If you scrolling through social media today, you’d think Kimberly Guilfoyle and Gavin Newsom lived in two different universes. She’s the firebrand U.S. Ambassador to Greece, appointed by Donald Trump. He’s the slick, progressive Governor of California and a perennial favorite for a future White House run. They are the north and south poles of American politics.
But back in 2001? They were the "New Kennedys."
Seriously. Harper’s Bazaar literally posed them on a rug in a Getty mansion and gave them that title. It’s wild to look at those photos now. They look like a couple plucked straight from a 90s legal drama—young, wildly ambitious, and deeply embedded in the San Francisco elite.
Honestly, the story of how they went from being the liberal power couple of the West Coast to leading opposite sides of a national culture war is more fascinating than any scripted political thriller. It wasn't just a breakup; it was a total ideological pivot that changed the map of American media and politics.
The San Francisco Power Years
They met in 1994. Kimberly was a rising star in the DA’s office. Gavin was a young businessman with the right last name and even better hair.
When they got hitched at St. Ignatius Church in 2001, it wasn't just a wedding. It was a coronation. The San Francisco Chronicle called it the "social event of the year." At the time, they were the ultimate Democratic dream team.
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- 2003: Gavin runs for Mayor of San Francisco.
- The Support: Kimberly quits her job as a prosecutor to stump for him full-time.
- The Win: He becomes the youngest mayor in a century.
People forget that Kimberly wasn't always the MAGA icon we see today. Back then, she was standing 100% behind Gavin when he made national headlines for issuing marriage licenses to same-sex couples in 2004. She was his fiercest defender on Charlie Rose, arguing that he was on the right side of history.
Why Did Kimberly Guilfoyle and Gavin Newsom Actually Split?
Basically, it came down to geography and ambition.
In early 2004, Kimberly got an offer she couldn't refuse: a TV gig in New York. She headed east to host Both Sides on Court TV. Gavin stayed in City Hall. You’ve seen this movie before. Bicoastal marriages are brutal.
They filed for divorce in January 2005. They cited the "strain of a bicoastal marriage," which sounds like the standard PR line, but in their case, it was actually true. You can’t be the First Lady of San Francisco from a studio in Manhattan.
There was some scandal later on, of course. In 2007, it came out that Gavin had an affair with Ruby Rippey-Tourk—the wife of his then-campaign manager—while he and Kimberly were in the middle of their divorce proceedings. It was messy. It was very San Francisco. But by the time that news broke, Kimberly was already building a brand-new life at Fox News.
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The Great Ideological Shift
This is where things get weird.
After the split, Kimberly didn't just change her zip code; she changed her entire political identity. Or maybe she just finally embraced who she always was? She told the Washington Post years later that she’d actually been a registered Republican since college.
While Gavin was climbing the ladder in Sacramento, Kimberly was becoming a staple on The Five. She transitioned from a San Francisco prosecutor to a conservative pundit who eventually became one of the most recognizable voices in the Trump orbit.
Where Are They Now in 2026?
It’s 2026, and the distance between them has never been greater.
Kimberly Guilfoyle recently started her tenure as the U.S. Ambassador to Greece. Following the end of her high-profile engagement to Donald Trump Jr. late in 2024, she’s leaned fully into her diplomatic role. Just a few months ago, she even joked about her 2004 honeymoon in Greece with Gavin during a meeting with the Greek President.
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"Fabulous honeymoon," she said. "The marriage? We'll work on getting a new husband."
Gavin Newsom, meanwhile, is still doing Gavin Newsom things. He’s navigating the final stages of his governorship and eyeing the 2028 landscape. Interestingly, reports from early 2025 suggested that he and Kimberly actually still talk. Some insiders claim she even helped him navigate some right-wing media appearances for his podcast.
They are a "transactional" success story. They don't have to like each other's politics to acknowledge that they both know how the game is played.
What We Can Learn From the Newsom-Guilfoyle Saga
The biggest takeaway here isn't the gossip. It’s how much the American political landscape has fractured.
- Politics is Personal: Their trajectory shows that political alignment is often as much about your social circle and career path as it is about core beliefs.
- The Bicoastal Trap: No matter how much power you have, you can't be in two places at once. Their marriage died because they both refused to play second fiddle to the other’s career.
- The Long Game: They’ve both managed to stay relevant for 25 years. That doesn't happen by accident. It requires a level of adaptability that most people simply don't have.
If you’re tracking the 2028 election cycle or just watching the current administration’s diplomatic appointments, keep an eye on how these two interact. They might be on opposite sides of the aisle, but their histories are permanently tangled.
Next Steps for Deep Diving into Their History:
- Check out the archived Harper’s Bazaar September 2004 issue for the "New Kennedys" photoshoot.
- Look up the 2004 Charlie Rose interview to see a version of Kimberly Guilfoyle that feels like a different person.
- Follow the current State Department briefings to see how Guilfoyle is handling the Greece post.