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Is Mark Leno’s Mayoral Campaign Doomed?

Everyone likes him. He has decades of experience. He’s an LGBTQ hero. So why does it feel like Mark Leno’s already lost the mayoral race?

It’s a sunny spring afternoon in the Castro, and Harvey Milk is smiling down on Mark Leno. From the second-story window of Milk’s former camera shop—now the San Francisco Human Rights Campaign Store—a painting of the martyred gay supervisor looks down at a small gaggle that has gathered around Leno. The mayoral candidate, as finely suited and smartly coiffed as ever, is here to announce endorsements from the city’s two most prominent LGBTQ political groups, the Alice B. Toklas and Harvey Milk clubs. The dozen or so supporters standing behind him with signs that read “Shake Up City Hall” include old friends of Milk’s who are now in their 60s, men who survived the plague that took Leno’s partner in 1990, along with so many others of their generation.

In his effort to become the city’s first gay mayor, Leno is channeling Milk’s legacy in ways that are both calculated and profound. Earlier in the day, his campaign released an ad that showed snapshots of a twenty-something Leno looking impossibly gorgeous. “Mark Leno came to San Francisco in 1978,” the narrator intoned over a four-on-the-floor beat. “Young, out, and proud.”

Yet on this day in the Castro, there are almost no reporters or television cameras. Only one other notable political figure is on hand: attorney Rafael Mandelman, who’s running a strong race to represent the Castro and the rest of District 8 on the Board of Supervisors. A passerby walking down the street turns to a man he’s walking with and, gesturing toward Leno, asks, “Who’s that?” The other man shrugs. One snaps a picture with his cell phone and they amble down the block.

As a campaign supporter later told me, it’s proved surprisingly difficult to rally voters to Leno on the basis of his becoming the first gay mayor of San Francisco. In spite of Leno’s insistence in interviews that his identity is “very important” to gay voters, polls suggest that it’s not a big enough deal. A February survey of 462 likely voters paid for by the firefighters’ union found Leno in third place with only 19 percent of the vote, behind supervisors London Breed at 29 percent and Jane Kim at 26 percent. (The union, for what it’s worth, has endorsed Breed.) Leno’s candidacy—which began in 2017 with a raft of early endorsements from across San Francisco’s ideological spectrum and a surge of donations that gave him a comfortable fundraising lead over his eventual rivals—has failed to incite much grassroots fervor. Voters who might have been motivated to elect a barrier-breaking mayor seem, in the era of #MeToo and Black Lives Matter, much more concerned about race and gender than sexual orientation. This has played to (white, male, 66-year-old) Leno’s disadvantage. “People who would have been ‘gay yay!’ are now ‘gay passé,’” says the supporter.

A former state senator and city supervisor, Leno was for a time considered the odds-on favorite to win the mayor’s seat after Ed Lee. He had won election to the state legislature five times, including two tough races against former supervisor Harry Britt and incumbent state senator Carole Migden, and has retained campaign consultant Ace Smith, who piloted winning campaigns for Jerry Brown, Kamala Harris, Ed Lee, and Gavin Newsom. The unfailingly polite Leno has decades of warm relationships to draw on, which helped him earn the endorsement of the local Democratic County Central Committee (along with Kim as their second choice).

But ever since Mayor Lee’s death in December launched a six-month race toward a June 5 special election, Leno’s long, loping stride has left him lagging behind Breed and Kim, who are running fast-twitch sprints to his right and left. This has led San Francisco’s chattering political class to wonder: With so much time to craft his campaign and so much money to do it with, why has Leno been running a marathon pace instead of a dash? And can he speed up in time to still become mayor?

Throughout the campaign, the notion that the long-serving Leno isn’t fitted to the present moment has dogged him. Leno seems to speak for—and to—a San Francisco of years past, not of the present. At a debate moderated by the Chronicle’s J.K. Dineen in March, he scolded young YIMBY activists to be more “respectful.” Change, he said, “takes time. It doesn’t take screaming, and it doesn’t take demeaning.” Leno is, in the best sense of the term, a political old hand, skilled at consensus building. He proved that on the Board of Supervisors for 4 years and for 14 in Sacramento, where he led fights to raise the minimum wage, exempt SROs from the Ellis Act, expand digital privacy rights, restrict solitary confinement for juveniles, and, in 2005, legalize same-sex marriage (Governor Arnold Schwarzenegger vetoed it).

