Stephen Sherrill, left, and Lori Brooke are running for San Francisco’s District 2 supervisor seat. Sherill is the sitting supervisor and Brooke is a community activist.
Manuel Orbegozo/For the S.F. Chronicle; Santiago Mejia/S.F. Chronicle
District 2 Supervisor Stephen Sherrill poses for a portrait at his office at City Hall in San Francisco, Tuesday, May 6, 2025
Manuel Orbegozo/For the S.F. Chronicle
Lori Brooke, a candidate for District 2 Supervisor, talks with a Chronicle Reporter in her home in San Francisco.
Minh Connors/For the S.F. Chronicle
Lori Brooke, a candidate for District 2 Supervisor, talks with Caroline Allen while canvassing in her district in San Francisco on Wednesday, April 22, 2026.
Minh Connors/For the S.F. Chronicle
Supervisor Stephen Sherrill, shown in a file photo at a community meeting, is fighting to retain his seat.
Carlos Avila Gonzalez/S.F. Chronicle
With just a week to go until ballots are due, the two-person race to represent the Marina, Cow Hollow and other northern neighborhoods in San Francisco City Hall is intensifying — in part due to a public intervention by two political insiders who had sought the seat.
Stephen Sherrill, a moderate who was appointed to the Board of Supervisors by former Mayor London Breed in 2024, is facing Lori Brooke, the longtime leader of a Cow Hollow neighborhood group, as he fights to retain his seat representing District 2.
The race has been animated in recent weeks by accusations from two of Breed’s former allies that she appointed Sherrill to curry favor with Michael Bloomberg, the billionaire philanthropist, Democratic party donor and former New York City mayor for whom Sherrill worked for several years.
Brooke is leaning into the allegations in ads, but it’s not clear whether the last-ditch attack is breaking through to voters.
Breed dismissed the accusations as “motivated by personal disappointment over not being selected.” She said she appointed Sherill based on who she “believed was most qualified and best prepared to serve the district and the city.”
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“People are entitled to disagree with my decision, but they are not entitled to manufacture false narratives about my integrity or decision-making process,” Breed said in a statement to the Chronicle.
Sherrill has denied there were any improprieties in his appointment and described the vetting process as rigorous.
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“Voters have been loud and clear [about] their politicians engaging in this kind of politics and they want people to get to work and solve problems,” he said.
In the year and a half he has occupied the office, Sherrill has become one of Mayor Daniel Lurie’s top allies and has backed legislation to build more housing and co-sponsored legislation to fill vacant retail spaces. Brooke and Sherrill share many of the same policy priorities for the district, such as street cleanliness and public safety, but disagree on Lurie’s “Family Zoning” plan, which Sherrill supports and Brooke opposes.
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The dispute over Sherrill’s appointment began when Conor Johnston, a former adviser and confidant to Breed, told two local news outlets that she had appointed Sherrill to appease Bloomberg, passing Johnston and several other contenders over for the position.
Now a retail cannabis entrepreneur, he was once known as Breed’s “guard dog” and was declared the “biggest mayoral race troll” by SF Weekly in 2018. The Chronicle reported recently that a mysterious van driving around San Francisco, emblazoned with messages blasting congressional candidate Saikat Chakrabarti, was registered to Johnston.
Another former Breed ally and contender for the appointment, Eric Kingsbury, told Mission Local and the San Francisco Standard that Breed had also informed him that she was considering her financial prospects in deciding who to pick for the job. Kingsbury declined the Chronicle’s request for comment.
Just weeks before the ballot deadline, Johnston went public with his account of the then-mayor’s 2024 appointment process to replace Catherine Stefani, who had been elected to the California Assembly.
Johnston, who was himself under consideration for the appointment to Stefani’s former seat, first told Mission Local and the Standard, and more recently the Chronicle, that Breed confided in him that she had decided to tap Sherrill in the hopes that it would help her secure a job with Bloomberg after she left office following her loss in the 2024 election.
Michela Alioto-Pier, a former supervisor who represented the district from 2004 to 2011, was also up for the job. Aliot-Pier told the Chronicle that after her interview with Breed, the then-mayor told her that, when it came to this appointment, “I have to think about me.”
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She didn’t know precisely what that meant and said Breed never discussed anything about Bloomberg or the possibility of getting a job from him. But she said Breed’s decision to tap Sherrill perplexed her and others in the district, particularly those who had hoped Stefani’s replacement would be another woman. Alioto-Pier has endorsed Brooke.
