Several San Francisco Supervisor Races, Notably D2, D4, D8 and D10, Volatile

Randy Shaw’s March 2 analysis concluded that multiple Board of Supervisors contests, notably Districts 2, 4, 8 and 10, are unusually unpredictable this year, raising the immediate prospect of rematches and short campaign cycles across neighborhoods from the Marina to the Sunset. Because the incumbents in District 2 and District 4 were both appointed to fill vacancies, they must stand for election in June to finish out the terms of their successors, and if they win they must run again in November to win full terms in office, creating compressed timelines for fundraising and voter outreach.

Shaw placed the volatility against a longer history of district voting patterns, noting that “since district elections resumed in 2000, only three districts have voted with ideological consistency: Districts 1 and 9 have always backed progressives, while moderates have controlled D2.” He warned that the June contests could spill into November: “As long as the June race is close, expect a rematch in November.”

District 2 has become ground zero for that dynamic. Supervisor Stephen Sherrill, the appointed incumbent, is reported to hold a roughly two-to-one edge in fundraising for the June race, part of “hundreds of thousands of dollars [that] have flowed to the leading candidates to represent District 2’s northern neighborhoods.” Shaw observed that “Sherrill got the San Francisco Democratic Party’s sole endorsement,” a factor that could matter if turnout skews partisan. Mission Local documented contentious rollout dynamics around Sherrill’s appointment, saying “the allegations regarding Sherrill’s appointment spurred bogus emails and fliers distributed to city residents’ inboxes and doorsteps, but did not derail his endorsement by the capital-D Democratic Party.”

The family zoning and growth fights have crystallized the D2 contest. Sherrill “voted for the zoning plan. He said it would satisfy state law, avoid a state takeover of local zoning rules, and create a more ‘welcoming, sustainable, family-friendly city.’” His chief rival, identified by Mission Local as Lori Brooke, has been portrayed as intensely focused on neighborhood-scale housing and development; Mission Local wrote that “His only major competitor is Lori Brooke. She is, perhaps monomaniacal[ly], fixated on neighborhood housing and development issues.” Shaw added that “No progressive has ever won D2. But Brooke’s prominence in leading the opposition to tall buildings makes her an atypical progressive,” and that “Brooke has shown she can raise enough funds to win. And that she has a strong campaign base.”

District 4 is similarly unsettled. Shaw called it “one of the most up in the air supervisor races of the past 25 years. A solid case can be made for each of three candidates to win.” On the west side, voters remain divided over the 2024 decision to close part of the Great Highway and create Sunset Dunes park. In District 4, newly appointed Supervisor Alan Wong “failed to meet a Tuesday deadline for getting the signatures he needed from three fellow supervisors to qualify a June initiative he had proposed just a week earlier to reopen Great Highway to vehicular traffic during weekdays.” SF Examiner coverage also names Jeremy Kirshner as a candidate and places a “Brooke” figure in D4 reporting as co-founder of Neighborhoods United SF and plaintiff in a lawsuit challenging the Family Zoning plan, while she has also been quoted calling GrowSF a “YIMBY-aligned astroturf organization.” The available excerpts show some ambiguity about which district that Brooke reference applies to, with Mission Local clearly placing Lori Brooke against Sherrill in D2 and SF Examiner describing Brooke-linked litigation and advocacy in the D4 paragraph.

Shaw singled out Districts 8 and 10 among the unusually unpredictable contests but the excerpts provided include no candidate names, fundraising figures or issue snapshots for those districts. Beyondchron framed the wider risk: “All of San Francisco’s November races face an unusual challenge: attracting attention from a voter base focused on Democrats retaking Congress and stopping Trump. This should benefit local candidates with the highest name recognition, which a Democratic Party endorsement and extensive personal contact with voters helps.”

The net effect is compressed campaign calendars, big early war chests, and local fights over growth, Great Highway access and Family Zoning that could decide close June contests and trigger decisive rematches in November.