SAN FRANCISCO — It is tempting to begin a story about this city’s mayoral race with an anecdote about the politically engaged, naked voter who took a few minutes to listen in on some street-corner campaigning on a recent afternoon, an easy cliche to capture the renowned out-there nature of the place. But let’s save that for later, because this is a serious, milestone moment in San Francisco’s political life.

Unfolding here is the most competitive race in a generation, an election that promises to be historic no matter its outcome. Whichever of the top three candidates wins in June will be a “first” — the first African American woman, the first Asian American woman or the first openly gay man to serve as this city’s mayor.

The central issues are how to oversee an enviable economy in a way that helps end the middle-class exodus caused by an exorbitant cost of living, preserve the prized idiosyncrasies of the city’s neighborhoods and its residents — both clothed and unclothed — and keep the big high-tech employers happy.


Simple — especially in a place that has, since the 1960s, celebrated its ability to make exuberantly clear what it does not like.

Given San Francisco’s sharp demographic changes over the past two decades, the shifting dynamics around race, ethnicity and sexuality may ultimately decide which of the front-runners goes on to lead this relatively small city with national influence. The Democrats — and they are all Democrats — chosen to lead this city often go on to lead the state in Sacramento and in Washington.

“There are no real ideological differences between the candidates, but each is a proxy for something larger,” said Corey Cook, a longtime political science professor at San Francisco State University and the University of San Francisco. “Even the bread-and-butter, micro issues like whether the buses are running on time are really about the question: ‘Whose city is it?’ ”


The essence of every San Francisco mayoral race, Cook said, is the “tension between the city that people arrived in and the city it is becoming.” What is different this year is the extraordinary gap between the rich and the poor that has emerged here since the last open mayor’s race nearly seven years ago.

Cook, now dean of the School of Public Service at Boise State University, said the worry then was “whether San Francisco was becoming a bedroom community to Silicon Valley, and now the worry is that San Francisco is becoming a part of Silicon Valley.”

“There is the growing sense that it has lost its protesting, alternative vibe, replaced by a tech economy whose public engagement is a whole different animal,” he said. “It is this uniqueness, historic and current, that now feels threatened by what some inside the city view as a sanitized tech economy that could pretty much exist anywhere.”


San Francisco has always managed to be cosmopolitan and parochial, a function of its role as an immigrant destination and of its confined geography. The city is bordered on three sides by water and to the south by the city limits. There is no place to grow.

But over the past two decades, San Francisco’s population has grown by nearly 100,000 people. That’s the equivalent of New York City gaining a million people over that time. (It added one-fifth that amount.)

The tech expansion began in the late 1990s during the tenure of Willie Brown, an African American political pioneer in this city who served previously as state Assembly speaker for 14 years.


Recruiting business was one thing, and Brown did it skillfully. But it was the subsequent “Twitter tax break” that has come to symbolize what to many here is the local government’s skewed relationship with the tech industry.


Six years ago, the city exempted Twitter from payroll taxes on new employees if it relocated its headquarters to a down-and-out neighborhood in the city’s south. Other industry giants jumped on board.

Soon the Mid-Market neighborhood was a tech hub, at a cost of tens of millions of dollars a year in local tax revenue. The mayor at the time was Ed Lee, whose sudden death in December prompted this special election.

Lee, the city’s first Asian American mayor, continued the pro-tech policies initiated by Brown as the city struggled to recover from the Great Recession. A pioneer on such socially liberal policies as the “sanctuary city” movement, Lee and his legacy are now viewed as leaning right on San Francisco’s left-heavy political spectrum.

“This city’s challenges are not solely on the shoulders of the tech industry,” said Supervisor London Breed, the candidate who could become the first African American woman to serve as mayor of the city. “Part of the problem is that our policies have not kept pace with the change.”


Breed, the slight front-runner according to recent polls, is the heir to Lee’s pro-business mantle. The only native-born San Franciscan among the top three candidates, she is the “moderate” in the race and, in a prospering city of newcomers, her story is a dispatch from what seems like another place entirely.

She grew up in Apartment 403 of the Plaza East public housing project, known in street shorthand as the “OC” for “out of control.” Police stayed away. So did taxis, leaving her reliant on public services to live, learn and move about the city. Her brother is in Vacaville State Prison for drug-related crimes.

“But for all that, the place still felt like a community,” Breed, 43, said during a recent interview at her campaign headquarters, carved out of the lobby of a movie theater.


The newly arrived have helped push up housing prices, which in turn have pushed out other longtime residents. The African American exodus has been especially pronounced, with blacks composing less than 4 percent of the city electorate, a lower share than statewide.


Breed has been close to the community for decades. She ran the African American Art & Culture Complex, an outreach hub for young blacks, and served on several of the city’s development commissions. In 2012, she won a seat on the Board of Supervisors and was reelected easily four years later.

As board president at the time of Lee’s death, Breed was made mayor until the next election. (Sen. Dianne Feinstein became San Francisco’s mayor following the assassination of George Moscone in 1978, giving her a leg up in the next election.)


But in January, the board voted to strip Breed of the title, ostensibly to avoid giving her an advantage in a special election only months away. Supervisor Mark Farrell was named mayor through the June election.

The appointment of Farrell, a white former Silicon Valley venture capitalist, infuriated Breed’s supporters. Even to those undecided on her candidacy, her treatment felt like the triumph of white, tech culture in the city.


“The white liberal clique talks a good game,” said Amos Brown, pastor of the historic Third Baptist Church and head of the city’s NAACP chapter. “But when it comes to working together in a coalition, they won’t do it. And that’s what they did to London Breed.”


