In the early 2000s, San Francisco had its own version of Camelot. They were young, incredibly polished, and practically radiated ambition from every pore. On one side, you had Gavin Newsom, the rising star of Democratic politics. On the other was Kimberly Guilfoyle, a fierce prosecutor with a wardrobe that screamed high society. They were the "New Kennedys," at least according to Harper’s Bazaar. But look at them now. One is a liberal governor often tipped for the White House; the other is the United States Ambassador to Greece, appointed by Donald Trump.
It’s a wild arc. Honestly, if you pitched this as a screenplay, an editor would tell you it’s too on the nose. How do two people go from sharing a bed and a political vision to standing on opposite sides of the deepest ideological chasm in American history?
The "New Kennedys" Era
They met in 1994 at a Democratic fundraiser. It makes sense. Back then, Kimberly wasn’t the firebrand speaker we saw at the 2020 RNC. She was a San Francisco native, a law student, and a rising star in the DA’s office. They married in December 2001. It was a Catholic ceremony at St. Ignatius Church, followed by a reception hosted by the Gettys. Yes, those Gettys.
When Newsom was elected Mayor of San Francisco in 2003, Kimberly was right there holding the Bible. She wasn't just a spouse; she was a partner in the "Newsomly" brand. But the cracks formed fast.
Career pressure is a real thing. In 2004, Kimberly moved to New York to host Both Sides on Court TV. Gavin stayed in City Hall. Bicoastal marriages are notoriously brutal, and theirs was no exception. By January 2005, they were done. They issued a joint statement citing the strain of their careers. It seemed amicable. They even went to events together after the split.
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The Pivot Nobody Saw Coming
Most people think Kimberly’s "MAGA" transformation happened overnight when she started dating Donald Trump Jr. in 2018. That’s actually not true.
The shift was gradual. After the divorce was finalized in 2006, she joined Fox News. You spend a decade in that environment, and your worldview is going to change. She wasn't just a legal analyst; she became a co-host of The Five. She was becoming a fixture of conservative media while her ex-husband was becoming the face of progressive California.
Then came the Trump years. She left Fox in 2018—reportedly under some pressure, though she’s always maintained it was her choice—to join the Trump campaign. This is where the narrative gets spicy. She didn't just join the team; she became family. Her engagement to Don Jr. in 2020 cemented her status as a MAGA heavyweight.
Current Status in 2026
Life comes at you fast. By late 2024, the engagement to Don Jr. was off. Rumors swirled about his relationship with a Florida socialite, but Kimberly didn't just fade away. In a move that surprised many, Donald Trump appointed her as the U.S. Ambassador to Greece.
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As of January 2026, she’s settled into her role in Athens. She recently made headlines for joking with the Greek President about her 2004 honeymoon in the country with Gavin. She called it "fabulous" but jokingly added that she was "ready for a new husband."
The Secret Phone Calls
Here is the part that drives political junkies crazy: they still talk.
Reports surfaced in 2025 that Gavin Newsom has actually consulted with Kimberly for help with his own political rebranding. It sounds like a conspiracy theory, but insiders suggest they’ve maintained a "transactional" connection for years. Gavin reportedly wasn't fazed by her political flip. He’s a pragmatist. She knows the "other side" better than almost anyone in his circle.
Think about that. The man leading the charge against Trumpism might be getting back-channel advice from a woman who was just part of the Trump inner circle. It’s either the ultimate "keep your enemies closer" move or proof that, at a certain level of power, party lines are just suggestions.
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Why the Kimberly Guilfoyle Story Matters
We love to put people in boxes. Kimberly is "the ex-wife." She’s "the Fox host." She’s "the Trump loyalist." But her career path shows a level of adaptability that is actually pretty terrifying if you’re her political opponent.
- She understands both playbooks. She knows how San Francisco liberals think because she was one. She knows how the MAGA base thinks because she helped lead them.
- She is a survivor. Most people would have been buried by the scandals and the high-profile breakups. Instead, she’s an Ambassador.
- The Newsom connection is a wildcard. If Gavin Newsom does run for President in the future, his history with Kimberly will be used as a weapon by both the left and the right.
If you’re trying to understand the current state of American politics, stop looking at the polls and start looking at this relationship. It’s a reminder that the people running the country are often much more interconnected than they’d like you to believe.
To stay updated on these high-level political shifts, keep an eye on official diplomatic appointments and the Federal Election Commission (FEC) filings for the 2028 cycle. The "transactional" nature of these relationships often shows up in who is funding whom. You can also follow the official "This Is Gavin Newsom" podcast, where he’s been increasingly bringing on voices that sound a lot more like his ex-wife than his current base.