Libby Schaaf, the Have-It-All Mayor of Oakland

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Children’s trash sprinkles the floor of this minivan, and the seats are less than new, worn by little bodies. The backseat is popped down for me to lumber into awkwardly. This could be just any soccer mom’s car, except there’s clearly an important woman in the second row, well-attired in a business jacket, followed by our camerawoman in the front row, rolling as I ask questions.

Under a dark-slate sky, just hours after sunset, we are in Oakland, the eighth largest city in California, with an outsize reputation and history, and this soccer mom is the honorable Mayor Libby Schaaf. We’re heading through neighborhoods with crime rates that would make a police chief’s blood curdle. But going through her packed schedule, the mayor isn’t noticing the surroundings much. She’s mentally scrolling her day: “Oh, I need to call Uber,” she says. Not to get a pickup — she’s got her mom-van for that — but because the multibillion-dollar giant has just announced plans to set up global headquarters here, a huge boost for the city, as it’ll come with 3,000 jobs if filled to capacity.

Schaaf has been mayor here for a year, a surprising victor who used an endorsement from Governor Jerry Brown to vault herself to a decisive 63 percent victory. Since then, her support has only risen, according to polls. But the 50-year-old former city councilwoman, whose profilers seem unable to describe her without mentioning her high school cheerleading record, might be putting it all on the line. In short, she’s making a big play for Big Tech that’s meant to attract jobs, and inevitably touches on one of the touchiest nerves around today: gentrification. Indeed, in some quarters, the arrival of Uber has only sharpened discontent, raising worries about rising rents, displacement and overpriced, fair trade coffee. Similar narratives have played out, over and over again, from Brooklyn to neighboring San Francisco, but Schaaf believes she can write a new growth story. It ends when she, and the city she leads, have it all, an economic revival that includes everyone. “The Oakland I dream of takes this moment of opportunity,” she says.

Naturally, big thinkers tend to attract even larger skeptics. Let’s not forget what leading Oakland entails. The city comes with the perpetual, unfortunate baggage of being one of the U.S.’s “most dangerous,” according to MarketWatch, CNN and Forbes; it’s tailed by ever-growing tensions between African-Americans and the police, and increasingly high rents as techies move to town. On the other hand, this is an underdog city, the home of the Golden State Warriors, the moneyballin’ A’s and the rascally Raiders. It’s an activist town, the old stomping grounds of the Black Panthers and not a place whose residents sit idly by. In this fiery city of 400,000, can a newly elected mayor make a change? And what might that change look like?

***

We arrive at Birdland Jazz Club, an unlikely spot for a meeting with a mayor in most cities, but here Schaaf’s delivering a version of her State of the City speech to 70 or so Oakland residents. Schaaf’s dressed a bit as though she were trying to please everyone — a business blazer atop a long artsy skirt. She speaks to a sea of white audience members at the meeting, not all that uncommon anymore in this racially divided city that lost a quarter of its African-American residents between 2000 and 2010.

Courting technology is a known narrative for Oakland — Schaaf’s predecessor, Jean Quan, says she helped expand Pandora’s presence and concluded the transfer of the Sears building to the developer who brought in tech-company bids, including Uber’s winning bid. Quan is a small Chinese-American woman who, like Schaaf, did not look like her constituency in full. Her difficulty (Schaaf defeated her to be elected), however, stemmed from her handling of Occupy Oakland. Everyone was mad at her, says Dan Siegel, an unsuccessful contender for the mayoralty: the police, their supporters, the occupiers, their backers. Quan says Occupy “was a perfect storm” and that Schaaf is “a better politician than me, probably.”

Tonight at Birdland, Schaaf fields questions of all sorts, dealing with the minutiae and the grand alike. A little boy raises his hand to ask about the future of his beloved Raiders. Lately there’s been talk that the Raiders want to decamp for another city, and the question arises often. Schaaf assures the boy she’ll do all she can to keep them close. She’s patient with all questions, often thanking the person for bringing up something so important to her mind. But when she speaks, she focuses on a few main issues: education, housing, policing and responsive government.

“Libby presents herself as a very attractive person,” says Siegel. “She speaks well, she’s pleasant.” Plus, she’s Oakland-grown; her parents were a flight attendant and a shoe salesman who had a meet-cute on a plane and fell for each other. Growing up in the wealthy Montclair neighborhood, Schaaf focused more on volunteering than politics, but when she was in high school, her godmother took her to League of Women Voters meetings, and she got bit by the politics bug. College led to law school, which led to all-too-familiar lawyer ennui.

