Politics usually has this weird way of turning people into statues—frozen, polished, and totally fake. But every so often, the polish chips. If you’re asking did Gavin Newsom have an affair, you’re digging into a story that actually fundamentally changed how he handles his public life. It wasn't some tabloid rumor or a "he-said-she-said" whisper campaign. It was a full-blown, front-page-of-the-Chronicle explosion that happened while he was the Mayor of San Francisco.
Honestly, it's a mess.
We aren't talking about a random stranger. We are talking about a betrayal that hit his inner circle. In late 2005, while Newsom was in the middle of a divorce from Kimberly Guilfoyle—yes, that Kimberly Guilfoyle—he had an affair with Ruby Rippey-Tourk.
The Ruby Rippey-Tourk Scandal Explained
Why does this specific name keep coming up? Because Ruby wasn't just some staffer. She was Newsom's appointments secretary. Even more complicated? She was the wife of Alex Tourk, who happened to be Newsom’s deputy chief of staff and his close friend.
It’s the kind of thing that makes people in City Hall still wince.
The truth came out in early 2007. Ruby was in a rehabilitation program for substance abuse and, as part of her recovery process, she confessed the affair to her husband. Imagine being Alex Tourk. You’re working your tail off to get your buddy re-elected as mayor, and then you find out this. He confronted Newsom and resigned immediately on January 31, 2007.
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The fallout was instant.
Newsom didn't try to hide it. He didn't issue some vague "mistakes were made" statement. He held a press conference and basically said: "Everything you’ve heard and read is true." He admitted he was deeply sorry. He admitted to a "personal lapse of judgment."
The Fallout and the "Catastrophic Illness" Pay
While the sex part of the scandal got the headlines, there was a secondary layer that nearly cooked his political career. After Ruby Rippey-Tourk left her job at City Hall, she received about $10,154 in "catastrophic illness" pay.
Usually, that money is reserved for people with terminal illnesses like cancer or AIDS.
The San Francisco City Attorney, Dennis Herrera, had to launch an investigation to see if Newsom had used city funds as "hush money." In the end, the report found that while the payment was "unusual" and showed a "pattern of favoritism," it wasn't technically illegal. Other employees had donated their own sick time to her. Still, the optics were terrible.
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Did Gavin Newsom Have An Affair With Anyone Else?
Once the Ruby story broke, the floodgates opened. People started looking at his entire dating history with a magnifying glass.
Before he married his current wife, Jennifer Siebel Newsom, there was Brittanie Mountz. In 2006, Newsom was 38 and the mayor. He was spotted out with Mountz, who was 19 at the time. It wasn't an affair in the "cheating" sense—he was single—but it raised a lot of eyebrows.
Then there was Sofia Milos, the CSI: Miami actress. They dated for a bit. It seemed like every week there was a new headline about who the "Bachelor Mayor" was taking to dinner.
Jennifer Siebel actually defended him during the 2007 scandal. She wasn't his wife yet, but she was his girlfriend. She even went on the SFist blog (under her own name!) to argue that Ruby was the one who instigated the "nothing incidents." She later had to apologize for those comments because, frankly, they were pretty harsh.
How He Survived Politically
Most people thought he was done. You don't usually survive sleeping with your best friend's wife and keeping your job. But Newsom did something smart: he went to rehab.
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He announced he was seeking treatment for alcohol abuse.
Fast forward to 2018, and he told the Sacramento Bee that he never actually did a 12-step program. He said, "There's no rehab. I just stopped." He claimed he just needed a "reset." Whether you believe that or not, it worked. He pivoted back to policy, leaned into the same-sex marriage issue, and eventually climbed the ladder to the Governor’s mansion.
Key Facts About the Scandal
- The Partner: Ruby Rippey-Tourk (Appointments Secretary).
- The Timeline: The affair happened in 2005; it went public in 2007.
- The Betrayal: Alex Tourk, the husband, was Newsom's campaign manager and close friend.
- The Resolution: Newsom apologized publicly, Alex Tourk received a settlement for his resignation, and Newsom eventually sought "treatment."
What Most People Get Wrong
A lot of people think this happened while he was Governor. It didn't. This is ancient history in political terms, but it’s the reason he is so guarded now. It’s also why his opponents bring it up every time he runs for something higher. They use it as a "character" argument.
The reality? The voters of San Francisco didn't care that much. He was re-elected easily. People seemed more bothered by the betrayal of a friend than the actual act of adultery.
If you're looking for lessons here, it’s basically that transparency—even when it's forced—is a powerful tool. Newsom didn't let the rumor mill grind him down. He stepped into the light, took the hit, and kept moving.
Actionable Insights for Researching Political History
- Check Local Archives: National news often misses the "hush money" details like the catastrophic illness pay investigation found in the San Francisco Chronicle.
- Look for Primary Statements: Don't rely on snippets. Newsom’s 2007 apology is a masterclass in crisis management.
- Cross-Reference Timelines: Note that he was legally separated/divorcing Kimberly Guilfoyle during the 2005 affair, which changed the "cheating on his wife" narrative to "sleeping with a friend's wife."
- Follow the Money: In political scandals, the "who slept with whom" is rarely what causes legal trouble; it’s always the payouts or city-funded benefits that follow.