Former Supervisor Vallie Brown, left, and current Supervisor Dean Preston will face off again in November. Preston narrowly defeated Brown in 2019. (Examiner file photos)

Former Supervisor Vallie Brown, left, and current Supervisor Dean Preston will face off again in November. Preston narrowly defeated Brown in 2019. (Examiner file photos)

District 5 race presents a challenge for moderates

Despite support for London Breed, neighborhood continues to lean progressive by most measures

By Eric Kingsbury

In what was the worst kept secret in San Francisco politics, former District 5 Supervisor Vallie Brown announced on May 29 she was seeking a rematch against Supervisor Dean Preston this November.

And it’s understandable why she’d want a second bite at the apple: After being appointed by Mayor London Breed to fill her former seat, Brown came a hair’s breadth away from winning re-election in the reliably progressive district. She lost by only 185 votes even after the race was rocked by a late-breaking scandal over her eviction of low-income, African-American tenants from a building she co-owned in 1994.

The fact that Brown — the candidate with the backing of The City’s moderate faction — came so close to beating a longtime progressive activist last time around is actually something of a shock. After all, this is the district that sent back-to-back members of the Green Party to the Board of Supervisors in the 2000s in Matt Gonzalez and Ross Mirkarimi and where, in 2011, John Avalos beat Ed Lee by 9% amongst first choice votes. Even in Lee’s re-election campaign in 2015, the 1-2-3 Anybody but Ed Lee slate of Francisco Hererra, Amy Farrah Weiss and the Examiner’s own Broke Ass Stuart outpolled him there by seven votes.

But things there do seem to be changing. The district elected the most moderate candidate running in the 2012 supervisorial race in Breed against a divided field of progressives, something that proved more than just a fluke when she managed to win re-election in a head-to-head matchup against Preston in 2016. Breed again had a strong showing in the 2018 mayoral election against two candidates running to her left, besting her closest rival in the district by 11% in No. 1 votes. Anecdotally, all of this would suggest that District 5 might be moving more towards the center, but is that really the case?

The data suggest the answer is a resounding no. In the 2019 district attorney’s race, Chesa Boudin handily beat Suzy Loftus by 14.6% in first choice votes in District 5, the district with the second highest turnout in The City in that election. Even in 2018, the combined first choice vote of Jane Kim and Mark Leno was 13 points higher than that of then-incumbent District 5 Supervisor Breed in the district (after ranked-choice was applied, Leno beat Breed in D5 by a little under 400 votes).

A more empirical approach makes an even stronger case. Using the Progressive Voter Index (PVI) — a one-number “score” of how progressive a San Francisco precinct is based off of how voters there have voted on ballot initiatives — we see that the most progressive parts of District 5 have not changed much at all. Both the Haight-Ashbury and the Western Addition have remained among the top-five most progressive neighborhoods in The City since the turn of the 21st century, and the district as a whole consistently jockeys with District 9 for the title of most progressive in The City.

So why is it that moderate-aligned candidates keep doing well in District 5? Well, in San Francisco, candidates, campaigns and identity voting matters. In 2012, Breed was a candidate with deep, lifelong ties to the district running against a divided progressive field that included an appointed incumbent who had managed to alienate both the moderate mayor who had appointed her and her longtime progressive allies in less than two years in office. She took home more than a quarter of the first choice votes in both the Western Addition and the Haight, and was the top second choice amongst most D5 voters.

By 2016, Breed was well established as an independent-minded moderate president of the Board of Supervisors. Even though she was facing a staunch progressive in Preston, she earned endorsements from a number of progressive organizations and two key progressive electeds — supervisors Aaron Peskin and Jane Kim — decided to stay neutral in the race. Again, the Western Addition and the Haight went to Breed and she was re-elected in a close race.

And it was Brown’s profile, too, that almost allowed her to pull off the same feat, with her longtime ties to the district as an activist and aide, a strongly independent-minded but progressive record, and split endorsements amongst progressives. But it was the eviction story that sunk her chances.

And what about 2020? It’s never smart to try and predict outcomes in San Francisco politics, but it should be noted that no elected incumbent has ever been defeated for supervisor since district elections returned in 2000. Surely anything could happen, but if progressives unite behind the leftmost candidate in D5, that person promises to be hard to beat.

Eric Kingsbury is a longtime San Francisco resident who writes about politics. His work has appeared in the Atlantic, the San Francisco Chronicle, and the New Republic.

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