Schaaf tells me the story of how she spent her time volunteering after those boring, billable hours as an entertainment lawyer. She cofounded a nonprofit, Oakland Cares, and one of her favorite mentees was a 9-year-old student named Nathan, whom she gave homework help to. “His mother had died when he was really young,” Schaaf says. “I could see him … start to see himself as someone who had potential. I just thought, I don’t get that kind of satisfaction from being a lawyer.”

I’d read about Nathan’s transformation in another piece about Schaaf, nearly word for word, but then again, Schaaf is preoccupied with transformation, to the point of obsession. Signs of change are all over Oakland, from work on the $1.5 billion project to revitalize the Brooklyn Basin to a “36 Hours” profile in The New York Times. The money is pouring in. But Schaaf believes that the right policies can use that money to make life better for Oaklandites: an education system that trains students for high-paying tech jobs, for instance, and affordable and market-rate housing.

Clear messaging is a priority for Schaaf, a lesson she credits to Brown, her mentor. Ask any expert on city development and they’ll tell you the same: No city has yet figured out a secret sauce to build up and not push vulnerable populations out. Schaaf’s play is a new page in the book to try to unite two Oaklands into one cohesive city. Her platform may sound like an “oxymoron,” as urban studies professor Samuel Zipp says — court tech money (historically seen as a gentrification instigator) and then use it to reverse gentrification — but Schaaf thinks Uber’s cash flow, and other money like it, matched with a commitment to inclusive diversity is the way to pull off what she calls — wait for it — “techquity.”

***

Before dawn on Schaaf’s 15th day in office, about 50 people gathered outside her house to protest police brutality and inequality, chanting “Wake up, Libby!” and “No sleeping on the job!” Schaaf’s children were in bed, asleep. “I’d be lying if I didn’t say it was scary and upsetting,” she says. She defends their right to protest, even at an ungodly hour. “Moving the conversation,” she says, “is much more important than my personal comfort.” Still, she stayed inside her house, for which she took plenty of flak.

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Schaaf at a May 2 press conference following May Day vandalism and violence.

Source Josh Edelson/Getty

Whatever their politics, most successful mayors tend to play to the consensus. From Michael Bloomberg to Bernie Sanders, they prioritize pragmatism and problem-solving over lofty ideas or partisanship, says Benjamin Barber, author of If Mayors Ruled the World. They can hang with a bunch of constituencies: activists, businesspeople, punks, soccer moms, yuppies, ex-cons, artists, coders, hipster babies. Indeed, Schaaf can go from genteel Berkeley to dicier Longfellow in a few minutes; she speaks at microbreweries and motorcycle clubs alike. And when she speaks, she does so in the vocabulary of an activist, though she doesn’t always have their support. Schaaf’s mayoralty might sound different, but when it comes to the police versus the people, it’s more of the same, says Robbie Clark, an activist at Causa Justa, in Oakland. “We’re seeing the same patterns and budgeting,” says Clark, and “the same … prioritization of the police.”

To be sure, she’s undertaking a nearly herculean effort. Other cities have tried to channel private growth into public gain, and some have fared better than others. Seattle is making a “very conscious effort to have its comprehensive plan and growth be truly inclusive,” says Victor Rubin, vice president of research at PolicyLink. Newark, meanwhile, benefited from the Cory Booker effect and used public-private partnerships to attract investment. But good intentions and investment are not panaceas. At the moment, Schaaf has a housing council implementing a development policy and has launched a plan to triple the number of low-income Oakland higher education graduates, but hardly anything has been put into place yet other than the recent Uber announcement.

On the other hand, experts caution that moving too quickly might have the worst results. Plus, some question whether Schaaf might be too late to the tech-industry bandwagon. “The market is softening, the tech boom is softening,” city planning professor Karen Chapple says. Softening is the least of it; a repeat of the dot-com crash would be devastating to Oakland’s progress. Still others question if tech is the right industry for Oakland at all, suggesting a better strategy would be to train residents for mid-level manufacturing jobs. But that might not be her biggest concern, Siegel says: She has an eight-person city council that Siegel describes as being “eight factions.”

As for Schaaf, her career seems to be on the rise, even if she can’t pull off a long-term turnaround for Oakland. Sitting in her wood-paneled office in marble-walled City Hall, Schaaf waves off the question of her ultimate ambition. She tells me to ask something more interesting.

Video by Charlotte Buchen.

Correction: An earlier version of this article misidentified the Jean Quan’s ethnic background. She is Chinese-American.

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