Libby Schaaf Claps Back

By subverting the Trump administration and protecting undocumented immigrants, the Oakland mayor has earned scorn from the feds—and love from a fractious city.

San Francisco magazine

May 17, 2018

At the Sunday farmers’ market in the parking lot of the Claremont DMV, two white men in red hats and American-flag hoodies fix Oakland mayor Libby Schaaf with dead-eyed stares. “We know those guys,” one of Schaaf’s aides says, gesturing at one of them. “He RSVPed on Facebook.” The aide calls up the man’s profile picture, in which he holds an assault rifle and stands in front of a Confederate flag. His name is Jeffrey.

I’m standing just to Schaaf’s right, close enough to hear her quietly say, “Oh, this is exciting,” as she glances at the men. These aren’t the typical folks who show up at her mobile office hours, which she holds monthly around the city. Mostly it’s grapefruit-and bok-choy-carrying Oaklanders bringing Schaaf their problems while she earnestly listens. A woman says her laptop was stolen from the Rockridge public library. A mother complains that Skyline High has canceled its International Baccalaureate program. An elderly woman has concerns about parking in the hills.

For each encounter, Schaaf dons her full Leslie Knope persona, burrowing deep into civic details that don’t matter much, unless they matter to you, in which case they matter quite a bit. One woman complains about the noise from the Suprema Meat Company, which wakes her up at four in the morning. She starts to tell Schaaf the company’s cross streets, but the mayor stops her. “Yes,” she says, “it’s right on the Emeryville border.” Another woman frets about graffiti at Mosswood Park. Delighted to show off some digital innovation, Schaaf calls up a new smartphone app that allows her to request graffiti removal through the city’s abatement program. “It works for potholes, too,” Schaaf says proudly. “Everything.”

For every constituent who wants to talk about larger issues like homelessness or housing prices, however, there’s another who simply wants to thank her. “I just want to thank you for what you did,” says a starstruck woman carrying a bag of produce. Schaaf clasps her hands in prayer against her chest and expresses her own gratitude. All morning long it’s like this: Schaaf pivoting between filler of potholes and resistance hero. What she’s being thanked—and protested—for is her decision, made just weeks earlier, to issue a public warning about an impending federal raid on undocumented immigrants. Her action drew praise from many of Oakland’s leaders, but it garnered the opposite reaction from President Donald Trump, who labeled her a “disgrace” during a White House meeting.

As the morning goes on, more and more right-wingers gather, several of whom protested earlier this morning at a coffee shop in Fruitvale that refuses to serve uniformed police officers. Some of them seem disconcertingly amped up. The guy who runs the farmers’ market pleads with the protesters to clear a path on the sidewalk. “We have families with strollers who can’t get through,” he says. An older white woman thrusts a poster toward Schaaf that reads “Lock Libby Up.” A blond college-age woman wearing a Black Sabbath T-shirt approaches the mayor while the older woman records them with a pink-encased iPhone, her fingers tipped with thickly lacquered nails.

“I know this is very emotional,” Schaaf says to the young woman as a greeting, calmly holding her gaze. Her name is Ashton Whitty, and she’s a Berkeley resident and minor YouTube star known for videos like “Why Liberals Can’t Date Me” and “Is David Hogg Leading a Leftist Dictatorship?” Whitty addresses Schaaf politely but insistently, with the nervous air of a student challenging a professor. Her premise is that Schaaf’s actions contravened federal policy on immigration—a power that a mayor shouldn’t have.

“Sanctuary laws are legal,” Schaaf says.

“But people would say that goes against the federal government,” Whitty replies.

“We’ve taken the position that we’ve not gone against the federal government,” Schaaf, a lawyer, counters, before launching into an exegesis on the vagaries of sanctuary law.

Whitty nods. Later she posts a video of their interaction spliced with her own exasperated commentary. Titled “Confronting Oakland Mayor Who Tipped Illegal Immigrants,” it currently has 62,000 views on YouTube.

In the distance, Jeffrey shouts, “I’m not a fascist or racist! Hitler was a socialist!” while a friend waves a big blue flag emblazoned with Trump’s name. One of Schaaf’s staffers pulls out his cell phone. I ask him if there are any police officers on hand. No, he says, but they are on their way. Like Whitty, Jeffrey has signed up to talk to the mayor. Fearing combustion, the staff try to shoo him away. He seems resigned to being pushed aside—he has the look of a guy who shouts because people tend not to listen to him. Schaaf intercedes: “If he signed up to talk, I’ll talk to him.”

