By Stas Voyager 
California Governor Gavin Newsom has been called a lot of things in the past few years — “Dark Gavin,” “Trump’s West Coast Nemesis,” and even “the Democrats’ secret weapon” should Joe Biden or Kamala Harris falter in 2028. But before he was the slick, gel-haired poster boy for West Coast liberalism and the embodiment of Trumpian resistance, he was simply Gavin — a mayor with ambition, a failing marriage, and a very messy scandal that nearly tanked his career before it even began.
Yes, before Newsom was sparring with Donald Trump over wildfires, COVID, and redistricting maps, he was making headlines for a more personal reason: having an affair with his best friend’s wife.
And not just any best friend. We’re talking about Alex Tourk, his deputy chief of staff — the kind of guy you’d expect to be at your side through thick and thin, the guy who clears your schedule, runs interference with angry donors, and maybe even holds your jacket during a late-night press scrum. That Alex.
The year was 2006. Gavin was Mayor of San Francisco, his then-wife Kimberly Guilfoyle was building her career in New York as a prosecutor-turned-TV personality, and their marriage had become something of a bi-coastal balancing act. Kimberly was glamorous, connected, and already showing signs of the woman who would later reinvent herself as a MAGA firebrand and Donald Trump Jr.’s fiancée. Gavin was ambitious, charming, and not-so-secretly living the kind of nightlife you’d expect from a handsome mayor in one of America’s most progressive cities.
Then came the bombshell: Newsom had been having an affair with Ruby Rippey-Tourk, Alex Tourk’s wife.
The Scandal Breaks
In early 2007, the San Francisco Chronicle broke the story. Ruby Rippey-Tourk, then working as a city program coordinator, had confessed the affair during rehab treatment, where disclosure is often part of recovery. Word traveled fast. And within days, Gavin stood at a press conference, slick hair intact, shoulders squared, and offered the kind of blunt admission politicians rarely make:
“Everything you’ve heard and read is true. And I am deeply sorry about that.”
He didn’t mention Ruby by name, nor Kimberly, nor the countless voters suddenly wondering if the photogenic mayor was just another cliché of political hypocrisy. But the damage was done. Alex Tourk resigned from his position as Newsom’s deputy chief of staff almost immediately. Kimberly Guilfoyle, by then separated from Gavin, had already filed for divorce a year earlier, citing “difficulties due to their careers being on opposite coasts.”
But it wasn’t hard to connect the dots.
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For a moment, it looked like Newsom’s career was over. Affairs in politics are nothing new, but sleeping with your best friend’s wife while holding public office? That’s the stuff of soap operas, not statehouses. The local press had a field day, late-night hosts feasted on the scandal, and the whispers in Democratic donor circles grew louder: Was Gavin too reckless, too entitled, too much of a liability to ever rise beyond San Francisco?
But here’s the thing about American politics: short memories, long ambitions.
Gavin did what many politicians in crisis do: he leaned in, apologized publicly, and tried to reframe himself as flawed but resilient. And perhaps most importantly, the political winds shifted in his favor. By 2010, America was consumed with the Tea Party wave, and the national conversation had moved on. In 2011, Gavin became California’s Lieutenant Governor. By 2018, he was the Governor of the nation’s most populous state.
As for Alex Tourk? He rebuilt his career as a political consultant and has largely avoided the spotlight since. Ruby Rippey-Tourk has kept a lower profile too. Kimberly Guilfoyle, of course, pivoted into full MAGA glam and is now planning her own wedding to Donald Trump Jr. Talk about everyone moving on in very different directions.
From Scandal to “Dark Gavin”
Fast forward to the Trump era, and Gavin Newsom has gone from scandal-tainted mayor to progressive warrior. His spat-filled exchanges with Donald Trump over everything from wildfire aid to COVID restrictions earned him the nickname “Dark Gavin” among online fans who saw him as the perfect foil to the then-president. He didn’t just spar with Trump — he used Trump’s own tactics back at him, offering snappy retorts, photo-ready defiance, and viral moments tailor-made for social media.
For Democrats disillusioned with Joe Biden’s age or Kamala Harris’s approval ratings, Gavin quickly became the “just in case” option. A West Coast liberal with Hollywood looks, Silicon Valley donors, and enough charisma to spar with Trump on the debate stage.
But political enemies haven’t forgotten. The affair scandal resurfaces every few years, often weaponized by Republicans eager to remind voters that “Dark Gavin” once had some very dark behavior of his own.
Why the Scandal Still Matters
So why revisit a nearly 20-year-old scandal now? Because in American politics — and Hollywood-style celebrity politics especially — character narratives matter. Gavin Newsom isn’t just a governor; he’s a brand. And brands are made of stories, both good and bad.
The story of the affair with Ruby Rippey-Tourk is, in a way, foundational to the Newsom myth. It’s the skeleton in his closet, the one he admitted to outright, the one that tested his political survival skills long before he had to navigate pandemics, recall elections, and national press speculation about a White House run.
If Newsom does decide to take on Trump directly in 2028 — or step in as the Democratic nominee should circumstances change — this scandal will almost certainly resurface. The irony, of course, is that his ex-wife Kimberly Guilfoyle will be on the other side of the campaign trail, arm-in-arm with Donald Trump Jr.
In a way, the whole saga feels almost Shakespearean: love, betrayal, ambition, revenge — with the added bonus of cable news and Twitter memes.
The Bottom Line
Gavin Newsom has managed to transform himself from scandal-plagued mayor to one of the Democratic Party’s brightest stars. But the story of his affair with his best friend’s wife lingers as a reminder that in politics, as in Hollywood, the past never truly stays buried.
As Democrats and Republicans alike look toward 2028, “Dark Gavin” will no doubt keep sparring with Trump-world — and whether voters care about his two-decade-old scandal or not could make the difference between Sacramento and the White House.
