San Francisco mayoral candidate Mark Leno would be the city's first openly gay mayor, but he's not the only candidate vying to be a "first." Eric Risberg/AP

The campaign has become as much about candidate biographies, super PAC money, and the city’s unique ranked choice voting system as it is about issues like homelessness and property crime.

“Why did the political establishment oust San Francisco’s first African American woman mayor?” The words are splayed across a wall of gilded portraits of San Francisco mayors past on the cover of a political mailer. The visible portraits are black-and-white shots of white men. In the bottom right corner, a young girl stands in the foreground, a shattered portrait at her feet of London Breed, San Francisco Board of Supervisors president, recently ousted acting mayor, and now mayoral candidate. The girl’s curly brown hair is divided into pigtails, and her skin tone matches Breed’s in the photograph below. Above her, a portrait of the current acting mayor, Mark Farrell, hangs to match the rest.

Breed’s biography—from a child raised in San Francisco public housing to, potentially, the city’s first African American woman mayor—makes for a compelling political narrative. But she isn’t the only candidate who would be a “first” for San Francisco. The other two leaders in the polls for the June 5 special election, Mark Leno and Jane Kim, would be the city’s first openly gay mayor, and first Asian American woman mayor, respectively. In the nation’s most progressive big city, where all the major candidates are liberal Democrats with similar policy prescriptions (clean the streets, combat homelessness, and build more affordable housing), identity stands out as a key differentiating feature. “There are no real ideological differences between the candidates, but each is a proxy for something larger,” Corey Cook, a political science professor at San Francisco State University told the Washington Post. Other non-policy factors, like each candidates’ perspective on super PAC money, and their strategy with regard to the city’s unique ranked choice voting system, have also played a major role in the election.

Attempts by Leno, Kim, and Breed to differentiate themselves have played out in the mailers and video ads that have flooded San Francisco residents’ mailboxes and consciousnesses over the past several weeks. These promotional materials, many of which are at once idealistic and cynical, paint a telling portrait of San Francisco in 2018, a city whose wealth and compassion exist in a tenuous balance, and whose values are in desperate need of a vessel, however symbolic.

Breed, the front-runner, might be the best embodiment of these complicated aspirations. The mailer depicting her shattered portrait was paid for by a super PAC called “It’s Our Time, SF Women for London Breed,” whose lead donors include Twitter co-founder Evan Williams and famed San Francisco socialite Dede Wilsey. Its message harkens back to December, when Breed was dubbed acting mayor after former Mayor Ed Lee died of a heart attack. About one month later, Breed was ousted by the Board of Supervisors, presumably to level the playing field for the upcoming special election, in which it was known she planned to run. However, many of her supporters saw this as an act of prejudice, especially in light of the fact that her replacement, Mark Farrell, is a white venture capitalist.

“Let’s return a strong and independent woman to the Mayor’s Office!” the words on the back of the pamphlet read. Below them, Breed’s portrait is restored to the wall, and the young girl tilts her head back to look up at her, a camera pressed to her face.

(It’s Our Time, SF Women for London Breed/Jurate Raulinaitis)

Kim and Leno are positioning their campaigns in opposition to Breed—so much so that they’ve allied themselves against her. They paint Breed as an extension of the city’s longstanding political power structure, and more importantly, as the only candidate who hasn’t rejected or discouraged super PAC spending on her behalf.

According the San Francisco Ethic’s Commission, independent expenditure groups that support Breed, but are technically unaffiliated with her campaign, have raised about $1.3 million, compared to around $422,054 for Kim, and just over $173,788 for Leno, over the past 85 days. Many of Breed’s super PAC donors are anonymous, but others are among the biggest names in the tech industry, including Williams, venture capitalist Ron Conway, and his wife Gail Conway. This money funds pamphlets and television spots that attest to Breed’s independence, her disadvantaged upbringing, and her leadership qualifications.

The extent to which big money interests have mobilized around Breed has become a huge part of both Leno and Kim’s campaigns. For Kim, who is currently polling in third place, her identity as a candidate during this phase in the race is closely tied in to her affiliation with national progressive movements. She is the only candidate to be endorsed by Bernie Sanders and his political action network, Our Revolution. The home page of her website is dominated by the slogan “The Resistance Lives Here,” and one of her mailers prominently features the phrase “Our city is ready to lead the resistance. Jane Kim will lead the way.”

Kim and Leno are attempting to jointly combat the money flowing into the Breed camp through an unusual political machination. The two are encouraging their respective supporters to vote for the other in the number two spot on San Francisco’s unique ranked choice ballot, which allows voters to select up to three candidates in order of preference.

The advertisement that announced the alliance does not mention Breed specifically, but rather the money being spent on her behalf. “The city belongs to us,” Kim says, “not the billionaires,” the two continue in unison. Their shared ideology is the stated purpose of the alliance, but detractors view it as a petty political tactic for two candidates who are trailing in the polls. The San Francisco Chronicle’s editorial board, which has endorsed Breed, said the move “projects an element of desperation.”

