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Inside San Francisco's Very Personal, Very Competitive, and Very Fascinating Race for Mayor

The first leg of the accelerated mayoral race has commenced. And it got real nasty, real fast.

And they're off! Mayoral racers Jane Kim, London Breed, Mark Leno, and Angela Allioto, being spurred on by Bernie Sanders, Willie Brown, Aaron Peskin, and Ron Conway.


A few days after being stripped of the most powerful public office in San Francisco, London Breed walks into an upscale Mexican restaurant near the Panhandle. With its $15 pozole and hipster rock over the speakers, the place feels a lot like San Francisco today. But what happens next feels a bit like San Francisco yesterday. Breed, who attended Benjamin Franklin Middle School, which stood nearby at Geary and Scott before shuttering more than a decade ago, notices one of her old teachers seated one table over. So before sitting down for lunch, she strides over to pay her respects. “I apologize,” she offers with a laugh, “for everything I did.”

The 43-year-old Breed doesn’t really need to apologize. If her teachers feel anything about her now, it’s likely unabashed pride. Because Breed has a hell of a life story to tell: She was raised by her grandmother in the Plaza East Public Housing project in the Western Addition, a handful of blocks from the thoroughly gentrified Divisadero commercial district we’re meeting in. Her older brother is currently serving decades in state prison for involuntary manslaughter and a number of other crimes. Her younger sister died of a drug overdose in 2004. Despite these circumstances, Breed went on to college at UC Davis and earned a master’s in public administration at USF. She was elected District 5 supervisor in 2012, reelected in 2016, and twice elevated by her peers to the presidency of the Board of Supervisors. Upon Mayor Ed Lee’s death on December 12, she assumed the status of acting mayor. And now she is not acting mayor.

This last bit wasn’t part of the plan. But it, too, adds to Breed’s compelling life tale, one that could lead her elliptically back to Room 200 this June. On January 23, Breed’s colleagues on the board took away her position of acting mayor and handed it, temporarily, to another supervisor, Mark Farrell. The stated rationale for the move revolved around the untenability of Breed’s acting as the head of both the legislative and the executive branches of government. But the dethroning was also clearly intended to undo the advantages of incumbency that Breed would have enjoyed as she sprinted toward June’s mayoral election. And as an added bonus, it painted Breed as a lackey of her highest-profile backer, Ron Conway—in progressives’ eyes, the living embodiment of tech’s malign influence on San Francisco—who’d been accused of strong-arming supervisors behind the scenes on Breed’s behalf.

By a 6–3 vote, Breed was toppled from the mayor’s seat in favor of Farrell, an affluent white venture capitalist who grew up in the Marina. Not 72 hours later, while splitting a taco plate with an aide, Breed is ready to earnestly discuss city issues. But one can detect the pain and indignation hovering just beneath the surface. That someone with her lived experience could come this far only to be accused by her board colleagues of being “owned” by some rich white man (i.e., Conway) is clearly rankling her. “The fact that my colleagues don’t understand how offensive that is, especially given my track record…” she says, shaking her head. “It’s not only offensive. It’s really disrespectful.”

Though Breed’s demotion came as a shock to many, in certain corners of City Hall it was no surprise. More than a week earlier, progressive supervisor Aaron Peskin had confided to San Francisco that a big move was in the offing. “I got a plan,” he said at that time. “And if it comes together, it’ll be apparent on January 23rd.”

Things came together, all right. But the racially tinged backlash that Peskin’s plan inspired, both in the moment at City Hall and later online (including fuming tweets from Democratic grandees Donna Brazile and Christine Pelosi), may actually have benefited Breed, at least in the short term. In the first few weeks of January, the candidate raised around $100,000 while serving as acting mayor. In the two weeks after her ouster, she more than doubled that, bringing in $218,000. What’s more, a poll conducted in January showed Breed surging ahead of her main opponents, former state senator and supervisor Mark Leno, District 6 supervisor Jane Kim, and former supervisor Angela Alioto. This snapshot diverged from internal polling commissioned by the Leno campaign (and undertaken by the same pollster), which put Leno and Breed in a dead heat. But regardless, it encapsulated why the progressive faction on the board was so hell-bent on stripping Breed of the mayor’s position. To avoid a Mayor Breed in June, they needed to rid themselves of Mayor Breed in January.


