City Limits As mayor of Oakland, Libby Schaaf has an impossible job. Just don’t tell her that.

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. Politico called 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 open a new office in 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.’”

One day in February, I joined Schaaf and Erica Derryck as they headed over to San Francisco for the Shift Forum, a business, technology, and policy conference, where Schaaf would join the mayor of Pittsburgh for an onstage Q&A. (Derryck took a new job in the spring.) Climbing into the passenger seat, Schaaf seemed energized and slightly punchy. When Derryck handed her a green folder full of pages marked with bullet points, she began to flip through it. “What is this conference?” Schaaf asked, squinting at the notes. “‘Capitalism at the Crossroads!’ Oh, is that where we are?”

The notes included an introduction that the moderator intended to use for Schaaf, in which he described her as “a thought leader.” “Do I have to be a thought leader?” Schaaf asked plaintively. “I’d rather be a do leader. Stop thinking! Let’s get some shit done!” Derryck and Schaaf have an easy camaraderie that often plays out like an old-fashioned comedy routine. Derryck is blunt, profane, and funny. Schaaf is earnest, goofy, and easily scandalized. Growing up, she often joined her mother doing community volunteer work, and she remains a committed civic booster. One of her earliest memories is of being 5 years old and wearing a sandwich board during intermissions at the Oakland Symphony, where she would walk up to strangers and ask them to donate to the symphony’s education program. “It was very good practice for being a politician,” she said. She was also an avid Girl Scout — she earned the gold award, the equivalent of Eagle Scout — and at one point organized a citywide scouting celebration and fundraiser for the Oakland Zoo. “The money was for an incubator for prematurely born spider monkeys,” Schaaf told me. “Doesn’t that sound random? But that was the project. And I was like, ‘Can I really organize something that hundreds of girls will show up at? Can I really raise hundreds of dollars to save a baby spider monkey’s life?’” She shook her head. “And I did it. I organized it, and people came, and it was successful. It seemed pretty heady at the time.” As we approached the conference, Derryck circled the block looking for parking. (Schaaf is notoriously thrifty when it comes to expenses like valet parking.) “We’re doing the loop of love,” Derryck said, as we crept through the downtown traffic. “The loop of love!” Schaaf said, delighted. Then she turned to Derryck. “What’s the thing you most want me to say? Techquity?” Derryck nodded. “What’s the thing you really don’t want me to say?” Derryck glanced at her. “I don’t want you to be finger-waggy,” she said with gentle sternness. “Don’t be finger-waggy in front of all these business and tech people, Libby Schaaf.” When we finally parked (valet, in the end), Schaaf hurried in and was quickly mic’d up. Onstage, with her swept-back auburn hair, clear brow, and high cheekbones, she looked a bit like a queen from a Lord of the Rings movie and conveyed some of the same authority. Her speech was polished and crisp, emphasized by a suite of professional-speaker gestures: the two-handed hatchet chop, the double pinch, the invisible ball weighed in one hand. Despite this, she can be tart. When Bill Peduto, the mayor of Pittsburgh, observed that Uber’s decision to focus on the bottom line “may cost them in the long run,” Schaaf remarked, “Well, it did cost them. Last week, when hundreds of thousands of people deleted their app.” Afterward, audience members swarmed Schaaf, hoping for a shared moment. A woman who teaches “entrepreneurship” asked for a selfie. A guy named Merlin from a company called HackerOne wanted god knows what. A woman in tight jeans and a white bolero jacket followed Schaaf into the elevator and out of the hotel, talking about education, mindfulness, and Native American religious practices. Schaaf engaged steadily with everyone (“I would really love to get you involved in the East Bay College Fund …”) until the valet came and Derryck politely but summarily put the mayor into the car. On the drive back to Oakland, Schaaf critiqued her own performance. She fretted that she hadn’t done as well when she let Peduto field the question first — “It sort of threw me off” — and also noted how doggedly he had stuck to his talking points. “During his first answer, I was like, ‘You’re not answering the question!’” She sounded indignant, then sighed and shrugged. “But he was putting out his key messages. I was more just answering the question.” I had already noticed that Schaaf, for all her abilities as a speaker, can at times be awkward. At the Piedmont Pines meeting, Schaaf brought up ballot Measure KK for an infrastructure bond and then described going on Spanish radio and hearing herself refer to Measure “caca.” The story got a laugh, but Schaaf persisted. “Does anybody know what ‘caca’ means in Spanish? For those of you who don’t speak Spanish, it means poop!” She gave a whooping laugh. Though Schaaf is generally popular — in a recent poll, 58 percent of respondents had a favorable opinion of her — she remains sensitive to such missteps, in part because she recognizes just how rapidly public opinion can shift. She noted that the city’s previous mayor, Jean Quan, a veteran school board member who had come to the job with broad support, saw her approval fall to 28 percent during her first year in office — partly due to her mishandling of the Occupy protests. “She was incredibly hardworking and brought very good intentions to the job,” Schaaf told me. “But she also left with people feeling that she had done very poorly.” She paused. “So that’s a pretty big cautionary tale.”