Before his elevation, Farrell pledged not to seek the office in June. And while prohibited from being identified as “mayor” on the ballot, Breed has probably benefited from her ouster, particularly among women and the progressive left most skeptical of her candidacy.

“Each candidate has a distinctiveness in identity politics,” said Robert Smith, a political science professor at San Francisco State University. The city’s demographics “put Breed at a numerical disadvantage, but she knows she has to put together a broader coalition, and she has Willie Brown’s help in doing so.”


Brown has endorsed Breed with the key constituencies he cobbled together to win two terms, including an Asian American population that accounts for a quarter of the city’s likely voters.

Pius Lee, an immigrant from Hong Kong who runs a real estate company, has thrown his support behind Breed. Framed photos of Lee with Willie Brown, a shaggy Gov. Jerry Brown during his first term in office, former mayor and now Lt. Gov. Gavin Newsom, and Ed Lee line his utilitarian, second-story office.

More important, the Chinatown Neighborhood Association that he runs has endorsed Breed. All three Chinese-language newspapers that circulate to more than 100,000 residents daily have followed suit.

The reason speaks to how local San Francisco politics can be: Breed has pledged not to allow a cannabis dispensary to open in Chinatown, a culturally conservative neighborhood whose immigrant residents recall the drug problems left behind in Hong Kong.

“It indicates that she honors Chinese culture,” Lee said, adding that he told her making that pledge publicly would secure her support.

There are campaign signs written in Cantonese in other parts of the city, some visible during a recent rush-hour morning in Portola, a battleground neighborhood in past elections. Those carrying them around the BART transit stop were volunteers for Supervisor Jane Kim.

A traditional Chinese immigrant enclave, Portola is becoming more Latino. It is young and working class — and many of the busy voters are confused that they are being asked to consider candidates now, rather than before a November election.

“The main question I get, though,” said Sandy Jiang, a Kim volunteer, “is ‘Why do I support Jane Kim?’ ”

Kim is Korean American, so there is no shared history with the Chinese immigrants that are far more numerous.

But she has done well with those voters in the past as an elected member of the school board and a supervisor, largely by working on housing and education issues important to them. Making community college tuition-free to city residents was an issue Lee helped drive.

Kim is a transplant to the city herself, a New Yorker who graduated from Stanford, moved here and began work as a community organizer. At 40, she is the youngest in the field, and her issues, including a focus on early-childhood education and the minimum wage, appeal to that barely-making-it element of the electorate. She is rising in the polls.

“What is interesting about being an Asian American candidate is the realization of just how much we’ve grown,” Kim said during an interview at Un Cafecito, a coffee shop in the Tenderloin, the traditionally down-and-out neighborhood she represents. “Part of why I have stayed in this city is because I am Asian.”

On the edge of the Castro District, a cradle of the West Coast gay rights movement, Mark Leno recently passed out pamphlets featuring his “Shake Up City Hall” slogan. He is running as the outsider, even though he is a highly successful San Francisco politician, winning races for supervisor, Assembly and state Senate in the past.

Leno is a generation older than his rivals, and at 66, he is seeking to culminate a career that began as a gay rights activist in the Castro and traces an arc similar to the city’s on that issue.

A rabbinical school dropout, Leno arrived from New York City in 1977, nearly a decade after coming out as gay. Doing so at the time, he points out, was the equivalent of admitting you were “a mentally ill criminal” given the statutes and psychiatric diagnoses then on the books. He opened a signmaking business, which is celebrating its 40th anniversary this year.

“It was a city known for creative, celebratory, oftentimes outcast communities,” Leno said. “In many ways, the city is much more sober today. Business, technology, the pursuit of profit — these are powerful forces that have certainly put pressures on the cost of housing, the cost of living.”

His arrival, part of what he described as the “historic queer migration” to San Francisco, coincided with the rise of gay political power in the city. Gay rights activist Harvey Milk had recently won a seat on the Board of Supervisors, and a year after Leno’s arrival, Milk was gunned down with Moscone at City Hall.

Involved in the gay men’s health movement at the time, Leno raised his profile with his work on the ground. His partner of a decade, the journalist Douglas Jackson, had AIDS and died in 1990. Leno has been single ever since.

He joined the Board of Supervisors in 1998, then eventually ran for and won the state Assembly seat that Milk had failed to win a quarter-century earlier. In doing so, he became the first openly gay man to serve in California’s legislature.

“The top line of my campaign is not ‘Vote for me, I’ll be the first openly gay mayor,’ ” he said, estimating the LGBT portion of the electorate at about 20 percent. “But it is certainly a very visible part of who I am and what my public career has always been about.”

Leno, like Kim and Breed, says the city could have negotiated better terms with some of the big tech companies that have arrived and reshaped neighborhoods near the Castro. But Leno proposes in future agreements to require that a certain percentage of new jobs and housing be set aside for San Francisco residents.

As he campaigns, Leno talks about ensuring that a portion of new tech jobs be reserved for San Francisco residents and more aggressively enforcing affordable housing construction as a part of any new business development.

“What about building higher?” Ted Edgerton, a 46-year-old professor, asked Leno as he took a pamphlet from him on a warm recent afternoon near Harvey Milk Plaza.

“You bet,” Leno said. “In the right places.”

Which brings us to the naked voter, who listened closely and quietly as Leno outlined his platform to passersby. (To be fair, the voter was not totally nude: A gold-sequined sock hid his genitals, and he wore flip-flops and sunglasses.) Leno appeared not to notice.

There’s still some San Francisco in San Francisco.

“So again change is upon us,” Leno said. “And no one’s suggesting it can be stopped. But how can it be most effectively and equitably managed?”