As The Atlantic’s Russell Berman reports, this is the first time in the history of ranked choice voting in San Francisco that two serious candidates have teamed up. The system was initially adopted to increase voter participation and save public money by eliminating the need for a run-off election. It works like this: If no candidate wins an outright majority of first choice votes, the lowest vote getters are eliminated one by one. The voters who selected losing candidates will then have their second choice votes added to the totals of the remaining candidates until one of them wins a majority. Ranked choice voting is supposed to be game-proof because second and third choices only count if a voter’s first choice candidate is eliminated.

Kim and Leno’s alliance could backfire, though. Breed’s campaign is spinning it as yet another instance of Breed being ganged up on: “Leno and Kim’s one-two strategy was announced to the world the day they orchestrated London Breed’s removal as mayor,” Breed spokeswoman Tara Moriarty told Berman. Breed has encouraged her supporters to vote for her in the one, two, and three spots, even though the latter two would not be counted.

The Leno-Kim alliance could also make the two candidates look the same to voters, a slippage the Breed camp is hoping to exploit. In one of its mailers, Breed’s campaign attempts to undercut Leno’s popularity as an erstwhile state senator by painting him as weak on crime because of his alliance with Kim, who is perceived as being the candidate furthest to the left.

(London Breed For Mayor 2018/ Jurate Raulinaitis)

To further distinguish herself, Breed has adopted a San Francisco-friendly version of “law and order” messaging in the campaign’s final days. In addition to criticizing Kim’s—and, by association, Leno’s—somewhat more permissive views toward tent encampments and policing, Breed has outlined harsher stances on these issues. In a 30-second TV ad, Breed connects her own journey from poverty to public office to her agenda on homelessness: “I know for me, tough love and a roof over my head made all the difference in the world,” she says.

Breed has pledged to end long-term tent encampments within a year of taking office, crack down on outdoor drug use, and add 200 officers to the police force. She has also championed conservatorship laws, which give the government more power to force people with mental illness to accept medical care or the supervision of a guardian. Kim and Leno have also supported such laws, but have been less vocal about them in their campaigns. By contrast, Breed has seemed almost intentionally provocative on this issue. “Taking away someone’s civil liberties is not something that I take lightly, but if we want to see a change on our streets we have got to do something different than what we’re doing now,” she said in a recent campaign speech. “I plan to introduce the kind of solutions that in some ways can be quite controversial, but are necessary.”

Leno has made his homelessness policy a point of distinction from Breed. One of his mailers is headed by the phrase, “London Breed on homelessness: a repeated record of inaction and empty promises.” The mailer cites Breed’s failure to create as many shelter beds as she promised this winter, her prior support of pro-landlord legislation, and the fact that, as a member and then president of the Board of Supervisors, she presided over a 10 percent increase in the city’s homeless population. (Kim was also on the Board during that period.)

When it comes to their plans on homelessness, however, the two candidates’ platforms are fairly similar. Leno’s pledge to end “street homelessness” by 2020 sounds a lot like Breed’s promise to clear tent encampments by 2019. There are rhetorical differences, but in broad terms, both plans include accelerating the production of affordable housing, building more navigation centers that connect the homeless to social services, expanding shelter access, and beefing up mental health services. The campaigns for Kim and Breed did not reply to CityLab's request for comment on their homelessness policies.

Kim is popular amongst the most progressive San Franciscans for making issues like eviction and subsidized housing key causes as a supervisor. But her platform looks nominally similar to her challengers’, too. In a TV ad, Kim states that her top priority is cleaning up the city’s streets—a goal that both her opponents have embraced—and her plan to “heal” homelessness in the city also includes more public health services, and expanding shelter access.

In the midst of these similarities, it seems the real difference between the candidates has more to do with their identities—and not just their race, gender, or sexual orientation. This is woven into Leno’s slogan, “A New Direction For San Francisco,” as well as his campaign materials, which not only point to flaws in Breed’s record on homelessness, but also seeks to paint Breed as a member of the old guard political establishment. “Homelessness is out of control. The status quo has failed us. We can’t afford any more empty promises,” one mailer reads.

(Mark Leno for Mayor 2018/ Jurate Raulinaitis)

While Breed’s supporters hold her up as an independent political operator with the odds stacked against her, Leno and Kim are sending the opposite message. As the heir apparent to Ed Lee, who was appointed by the previous Mayor Gavin Newsom, who was himself championed by his predecessor, Willie Brown—all of whom were moderates in San Francisco parlance—Breed looks to many as anything but the “change” candidate.

The question is, do San Francisco voters really want change, or do they want tangible improvements to their daily lives? Or perhaps a symbol of uplift and resistance in the Trump era? More than likely, any of the three could play those roles. San Franciscans, rank your choices.

CORRECTION: An earlier version of this article incorrectly stated that Jane Kim was endorsed by the local chapter of the Democratic Socialists of America.

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