Shortly after Schaaf and I spoke, the city weathered yet another series of setbacks. In March, Uber scaled back its planned move to Oakland, undercutting Schaaf’s hope of attracting more tech firms. Not long after, the city lost one of its two remaining sports teams, the Raiders, to Las Vegas after months of contentious negotiations. (The Warriors had previously announced that they were decamping to a new arena in San Francisco.) A few weeks later, another fatal fire gutted an apartment building in West Oakland, killing four people; a subsequent investigation revealed that a fire captain had spent months warning his superiors about code violations in the building to no effect. Then, in March, Schaaf came under criticism for suggesting that revenue from the city’s new soda tax be used for programs not directly related to nutrition — contradicting what supporters of the bill had been promised and prompting censure from the City Council. Although Schaaf walked back her proposal, the misjudgment showed how quickly political alliances can turn. In the wake of these events, Schaaf vowed to overhaul the fire department, while also doubling the number of inspectors. Still, critics on the City Council argued that she had been slow to address the department’s dysfunction, acting only after the second fire had forced her hand. Several people pointed out to me that Schaaf had long been aware that the existing fire chief, Teresa Deloach Reed, was “a disaster.” It had been a subject of discussion when Schaaf was on the Council, and department officials had warned Schaaf before her election that “if this chief stays, people are going to die.” Schaaf acknowledged that Reed had cost the city millions of dollars because of her poor financial management and at one point had allowed the number of firefighters to fall to 394 from the budgeted number of 508, leaving the department dangerously understaffed. The problem, according to three people familiar with the situation, was that Schaaf had been unwilling to fire Reed, the first female African American fire chief of a major city, who was scheduled to become eligible for a city pension in 2017. “In the end, Libby chose to gamble by keeping Reed on, rather than risking her political capital,” one person told me. “Libby’s weakest point is her standing in the black community. Ultimately, Libby just wasn’t willing to take the political heat over replacing her.” (The mayor’s office declined to comment; Reed retired in May.) When I spoke with Ignacio de la Fuente, a former City Council member who hired Schaaf for her first political post — she worked as his assistant — he said that he thought Schaaf was doing a good job but also suggested that she had so far gotten something of a “free ride.” For one thing, after years of budget cuts, the economy was finally growing, which meant that the city could hire more police officers and put more money into capital projects. Ironically, Trump’s election had also helped by drawing activists’ ire away from the city. “She’s been lucky, in a sense,” de la Fuente told me. “I think the second half of her term could end up being more difficult.” This prophecy was at least partly borne out when a scathing report into the police prostitution scandal criticized Schaaf and her city administrator. Noting that Schaaf had not been informed of the problem or the subsequent intradepartmental investigation for several months, the court-appointed investigator chastised the mayor for failing to look into the source of that delay. A consistent criticism of Schaaf is that her focus on popularity makes her overly cautious: circumspect in her speech and conservative in her actions. (I once asked Schaaf what she was like growing up, and she somewhat bafflingly insisted that she couldn’t answer that question.) While that approach has helped Schaaf avoid the trap of polarization that afflicted many of her predecessors, it has also left some feeling frustrated by what they perceive as a tentative governing style. One person who interacts with the mayor observed that she is “not courageous. She’s not willing to take the hard stance. She triangulates a lot.”