Jeffrey walks up to the mayor, the staffers watching warily. Schaaf takes his gaze, and Jeffrey suddenly becomes shy, stumbling over his words. “These people are here illegally. Don’t you have a duty to American citizens?” he asks, sounding genuinely anguished. Schaaf waits for him to finish and carefully responds. “All I was doing,” she says, “was informing people of their legal rights and responsibilities.”

Later, I ask Schaaf what it felt like to talk to the protesters. It would be so easy—and understandable—for her to avoid such fraught confrontations. But that approach doesn’t seem to interest her. “I believe that a huge part of my job is trying to understand where people are coming from,” she says. “One man asked me, ‘Why are you putting these undocumented criminals in front of Americans?’ I sincerely said, ‘I’m sorry if my actions made you feel that way, because that was not my intent. My intent was not to make you feel like you were put behind someone else.’ I can say that with honesty. I can say that because I was listening to how he felt.” 

Forty-five years ago
, while Schaaf was in elementary school, two political scientists at UC Berkeley wrote a book about Oakland titled Implementation. It has a long subtitle that begins, How Great Expectations in Washington Are Dashed in Oakland. In the book, written as a rejoinder to the more hagiographic Oakland’s Not for Burning, Jeffrey Pressman and Aaron Wildavsky explain why a Great Society program designed to pump money into Oakland and bring jobs to African Americans utterly failed. Even in the best of circumstances—money ready to be spent, federal-local agreement, and a policy’s widespread popularity—the federal initiatives fell apart. If it’s that hard for Washington to carry out programs in a city under the best of circumstances and with the best of intentions, the authors say, imagine how hard it is when a city chooses “to oppose, delay, and reject federal initiatives.”

Oppose, delay, and reject. You could write a dissertation about l’affaire Schaaf and not change a word. By Tuesday, February 27, agents from U.S. Immigration and Customs Enforcement had arrested more than 150 suspected undocumented immigrants across the Bay Area. ICE acting director Thomas Homan told the Washington Post that the agency could have arrested more, except that on the Saturday before the raids, the renegade mayor of Oakland had announced the impending roundups via Twitter and press release. The acting director claimed that 864 “criminal aliens” would have been arrested but “were able to elude us thanks to the mayor’s irresponsible decision.” (A few days later, an ICE spokesperson resigned, saying he had been pressured to inflate the number of immigrants said to have escaped arrest.)

In the days that followed the raid, the conservative Internet, talk radio, and television apparatus pilloried Schaaf, with few national Democrats, if any, running to defend her. “What she did is no better than a gang lookout yelling, ‘Police!’ when a police cruiser comes into the neighborhood, except she did it to a whole community,” Homan told Fox News. “These are American heroes that strap a gun to their hip every day to defend this nation, and to tell the criminals that we’re coming in the next 24 hours is just incredible.”

On March 1, White House press secretary Sarah Huckabee Sanders said that the Department of Justice would review Schaaf’s actions, calling them “outrageous.” Attorney General Jeff Sessions delivered a speech in Sacramento on March 7 in which he called out the mayor personally: “How dare you needlessly endanger the lives of law enforcement just to promote a radical open-borders agenda.” The administration’s threat, however remote, was that Schaaf could face criminal charges for obstruction of justice.

Schaaf may or may not have expected the volume of criticism leveled at her, but she certainly anticipated some personal recriminations, saying in January that she would be willing to go to jail to “protect all of our residents, regardless of where we come from.” Pulled by her own political instincts as well as by the explicit wishes of the community, she also may have been pushed to atone for a previous mistake by the city.

Despite Oakland’s decade-old “sanctuary city” policy, which declares it “a City of Refuge for immigrants from all countries,” in August 2017 members of the Oakland Police Department actively collaborated with ICE, directing traffic as the federal agency carried out a smaller raid of undocumented immigrants. Afterward, Schaaf was incensed at what she saw as the department’s complicity, as was the Oakland City Council, which voted unanimously on January 16 to end cooperation with ICE. The very next day, a story in the Chronicle suggesting that another, much larger raid was in the works raised the level of concern within the mayor’s office.

