Sunday, October 18, 2026

The rise and fall of SF's 21st century power couple: Gavin Newsom and Kimberly Guilfoyle

They were 'the New Kennedys.' 
And then they were done.
By Kendra Smith, 
Deputy Managing Editor
Oct 18, 2026

More than two decades ago in 2004, then-San Francisco Mayor Gavin Newsom and his wife Kimberly Guilfoyle were given the label “the New Kennedys” in an infamous Harper’s Bazaar profile for which they posed lying seductively on a maroon and gold rug. It may have sounded like hyperbole, but it was clear even then that the two could take their San Francisco roots to greater heights. Gordon Getty, the prominent American philanthropist and oil heir, also a longtime family friend of Newsom, had told W magazine the year before that the couple was “destined for greatness,” in both SF and D.C.

Just apparently not together. 

By 2006, SF’s “Camelot couple” had unceremoniously divorced and begun to their ascent to new heights, albeit ones that were in political opposition. Guilfoyle became a MAGA superstar who was engaged to Donald Trump Jr. for three years and served as ambassador to Greece until she resigned this week after accusations of misconduct, which she denies. Newsom became California’s lieutenant governor in 2011, was elected governor in 2019, and has a much-speculated-about 2028 presidential bid on the horizon.

Gavin Newsom takes the oath of Office of Mayor from his father Judge William Newsom as his wife Kimberly Guilfoyle Newsom holds the Bible, Jan. 8, 2004.

Gavin Newsom takes the oath of Office of Mayor from his father Judge William Newsom as his wife Kimberly Guilfoyle Newsom holds the Bible, Jan. 8, 2004.

Michael Macor/The San Francisco Chronicle via Getty

But before their comparison to America’s iconic first couple, Jackie and Jack, they were just Kimberly and Gavin, a model turned attorney and a wine entrepreneur turned county supervisor who were falling in love. 

In his memoir, “Young Man in a Hurry,” Newsom references bringing Guilfoyle on a group trip with Billy Getty as his date in the late 1990s (Getty had dated Guilfoyle, but he had a new girlfriend by then, and she was invited to Maui, too). The couple were first introduced to each other at a political fundraiser by Art Groza, a part owner of Newsom’s PlumpJack business and known San Francisco connector, according to the San Francisco Chronicle. One of the first times the pair appeared together in print as a couple seems to be with the senior Gettys, Gordon and his wife Ann, at a 2000 San Francisco Symphony gala, but with no Billy in attendance — a potential slight, given that the two young men had been best friends and business partners. By May 2001, they had fallen out, according to San Francisco Chronicle columnists Phil Matier and Andy Ross. 

FILE: Right to left, San Francisco District Attorney Terence Hallinan, Assistant District Attorney Jim Hammer, Assistant District Attorney Kimberly Guilfoyle Newsom, and Carlos B. Sanchez, assistant bureau chief for the San Francisco bureau of criminal investigation, listen as jurors speak to reporters about their deliberations after the jury delivered the verdict in the San Francisco dog mauling trial in Los Angeles, March 21, 2002. 

FILE: Right to left, San Francisco District Attorney Terence Hallinan, Assistant District Attorney Jim Hammer, Assistant District Attorney Kimberly Guilfoyle Newsom, and Carlos B. Sanchez, assistant bureau chief for the San Francisco bureau of criminal investigation, listen as jurors speak to reporters about their deliberations after the jury delivered the verdict in the San Francisco dog mauling trial in Los Angeles, March 21, 2002. 

AFP via Getty Images

Guilfoyle had moved back to the city from Los Angeles the year before to reclaim a role in District Attorney Terence Hallinan’s office. Born and raised in the Mission and then Daly City, she attended Mercy High School and then UC Davis, where she worked in retail at a Clothestime store making $6 an hour. A spontaneous offer to model brought her hourly up to $300, and helped pay her way through University of San Francisco Law School. 

She built up an impressive portfolio of everything from lingerie work to ads for soap, but it was always just a side hustle to her legal career. Guilfoyle’s assignment to the 2001 Diane Whipple dog-mauling case, a trial that captivated the city and the nation, eventually thrust her into the spotlight and appearances on “Dateline,” “The Today Show,” “Geraldo Rivera” and “Good Morning America.”

“I think about Diane Whipple every day,” she told the San Francisco Chronicle in 2001 of the case, knowing that the lacrosse teacher’s death was preventable with better laws. A June profile of her from the outlet in the same year calls her “a damn serious lawyer.”

Meanwhile, two years before he would even run, Newsom was already considered the front-runner to replace Mayor Willie Brown. The engagement rumors were swirling.

Gavin Newsom at home in the kitchen with wife Kimberly Guilfoyle Newsom, Jan. 25, 2003.

Gavin Newsom at home in the kitchen with wife Kimberly Guilfoyle Newsom, Jan. 25, 2003.

Christina Koci Hernandez/San Francisco Chronicle by Getty

Newsom proposed to Guilfoyle in Cabo San Lucas over Memorial Day weekend, 2001. He asked her dad, Tony, for her hand in marriage in advance, earning access to the ring Tony had presented Kimberly’s mother Mercedes with 30 years prior. Guilfoyle told columnist Rob Morse that the couple were “best friends who both hope they can do great things for San Francisco.” 

