense.

Guilfoyle embraced the effort, alienating other hosts, including Megyn Kelly, who complained about her to the Murdoch family, which controls the conservative-leaning network, according to four people familiar with the incident. After Ailes was forced out of Fox News in July 2016, amid repeated allegations of sexual harassment, Guilfoyle felt she received less airtime on “The Five,” even though the show is divided equally between the five co-hosts.


TV personality Alex Trebek and hosts of “The Five” including Kimberly Guilfoyle, on set. (Noam Galai/Getty Images)

Donald Trump Jr. and Guilfoyle attend the D.C. premiere of the film “Death of a Nation.” (Shannon Finney/Getty Images)

The story of her departure last month from Fox News is in dispute. Sam Nunberg, an early campaign adviser to Trump, says that her tenure at Fox ended unfairly — that colleagues were jealous of her star power and that the Murdochs frowned upon her loyalty to both Ailes and Don Jr.

That’s one version. The other, according to two people aligned with Fox News who were not authorized to speak to the media, is that she engaged in inappropriate workplace communication with colleagues that was no longer acceptable in the post-Ailes era. Guilfoyle declined to comment on any Fox News matters, but a representative pointed to her “bitter-sweet” Twitter announcement saying she had “decided to leave Fox News Channel.” Fox News declined to comment beyond their initial statement that they had “parted ways” with Guilfoyle.

As her star dimmed at Fox, it brightened in Trump world, says Stephen K. Bannon, the former Trump adviser, who says she was considered for Trump’s press secretary during the presidential transition.

While she was negotiating her exit from Fox in June, Guilfoyle gave a fiery speech in Dallas at a conservative leadership summit for young women. She cha-cha’d onstage in a bright red dress, through a cloud of pink confetti, to “Let’s Get Loud.” She declared at the microphone that Jennifer Lopez was “my Boriqua hermana” (or, my Puerto Rican sister), and then delivered a strident defense of Trump’s treatment of women.

Then, at a D.C. event for high school conservatives last month, she threw red-meat talking points at the mostly male crowd, with a dash of sexual innuendo. Between chants of “Build that wall” and “Lock her up,” Guilfoyle said: “Some of you may have heard I recently started dating” the president’s son. “I mean what can I tell you? Mama’s a closer, you know what I mean?” The crowd howled as she brushed her long brown hair out of her face.

Bannon says that “she makes me look like a wimp.”

“I said she should be doing it three times a day,” he says of Guilfoyle’s campaigning. “She can do the high donor stuff, but there are a lot of people who can do that. What she really can do is fire up the people who are the volunteers and the people who are the backbone of this movement.”

Nunberg is more succinct: “Those legs got ratings, and I think those legs can get votes.”

On the Fourth of July, when she was still appearing on “The Five,” Guilfoyle posted on Instagram a photo of herself holding hands with Don Jr. on the West Wing colonnade. And there it was: a symbolic portrait of Fox News hand in hand with the Trump family. Two days later, on Breitbart News radio, Guilfoyle praised her boyfriend’s political potential — “I think he is the No. 1 up-and-coming political figure, for sure, on the right” — just as she had done with Gavin Newsom years ago.

Onstage in Cincinnati, she extols the world of President Trump.

“Your pockets may feel a little heavier,” she says to a muted daytime crowd, before introducing Pence. “You can thank the president for that.”

On the six-seat private plane back to Washington, Guilfoyle critiques White House press secretary Sarah Huckabee Sanders’s performance. Sanders had just said she’d never heard the president use the n-word but could not guarantee there was no tape of him uttering the slur.

The president is “not going to be happy about that,” Guilfoyle says.

Guilfoyle’s former boss at Fox News, Bill Shine, is now in the White House communications shop, and although he hasn’t tried to recruit her, she says, he’s “a big fan of mine, let’s put it that way.”

Whatever comes next, there may be tricky territory ahead.

This week’s courtroom drama involving Trump associates, as well as the ongoing investigation into the campaign’s alleged coordination with Russia, have darkened the cloud of suspicion surrounding the president and Don Jr. And the watchdog group Citizens for Responsibility and Ethics in Washington (CREW) is concerned that Guilfoyle is both working for a group that’s prohibited from coordinating with the Trump campaign and dating a top surrogate for the campaign.

“It raises eyebrows,” says Jordan Libowitz, CREW’s communications director, adding: “If you look at the overlap between the Trump administration, the Trump campaign, the Trump Organization and the Trump family — the lines are very blurred between them.”

One person’s blurred lines are another’s clear road map. Guilfoyle says she can be both campaigner and romantic partner, though it’s the latter that has been getting big play.

On Instagram, she posts photos of herself fishing with Don Jr. off Montauk, N.Y., and jetting with him to Monaco. In speeches, she calls him “Junior Mints” because he’s “sweet as candy.”

At one point on the flight home, she puts her hands to her cheeks and lets out a near-squeal that fills this plane.

“I love him so much!” Guilfoyle says of Don Jr. “I love spending time with him. And I have no apologies. We love each other very much.”

Indeed.

“We are best friends.”

It’s clear.

“I absolutely adore him.”

Intent on making her case, Guilfoyle adds that their relationship is for keeps, that the Guilfoyles and the Trumps will merge like “The Brady Bunch.” Except it will be “The Donberly Bunch,” she says — which sounds like a strange sequel to a short-lived show, set in San Francisco, called “The New Kennedys.”