One month later, Schaaf received information from what she describes as multiple credible sources that raids were coming. (She has consistently refused to divulge her sources.) Right away, Schaaf saw two possible courses of action: to disseminate the information to the broader public or to pass it along through private channels. As she agonized, Schaaf reached out to an old friend, Emma Paulino, an organizer with Oakland Community Organizations, a nonprofit advocacy group. The women had met two decades ago, when Schaaf worked for Councilmember Ignacio De La Fuente, who represented Fruitvale, one of the centers of Oakland’s Latino community. Back then, Paulino was pushing for a new elementary school and traffic islands to combat speeding, and Schaaf was one of her first points of contact within city hall. Now, decades later, Schaaf had a question for Paulino: What would Oakland’s Latino community want her to do in response to a rumored ICE raid?

Paulino convened a conference call with Father Stephan Kappler, the pastor of St. Jarlath Catholic Church in Fruitvale; Cristina Hernández, a representative for the Catholic diocese in Oakland; and Paul Chavez, the executive director at Centro Legal de la Raza, a legal services organization in Fruitvale that serves the Spanish-speaking community. During the call, the ad hoc task force debated how to advise the mayor, who awaited their recommendation. The group quickly dismissed advising Schaaf to do nothing. “There are some matters of social justice that don’t require a whole lot of weighing,” Kappler says. His gut reaction was that “maybe it’s best not to reveal this” in public because “it might create anxiety in the community,” and Paulino agreed. But as the group mulled it over, they began to see the wisdom in going public. “If this is credible information, and we are not sharing this with our families,” Kappler says, “then that would create a lack of trust.” The group soon arrived at a decision: Tell the mayor to go public.

Late on Saturday afternoon, Schaaf was in the middle of packing up her son’s bookshelves (“It’s a long story,” she says) when she received the expected call from Paulino’s advisory group. That evening, just prior to sitting down for a meal with some longtime friends, she issued the press release: “I literally was pressing send on the message while our dinner was starting.”

The next morning, Schaaf’s office was overwhelmed with media inquiries. Hastily, her staff called a press conference at a senior citizen center in Fruitvale run by the Unity Council, a nonprofit service provider. Schaaf was scheduled to attend a separate event there, announcing a community resiliency strategy—fire safety, building upgrades, and the like—that stemmed from the 2016 Ghost Ship fire, which occurred nearby. Her office asked Chris Iglesias, the council’s director, if the mayor might hold a separate event upstairs just before the scheduled one. He asked what it would be about. “‘Oh,’ they said, ‘she just wants to get some information out to the public,’” he says.

When the press arrived, Iglesias teed the mayor up and then left to set up the other press conference, to be held downstairs. “I was going back and forth,” he says, and it took some time for him to realize the magnitude of what Schaaf was facing. Schaaf’s message was terse: She had reason to believe that a raid would happen soon. She directed people to Centro Legal de la Raza and outlined how Oakland’s schools and police would respond. “We want residents to prepare,” she said—to know their legal rights, to have a family plan in case one person ended up in jail, and to look out for their neighborhoods—“not to panic.”

The symbolism of the moment—as full-throated an act of resistance as the Bay Area has seen since the 2016 election—seems to have hit Iglesias before it even hit Schaaf. “‘Whoa, that’s pretty ballsy,’” he says he thought as she fielded questions from the media. “It was 100 percent baller. She’s an Oakland baller, right there.”

Schaaf believed she had the legal and moral right to act as she did—a position she maintains to this day. “Who am I, as a person of power and privilege, to be so condescending to think that the community cannot handle the truth?” she asks. “They live in fear every day. The difference was that now they had information.”

Aside from some wan criticism from local political rivals, it was a decision that most Oaklanders appear to support. “At the beginning, I felt it might be a political move,” says Alicia Contreras, the head of the Spanish Speaking Citizens’ Foundation. “But when the raid actually happened, to see a white mayor say she would go to jail if she had to, that she would do everything she could to protect us, was a powerful message.”

The following Sunday, in the parking lot of her church, an undocumented man approached Paulino. “Tell the mayor thank you,” he said. “Tell her that she’s our champion.” 

