When canvassing, Sherrill\u2019s opening line is a series of questions: \u201cWhat\u2019s on your mind? For the neighborhood? For the city? That you\u2019d like me focused on for you?\u201d<\/p>\n
If the voter has a concern \u2014 maybe the sidewalk in front of their house is uneven and needs repair \u2014 Sherrill writes it down on a post-it note along with their contact information and a promise to email the relevant city department.\u00a0<\/p>\n
Once that\u2019s done, Sherrill asks for their vote.\u00a0<\/p>\n
\u201cI\u2019m your guy in City Hall right now,\u201d he\u2019ll say. \u201cI\u2019ve got an election in June, I want your support.\u201d\u00a0<\/p>\n
Sherrill has been knocking on doors since January, he says, because \u201cthat\u2019s how you learn what people need.\u201d\u00a0<\/p>\n
When he first started, \u201cquality conversations\u201d were the main goal. \u201cI\u2019d probably have more conversations just talking to people on the street than actually knocking on doors,\u201d he said.\u00a0<\/p>\n
But now with the election approaching, Sherrill knocks with determination. He\u2019ll 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.<\/p>\n
When voters can\u2019t think of something Sherrill can do for them,\u00a0he\u2019ll point to his email address listed on the back of his flyers.\u00a0<\/p>\n
Though Sherrill is making an effort to respond to constituents, his opponent, Brooke, is counting on the fact that they won\u2019t feel heard.\u00a0<\/p>\n
\u201cWhat I\u2019ve been experiencing as a neighborhood leader is that City Hall is not always listening to us,\u201d she told voters while canvassing in Pacific Heights on a recent Saturday. \u201cA lot of things just get pushed upon us and they really aren\u2019t hearing our voice.\u201d<\/p>\n
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.\u00a0<\/p>\n
\u201cWe tried to tell Stephen, he said he would follow up and he never did,\u201d they told Brooke. \u201cSo then I was like, \u2018Who\u2019s running against this guy?\u2019\u201d<\/p>\n
This was a question Brooke liked to hear. \u201cI\u2019ve been the Cow Hollow Association president,\u201d she told the couple, \u201cand that\u2019s exactly the kinds of things that I was dealing with all the time, quality-of-life issues.\u201d\u00a0<\/p>\n
But fixing seemingly simple<\/a> quality-of-life issues isn\u2019t always easy. Sherrill\u2019s office said that it forwarded the streetlight request to two city departments involved in installing lights. But \u201cfunding for projects like this is limited\u201d and \u201cinfrastructure requests can take time to install.\u201d<\/p>\n Nevertheless, the couple seemed eager to boost Brooke: \u201cWe\u2019re excited to have somebody who\u2019s in the neighborhood and understands we could have a streetlight on that corner.\u201d\u00a0<\/p>\n Being a longtime neighbor \u2014 and not a career politician \u2014 is a core part of Brooke\u2019s doorknocking pitch. \u201cI\u2019m your neighbor, and I\u2019m running to be District 2 supervisor,\u201d she\u2019ll say. \u201cI wanted to come by and say hi and introduce myself in person.\u201d\u00a0<\/p>\n And neighbors are receptive. On that Saturday, one couple invited her into their living room to chat for half an hour \u2014 something Brooke says happens regularly.\u00a0<\/p>\n \u201cI\u2019ve had tea, I\u2019ve had coffee, I\u2019ve had cookies,\u201d she said.\u00a0<\/p>\n The main issue for Brooke\u2019s campaign \u2014 and the subject that she feels Sherrill and City Hall are deaf to \u2014 is the city\u2019s upzoning plan<\/a> to allow taller buildings and YIMBYism<\/a>. She\u2019s decidedly against both.\u00a0<\/p>\n As she walked down Fillmore Street, she gazed skeptically at a six-story apartment building, which the city\u2019s upzoning plan<\/a> now allows on every parcel on the street.\u00a0<\/p>\n \u201cWhen it\u2019s just one and you\u2019re used to it, it doesn\u2019t seem to be as jarring. But when you imagine if it\u2019s on both sides, then it starts to become quite overwhelming and imposing,\u201d she said ruefully.\u00a0<\/p>\n Brooke\u2019s focus on housing has allowed her to pull together an unusual coalition \u2014 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.