The couple paired this class act with the purchase of a five-bedroom, four-and-a-half-bath William Wurster home at 2780 Pacific Ave. in Pacific Heights for $3 million, using a $1 million loan from the Gettys. Unfortunately, it wouldn’t be the only private loan Newsom took on at the time — there were a total of five, dating back to 1997, in the amount of nearly $11 million, which got him into hot water with the Ethics Commission later when he ran for mayor. Ironically, the house was right next door to Billy Getty’s. 

Mayor Gavin Newsom and his wife Kimberly Guilfoyle are photographed by camera crews as they arrive. The mayor is in the national spotlight since allowing same-sex marriage, March 5, 2004.

Mayor Gavin Newsom and his wife Kimberly Guilfoyle are photographed by camera crews as they arrive. The mayor is in the national spotlight since allowing same-sex marriage, March 5, 2004.

Deanne Fitzmaurice/San Francisco Chronicle via Getty

The engagement was a whirlwind six months and change that included an engagement party thrown by his sister’s best friend Lori Puccinelli (now Stern) at Presidio Bowl. By the time of the couple’s lavish December 2001 wedding, SF and the U.S. were reeling from a financial crisis made worse by the Sept. 11 attacks just a few months earlier. The average rent for a one-bedroom in San Francisco was about $1,500 ($2,900 in today’s dollars), driven by the dot-com boom in spring 2000. 

But a 500-person Getty-hosted nuptial extravaganza was apparently not out of the question.

The couple had first conceived a small, private ceremony in Mexico, but moved the event to San Francisco to open the door for more family and friends to attend. Everyone who was anyone among the SF elite was there: Angela Alioto, Clint Reilly, Mark Leno, Danielle Steel, Trevor Traina, Summer Tompkins Walker (of Esprit and North Face Tompkins), Stanlee Gatti (who did the flowers) and both mayors Brown (Willie and Jerry, the former governor, who at the time was mayor of Oakland). 

Columnist Morse called the “two hottest public servants in San Francisco” tying the knot a “royal wedding.” 

“Julia Roberts only wishes she was played by Kimberly in a wedding flick,” he added.

FILE : Gavin Newsom and his wife Kimberly Guilfoyle Newsom are photographed together in 2003. 

FILE : Gavin Newsom and his wife Kimberly Guilfoyle Newsom are photographed together in 2003. 

Justin Sullivan/Getty Images

The perfume of a plethora of gardenias filled the towering, ornate St. Ignatius Church on Fulton Street for the ceremony. The bride wore Vera Wang. Guests bawled as Tony walked her down the aisle to Pachelbel’s Canon in D. Actor Ed Asner and his wife Cindy, Newsom’s aunt, were conscripted to read a sensual Bible passage that mentioned breasts; they flew in from LA via Rome, where Ed was playing the pope in a movie, and had to rehearse the torrid stanzas on the plane.

A bash followed at the Getty mansion, where they covered the pool with a floor to create an outdoor jazz grotto and erected a tent of aqua-colored velvet. The Gettys’ chef put six days into the preparations, serving guests lobster, beef and duck alongside sushi, dim sum and Cowgirl Creamery cheeses. The wedding cake was chocolate, had nine tiers, and apparently slumped slightly. 

Two years later, Newsom would win a December runoff election and become San Francisco’s mayor. Then Guilfoyle made a bombshell announcement: She was moving to New York in January 2004 to pursue a TV career doing legal commentary, and the marriage would be bi-coastal. (The couple sold the house in 2004 for a modest gain, at $3.62 million.)

FILE: San Francisco Mayor Gavin Newsom listens to remarks during a news conference at City Hall in San Francisco, Feb. 23, 2004. 

FILE: San Francisco Mayor Gavin Newsom listens to remarks during a news conference at City Hall in San Francisco, Feb. 23, 2004. 

Justin Sullivan/Getty Images

February 2004 marked the start of Newsom’s “winter of love,” when the city granted 4,000 marriage licenses to same-sex couples who previously could not legally wed. By October of that year, Guilfoyle was in the news again, in the New York Post and the San Francisco Chronicle, for off-the-cuff comments she made after accepting an award for her husband at a New York Pride event, where she reportedly described him as “hung” and implied he would be with men only if they were “better than me” and made a gesture some interpreted as sexual. She shrugged off the situation, telling Matier and Ross, “I was falsely accused.”

Three months later, she and Newsom would announce the end of their marriage. Newsom notes in his book that his sister saw “signs of trouble ahead,” as far back as their courtship. His mother, he wrote, felt the same, but kept it from him during the engagement and wedding.

The couple’s divorce records are sealed, and it’s unknown what was the first or last straw in the unraveling: The career change, the last three irreverent seconds of a speech, or something else. At the time of the finalized divorce in 2006, gossip rags rumored that Newsom had been going after actor Sofia Milos, who was in the show “CSI: Miami.” (His notorious affair with married aide Ruby Rippey, which resurfaced earlier this year, didn’t happen until 2005.) Like most marriages that go awry, it was probably a lot of things. Whatever the cause, San Francisco’s brief days of Camelot were finished.

Photo of Kendra Smith
Deputy Managing Editor

Kendra Smith was born and raised in the Bay Area and has lived in San Francisco for nearly 20 years (in two stints). She has a degree in journalism from the University of Oregon and previously worked for Sunset Publishing, Weldon Owen Publishing, Future US and Healthline, among others. Her favorite day in the city would have to include dim sum and an urban hike. As a deputy managing editor, she supports SFGATE’s food, culture, travel and local editorial teams. Send her a tip by email.

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