At least on paper
, Libby Schaaf seems an unlikely avatar of the resistance. She is, by Oakland’s standards, a moderate Democrat—a straight, white, 52-year-old Jewish attorney who grew up in the Oakland Hills and who, according to some friends, might be a partner at a white-shoe law firm had she not been captured by politics. Politically, she draws support from the same coalition of voters that swept Jerry Brown into the mayor’s office in 1999—homeowners, business owners, whites and Asian Americans, and League of Women Voters types. She lacks deep support among African Americans, progressives, and voters who live in West and East Oakland.

Schaaf came into office in 2014 after two disastrous predecessors: the hardworking but poorly performing Jean Quan, whose equivocating response to the Occupy protests alienated both the left and the center, and the not-so-hardworking former congressmember Ron Dellums, who rarely showed up to city hall. Schaaf took first place after a bumper car ride of an election with 14 candidates, including the incumbent Quan. Of the seven most credible, Schaaf stood in the ideological center, not as progressive as her fellow councilmember Rebecca Kaplan and not as law-and-order as San Francisco State professor Joe Tuman. An endorsement from Brown helped voters converge on her in the confusion, and Schaaf defeated Kaplan in the final round of ranked-choice voting by 63 to 37 percent. (Kaplan is said to be planning another mayoral bid against Schaaf in the 2018 election, but the filing deadline is not until August.)

After a brief honeymoon period, Schaaf’s time in office became marked by troubles both chronic and acute. The school district, which the state took over from 2003 to 2009 after a fiscal crisis, continues to underperform both educationally and financially; it made $11 million in budget cuts in November 2017. The police department has been under federal over sight since 2003, and its problems were compounded after a suicide note written by one officer in 2016 led to the discovery that at least 14 others had sexually abused an underage prostitute. After the chief of police resigned on June 9, 2016, the department cycled through three chiefs in eight days before being put temporarily under the control of city administrator Sabrina Landreth. On January 4, 2017, six months after issuing her instantly iconic dig at macho cop culture—“I am here to run a police department, not a frat house”—Schaaf appointed the first woman to officially head the department, Anne Kirkpatrick.

In the midst of this turmoil came the Ghost Ship fire, which killed 36 people on the night of December 2, 2016, at an unlicensed warehouse in Fruitvale that had been converted into an artists’ collective. In the wake of the fire, Schaaf offered both carrots and sticks—a $1.7 million grant to help artists secure affordable spaces, but also a crackdown on unpermitted and unsafe live-work environments.

Any one of those events could have sunk a mayor, but they didn’t sink Schaaf. The city’s roaring economy and her adroit handling of the crises have kept her popularity high. An Oakland business group called the Jobs and Housing Coalition, which has conducted two polls a year for the last decade, completed its most recent survey on March 3; out of 400 likely voters, 61 percent approved of her performance. Schaaf’s favorables have stayed high throughout her term, hitting 72 percent in December 2017 and never dipping below the high 50s.

Not everyone in Oakland feels buoyed, though. Schaaf is the mayor of a diverse city in which Latinos, African Americans, Asian Americans, and whites each make up roughly a quarter of the residents. But Oakland’s demographics have always been changing. An overwhelmingly white city prior to World War II, it transformed into one in which a plurality of residents were black, then into the current one, in which the percentage of African Americans has been dropping for almost 40 years and the composition of the power structure has changed accordingly. The March 3 Jobs and Housing Coalition poll found that only 34 percent of black likely voters would reelect Schaaf, while 41 percent would choose to replace her. It was the worst she fared among any racial group. (In the city as a whole, 45 percent favored reelection while 30 percent favored replacement.)

Jorge Lerma, a member of Oakland’s neighborhood police advisory board and the Latino Task Force and a veteran of the Chicano power movement, sums up both the knock against Schaaf and her defense against it. “People sometimes say she’s the little white girl from the hills, a privileged little princess having her day in the slums and the ghettos,” he says. He disagrees. “She’s deeper and stronger than that.”

This is certainly true of her standing in the Latino community. Schaaf’s Spanish is good enough for her to do a regular call-in show—with some assistance—on a Spanish-speaking radio station and to conduct interviews with the Latino press without a translator. And Schaaf’s name adorns one of the steel beams at the Fruitvale Transit Village, a celebrated mixed-use development near the BART station that she worked on for decades. “She could have stayed in the hills,” Lerma says, “but she took her privilege as an opportunity to give back, not to run away.”

