The most lopsided result in San Francisco’s election yesterday was Supervisor Stephen Sherrill’s commanding victory over longtime neighborhood activist Lori Brooke, by a margin of about 70 to 30, in District 2, which includes Pacific Heights, Cow Hollow and the Marina.
Despite Sherrill’s support by Mayor Daniel Lurie and allied groups, and a roughly 3 to 1 fundraising advantage, the outcome was far from certain. Brooke window signs were prevalent throughout the district, a testament to her 20-year leadership of Cow Hollow Association leading fights for local control and quality-of-life issues (the numbers of visibly unhoused people in its neighborhoods are much lower than in other parts of the city).
Sherrill is 39 years old, wealthy, and a newcomer to San Francisco politics, appointed to his seat by then-Mayor London Breed in December 2024 after directing her Office of Innovation. He came from New York City where he worked for then-Mayor Michael Bloomberg, whose 2009 campaign he worked on fresh off graduating from Yale.
Even worse for his San Francisco political prospects, Sherrill was a registered Republican until 2009 and first registered as a Democrat in 2023. Sure, District 2 is San Francisco’s wealthiest district and probably its most conservative, but neither candidate called for taxing the rich more.
So why was this outcome so lopsided and what does that portend for San Francisco?
Retail politics
Part of it is personality and retail politics. Those who interact with Sherrill say he’s charming, smart, engaged and empathetic — striking qualities I’ve also observed during some random interactions I’ve had with him in recent weeks, from the Fort Mason Night Market to his campaigning on Union Street on election day.
The best testament to Sherrill’s personality and political skills comes from Kat Anderson, president of the San Francisco Parks and Recreation Commission, who ran for D2 supervisor twice (in 2010 and 2017) and was angling to have Breed appoint her to the seat in 2024 after Catherine Stefani was elected to the Assembly.
Anderson has long coveted the D2 seat and had every reason to oppose and resent Sherrill, who reached out to her to set up a meeting shortly before his appointment was announced. Instead, she ended up supporting Sherrill and campaigning for him, as she told me last night during his election party at Lobalita.
“He was so authentic and so empathetic,” Anderson told me. “And then he said, ‘I want to work with you.’ He completely charmed and disarmed me.”
Anderson attributed Sherrill’s popularity and success to a focus on listening to his constituents and responding to their requests, whether it’s fixing a speed bump or getting more beat cops onto a particular street or just making them feel heard.
“I like Stephen because he’s all about constituent services. As a 32-year district resident, that’s what I like to see,” Anderson said. “I also feel like he’s the next generation of leaders and we should support them.”
Housing division
The biggest issue dividing Sherrill and Brooke was housing. As I wrote in February, Brooke is animated by an anger over the so-called YIMBY state laws that seek to accelerate housing development and prevent neighborhood groups like hers from challenging projects.
By contrast, Sherrill supports accelerating housing development and was a key vote in favor of Lurie’s controversial Family Housing Plan, which aims to build 82,000 housing units by 2031 largely by increasing building heights and density on the westside in the Sunset and Richmond neighborhoods, and in District 2.
So, it’s no surprise that Lurie showed up at Sherrill’s election party to sing his praises. “He’s put the time in, he’s put the effort in,” Lurie said of Sherrill. “He’s focused on housing, he’s focused on public safety, and he’s focused on District 2.”
Sherrill spoke next and returned the praise.
“People are happy with the direction of the city and that starts at the top,” Sherrill said to Lurie. “Tonight was about results.”
Sherrill dexterously name-checked the politicians, political groups, staffers and volunteers during his speech, including Anderson.
“This is about the community,” he said. “It’s about all of us working together for the good of the city.”
But Sherrill is still clear-eyed about the challenges ahead, particularly as they relate to managing and mitigating the housing growth he supports. In his speech, he called affordable housing and public transit “the elephant in the room,” acknowledging the challenge of ensuring their expansion keeps pace with market-rate housing development.
To that end, Sherrill said he’s actively involved in crafting a parcel tax to increase funding to the San Francisco Municipal Transportation Agency, slated to go before San Francisco voters in November. Sherrill told me proudly that he’s trying to make the tax progressive, so that big commercial properties that burden the transit system most pay more than residential properties.
“We have a lot of work ahead of us,” Sherrill said in his election night speech. “But this is a great night for San Francisco.”
Sherrill’s campaign work also isn’t over yet. This week’s victory was only to finish out the remainder of his appointed term. Sherrill is running again in November for a full term, likely facing Brooke again, and at least four others who have filed for candidacy. But the political wind likely will be with Sherrill after this lopsided victory.