S.F. mayoral candidates wade into District 5 race vs. Dean Preston

San Francisco’s mayoral candidates are beginning to show a particular interest in District 5, as Mayor London Breed and former Supervisor Mark Farrell pick their favorite among those running for supervisor against incumbent Dean Preston. 

Political newcomer Scotty Jacobs today announced he received Farrell’s endorsement, and earlier this month, Breed threw her support behind Bilal Mahmood, another relatively new arrival. Preston, meanwhile, has long had the support of fellow Supervisor Aaron Peskin, who appeared at Preston’s re-election campaign event before he announced his candidacy for mayor.

Other districts haven’t yet seen the same interest from the mayoral hopefuls: Farrell has not made endorsements in any of the five other ongoing supervisor races, and Daniel Lurie has made no endorsements. Breed and Peskin, meanwhile, have made sporadic endorsements around the city.

District 5 is one of the most-watched supervisor races this election, in which candidates vying to represent a diverse swath of the city from Haight-Ashbury to the Tenderloin have raised nearly $1 million in contributions and public financing, and outside groups have raised even more to remove Preston, the city’s most progressive elected politician, from office. 

Peskin’s support for Preston is a logical step as the two are longtime colleagues and politically aligned; progressive District 5 voters are expected to support both Preston for supervisor and Peskin for mayor.

Political analysts and observers, however, said they doubted that the endorsements of mayoral candidates would have much impact for the District 5 supervisor hopefuls. Instead, they said, the benefits could lie with the mayoral candidates.

Farrell, for example, is little known in the progressive-leaning district. And his conservative-leaning policies as a former supervisor, like Prop. Q, which he co-sponsored in 2016 to prohibit tents on public sidewalks, have been rejected by residents there. 

“It’s to get votes from [Jacobs], as opposed to giving and getting [him] votes,” said Jim Stearns, Peskin’s consultant, regarding Farrell’s motivation for endorsing Jacobs — who is canvassing and campaigning across the district. Farrell might be hoping Jacobs could “carry a message” for him.  

Jacobs, who has leaned into harsher public safety approaches like deporting drug dealers and compelled treatment, confirmed that he supports Farrell’s campaign for mayor. As of June 30, Jacobs had raised $23,355. 

“I’m honored to have Mark’s sole endorsement. With Mark’s pragmatism and perfect blend of public and private sector experience, I know that, together, we will do great things to get San Francisco back on track,” said Jacobs, a 30-year-old who left his job as a brand manager to run for office. 

Jacobs called District 5 the “ground-zero of the rapidly shifting political landscape across San Francisco” and emphasized his and Farrell’s “aligned policies,” like bolstering the police department to supporting encampment sweeps and the March ballot measure Prop. F to drug test welfare recipients. 

Another longtime political observer said that Farrell could be joining the high-profile supervisor race in District 5 to “create a distinction” between himself and Breed, and appeal to other potential supporters. 

“It’s not about winning D5, necessarily,” the observer said. “It’s about, who are the other people that he’s signaling, by endorsing” Jacobs. Where Mahmood has used progressive rhetoric to court voters in District 5, Jacobs has embraced a rightward shift in city politics. 

The political observer said Breed, who lives in the district and once led it as supervisor, likely had similar motivations — in addition to her open disdain for Preston, who has “always been a thorn in London Breed’s side.”

“I would look at it through the lens of: What does it get her?” they said. “She may also be feeling like she needs to endorse [Mahmood] in order to keep other people who are also supporting her, to keep them happy, because he does well with that wealthy crowd.”

Mahmood has received support from major tech figures like crypto billionaire Chris Larsen and angel investor Ron Conway — both of whom financially backed Breed’s successful police ballot measure, Prop. E, in March. Mahmood is also an elected member of the local chapter of the Democratic Party, which recently endorsed Breed. 

But at the same time, while the endorsement could work in Breed’s favor, Stearns said, her unpopularity could hurt Mahmood. (Breed’s ratings have, according to a San Francisco Chronicle poll, improved in recent months.)

“Being endorsed by an unpopular mayor can be a drag on a candidate such as Mahmood,” Stearns said, “because people … don’t want to elect a supervisor who they believe would be a rubber stamp for that mayor.” 

Both candidates, if they win, do seem to expect cooperation from the candidates they are endorsing. 

“I need a supervisor of my home neighborhood that actually wants to work with me,” Breed said at Mahmood’s field campaign kickoff event on Aug. 17. She acknowledged it “took a minute” for her to make an endorsement as she assessed all the candidates in the race, and even gave Jacobs a shoutout. 

Farrell, for his part, said he could relate to Jacobs “as a former underdog candidate for supervisor” and called him the change needed to replace Preston. 

“He is focused on the top issues facing the district and we desperately need a new voice that represents the future of San Francisco,” Farrell said in a statement, calling Jacobs a “critical and necessary partner” in City Hall. 

This article has been updated to reflect that Breed has made endorsements in other districts.