Zachary Norris, executive director of the Ella Baker Center, the nonprofit founded by CNN’s Van Jones, has a more nuanced view. An African American, Norris praises the mayor for her handling of the ICE raids. Yet there is something about Schaaf and other Oakland leaders that many in the African American community have found difficult to trust. “People can see through the glad-handing,” Norris says. “I’m not accusing her of that, but [that suspicion] is a challenge that has to be met with sustained attention.”

For her part, Schaaf argues that she has put in the work with communities of color—and not just when she got elected. When I start to offer a comparison between her upbringing in Montclair and mine in predominantly white Moraga, she bristles. “I think I had a different upbringing,” she says. “And I haven’t lived in Montclair since I was 17 years old.” After Schaaf graduated from college, she and her mother started a nonprofit that took them across the city. “I have an old picture of us in deep East Oakland at a school-supply giveaway,” she says. As a young lawyer, she did pro bono work for political asylum seekers from El Salvador. And her first job in politics was not with a white council­member in the hills but with a Latino officeholder representing Fruitvale. She adds, a bit defensively: “My best friend growing up lived off of High Street and was African American.”

Schaaf’s stand against the raids had a double effect. In addition to being, in her mind, the right thing to do, it was also unimpeachably good politics. As Robert Gammon wrote in the East Bay Express, “It was pure political gold. In the liberal East Bay, nothing beats getting called out by Donald Trump.” Every time Trump says her name, Schaaf moves that much closer to reelection, agrees developer John Protopappas, a longtime supporter and friend. (“House money” is how one aide describes the presidential disses.) She also moves closer to the race she may choose to run next. “She has created a platform for future offices that is true to who she is,” Protopappas says.

According to published reports, Schaaf explored running for lieutenant governor of California in the upcoming election before deciding against it. When she does choose to run statewide or for Congress (Dianne Feinstein, 84, and Barbara Lee, 71, have to go sometime), her famous act of defiance could permanently elevate her in the same way that San Francisco mayor Gavin Newsom’s stand for gay marriage in 2004 helped propel him to the lieutenant governor’s office and, perhaps, to the governor’s seat. A poll by UC Berkeley’s Institute of Governmental Studies indicates that 56 percent of the state’s voters favor the statewide sanctuary law, while 41 percent oppose it. (More than 8 in 10 Democrats support it.) If Schaaf has ambitions, standing up to Trump only helps them.

But in so doing, has Schaaf raised the risk of a retaliatory raid? Could, as the Chronicle editorial board fretted, “the mayor’s defiance…increase the odds that a notoriously thin-skinned and vindictive president will order Oakland to be targeted”? “I don’t know about that,” Iglesias says, pointing to the distractible Trump’s lackluster record of turning bluster into action. “I think he just likes to bash people.” For her part, Schaaf doesn’t spend her days war-gaming the president’s next moves. “I have a job to do as the mayor, and it’s not to revise immigration policy,” she says. “I cannot let President Trump’s strange proclivities for revenge distract me from the job that I have to do.”

And that job is daunting. Although crime has dropped precipitously—the number of murders in 2017 was the lowest since 1999, according to FBI statistics—Oakland’s per capita crime rates remain among the highest in the country. Despite the construction cranes that clog Uptown and Brooklyn Basin, economic prosperity still has not reached communities ravaged by generational poverty. And the raw cost of housing has pushed a growing number of Oaklanders out into the streets, leading to a sudden spike in homelessness that Schaaf calls “soul scathing.”

None of these problems lend themselves to easy solutions or grand moments of moral clarity. Wary of this quandary, the mayor shies away from even describing them as problems that will be solved: Rather, they’re chronic conditions that can be gradually improved, but never eliminated. “The day you take the office, you are responsible for all the ills of the city,” Schaaf says, noting the irony that these ills are the same things that compelled her to run for office in the first place. “So you find yourself being yelled at, protested against, for the very causes that you have been yelling and protesting about. That’s your journey to a position of leadership. That day you take the title, you’re responsible. It feels hard, but it feels like it’s what I signed up for.”

There will be plenty of opportunities for Schaaf to be protested again. But at least for one moment, her stand on the immigration raids unified a fractious city. As Norris, who disagrees with her on many issues, puts it, “She took a stance. That’s important and should be acknowledged. I’ll tell you all the things I don’t think she’s doing well. But people should recognize that on this, she’s standing with the community.”