Sherrill registered with the Democratic Party in 2023 after identifying as “no party preference” since first registering in San Francisco in 2016.

He has longstanding connections to former New York City Mayor Michael Bloomberg, an ally and supporter of Breed. After college, Sherrill worked as an assistant for the New York deputy mayor for operations and later was promoted to senior policy advisor during Bloomberg’s tenure.

Bloomberg contributed more than $1 million to an independent expenditure committee supporting Breed’s failed reelection bid this year; likewise, she endorsed Bloomberg during his unsuccessful presidential run in 2020. The San Francisco mayor’s office of innovation is funded by Bloomberg Philanthropies, his charity.

Sherrill denied that political ties between Bloomberg and Breed were a factor in his appointment, saying both care deeply about building cities and hiring great talent.

Not all District 2 community leaders were convinced. Jason Pellegrini, a former human rights commissioner and District 2 resident, said he will support Sherrill’s success in office, for the sake of the district. However, he said, Breed’s choice carries the whiff of a political favor, and Sherrill wasn’t the most experienced pick on the short list of possibilities.

“I’m extremely disappointed in Mayor Breed, the daughter of San Francisco, as she’s leaving office,” Pellegrini said. “I feel this is a slap in the face not only to District 2 but to San Francisco.”

Patricia Vaughey, president of the Marina-Cow Hollow Neighbors & Merchants Association, was skeptical of Sherrill’s appointment and said she had not seen him at community meetings.

“Here we go again with someone who doesn’t know what the fuck they’re doing,” Vaughey said. Still, she said she will do her best to support him: “I have to work with whoever I have to work with.”

Through a spokesperson, Breed’s office said, “The mayor made the appointment based on her belief in Stephen’s qualifications and abilities, nothing else.”