San Francisco’s appointed District 2 supervisor, Stephen Sherrill, is sitting pretty going into the June 2 special election to keep his seat: He has fundraised more than twice his opponent. 

Sherrill, a former staffer to New York City Mayor Mike Bloomberg appointed by outgoing Mayor London Breed, received $223,279 in contributions as of Dec. 31, according to the latest campaign finance filings. Lori Brooke, a longtime community organizer challenging him for the district seat, which represents the ritzy Marina, Pacific Heights, Cow Hollow and Presidio Heights areas, raised $100,756 in that same period.

Though Sherrill received many more donations of $500 or less than his opponent, he is also the beneficiary of an outside PAC that has turned to some of his most intimate supporters: his own relatives. 

The political pressure group GrowSF, which has grown close to Mayor Daniel Lurie, an ally of Sherrill, spun up a political action committee that raised $17,200 for Sherrill last year.

Campaign contributions in San Francisco are strictly capped at $500. But because the GrowSF committee is regulated at the state level, it is a (legal) end-run around the city’s donation limit — which is at the same dollar figure as it was in 1972. The bulk of the GrowSF funding comes in four-figure sums from the Sherrill family: Stephen C. Sherrill, the supervisor’s father, gave $4,900. His mother, Katherine, gave another $4,900, and William Sherrill, relation unknown, pitched in $2,500.

Each has also given the city-imposed limit of $500 to Sherrill directly. Sherill also received $500 each from Miriam “Mimi” Haas, Lurie’s mother, and Walter Haas, her brother. He got $500 from venture capitalist and “Godfather of Silicon Valley” Ron Conway, a San Francisco moderate power broker, and hundreds more from other members of the Conway family.

The District 2 race is one of two contests on the special June 2 ballot. Both Sherill and District 4 Supervisor Alan Wong, who was appointed by Mayor Daniel Lurie, must win a vote of the people to fill out the remainder of the current term — and, if successful, will run again in November.

Both Sherrill and Brooke have also received $60,000 in public financing, which the city gives candidates if they raise money from residents in small amounts. 

Smiling woman with long blonde hair wearing hoop earrings and a dark pinstripe blazer, posed in front of a pink background.Lori Brooke.

Sherrill, anticipating a win in June, also has a separate campaign committee for the November general election that has already raised $103,104. That money cannot be used for the June race.

Sherrill ended the year with $167,889 cash on-hand, while Brooke had $65,300.

Housing and last year’s upzoning vote are sure to play into the race. Brooke, the only other contender for District 2, has condemned the vote and said city officials should fight state laws that have forced San Francisco to add housing supply. She described the upzoning as “transforming 4-story human scale, sunny corridors into 8- to 14-story walls.”

Sherill, meanwhile, has walked a tightrope on housing: He voted for Lurie’s upzoning plan last year, but implied the city was backed into a corner — voting “no,” he said, would mean a far-worse “state takeover.” He is backed by the YIMBY group GrowSF but, like Lurie, he has come out against the 800-unit waterfront Marina Safeway proposal in his backyard.

Sherrill is a former Republican who worked for the George W. Bush administration before becoming an Independent in 2009; he only registered as a Democrat in 2023. His father is a longtime GOP donor who has given hundreds of thousands to national Republican candidates, according to the Federal Elections Commission.

Sherrill was a Bloomberg acolyte and former staff member. He then moved to San Francisco and worked in the Mayor’s Office of Innovation — a body funded by Bloomberg Philanthropies — from 2022 until he was last year appointed by Breed.

Brooke is the former president of the Cow Hollow Association, a neighborhood group with a mission to “preserve and enhance the residential character” of Cow Hollow, and touts years of community organizing, including public-safety initiatives, trash clean-ups, and tree planting.

The money behind Brooke is entirely in amounts less than $500, and she has no outside PAC backing her.