As SFist celebrates its 20th anniversary, we remember the ridiculous San Francisco City Hall scandals that made us a go-to destination for salacious political gossip and mockery in our early days.

We are celebrating our 20th anniversary at SFist this week, and in looking back, we acknowledge that some of our critics have called our tone perhaps a little unprofessional in the early years. But those early years were a time when San Francisco had a famously philandering mayor, a supervisor who used the word “fuck” at every board meeting, and another supervisor who secretly did not even live in San Francisco but still shook down local boba shops for $80,000 bribes. So really, our unprofessional tone was perfect for covering such an unprofessional era at SF City Hall.

SFist published its very first post just six months after Gavin Newsom was sworn in as Mayor of San Francisco in 2004. At the time, Newsom was married to a certain Kimberly Guilfoyle, who is (sigh) that Kimberly Guilfoyle. But back then, Guilfoyle was a highly respected SF assistant district attorney known for winning a conviction in a high-profile dog-mauling case.

The two had a dignified break-up in 2005. But the path going forward for both was anything but dignified.

The then-38-year-old Newsom quickly developed a reputation for dating much younger women. The most infamous of these paramours was a 20-year-old Brittanie Mountz (seen above), who appeared to have used a fake ID to get into events at which she drank with Newsom.

But there were others! So many others that SFist ran updated power rankings on the always fluid pecking order of Newsom’s various side-pieces: CSI: Miami bit-part player Sofia Milos, reality TV personality Erin Brodie, and the eventual winner of the Gavin girlfriend sweepstakes, Jennifer Siebel (now Jennifer Siebel Newsom).

This all hit fever-pitch in January 2007, in a bombshell incident that spurred the greatest SFist headline of all time. News broke that Newsom had an extramarital affair with his own campaign manager’s wife Ruby Rippey-Tourk. Her husband Alex Tourk had been Newsom’s deputy chief of staff before being named reelection campaign manager in September 2006. And for months after that, it became appointment reading to catch each day’s developments as side-splittingly summarized by SFist writers Eve Batey and Rita Hao in their As the Gav Turns series.  

Newsom blamed the behavior on alcohol and entered treatment. But many SFist commenters alleged that it was fake rehab and Newsom never really stopped drinking (which was confirmed by the Sacramento Bee years later).

It was during this phase that Newsom dealt with the fallout of a very hilarious photo of him staring at a woman’s breasts that became public. The image was from the political hit-job mailer against Newsom from the 2007 mayoral election seen below, and its origin, and degree of authenticity, are still unknown.

Just one week before the Rippey-Tourk affair scandal broke, Newsom’s campaign was reeling from a separate scandal, unearthed here at SFist.

SFist discovered that Newsom’s press secretary Peter Ragone had been posting sock puppet comments in the SFist comments section under someone else’s name, a scandal came to be known as SFistGate.

So at this point, SFist wasn’t just covering the scandal, we were part of the unfolding scandal.

Despite all of this mortifying behavior, Newsom still easily won reelection that year with a landslide 74% of the vote. This was likely because his opponents were a cast of gag-candidate characters like Chicken John, and Power Exchange bondage club owner Michael Powers.

There were other ongoing scandalous matters which obsessed SFist and our readers during this mid-to late-2000s era.

We chronicled the exploits of foul-mouthed then-supervisor Chris Daly in a series called Everybody Hates Chris. A reckless driving incident from then-state Senator Carole Migden inspired the How’s Carole Migden’s Driving? series. And surely the most bizarre ongoing SFist series of that day was Oh No, Ed Jew!, the saga of the then-District 4 SF supervisor who secretly did not even live in San Francisco, but more significantly, solicited an $80,000 bribe from a Quickly boba shop. He was sentenced to more than five years in prison.  

On a personal note from this SFist correspondent, one day I was called to serve on a jury duty pool with Ed Jew, and at the height of the Ed Jew scandal at that. I wrote a lengthy SFist comment about the experience, and SFist co-founder Rita Hao emailed me later that day and offered me an (unpaid) position as an SFist contributor. And I’m proud to once again be an SFist contributor today.

So in some ways, some of these scandals truly did, to some degree, make SFist what it is today.

SFist Turns 20: Here’s to 20 Years of Gossip, Snark, and Covering This Beautiful City [SFist]

Image: From a political hit piece, origin/authenticity unknown