mayor of Oakland, Libby Schaaf

On a cold day in an unusually rainy winter, Oakland Mayor Libby Schaaf took the stage in an underheated school auditorium high in the Oakland hills. The event was the annual community meeting for a neighborhood known as Piedmont Pines, a woodsy enclave bordered by parkland and hiking trails. Despite the weather, the room was full. Onstage, Schaaf, wearing a dark brocade jacket and black slacks, stood very straight. 

Schaaf’s election in 2014 had sur­prised some who assumed that a mayoral campaign by an upper-middle-class, middle-aged white woman was unlikely to play well in a city with an active protest culture and a long history of racial tension. Tonight was something of a victory lap for Schaaf, who had grown up in the neighborhood and attended the high school where she was now speaking.

Gazing out at the crowd, Schaaf beamed. “It’s hard not to break into a Guys and Dolls routine, which is the last thing I performed on this very stage,” she began, “and it’s hard to stay mayoral in front of so many old friends.” Then Schaaf proceeded to stay quite mayoral, indeed. She highlighted a new infrastructure bond, emphasized dropping crime rates, and reflected on the city’s startling growth. “Around the office, we’re calling this halftime,” Schaaf said. “We’re having locker room talks.”

Still, for all the optimism, it was hard not to be aware of Oakland’s troubles. Eight months earlier, a group of police officers were accused of soliciting an underage teenage sex worker — who happened to be the daughter of a dispatcher — while providing her with information about undercover prostitution stings. (In May, the city settled the claim for $989,000.) In the wake of the scandal, Schaaf replaced the existing police chief, only to have her two subsequent appointments step down within days. The episode made national headlines — Fox News: “Three chiefs in nine days!” — but the turnover wasn’t even a city record. In 2013, Mayor Jean Quan was forced to appoint three chiefs in three days.

Then, in December, a fire at the two-story warehouse and artist collective known as the Ghost Ship killed 36 people who had gone to hear an electronic music show. After it was reported that the fire department had not inspected the building in more than a decade, Schaaf was criticized for negligence while being berated by residents who worried that she would use the fire as an excuse to evict them and shut down unpermitted units. When Schaaf appeared to defend the fire department, she was perceived as being conciliatory and clueless. Politicocalled her “a deer in the headlights.” Speaking at the Ghost Ship memorial a few days later, she was booed so loudly that an organizer had to intervene. 

At the Piedmont Pines meeting, though, Schaaf seemed to be at ease, lingering until nearly everyone else had left. In high school, Schaaf was head cheerleader, and she often exhibits a tireless enthusiasm. Although the meeting had run past 9 p.m., and Schaaf was scheduled to join the city homeless count the following morning at 4:45 a.m., she appeared unconcerned, pausing at the door, and then again in the parking lot, as various audience members aired their thoughts on everything from bike lanes to immigration. Schaaf listened to each person attentively, sometimes lightly resting a hand on the person’s arm, until Erica Derryck, the mayor’s communications director, herded her away.

SCHAAF OVERSEES a city that is wrestling with nearly every issue facing urban America: rapid gentrification, a black community that feels increasingly marginalized, a troubled and historically racist police force (it’s been under federal oversight for 14 years), and a growing homeless population (up 25 percent over the past two years). Even now, large swaths of the city remain devastatingly poor. The 5-square-mile section known as Deep East continues to have a high homicide rate; last year the area accounted for nearly half the homicides in the city. A recent Reuters study revealed that more children in the Fruitvale neighborhood have dangerous levels of lead exposure than do children in Flint, Michigan. 

The city is also home to a number of extremely vocal factions, including the Anti Police-Terror Project, which protested outside Schaaf’s home at 5 a.m. on Martin Luther King Day, two weeks after her inauguration. Since Schaaf took office, the city has seen roughly 45 demonstrations, including several in which marchers flooded nearby freeways, stopping traffic for hours. The factions are also ideologically disparate, to the point where appeasing one group invariably means aggravating another. Different coalitions have complained that the mayor has not hired enough new police officers and, conversely, that she has hired too many; that she has stacked the planning commission with developers and that she has discouraged development.

While the city charter officially provides for a strong mayor, in practice the position has limited influence. Schaaf can’t veto bills the City Council passes, has no say over the school board, and can’t fire department heads (except the police chief).

“Being mayor of Oakland is thankless,” observed Don Perata, former president pro tempore of the state Senate. “You get blamed for things you have no control over, and when something gets better, you don’t get any credit.”

