by JOE ESKENAZI DECEMBER 18, 2024, 9:30 AM (MissionLocal.org)
Short-timer mayor London Breed today, at long last, named her choice for the District 2 supervisor seat vacated by Assemblywoman Catherine Stefani: Stephen Sherrill. And, like most everyone in District 2, you’re probably asking “Who’s Stephen Sherrill?”
That’s a good question. But the more relevant question might be, “Why Stephen Sherrill?”
But first, the former: Sherrill is a 38-year-old who has resided in District 2 since 2016 — though only in August 2023 did he change his registration from “no party preference” to Democratic. Oddly enough, on that same 2023 re-registration, his birthplace was changed from New York to California.
This was, presumably, an error. In San Francisco, political affiliation may at times seem immutable, but it’s malleable. A birthplace really is immutable.
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Sherrill has, since 2022, worked in the Mayor’s Office of Innovation and, since April of this year, been its director. That office is funded by Bloomberg Philanthropies. Sherrill, a Michael Bloomberg protégé, previously worked in the Bloomberg mayoral administration. In between working for Bloomberg and Breed, Sherrill worked in private equity, marketing and e-commerce.
Bloomberg, a self-made billionaire and former New York City mayor, has put at least $28.9 million into San Francisco political causes. That includes $1.5 million he dropped into Breed’s ill-fated re-election campaign.
Breed, of course, endorsed Bloomberg for president in 2020, and attended his “Mayors for Mike” Harvard University program.
Come Jan. 8, she will find herself in need of gainful employment.
So, very briefly, that’s a bit of the who. But do these connections explain why Breed gave Sherrill this job? Certainly nobody with an ounce of sense, political or otherwise, would say anything like that on the record. And, absent hard evidence of a specific quid-pro-quo — in writing or uttered to a witness or into a tapped telephone line or wire, Rod Blagojevich-style — then nothing illegal transpired here.
But that doesn’t make it look great.
“He is dedicated to making San Francisco safer and more affordable for everyone,” Mayor Breed said in a statement this morning, “including supporting the housing, transit and infrastructure we need … With his experience in both the public and private sectors, I know he will be a strong addition to the Board of Supervisors, and a committed neighborhood advocate.”
Yet it warrants mentioning that no appointment like this would come to pass in other California cities. Despite what many well-funded, ridiculous people were telling you this election season, San Francisco’s mayor is already clothed in immense power. Unlike other cities in this state, her appointment powers for vacant elected positions are unilateral. They are also far broader than those of most any other mayor.
For the vast majority of District 2 residents, this is likely the first they’re hearing of Sherrill. He may turn out to be a whiz at legislation and a sympathetic ear for all the problems District 2 residents bring to their elected representatives. But he is not well known among neighborhood groups, and has not yet made a palpable effort to become better known. Notably, Sherrill’s introductory press release quotes San Francisco royalty and a YIMBY, but no District 2 neighborhood leaders.
Separate and apart from his personal qualities and professional competencies, the series of political connections recounted earlier do not elicit great confidence in government.
By the next scheduled election in June 2026 (though it could potentially come sooner), this may not matter, if Sherrill turns out to be a fine public servant. He may yet establish a great rapport with Mayor-elect Daniel Lurie. Otherwise, he’s an easy target for an opposition researcher.
District 2 is one of the more old-school enclaves of the city. Rarely is a Yale University degree, which Sherrill possesses, a handicap. But for many D2 residents, “Yale” is not the correct answer to the age-old San Francisco question, “Whereja go to school?”
“Marina Middle School” might go down better. “Marina Middle School … with your goddaughters Theresa and Isabella” might go down better still. Sherrill does not have answers like those.
Mayor Breed won only four of the 47 precincts in District 2. She performed worse here than 2019 DA candidate Chesa Boudin — and he did not do well. Any associations with the deeply unpopular incumbent will not be helpful to her new District 2 supervisor, moving forward.
Sherrill’s YIMBY bona fides were appealing to Breed. Regardless of what one feels about constructing all levels of housing citywide, this will not put Sherrill in good stead with his constituents in the Marina, Jordan Park, Pacific Heights, etc. If the goal is passing pro-housing legislation leading up to the scheduled June 2026 election, that makes some sense. But, beyond that, trouble is brewing. A more well-known community candidate could’ve likely gotten away with not being on the same page as much of District 2 on development issues. But that’s not Sherrill.
Breed gave a long look at putting her former legislative aide Conor Johnston in the vacant District 2 seat. Johnston is a smart and experienced legislative hand, but he is also an emphatic, and even vitriolic, Breed partisan who has carved out a persona, both online and in person, as something of a professional wrestling heel of San Francisco politics.
Also relevant: He doesn’t live in District 2.
That the two apparent finalists for this position were Johnston and Sherrill does not, on its face, indicate an overriding level of respect or concern from the mayor for the voters of District 2, who have already indicated how they feel about her.
And while, again, there is nothing yet provably wrong here, today’s appointment carries the whiff of transactionality. It will be more than a mere whiff if Breed assumes a future role under the aegis of Bloomberg. Vamos a ver.
San Francisco’s mayor — again, clothed in immense power — has a uniquely free hand at making appointments.
“Of the ten cities surveyed here, no other city among the most populous grants total discretion for appointments, let alone without strict time parameters for action necessary, to one individual,” reads a 2013 San Francisco study on various cities’ processes for filling vacant elected positions.
“It is perhaps best summed that the City and County of San Francisco, when filling vacancies to publicly elected positions, takes action through Mayoral appointments that are unchecked in a manner that supersedes most all other governing body’s [sic] functions surveyed herein, including offices of considered ‘higher status’ at the statewide level.”
Well, that’s what it is to be a strong mayor in a strong mayor system: Nice work if you can get it. As for the discontents: The next scheduled election is June 2026.
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JOE ESKENAZI
Managing Editor/Columnist. Joe was born in San Francisco, raised in the Bay Area, and attended U.C. Berkeley. He never left.
“Your humble narrator” was a writer and columnist for SF Weekly from 2007 to 2015, and a senior editor at San Francisco Magazine from 2015 to 2017. You may also have read his work in the Guardian (U.S. and U.K.); San Francisco Public Press; San Francisco Chronicle; San Francisco Examiner; Dallas Morning News; and elsewhere.
He resides in the Excelsior with his wife and three (!) kids, 4.3 miles from his birthplace and 5,474 from hers.
The Northern California branch of the Society of Professional Journalists named Eskenazi the 2019 Journalist of the Year.