Before taking over the job representing District 2, Sherrill was little known outside City Hall, where he ran the Mayor’s Office of Innovation, which is funded by Bloomberg Philanthropies. He had previously worked for Bloomberg’s mayoral administration in New York.
Bloomberg was the top financial backer behind Breed’s failed reelection campaign, spending roughly $1.5 million to support her.
Johnston said the close ties between Bloomberg and Sherrill “set off a five alarm fire in my head” and, after hearing she planned to announce Sherrill as her pick, he tried to dissuade Breed from moving forward with it, including at a Dec. 3 meeting in Breed’s City Hall office.
“I went in and laid all this out and said, ‘You can’t do this,’” Johnston said. “It’s terrible for your legacy, it’s going to look awful.”
After leaving office, Breed had a temporary, part-time role as a “civic innovation” adviser-in-residence for the Aspen Policy Academy, a branch of the Aspen Institute think tank, which has ties to Bloomberg’s charitable organization. Breed said in her statement that she currently runs her own company and has “active clients” she did not name.
Johnston said he decided to go public less than a month before the election because he believes voters should hear his account of the incumbent’s selection. A pro-housing moderate, Johnston is hardly an obvious ally for Brooke, who is opposed to taller and denser housing in parts of District 2, but Johnston said that “some things are bigger than politics.”
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“The sanctity of our system of government to me is more important than what you think of the Family Zoning plan,” he said.
Johnston’s place on the shortlist for the appointment also worried some City Hall insiders at the time: He frequently antagonized his political opponents, including Lurie, who had just been elected to replace Breed in City Hall.
Former Supervisor Aaron Peskin, who is backing Brooke, penned a letter to the city’s inspector general requesting that the office investigate Johnston’s claims. Peskin, who authored the ballot measure that created the inspector general’s office, said he questioned why no one in City Hall had yet spoken out about the allegations.
“The fact that not a single person in the government — not the mayor, who ran on an anti-corruption platform, or anyone else — has said a word is deeply disturbing,” Peskin said. “If there’s nothing there, they should welcome an investigation. They should be calling for an investigation.”
Lurie’s office declined to comment.
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Alyssa Sewlal, a spokesperson for the Controller’s Office, which oversees the inspector general, declined to say whether it was pursuing an investigation.
“The Inspector General reviews and considers all complaints brought to the office, and multiple factors determine whether it’s appropriate for the I.G. to pursue a formal investigation,” Sewlal said in a statement.
A committee supporting Brooke’s campaign has printed mailers proclaiming Sherrill’s appointment “a story of city hall corruption.”
“City Hall has done nothing,” the ad says. “They want voters to look the other way. Don’t.”
Voters “have the ability to right this wrong,” Brooke said in a statement. “In the past few weeks, support for our campaign has continued to grow immensely. We are hearing more and more cases of voters who have changed their votes because they want transparent, independent leadership.”
Sherrill brushed off the ads as the “tactics of the politics of the past.” He has had “a couple people ask quizzically” about Johnston’s claims but said voters with whom he has spoken are generally more concerned about policy issues like the cost of housing and public transit.
“Voters aren’t stupid,” he said. “They see the timing. … They want to talk about problems that affect their everyday quality of life.”
Brooke isn’t the only player in the race to go on the attack. GrowSF, a moderate pro-housing group allied with Lurie that has spent nearly $189,000 to back Sherrill, has tried to cast Peskin’s support for Brooke as a liability in digital ads equating the two. In some respects, they make an unusual pair: Peskin is a progressive and Brooke is a pro-public safety moderate.
Uniting them is a skepticism of the mayor’s zoning reforms, which respond to state requirements that cities build more housing to combat the affordability crisis.
Brooke has said she isn’t opposed to building more housing but worries about what the construction of tall, dense development would mean for the Marina. She has publicly criticized the plan to convert a Safeway store in the Marina into a highrise apartment complex. Sherrill and Lurie also oppose the project, but Brooke and her supporters say the incumbent could do more.
The Safeway project is among the reasons Alioto-Pier has thrown her support behind Brooke. She said she would have succeeded in killing the planned development if she had been the district’s supervisor when it was launched.
“You get really aggressive about it,” she said. “You’re a member of the Board of Supervisors — you can hold hearings on anything you want. You’ve got a bully pulpit.”
Sherrill said he has “been working very hard” to respond to the project, including on a trip last week to Sacramento, where he met with leadership at the California Department of Housing and Community Development.
On Friday, he filed a request with the city’s planning department to reassess the project’s eligibility for streamlined approval under state law, he said.