One morning I joined Schaaf for the 9 a.m. Sunday service at Shiloh Church in the Laurel neighborhood of Oakland. Much of Laurel is in District Four, which Schaaf represented during her term on the City Council. With a multiracial, largely blue-collar population, it’s far from Piedmont Pines. When Schaaf was brought up to speak, she praised Shiloh’s diversity, adding, “When I look out at this church, I see beauty and strength.” She closed by asking the congregation to pray for her and for “this wonderful community that we are blessed to call home.” After the service, Schaaf suggested that we go to World Ground Cafe, on nearby MacArthur Boulevard, to talk. As we took a seat at a battered table, Schaaf recalled holding monthly office hours at the café when she was on the City Council. “We’d commandeer a table, and people would just talk for hours.” She looked briefly melancholic. “That’s one thing I kind of miss as mayor: You can’t be as deep into a community as you can when you’re a council member.” Another knock on Schaaf’s work is that she has focused more on the wealthier, more gentrified segments of Oakland, while ignoring the city’s most troubled areas — concentrating on concerns like pothole repair rather than the slow police response time (up to several days) for robberies in the poorer neighborhoods. John Jones III, a community organizer who works on affordable housing and criminal justice issues, said that “Schaaf’s legacy will be defined by the displacement crisis.” While he acknowledged that there were larger forces at work, he also noted, “It happened on her watch. She could have done more to stop the bleeding.” When I mentioned this perception to Schaaf, she frowned. “I think that every mayor, and probably every public figure, feels a little misunderstood by certain factions of the city,” Schaaf said. “I am a middle-class, middle-aged white lady, and I cannot help that.” She shook her head. “I think it helps that I grew up here and that I’ve been volunteering in the community for years. But you can never do enough to convince people that you get them. That you understand their problems. That you’re committed to helping their particular situation.” At the Shift Forum, Schaaf had been asked about the city’s rapid gentrification and its impact on the city’s poorer residents. At the time, Schaaf had emphasized her own talking points (techquity!), but later on she was more reflective. “In some ways, I wanted to be the mayor because I had seen all these moments of opportunity pass Oakland by, and I could see that we were in another one of those moments,” she told me. “But I did not anticipate that we would be so successful in actually catching this one.” She paused. “I’d like to think that as Oakland begins to prosper, the biggest beneficiaries will be the people who’ve been here through the hard times. But the truth is that we’ve become too successful too quickly.” She smiled wanly. “It’s ironic that our biggest success is also our biggest failure.” In the wake of the Ghost Ship fire, Schaaf told me, she had felt depressed — partly because of the tragedy itself but also because of “this feeling that people hate government. They hate it getting into their private lives, they don’t want us in their homes, they don’t want us raising their taxes, they don’t want us inspecting them all the time. Until something bad happens, and then it’s our fault. It’s like you cannot win.” Despite this, Schaaf remains uncynical — at times, almost eerily so. At one point, while we were talking in her office, I tried to ask Schaaf why she found it so gratifying to do things like attend community meetings. Schaaf seemed mystified by the question. She quoted Margaret Mead (“Never doubt that a small, committed group of citizens can change the world”) and then talked about the value of the commons and the idea that government represents our best collective selves. Not long after, she launched into a saccharine account of “Luis, who is going to college thanks to the Oakland Promise.” She finished by fetching a commemorative album and showing me a photo of Luis, adding, “I cannot tell you how incredible I felt the day we launched the Oakland Promise. I always say it comes in second only to my wedding day.” When I repeated the question, Derryck, who had been listening, jumped in. “Like, on the worst days, why do you get up?” she asked the mayor. Schaaf nodded but then pivoted into what sounded like a rehearsed speech. “To me, Oakland represents diversity and inclusion. It represents what cities should be: places of opportunity for everyone.” She went on to describe the city’s “gritty authenticity” and progressive values. “I believe that the success of this city stands for the success of those values,” she finished. Then she looked at me hopefully. “Does that help at all? Am I getting any closer?” Talking with Derryck later, I tried to make sense of the exchange. Did Schaaf understand how canned — how fake sincere — she sounded? Derryck shook her head. “I spend every day with her, and all the time, I’m like, ‘Really? You can’t really think that.’” She paused. “It took me a long time to understand that she’s not just being a Pollyanna. She actually believes it.” In today’s political climate, where fabulist populist rhetoric and blunt-spoken “authenticity” are paramount, it’s possible that Schaaf’s devout do-gooderness may read as artificial. This is ironic, given that Schaaf almost certainly is being authentic. It’s just that her authentic self happens to sound like a politician giving a cheesy speech about civic pride. One person familiar with Oakland politics told me that “she’s sort of like Hillary Clinton, in that she’s good in person, but the minute she’s onstage, you start looking for her power cord.” Several people I spoke with said that Schaaf would likely have taken a cabinet position in Clinton’s administration had the election gone differently. When that fell through, one person told me, Schaaf tried to line up support for a 2018 run for lieutenant governor, but the campaign “didn’t go well.” (Schaaf’s office denies that she was considering such a run.) Not long after, Schaaf announced her intent to run for a second term. “When Schaaf ran for mayor, she was the least disliked,” Larry Tramutola, a political strategist based in Oakland, told me. “But at this point, I don’t think there’s anyone who could go head to head with her and beat her.”