Besieged by rising regional unaffordability, persistent homelessness, and soaring rates of property crime, San Francisco voters have never needed answers more than they do now. But in the coming months, they may not hear a lot of legislative prescriptions for what ails their city. Instead they can expect a lot of anger, fulminations, and finger-pointing.

Veteran political consultants are already anticipating that this mayoral election may be the least substantive and, as one campaign adviser put it, the most “story-driven election we’ve ever seen. Stories are going to matter so much more than they usually do.” And Breed doesn’t hold a monopoly on compelling life stories. In Leno, her foremost rival, you have a gay former rabbinical student, a smallbusiness owner who lost his life and business partner in the AIDS pandemic, and a former supervisor, assemblyman, and state senator who’s never lost a political race. If elected, he would be San Francisco’s first LGBTQ mayor. And while many younger city voters may not fully appreciate the specialness of that prospect, Leno certainly does. “Within the queer community,” he notes with a wry laugh, “this campaign is very important.”

For two solid days a week for many weeks, Leno, who is 66, has been locking himself inside a glass-walled conference room at SCN Strategies, the blue-chip campaign shop that has previously notched wins for Kamala Harris, Jerry Brown, Ed Lee, and Libby Schaaf. There, the candidate places fundraising call after fundraising call. Leno was the first major candidate to declare his intention to run for mayor, all the way back in May 2017, and ever since he has been methodically lining up supporters and raising cash. He aimed to amass $1.475 million by 2019 but is now sprinting to hit that goal before this June.

In many ways, Leno makes for an odd antiestablishment candidate, which is how he’s positioning himself. Like Breed’s, his political origins are linked to Willie Brown. (Da Mayor appointed Leno to the Board of Supervisors in 1998.) He is a consummate insider who’s played politics at the city and state level for nearly three decades. He is no bomb thrower, but rather a calculated-risk taker, having bewildered San Francisco’s left by pulling out of the 2015 mayoral race out of wariness over Ed Lee’s poll numbers and fundraising prowess. San Franciscans in 2015, Leno maintains, were not in a revolutionary mood. Leno’s gut tells him that 2018 stands to be very different.

As he talks about the prevailing disgruntlement that has taken hold citywide, one can make out a familiar silhouette inside a glass-walled conference room on the other side of the SCN offices. Clearly visible is the pomaded head of former mayor and current gubernatorial candidate Gavin Newsom, like Leno a client of SCN partner Ace Smith. But the fact that Newsom and Leno rely on the same campaign consultants doesn’t mean that Leno would run the city the same way as his predecessors. “The same cloud of people have been around the Mayor’s Office for 22 years running,” explains one longtime political operative regarding the uninterrupted handoff of advisers and personnel between the Brown, Newsom, and Lee administrations. “When Mark says he’s going to ‘shake up City Hall’”—his campaign slogan—“this is what he means. He doesn’t have a huge government-in-waiting. He doesn’t have a shadow government.”

Left unsaid is this: The ideological differences between the Breed and Leno factions of city politics aren’t vast (this is San Francisco, after all), but the devil emerges in the details of municipal policy. To those whose livelihoods depend on it (to say nothing of the rest of the citizenry), it matters enormously who appoints scores of commissioners. It matters who negotiates union contracts. And it matters whose calls you take—and whose cries for help you ignore.


At the time of his death, Mayor Lee’s favorability numbers were at George W. Bush levels. But sentimentality is a powerful thing, and polling has since revealed a posthumous increase in his popularity. This presents a challenge for San Francisco’s mayoral aspirants. All must, to an extent, run as agents of change, highlighting the city’s shortcomings, while also respecting Lee’s legacy.