\u00a0<\/p>\n \u201cLeague of Pissed Off Voters, Working Families Party, they all support me,\u201d Brooke said, naming a few progressive groups. \u201cThen I have Neighbors for a Better San Francisco and Connected SF and they love me,\u201d she said, naming some more conservative groups.\u00a0<\/p>\n \u201cI\u2019m probably not necessarily Lori the progressive, Lori the moderate. I\u2019m Lori the issue,\u201d she said. She\u2019s declined to take stances on other city issues including public power<\/a> and raising taxes to save public transit<\/a> and plug the deficit<\/a>.\u00a0<\/p>\n But is opposing housing enough to deliver her victory?\u00a0<\/p>\n District 2\u2019s 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.\u00a0<\/p>\n \u201cMost District 2 voters are concerned about housing affordability and generally pro-housing, but they are also conscious about where housing goes,\u201d Kingsbury said.<\/p>\n People might be skeptical of proposals like the Marina Safeway<\/a> development, a 25-story housing complex planned on the waterfront. But they may not be opposed to upzoning<\/a> for taller buildings on busy commercial streets like Lombard<\/a>.<\/p>\n \u201cIt has to do with the look and feel of the place,\u201d Kingsbury said.\u00a0<\/p>\n A recent poll<\/a> of District 2 residents, commissioned by pro-development political pressure group GrowSF<\/a>, backed that up \u2013 58 percent, a majority, approved of the Marina Safeway<\/a> and a whopping 84 percent approved of upzoning.\u00a0<\/p>\n Nevertheless, Sherrill has avoided taking a strong pro-housing stance, even though he voted for the upzoning<\/a>, is a member of the YIMBY group Northern Neighbors, and often says that the city needs to build more housing.\u00a0<\/p>\n He declined to give a straightforward answer last week when asked whether politicians should oppose housing projects that block people\u2019s views<\/a>. He also doesn\u2019t support<\/a> the Marina Safeway<\/a> development.\u00a0<\/p>\n Though thus far much of Brooke\u2019s campaign has focused on Sherrill\u2019s YIMBY affiliations and political ambitions, if she wants to go negative she has options. A recent poll texted to voters\u2019 phones in District 2 tested two attack messages against Sherrill:\u00a0<\/p>\n \u201cStephen 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,\u201d read one.<\/p>\n \u201cStephen Sherrill was appointed<\/a> as Supervisor by Mayor London Breed, in a series of shady back-room dealings<\/a>, so she could get a job with Michael Bloomberg when she left office. It\u2019s time to say no to more corrupt politicians in City Hall,\u201d read the second.\u00a0<\/p>\n Still, Sherrill is largely considered the favorite.<\/p>\n For one, his campaign has lots and lots of money<\/a>. He\u2019s raised $475,000 on his own and three different independent expenditures<\/a> \u2014 GrowSF<\/a>, an IE linked to Mayor Daniel Lurie, and an IE specifically to his campaign \u2014 are backing him. GrowSF alone has already committed $252,000. Brooke has raised $304,000 and thus far has no independent expenditure support.\u00a0<\/p>\n Sherill\u2019s also put together a broad coalition of endorsements<\/a> including labor unions, YIMBY groups, local Democratic groups, neighborhood leaders, politicians across the state, and, perhaps most importantly, the mayor.\u00a0<\/p>\n \u201cThis mayor especially goes very far with voters in District 2,\u201d Kingsbury said. \u201cHe\u2019s a native son. \u2026 They like his agenda and they like the direction the city is going.\u201d<\/p>\n![\"Campaign](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/04\/IMG_1960-2-853x640.jpeg\")
Lori Brooke\u2019s campaign flyer. Photo by Io Yeh Gilman.<\/p>\n![\"A](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/04\/IMG_1964-480x640.jpeg\")
Lori Brooke gazes up at a 6-story apartment building on Fillmore Street on March 28, 2026. Photo by Io Yeh Gilman<\/p>\n
![\"A](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/04\/IMG_1957-2-853x640.jpeg\")
Stephen Sherrill\u2019s campaign flyer. Photo by Io Yeh Gilman<\/p>\n