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

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  The RISE and Fall of S F's twenty first century power couple,
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  Gavin Newsom and Kimberly Guilfoyle Written by Kendra Smith This
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  article is being read by an automated voice generated by Everlett. More
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  than Tou decades ago in two thousand four, then San Francisco Mayor
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  Gavin Newsom and his wife, Kimberly Gilvehole, were given the label the
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  New Kennedys in an infamous Harper's Bazaar Profile, for which the posed
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  lying seductively on a maroon and gold rug. It may have sounded
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  like hyperbole, but it was clear even the that the Tou could
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  take their San Francisco routes to greater heights. Gordon Getty, the prominent
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  American philanthropist and oil heir, also a longtime family friend of Newsom,
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  had told W Magazine the year before that the couple was destined
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  for greatness, in both SF and DC just apparently not together. By
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  two thousand six, SF's Camelot couple had unceremoniously divorced and begun to
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  their ascent to new heights, albeit ones that were in political opposition.
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  Gilfoyle became a MAGA superstar who was engaged to Donald Trump Jr.
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  For three years and served as ambassador to Greece until she resigned
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  this week after accusations of misconduct which she denies. Newsom became California's
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  lieutenant governor in twenty eleven, was elected governor in twenty nineteen, and
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  has a much speculated about twenty twenty eight presidential bid on the
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  horizon. But before their comparison to America's iconic first couple, Jackie and
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  Jack, they were just Kimberly and Gavin, a model turned attorney, and
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  a wine entrepreneur turned county supervisor who were falling in love. In
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  his memoir, Young Man in a Hurry, Newsom’s references bringing Guilfoyle on
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  a group trip with Billy Getty as his date in the late
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  nineteen nineties. Getty had dated Gilfoyle, but he had a new girlfriend
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  by the and she was invited to Maui too. The couple were
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  first introduced to each other at a political fundraiser by Art Groza,
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  a part owner of Newsom's plumpjack business and known San Francisco Connector,
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  according to the San Francisco Chronicle. One of the first times the
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  pair appeared together in print as a couple seems to be with
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  the senior Geddes, Gordon and his wife Anne, at a two thousand
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  San Francisco Symphony Gala, but with no Billy in attendance, a potential
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  slight, given that the two young men had been best friends and
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  business partners. By may two thousand one, they had fallen out, according
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  to San Francisco Chronicle columnist Phil Mateer and Andy Ross. Gilfoyle had
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  moved back to the city from Los Angeles the year before to
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  reclaim a role in District Attorney Terrence Hallanan's office. Born and raised
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  in the Mission and the Daly City, she attended Mercy High School,
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  and then UC Davis, where she worked in retail at a clothes
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  time store, making six dollars an hour. A spontaneous offer to model
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  brought her hourly up to three hundred dollars, and helped pay her
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  way through University of San Francisco Law School. She built up an
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  impressive portfolio of everything from lingerie work to ads for soap, but
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  it was always just a side hustle to her legal career. Gilfoyle's
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  assignment to the two thousand one Diane Whipple dog mauling case, a
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  trial that captivated the city and the nation, eventually thrust her into
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  the spotlight and appearances on Dateline, The Today Show, Geraldo Rivera, and
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  Good Morning America. I think about Diane Whipple every day, she told
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  the San Francisco Chronicle in two thousand one of the case, knowing
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  that the Lacrosse teacher's death was preventable with better laws. A June
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  profile of her from the outlet in the same year calls her
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  a damn serious lawyer. Meanwhile, two years before he would even run,
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  Newsom was already considered the front runner to replace Mayor Willie Brown.
