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Is Libby Schaaf the Answer to Oakland's Problems?

Justin Berton | December 16, 2014 | Story Politics

“The things I do for my city. Jean Quan wouldn’t do this.”

Libby Schaaf, the mayor-elect of Oakland, has spent all afternoon talking about how she plans to solve the city's problems of crime and gentrification, how she'll correct the deficiencies of her predecessor's administration, and how she'll keep the A's and Raiders from skipping town. She's been walking me through her campaign talking points, each delivered with the crisp, authoritative detail that garnered key political endorsement and made Oakland's voters swoon. And now she's posing for a photographer who is giving her oddly precise directions, like “Use your chin to follow my hand on this axis, throw your head back and laugh, and then close your eyes.”

And so Schaaf, understandably, is running out of steam. But then, before her patience is depleted completely, she digs into some deep well of enthusiasm known only to retail politicians and former high school chearleaders and laughs—hard. It's a laugh that signals that Schaaf is aware of both the silliness of the photo shoot and the lengths to which breakout politicians must go to manage their image—and it’s one that she’s been unleashing a lot lately, now that she has survived an arduous, come-from-behind election and is preparing to take the reins of one of the country’s most ascendant, yet still very troubled, cities.

“Have you seen this view out here?” Schaaf yells from atop downtown’s Tribune Tower. She jumps up to the balcony’s edge and takes a seat, 300 feet above her city. Then she leans over the edge to snap a selfie with her iPhone.

Energized by the dangerousness of what she’s doing, Schaaf starts to have some fun—which, for her, means calling the shots. “Now you go on that side of the clock, and let’s see if we can take each other’s picture.” I can hear that fantastic laugh from the other side of the massive clock as she extends her arm into the darkness and we take each other’s portrait.

As we compare the blurry photos, I tell Schaaf that I’m going to tweet them out. She immediately reaches over to scroll through the images. “OK...OK,” she mumbles, until she gets to one picture: “No.” The photo in question shows Madame Mayor-Elect beginning an awkward slide down from the balcony’s edge, looking a bit like she’s trying to pedal an invisible bicycle while in the throes of a seizure.

“I’m just going to delete that one right now for you,” Schaaf says, and before anyone can debate her about freedom of the press, she taps the delete button on my phone and swoooosh: gone. And then: her biggest, boomingest laugh yet.

Nobody was more surprised by her margin of victory in November's election than Schaaf herself: She garnered 29 percent of first-place votes in the ranked-choice election, then trounced runner-up Rebecca Kaplan, her city council colleague, in the final round, 63 to 37 percent. In the months leading up to November, every poll showed Kaplan with a large lead, followed by Quan and Schaaf more or less neck and neck. Then, with Election Day just weeks away—much like a poker player who conceals pocket aces while slow-rolling her opponents—Schaaf began playing her hand: First came an endorsement from Senator Barbara Boxer, then another from Governor Jerry Brown, for whom Schaaf served as an aide during his mayoral term. “His imprimatur,” Schaaf tells me over tamales a few hours before our selfie standoff, “was the biggest boost to getting elected. People were nostalgic for his kind of competence at city hall.”

Schaaf is too politic to name names, but it’s clear whom she’s referencing: After Brown was termed out in 2006, former congressman Ron Dellums rode his name recognition into office, promising salvation from the hills to the flatlands. But he rarely bothered to show up at the office and contributed little of substance to the city’s nascent renaissance. Quan’s 2010 election over Councilmember Don Perata was more an indictment of machine politics—we won’t get fooled again!—than evidence of broad support for the charisma-challenged candidate. Still, Quan dove headlong into the job and won high approval marks—until, that is, she very publicly bungled the city’s response to Occupy Oakland. Over time, her tortured and defensive communication style came to eclipse her formidable work ethic and wonkish intellect; by the end of her term, her approval rating had fallen to the low end of the 20 percent range.

Compared to her predecessors, then, Schaaf is indeed a sight to behold: charismatic, optimistic, effervescent. Like Quan, she has a deep background in local governance, a native's nuanced understanding of the city, and, her allies say, the toughness to handle a job that's arguably the most difficult in Bay Area government. But she’s also a born storyteller, a message crafter, and a pom-pom waver (Skyline High Titans cheerleading squad, class of ’83)—and that may just be what Oakland needs right now.

