As weary eyes scroll back and forth between the presidential and mayoral races, another San Francisco election is buoyed by an outstanding amount of cash and attention from some of the nation’s biggest politicians and tech overlords.
To his fans, Supervisor Dean Preston has made himself an outlier in local politics as a staunch progressive, receiving endorsements from national figures like Rep. Nancy Pelosi and fellow democratic socialist Sen. Bernie Sanders. To his critics, Preston is the personification of everything wrong with San Francisco, a NIMBY who slings an array of policies soft on crime, addiction and homelessness that polls have shown city voters are moving away from.
His main challenger, Bilal Mahmood, is a tech entrepreneur and relative newcomer who first made waves in his unsuccessful run for state Assembly in 2022, where he clinched a third-place finish despite his lack of experience as a candidate.
Another challenger, Autumn Looijen, who led the recalls of progressive school board members in 2022, has emerged as a more moderate, if not conservative voice to the race compared to Mahmood and Preston. For example, she received the endorsement of the San Francisco Republican Party earlier this week.
While Preston is not the only progressive incumbent facing a significant challenger in San Francisco — District 1 Supervisor Connie Chan is being challenged by moderate Marjan Philour — the District 5 race is raising eyebrows for its enormous cash flow. According to campaign finance filings released in July, Preston raised $426,000 so far, 38% of which came from city-matched funds, while Mahmood garnered $437,000, 58% of which came from city-matched funds. The District 5 election is the only supervisorial race where two candidates broke $400,000.
Mahmood said the upwelling of national and local attention to this election comes as no surprise. He said Preston has had to resort to currying the favor of big-time politicians to make up for a lack of local support, citing his own local endorsements like the Democratic County Central Committee, the Alice B. Toklas LGBTQ Democratic Club and the Chinese American Democratic Club — the latter of which endorsed him behind Looijen.
“I think Dean is out of touch when it comes to things like housing,” Mahmood said. “When I talk to voters, they want housing at all incomes, and voters know that, and he is trying to run away from his housing record.”
That’s not all. A political action committee affiliated with the moderate group Grow SF, Dump Dean, has gathered $297,000 to unseat the incumbent. In Chan’s district, the group also raised $62,000 under a PAC called Clear Out Connie.
Founded in 2020 by former tech workers Steven Buss Bacio and Sachin Agarwal, Grow SF is one in a bumper crop of new moderate political groups working to boot progressives and reshape San Francisco government.
The group previously backed the successful recalls of former District Attorney Chesa Boudin and three school board members in 2022. But it’s unclear whether voters in District 5 — encompassing the Haight-Ashbury, Fillmore and Tenderloin neighborhoods and one of the most progressive areas — are willing to oust a die-hard lefty.
Buss Bacio criticized Preston and Chan for stonewalling housing projects and supporting defunding the police.
“All of that is out of step with San Franciscans,” he said. “They both don’t want to do their job.”
Buss Bacio declined to reveal how nearly $300,000 would be spent over the next several months but said San Franciscans can expect to see the funding results of Dump Dean in “the next couple weeks.”
Ousting an elected incumbent supervisor has only been done once before since district elections were reintroduced in 2000. In 2022, District 4 Supervisor Joel Engardio toppled incumbent progressive Gordon Mar by a narrow margin of 460 votes. Grow SF shoveled $50,000 into the campaign, which included billboards, mailed flyers, newspaper ads and more, primarily in Mandarin and Cantonese due to the preponderance of Chinese residents on San Francisco’s west side.
Preston is no stranger to detractors with cash. Tech tycoons, including billionaire and X owner Elon Musk and Y Combinator president Garry Tan, have skewered Preston on social media. But removing a progressive incumbent in District 5 may be a tougher sell.
The district’s progressive leanings were on display in the March primary election, when those voters opposed increasing police powers, standing in stark contrast to a majority of the city, according to data gathered by the San Francisco Chronicle.
Katie Marocco has lived around the Panhandle for the past two and a half years. She said Preston gets a bad rap in his management of places like the Tenderloin. But she also said she’s felt less safe in her own neighborhood lately and wants to learn more about Mahmood’s policies.
“I would definitely like to see that improve,” she said. “I love San Francisco. I think it’s a very community-based city. I personally want to feel safe in my community.”
When it comes to stopping the Tenderloin’s fentanyl crisis, which claimed nearly a quarter of the city’s 810 overdoses last year, the two candidates employ methods that are built on arresting drug dealers, but give deference to first-time, nonviolent offenders.
Mahmood has endorsed a three-step drug market intervention plan, whereas Preston’s has championed what’s called a “four pillars” strategy. Originating from Zurich, the strategy includes arresting and prosecuting drug dealers but also providing safe usage sites.
Still, Preston has been critical of the city’s push to bolster police staffing and enforcement, opposing arresting drug users.
“I think that is completely counterproductive,” Preston told The Standard. “We should be moving them off the streets and into overdose prevention sites. I have been very critical of an approach that is trying to lead with law enforcement to address an addiction crisis.”
Preston also said that when it comes to his hotly debated housing record, his slate is clean, referencing a lawsuit by housing advocate Corey Smith, who claimed the incumbent’s voter pamphlet was embellished to reflect more homes in his housing voting history. Last month, a Superior Court judge shot the case down.
“[Mahmood] just moved to the district last year and maybe is unaware of our work on these issues,” Preston said. “We’ve got a very clear record on housing, for example.”
Mahmood said that while growing up in the Peninsula, the Tenderloin is where his family visited each weekend, partly because it had some of the best Pakistani food. The neighborhood has always been “a home away from home,” Mahmood said.
Mahmood also faced attack ads while running for the Democratic County Central Committee seat for embellishing his credentials as a neuroscientist and being funded by the same tech money attacking Preston. In March, a group of neuroscientists sent a letter to Mahmood questioning the legitimacy of his claims as a neuroscientist, which were subsequently removed from his campaign’s website.
Jason McDaniel, a political science professor at San Francisco State University, said that although voters citywide have gravitated away from progressive policies in the past few elections, it may not unfold that way in Preston’s district. Voters have taken out their frustrations on incumbents in recent elections, he said, but that doesn’t mean they’ll embrace Mahmood.
“It’s worth watching to see if that’s where the city is going with these last few elections, sort of moving away from some of the progressive positions,” McDaniel said. “Does that continue?”
Voter turnout in District 5 is among the highest in the city, and registration has only risen since 2022, according to the latest data by the city. In 2020, Preston won 21,484 votes, with his biggest competitor being Vallie Brown with 16,777 votes. In a poll conducted by Change Research that surveyed 429 District 5 voters, which was paid for Mahmood’s campaign, data showed Preston ahead throughout the first few rounds of voting but the candidates neck and neck in the final round.
McDaniel added, “There’s been a lot of discontent with incumbents. You know, voters rarely turn to newcomers.”