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  The engagement rumors were swirling. Newsom proposed to Gilfoyle in Cabo San
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  Lucas over Memorial Day weekend, two thousand one. He asked her dad,
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  Tony, for her hand in marriage in advance, earning access to the
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  ring Tony had presented Kimberly's mother Mercedes with thirty years prior. Gilfoyle
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  told columnist Rob Morse that The couple were best friends who both
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  hope they can do great things for San Francisco. The couple paired
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  this class act with the purchase of a five bedroom, four and
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  a half bath William Worcester home at twenty eight seventy Tech Pacific
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  Avenue in Pacific Heights for three million dollars, using a one million
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  dollar loan from The Gedys. Unfortunately, it wouldn't be the only private
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  loan Newsome took on at the time. There were a total of
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  five, dating back to nineteen ninety seven, in the amount of nearly
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  eleven million dollars, which got him into hot water with the Ethics
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  Commission later, when he ran for mayor. Ironically, the house was right
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  next door to Billy Geddy's. The engagement was a whirlwind six months
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  in change that included an engagement party thrown by his sister's best
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  friend Lori Puccinelli, now Stern, at Presidio Bowl. By the time of
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  the couple's lavish December 2001 wedding, SF and the US were reeling
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  from a financial crisis made worse by the September eleventh attacks just
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  a few months earlier. The average rent for a one bedroom in
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  San Francisco was about one thousand five hundred dollars, two thousand nine
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  hundred dollars in today's dollars, driven by The
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  dot com boom in spring two thousand. But a five hundred person
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  getty host dude, nuptial extravaganza, was apparently not out of the question.
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  The couple had first conceived a small private ceremony in Mexico, but
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  moved the event to San Francisco to open the door for more
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  family and friends to attend. Everyone who was any one among the
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  SF elite was where Angela Aliotto, Clint Rayleigh, Mark Leno, Danielle Steele,
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  Trevor Traina, Summer Tompkins Walker, of Espree and North Face Tompkins, Stanley
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  Gaddy, who did the flowers, and both mayors Brown, Willie and Jerry,
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  the former Governor, who at the time was Mayor of Oakland. Columnist
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  Morse called the two hottest public servants in San Francisco, tying the
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  knot a royal wedding. Julia Roberts only wishes she was played by
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  Kimberley in a wedding flick, he added. The perfume of a plethora
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  of gardenias filled the towering, ornate Saint Ignatius Church on Fulton Street
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  for Then ceremony. The bride wore Vera Wong. Guest bald as Tony
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  walked her down the aisle to Patchel Bell's canon in D actor
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  Ed Asner and his wife Cindy, Newsom's aunt, were conscripted to read
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  a sensual Bible passage that mentioned breasts. The flew in from LA
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  via Rome, where Ed was playing the Pope in a movie, and
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  had to rehearse the torid stanzas on the plane. A bash followed
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  at the Getty Mansion, where the covered the pool with a floor
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  to create an outdoor jazz grotto, and erected a tent of aqua
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  colored velvet. The Geddes chef put six days into the preparations, serving
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  guests lobster, beef and duck alongside sushi, dim sum, and cowgirl creamery
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  cheeses. The wedding cake was chocolate, had nine tiers, and apparently slumped
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  slightly. Two years later, Newsom would win a December runoff election and
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  become San Francisco's mayor. Then Gilfoyle made a bombshell announcement. She was
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  moving to New York in january two thousand four to pursue a
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  T V career doing legal commentary, and the marriage would be bi
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  coastal. The couple sold the house in two thousand four for a
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  modest gain, at three point six two million dollars. February two thousand
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  four marked the start of Newsom's winter of love, when the city
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  granted four thousand marriage licenses to same sex couples who previously could
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  not legally wed. By October of that year, Gilfoyle was in the
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  news again, in the New York Post and the San Francisco Chronicle,
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  for off the cuff comments she made after accepting an award for
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  her husband at a New York Pride event, where she reportedly described
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  him as hung and implied he would be with men only if
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  they were better than me, and made a gesture some interpreted as
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  sexual. She shrugged off the situation, telling Matthieu and Ross I was
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  falsely accused. Three months later she and Newsom would announce the end
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  of their marriage. Newsom notes in his book that his sister saw
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  signs of trouble ahead, as far back as their courtship. His mother,
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  he wrote, felt the same, but kept it from him during the
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  engagement and wedding. The couple's divorce records are sealed, and it's unknown
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  what was the first or last straw in the unraveling, the career
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  change, the last three irreverent seconds of a speech, or something else.
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  At the time of the finalized divorce in 2006, gossip rags rumored
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  that Newsom had been going after actor Sophia Milos, who was in
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  the show, token name, Miami. His notorious affair with married aide Ruby
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  Rippy, which resurfaced earlier this year, didn't happen until two thousand five.
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  Like most marriages that go awry, it was probably a lot of
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  things. Whatever the cause, San Francisco's brief days of Camelot were finished.
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  Editors Note. This article was upated at ten AM, october twentieth, to
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  correct the address of the Pacific Heights home Gavin Newsom bought in
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  two thousand one.