Throughout her rise to the executive seat, Schaaf has displayed an uncanny ability to pragmatically promote her city and, by extension, herself. At the photo shoot, she wears a skirt and blouse made by West Oakland designer Babette (whose name she mentions three times), as well as a pair of locally manufactured earrings that bear the city’s oak tree logo. Even the tamale place she picked out, La Snackeria, serves as an entry point into her Oakland narrative: It opened with the help of Schaaf-sponsored legislation that supports microlending at the city level.

“You’ve got to show the story of Oakland,” Schaaf says. “It can’t just be told.” The consensus seems to be that she’s the person to do it.

“Clearly, she’s got a mandate from our voters,” says longtime councilmember Larry Reid, who did not endorse any candidate. “And she got it because they saw what I saw: She’s smart, she does the homework, and she makes intelligent decisions.” In fact, Reid recalls that after watching Schaaf work on the council two years ago, he told her that she’d be mayor one day. “But I didn’t expect it to happen this quickly.”

Schaaf grew up in the Piedmont Pines neighborhood of Oakland—a fact that she’s made smart use of in this authenticity-obsessed town, adopting the campaign slogan “Made in Oakland” and repeatedly reminding voters that her two children attended the same public elementary school that she did. She moved to Florida for college and attended law school to become an entertainment lawyer. In 1992, she returned to Oakland to work at one of its largest law firms, Reed Smith. But while volunteering at the Boys and Girls Club, she says, she had a life-changing moment: A nine-year-old student she was mentoring spontaneously embraced her in front of his friends. “I thought, ‘They don’t hug me like this at the law firm,’” she tells me.

So Schaaf ditched the corporate life and did the community thing, volunteering at schools and sitting on nonprofit advisory boards. She soon took a job as chief of staff to one of Oakland’s most powerful politicians, Councilmember Ignacio De La Fuente, and then another with Brown’s administration, before running for city council four years ago.

As a councilmember, her pragmatic reasoning distinguished her from her more ideological peers: She was against youth curfews not because they target people of color, as critics railed, but because she’d run the numbers and concluded that Oakland police could not enforce them and achieve meaningful results. When candidate Kaplan boasted about a new lease deal with A’s honcho Lew Wolff and Quan opposed it, it created a campaign wedge issue. In a shrewd political calculation, candidate Schaaf took a seat on the sidelines, deeming the headline-grabbing debate a no-win for her candidacy—and at a time when she could have used the easy name recognition.

All told, Schaaf ’s politics are palatably middle-of-the-road, at least by Oakland standards: progressive enough to satisfy Oakland’s left—she surprised many when she won the endorsement of the East Bay Express, the city’s left-of-left alt-weekly—but not so far out as to alienate the city’s sizable bloc of older, wealthier, more conservative hill dwellers. And, like any good Oakland politician, Schaaf can’t pass up an opportunity to rib San Francisco; she told reporters during the campaign that the city had “sold its soul,” its elected officials acting in ways that ensure that San Francisco, unlike Oakland, will become a monoculture catering in large part to the elite.

It’s easy enough to come out against gentrification in a city like Oakland—the message plays well with the progressive base while soothing the liberal guilt of the gentrifiers themselves—but Schaaf is mayor now. And mayors don’t stay mayors without boosting the tax base. Schaaf knows that she will need to thread the develpment needle, ushering in economic growth without turning the city into the kind of place that she has so persistently railed against. “We can’t build a wall around the city,” she says. “Nor would we want to.”

Instead, Schaaf wants to get in front of the gentrification tidal wave, building affordable housing and creating tax abatements to encourage property owners to retain tenants who qualify for rent subsidies. She’s an advocate for community policing and wants to keep the A’s and the Raiders from moving elsewhere (though she’s opposed to offering public money for their stadiums). The idea is to keep Oakland the way it is—or, better yet, to restore it to the town that Schaaf grew up in, one that’s economically, socially, and culturally diverse. “Our soul is too beautiful to sell for growth,” she says.

Despite her optimism—and her enviable image—Schaaf knows that she’s in for a rough ride. The honeymoon ends for her with the first riot, or violent crime spike, or black kid shot dead by the cops. In that moment, it won’t be enough to not be Jean Quan, nor will enthusiasm alone win the day. Schaaf will have to govern a city that is not easy to govern and has a history of losing faith in its leaders.

Back at the photo shoot inside the Tribune Tower, the photographer mentions that in all the photos that he has seen of her, she’s smiling.

Schaaf laughs, again. “Talk to me in a year,” she says. “We’ll look at the photos then.”

Originally published in the January issue of San Francisco

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