Of all the candidates, the 40-year-old Kim is most eager to close the book on the Lee era—although even she supports renaming Portsmouth Square after him. She’s the prolific legislator who pushed to make City College free and extracted affordable housing concessions from some of the city’s biggest developers. Sensing the foul mood of an electorate unnerved by rampant homelessness, public drug use, and general filth, she’s the candidate who’s said she doesn’t “want to support any new full-time city employees who aren’t street cleaners.” To Kim, the real definition of progressivism is putting the city’s vast resources behind its ideological fixations. “We’re not only a liberal city, we’re also extremely wealthy,” she said in late January at a café across the street from City Hall. “We can aff ord to enact policies other municipalities can’t even fantasize about.”

The District 6 supervisor, who made much of Bernie Sanders’s endorsement and joint appearances during her failed run for state senate in 2016, is again framing herself as this city’s Bernie. She wants to expand subsidies to more of San Francisco’s poorest residents, a philosophy she describes as “investing in our citizens.” The only problem— for progressives, at least—is that having Kim and Leno both duking it out for the top slot at City Hall could shake out poorly for both of them.

“It clouds the race a lot to have them both there,” says a veteran political strategist. The progressives are well aware of the danger of Leno and Kim draining each other’s pools of support and effectively clearing the field for Breed, but there’s not a lot they can do about it. “Right now, London has the biggest team of loyalists,” the strategist continues. “The moderate forces have all gotten in line behind her.” But where will those forces be led? So far, Breed has tried to capitalize on the outrage over her ouster, ending a speech in early February commemorating Black History Month with the provocation “I am nobody’s slave—no white man millionaire slave.” But, says one experienced campaigner, Breed’s team can’t let rage alone suffi ce: “They need to get all those angry folks who are good at yelling and screaming to go out and walk precincts five hours a day, collecting names…. You can’t win with an outside game. You can’t have Ron Conway come in and spend a lot of money if you don’t have an inside game to take advantage of, target, identify, and activate your supporters.”

For Breed, the backing of Conway has been a double-edged sword. Just as she once raged at the suggestion that she was controlled by a powerful man (“Willie Brown didn’t wipe my ass when I was a baby…. I don’t do what no-motherfucking-body tells me to do,” she spat in 2012), so too does she bridle at being lumped in with Conway . Although now her vitriol is reserved for her accusers. “That’s their playbook,” she says of the city’s left. “They always blame the man behind the curtain.” The problem for Breed is that there is a man behind the curtain.

And he’s got both a big wallet and a big mouth. (Conway reportedly began stumping for Breed at Lee’s private family funeral.) “The other candidates don’t even have to run against London,” notes longtime consultant Jim Ross, who ran Newsom’s 2003 mayoral race. “They can run against Conway.” In essence, this is already happening. When a pro-Breed PAC was launched in late January, Leno fired off a tweet noting that he had pledged to reject ads from outside groups, stating, “It’s time to let the people select their leaders without the corrupting influence of special interest money.”

But just as Leno and Kim needn’t run against Breed, Breed needn’t run against Leno and Kim. “If I was London,” says Ross, “I’d run against Mark Farrell.” The man chosen to replace her is the “poster child for white privilege,” as one wary progressive puts it. The optics of deposing a black woman raised in public housing to empower a well-off white man—and couching this as a move in defense of the city’s have-nots—are abysmal.

And so, when asked about Conway’s influence on her candidacy and her potential mayoralty, Breed immediately turns the tables. Her foes have no standing to criticize her: “The hypocrisy of it all is who they put in the Mayor’s Office.” Still, Breed professes to want to avoid this particular story line altogether. “We’ve got to move on,” she says at the restaurant. “We’ve got to channel that anger into getting the results we want.”

If she can achieve this, she’ll earn plenty of supporters in San Francisco—because people are angry, and about so many things. The city is awash in money, yet drowning in high levels of deprivation and despair. No mayor can change all this. But the candidate who can harness our collective anger, fear, and hope and convert it into action will be the one who runs away the victor.

Read more: The Mayor's Race Drinking Game 


Originally published in the March issue of San Francisco

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