The city has also changed dramatically in the past decade. Wealth from the Bay Area tech boom has overflowed into downtown, attracting restaurants and boutiques and drawing companies like Uber, which in 2015, made a high-profile announcement that it would move its headquarters from San Francisco to Oakland, eventually bringing 3,000 employees to the already crowded city. In the first quarter of 2016, office rental prices in Oakland went up by 34 percent — a rate that put the area in first place worldwide, ahead of Stockholm and Dubai. At the same time, rents and home values have soared, while the number of black residents has plummeted by almost a third since 2000.

In her first two years, Schaaf has appointed a new city administrator, helped to pass a $600 million infrastructure bond, brought in more than 150 new police officers, created the city’s first Department of Trans­portation, and begun to establish a public database of every street-paving project. (Although Schaaf doesn’t promote this fact, her administration has women occupying almost all its top positions.) In 2016, she also launched an ambitious program known as the Oakland Promise, which aims to triple college graduation rates among Oakland public school students, from its current abysmal level of 10 percent, through a mix of scholarships and academic support.

“During the first half of the game, a lot of what we’ve been doing is just trying to stabilize the organization,” Schaaf told the crowd at Piedmont Pines. “We’re creating a rainy day fund, socking away money for our unfunded pension liabilities.” She added with apparent sincerity, “If you have questions about this, please ask. I love geeking out about unfunded pension liabilities.”

She has also shown some unexpected moments of grit. After then-presidential candidate Donald Trump described Oakland as one of the most dangerous places in the world, Schaaf promptly tweeted: “Let me be clear … the most dangerous place in America is Donald Trump’s mouth.”

For the most part, though, Schaaf has focused on balancing seemingly contradictory demands: preserving affordable housing, while encouraging development to bring more money into the city. Schaaf likes to talk about “techquity” — the idea that tech companies should invest in their community —  and points out that she recently raised $1.7 million to fund below-market rentals for artists. The city is also building more than 3,000 housing units — more than in the past six years combined. 

Despite this, development has proceeded unevenly. Like other, larger cities — Los Angeles, New York — Oakland is less a unified metropolis than a patchwork of individual neighborhoods that got stitched together over the years, where remnants of an industrial past (train yards, warehouses, the port) mix uneasily with pockets of affluence (riding stables and multimillion-dollar homes). The result is a kind of wealth gradation, with the richer hills to the north and east bleeding gradually into the poorer flatlands at the city’s southern end.

This geography is overlaid by a series of complex racial shifts. At the start of World War II, Oakland was 95 percent white — a demographic that changed when tens of thousands of African Americans arrived to fill jobs building ships and tanks. In the 1950s, as whites began to abandon the city for the suburbs, the police department started recruiting white officers from the South. Racial tensions rose as the economy faltered. 

By the time Schaaf left for college in 1983, downtown Oakland had largely been abandoned, becoming, in her words, “a shuttered ghost town.” Schaaf’s parents thought about leaving but didn’t, mostly thanks to her mother, a former flight attendant who felt committed to the city. Schaaf says she remembers that period of white flight even though she was sheltered from most of the city’s decline. Growing up in Piedmont Pines, Schaaf attended Head-Royce, a private school, where she “felt like one of the poor kids,” then transferred to a nearby public high school, Skyline, where she felt uncomfortably wealthy.

That experience, Schaaf told me, had a profound influence on her. At Head-Royce, competition to get into the best colleges had been high, but at Skyline, Schaaf said she was often teased for sitting in the front row. “It was quite shocking for me to see that,” she added. “The difference in culture, not just among the adults, but among the students themselves.” Even as a teenager, Schaaf recalled, she “felt very much affronted by the idea of ‘the two Oaklands.’”

After finishing college, Schaaf attended law school, then returned to Oakland and took a job at Crosby Heafey LLP, where she negotiated product liability settlements on behalf of Suzuki and watched as the city ineffectually tried to woo a single department store, Macy’s, to downtown. After a few years, Schaaf quit her law job, first to work for an educational nonprofit and then to serve as an aide to Jerry Brown during his second term as mayor in the mid 2000s. Brown was aggressive about courting developers — often without much concern for the city’s working-class populations. “This might get me in trouble,” Schaaf told me, “but Jerry didn’t always make preserving diversity a priority.” 

Despite Brown’s efforts, the city effectively sat out the first dot-com boom, even as nearby Emeryville and San Francisco were transformed. According to Schaaf, it was her frustration with Oakland’s perpetual bystander status that ultimately drove her decision to run for mayor after serving on the City Council. “There was literally this moment where I went from ‘Hell, no, I won’t even consider this’ to ‘I’m doing this.’ So much of it was just feeling, ‘I cannot let this opportunity go by us again.’”

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