All politics are local, but some are more local than others. When Ed Lee, then in his second term as the mayor of San Francisco, had a fatal heart attack in a supermarket, this past December, city leaders gathered to exchange an old civic emotion: sentiment buoyed by opportunism. Within hours, London Breed, the president of the Board of Supervisors and Lee’s acting successor, had hosted a press conference to praise the fallen leader and set a strong course. “He believed in a city where a poor kid from public housing could become mayor,” Breed, who grew up in public housing, said. “Our city’s values have never been more important!” A swift response across the political landscape made that clear enough. Although the conference was hastily assembled, its attendees included Lieutenant Governor Gavin Newsom, a former mayor who is running in this year’s gubernatorial election. California’s junior senator, Kamala Harris, reportedly called Breed that day to talk.

Since then, the mayoral race has become charged in a very Bay Area way. As locals mourned Lee’s death in their various fashions (“Say hi to Jerry,” one Deadhead wrote), the city’s liberal ranks began to come apart like thistle blooms. On January 23rd, Breed was voted out of her acting-mayor role by the Board of Supervisors. Ostensibly, this was to level the field in advance of the June 5th special election for the permanent seat. To many of Breed’s supporters, however, it looked like a demotion fuelled by prejudice: Breed is black, while her replacement in the acting role, the former supervisor Mark Farrell, is white. Much of San Francisco was, briefly, aghast.

Actually, structural factors did make Breed’s triple role as board president, acting mayor, and candidate awkward. She could become a one-stop shop for lobbying, some observers noted, and, because many appointments on boards, commissions, committees, and task forces are divided among supervisors and the mayor, she could theoretically wield power with both hands. The greater issue, though, was also a light irony: by voting Breed off the path into incumbency, supervisors sought to make it possible to swing the mayorship left.

All of San Francisco’s eleven supervisors are liberal Democrats. The city has not had a Republican mayor since 1964. Somehow, rather than bringing unity, this common ground is scored with difference. The supervisors are said to be divided into progressives, who lean furthest left, and moderates, who lean somewhat less so. The distinction mostly comes down to positions on development (progressives are bullish on subsidized housing; moderates accept more market-rate), local business (moderates embrace growth), tech (progressives are wary), and policing (moderates favor heavier enforcement, sometimes for managing homelessness). You could barely fit a pamphlet between many of these views, and yet their holders struggle to see eye to eye. Progressives lament the moderates’ iron grip on the mayorship since 1992, and blame it for incursive wealth and housing costs. Moderates fear that a progressive mayor would smother one of the few midsized American cities finally prospering, powerful, and positioned to solve big problems. To an eerie degree, the sectarian turf wars riving San Francisco are a microcosm of left-of-center divisions growing nationwide.

Breed is seen as a moderate. The other two high-polling candidates among eight, Supervisor Jane Kim and the former state senator Mark Leno, are known as progressives; although Breed leads, any of the three could win. The slate is, in a lot of ways, one to be proud of. When Willie Brown was elected, in 1995, the line around town was that San Francisco had seen its last straight white male mayor. Aside from Newsom, who could be described as quite straight, white, and male, that has been true. Lee was the city’s first Asian-American mayor, and his elected successor looks likely to be an African-American woman (Breed), an Asian-American woman (Kim), or a gay man (Leno). Oddly, in a left-leaning city, this abundance of bright choices has turned the contest confusing and dark.

The issue came to a head earlier this month, when the San Francisco Chronicle e-mailed Kim a series of biographical questions, seeking response. By many measures, Kim has the left-most credentials of the main contenders. As a supervisor, she has made eviction and subsidized housing key causes; before becoming a Democrat, in 2008, she was a Green. She famously refused to recite the Pledge of Allegiance in office until the Supreme Court struck down the Defense of Marriage Act, and she spearheaded a successful effort to make the city’s community college tuition-free. The Chronicle’s queries centered on Kim’s early education (she grew up in New York and went to Spence), a Manhattan condo that she co-owns, and her father’s job (at Kiss, the cosmetics corporation). The paper asked, “Couldn’t someone looking at all these details about your life draw a different conclusion about your background than the one presented in your campaign narrative — that you’re more of a child of privilege than you paint yourself?”

Instead of answering the paper’s e-mail, Kim posted her replies on Medium. She suggested that the Chronicle was being fed opposition research. (She mentioned Ron Conway, a venture capitalist and political kingmaker who endorsed Breed from the lectern at Lee’s funeral and is now funding her campaign; I spoke with both Conway and Kim a few years ago, for a story about tech’s growing presence in town.) A small tempest ensued. The Chronicle’s editor, Audrey Cooper, published a letter suggesting that the e-mail came about because Kim had avoided questions on the phone; she conceded, however, that the queries were “inappropriately worded and insufficiently researched” and swapped out the reporter and the editor on the beat. For a while, the matter seemed closed. Yet the question lingered: Did Kim have a sufficiently humble biography to bear out her political work?

Recently, there has been a national reckoning with the idea that lived experience matters—that someone who grew up in public housing knows something about local poverty that someone who went to fancy schools does not, or that a member of a community heavily targeted by law enforcement has firsthand insight into predatory policing. That reckoning is important and, in its best practice, a source of nuance. Kim isn’t wrong, however, to suggest that there is something slippery in making that kind of identification the basis of voter choice. Electoral politics are about secondhand representation, after all. Our representatives aren’t supposed to be governing from their personal experience; they’re supposed to be studying and synthesizing the needs of all people whom they represent and plotting a course accordingly. Leadership, when it’s done in good faith, is an exercise not of personal history but of policy.

San Francisco’s mayoral race makes clear how obfuscating it can be to assume that one implies the other—and how confusing campaign politics get when policy history and personal history are both in play but don’t line up. Breed, the candidate with the most underprivileged background of the three, has drawn support from the most privileged figures in the city and, although she has a brother in prison, seems to favor the strongest policing platform. (Bizarrely, in the eyes of many people, George Shultz, Ronald Reagan’s Secretary of State, has been sending out enthusiastic endorsement mailers on her behalf.) Kim, a first-generation product of élite schools, has focussed her policy on inequality. In this respect, Leno, an L.G.B.T.Q. activist, rabbinical-school dropout, and onetime Art Garfunkel lackey, may be the least vexed candidate of the three—even the most conventional, by San Francisco standards. At sixty-six, he has a deep place memory (unlike Breed and Kim, he was politically cognizant when Harvey Milk and George Moscone were assassinated), and he has emerged, intentionally or not, as an avatar of pre-tech San Francisco. (It may help that he was working in Sacramento during many of City Hall’s fraught recent decisions.) Chinatown, whose political clout helped Lee win, appears to support Breed. Both Breed and Leno, curiously, claim endorsements from Kamala Harris. In the matter of practical political alliances, at least, biography seems to be off the table.

Will voters see it that way? It is hard to think about Bay Area politics right now without considering the state of American liberalism more broadly; the sorts of squabbles that used to be eccentrically San Franciscan have become large-scale factional disputes. We see it in the growing electoral rift between a centrist liberalism and an influential left wing—in Pennsylvania, recently, three Democratic Socialist candidates won primary races. San Francisco’s mayoral election next month will be a litmus test for the way an atomized left is thinking as a collective. And the outcome will be less important than the terms on which the victory occurs.