Do District 2 residents feel listened to? That’s the essential question driving the two campaigns for District 2 supervisor.
Appointed incumbent Supervisor Stephen Sherrill wants the answer to that question to be “yes.”
He was tapped in December 2024 by then-Mayor London Breed to fill a vacancy left by Catherine Stefani’s matriculation to Sacramento. June’s election will decide who gets to fill out the remainder of her term — Sherrill, or longtime neighborhood organizer Lori Brooke. Whoever wins in June will have to run again in November for a full four-year term.
When canvassing, Sherrill’s opening line is a series of questions: “What’s on your mind? For the neighborhood? For the city? That you’d like me focused on for you?”
If the voter has a concern — maybe the sidewalk in front of their house is uneven and needs repair — Sherrill writes it down on a post-it note along with their contact information and a promise to email the relevant city department.
Once that’s done, Sherrill asks for their vote.
“I’m your guy in City Hall right now,” he’ll say. “I’ve got an election in June, I want your support.”
Sherrill has been knocking on doors since January, he says, because “that’s how you learn what people need.”
When he first started, “quality conversations” were the main goal. “I’d probably have more conversations just talking to people on the street than actually knocking on doors,” he said.
But now with the election approaching, Sherrill knocks with determination. He’ll ring multiple times to make sure no one is home, wait patiently even if a large-sounding dog barks and growls from behind the door, and have whole conversations over the intercom with apartment dwellers reluctant to come downstairs.
When voters can’t think of something Sherrill can do for them, he’ll point to his email address listed on the back of his flyers.
Though Sherrill is making an effort to respond to constituents, his opponent, Brooke, is counting on the fact that they won’t feel heard.
“What I’ve been experiencing as a neighborhood leader is that City Hall is not always listening to us,” she told voters while canvassing in Pacific Heights on a recent Saturday. “A lot of things just get pushed upon us and they really aren’t hearing our voice.”
That message resonated with one couple Brooke ran into on the street that day. They wanted a streetlight installed on their block to deter car break-ins.
“We tried to tell Stephen, he said he would follow up and he never did,” they told Brooke. “So then I was like, ‘Who’s running against this guy?’”
This was a question Brooke liked to hear. “I’ve been the Cow Hollow Association president,” she told the couple, “and that’s exactly the kinds of things that I was dealing with all the time, quality-of-life issues.”
But fixing seemingly simple quality-of-life issues isn’t always easy. Sherrill’s office said that it forwarded the streetlight request to two city departments involved in installing lights. But “funding for projects like this is limited” and “infrastructure requests can take time to install.”
Nevertheless, the couple seemed eager to boost Brooke: “We’re excited to have somebody who’s in the neighborhood and understands we could have a streetlight on that corner.”
Being a longtime neighbor — and not a career politician — is a core part of Brooke’s doorknocking pitch. “I’m your neighbor, and I’m running to be District 2 supervisor,” she’ll say. “I wanted to come by and say hi and introduce myself in person.”
And neighbors are receptive. On that Saturday, one couple invited her into their living room to chat for half an hour — something Brooke says happens regularly.
“I’ve had tea, I’ve had coffee, I’ve had cookies,” she said.
The main issue for Brooke’s campaign — and the subject that she feels Sherrill and City Hall are deaf to — is the city’s upzoning plan to allow taller buildings and YIMBYism. She’s decidedly against both.
As she walked down Fillmore Street, she gazed skeptically at a six-story apartment building, which the city’s upzoning plan now allows on every parcel on the street.
“When it’s just one and you’re used to it, it doesn’t seem to be as jarring. But when you imagine if it’s on both sides, then it starts to become quite overwhelming and imposing,” she said ruefully.
Brooke’s focus on housing has allowed her to pull together an unusual coalition — progressives who worry that new housing will lead to gentrification as well as more moderate and conservative groups that are concerned about preserving neighborhood character.
“League of Pissed Off Voters, Working Families Party, they all support me,” Brooke said, naming a few progressive groups. “Then I have Neighbors for a Better San Francisco and Connected SF and they love me,” she said, naming some more conservative groups. Neighbors for a Better San Francisco and Connected SF have yet to make endorsements in the District 2 race.
“I’m probably not necessarily Lori the progressive, Lori the moderate. I’m Lori the issue,” she said. She’s declined to take stances on other city issues including public power and raising taxes to save public transit and plug the deficit.
But is opposing housing enough to deliver her victory?
District 2’s reputation for being anti-development is not fully accurate, said Eric Kingsbury, a former longtime Marina resident and past president of the Marina Community Association.
“Most District 2 voters are concerned about housing affordability and generally pro-housing, but they are also conscious about where housing goes,” Kingsbury said.
People might be skeptical of proposals like the Marina Safeway development, a 25-story housing complex planned on the waterfront. But they may not be opposed to upzoning for taller buildings on busy commercial streets like Lombard.
“It has to do with the look and feel of the place,” Kingsbury said.
A recent poll of District 2 residents, commissioned by pro-development political pressure group GrowSF, backed that up – 58 percent, a majority, approved of the Marina Safeway and a whopping 84 percent approved of upzoning.
Nevertheless, Sherrill has avoided taking a strong pro-housing stance, even though he voted for the upzoning, is a member of the YIMBY group Northern Neighbors, and often says that the city needs to build more housing.
He declined to give a straightforward answer last week when asked whether politicians should oppose housing projects that block people’s views. He also doesn’t support the Marina Safeway development.
Though thus far much of Brooke’s campaign has focused on Sherrill’s YIMBY affiliations and political ambitions, if she wants to go negative she has options. A recent poll texted to voters’ phones in District 2 tested two attack messages against Sherrill:
“Stephen Sherrill previously worked for Michael Bloomberg and in the George W. Bush Administration and only became a registered Democrat in 2023. We should not trust a former registered Republican, who dedicated part of his career to conservative causes, to represent the values of our community,” read one.
“Stephen Sherrill was appointed as Supervisor by Mayor London Breed, in a series of shady back-room dealings, so she could get a job with Michael Bloomberg when she left office. It’s time to say no to more corrupt politicians in City Hall,” read the second.
Still, Sherrill is largely considered the favorite.
For one, his campaign has lots and lots of money. He’s raised $475,000 on his own and three different independent expenditures — GrowSF, an IE linked to Mayor Daniel Lurie, and an IE specifically to his campaign — are backing him. GrowSF alone has already committed $252,000. Brooke has raised $304,000 and thus far has no independent expenditure support.
Sherill’s also put together a broad coalition of endorsements including labor unions, YIMBY groups, local Democratic groups, neighborhood leaders, politicians across the state, and, perhaps most importantly, the mayor.
“This mayor especially goes very far with voters in District 2,” Kingsbury said. “He’s a native son. … They like his agenda and they like the direction the city is going.”
Sherrill frequently emphasizes his collaboration with Lurie and his endorsement is prominently featured on Sherrill’s flyers.
In the end, having the mayor’s support could make all the difference.
It was the first thing one voter noticed, tapping the emblem with the endorsement in it: “Oooh, Lurie, nice!”