But his insistence on civility and decorum may end up being a liability in an election season dominated by disgust, fear, and anger. This is a time when screaming for change and demeaning those resistant to it may be a winning strategy. Leno, perhaps sensing that shift, has taken to proclaiming at each campaign stop that he’s the candidate of change. That’s paradoxical coming from a man who’s been an inside operator for so long. “The thing is, an old white guy in a really nice three-piece suit really doesn’t scream change,” says campaign consultant David Latterman, who briefl y worked for another mayoral candidate, Angela Alioto, this cycle. “The narrative this year is not about gay liberation,” echoes another longtime San Francisco political observer. “It’s about sexual assault, and how when power plays happen, the person who comes out on top is not a woman.”

That was especially true after a Leno ally, District 3 supervisor Aaron Peskin, engineered Breed’s ouster as acting mayor in January, replacing her with Mark Farrell, the white, male Marina district supervisor. Breed was able to flip this short-term setback into what could be a long-term gain, garnering campaign donations, celebrity endorsements, and priceless momentum on a narrative of a black woman done dirty by back-room-dealing white men. Once an appointee of moderate mayor Willie Brown, in both his contested races Leno defeated progressives—Britt in 2002 and Migden in 2008. Although he could have played for moderate voters this time, Latterman says Leno made an early choice to tack left, a bet predicated on the weakness of Kim’s candidacy. That hasn’t come to pass, and Breed’s support from moderates means there’s no room for him to move to the center.

Today Leno’s challenge is this: He’s endorsed by the long-battling progressive Peskin and the moderate state senator Scott Wiener (who has since also endorsed Breed). How can Leno credibly reach out to both of their voter bases when each block has a more natural fit with Kim and Breed, respectively?

For Leno to win—and he certainly still has a chance—he’ll have to prevail in what’s essentially a hidden progressive primary that will happen simultaneously with the election on June 5. This is where San Francisco’s ranked-choice voting system could make a difference. If Leno finishes ahead of Kim but behind Breed, he could take enough votes from the third-place Kim to vault into first. However, should Kim finish ahead of Leno, it dooms his chances. That may be why, according to at least one well-positioned source, Leno tried at least twice to convince Kim to stay out or drop out of the race, telling her that she would only amount to a spoiler.

John Avalos, the progressive former supervisor who ran to a second-place finish against Lee in 2011, still sees a lane for Leno among the city’s leftmost-leaning voters. “Leno is a mensch and has quite a progressive record of major accomplishments on a wide range of issues in the state of California,” Avalos says. “I don’t see him being squeezed so much from the left.” Avalos praises Kim and Leno for “running cooperatively” and saving their attacks for Breed.

But not attacking Kim (at least in public) and throwing only glancing blows at Breed may become a problem for Leno, says Jason McDaniel, a political science professor at San Francisco State. “Leno may be suffering from second-choice syndrome,” he says. “He’s broadly acceptable to many, but doesn’t engender much passionate support.”

Leno at times seems as if he’s running for mayor of the city he departed 15 years ago, not the city he returned to. Insiders trade stories about an early campaign event during which he spent what felt like 20 or 30 minutes detailing the minutiae of a statewide fight to eliminate certain kinds of toxic flame retardants from couches and other kinds of furniture. Important? Yes. Among the voters’ top issues this year? Not so much.

It’s easiest to catch that disconnect in Leno’s smallest moments, like the one in front of the Potrero Hill Democratic Club in February when, in talking about the Twitter tax break, he posed a rhetorical question: “Imagine if instead of bringing all these new folks from out of town…” Then he paused, his voice trailing off for a moment, before adding, “…they are welcome to come, of course.” It was the pause of a man who hasn’t made up his mind about the new San Francisco—a city that may have left him behind.

Originally published in the May issue of
San Francisco

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