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Oakland's Libby Schaaf Is the Talk of the Town

Up for reelection this fall, the charismatic mayor is an unabashed cheerleader for her city, even when it means taking scathing criticism for her actions.


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By the time Oakland Mayor Libby Schaaf arrives at Jack London Square for one of her regular community visits, a crowd of her constituents has already gathered. They’re here for Mobile Mayor, a series of pop-up events where residents can speak directly with the city leader about everything from the housing crisis, to parking tickets, to her bold decision that infuriated the Trump administration.

It’s been a few months since Schaaf shot to national prominence—not a bad thing in a reelection year, even though she was both praised and pilloried—for her polarizing stance on immigrants’ rights. But during the Mobile Mayor forum, the charismatic and controversial commander in chief of the East Bay’s biggest city gushes with residents about nooks and neighborhoods as if they were chatting over the garden fence.

During her three-plus years in office, Schaaf, 52, has led Oakland through some of its most promising—and most devastating—moments. On the positive side: The city has seen a building boom; investment is up; crime is down; and the city has steadily burnished its reputation as a hip and happening locale, à la Brooklyn’s Williamsburg or Los Angeles’ Silver Lake. But there are many residents in Oakland’s diverse mosaic that will never benefit from these improvements, and the city has experienced some significant downsides on Schaaf’s watch: The Oakland Police Department has been rocked by scandals and revolving leadership; the recent NBA champion Golden State Warriors and the NFL’s Oakland Raiders have announced imminent moves (leaving only the Oakland Athletics to represent the East Bay in professional sports); and most tragically, the Ghost Ship warehouse inferno—the city’s deadliest fire—killed 36 people in December 2016.

Now, her constituents are asking tough questions. For instance, how can low- and middle-income residents afford a home in Oakland’s searing real estate market, and what does the city plan to do about the swelling homeless population living on sidewalks and beneath freeway overpasses?

A thirtysomething woman named Sandra and her husband step forward for their turn with the mayor. “First of all, I just wanted to say thank-you for standing up for the community,” Sandra begins. Schaaf smiles and nods, as Sandra recounts her long, labored house hunt.

Lately, the mayor has heard a lot of thank-yous for the public notice her office published on a Saturday night in February. Credible sources alerted Schaaf, the bulletin read, that U.S. Immigration and Customs Enforcement (ICE) was planning raids in the Bay Area—including in Oakland—that would begin as soon as the following day. “As mayor of Oakland, I am sharing this information publicly not to panic our residents but to protect them,” Schaaf wrote in the release, which she posted to her thousands of Twitter and Facebook followers. The notice went on to include resources for legal aid, and to outline local and statewide sanctuary policies.

The response was swift, divided, and inescapable: calls and even death threats from residents and, more often, from out-of-towners; relentless social media chatter; and—loudest of all in its media reverberation​—​blasts from President Donald Trump, Attorney General Jeff Sessions, and acting ICE Director Thomas D. Homan, likening Schaaf to a “gang lookout” and accusing her of obstructing justice.

But in Oakland, where Trump received less than 5 percent of the vote, Schaaf also hears plenty of gratitude and support from locals, even as the White House steadies its aim at sanctuary cities in response. (Ironically, the Oakland Police Department was criticized for cooperating with an immigration raid in August 2017; the public outcry prompted the city council to cut all future ties with ICE.)

Months later, Schaaf and her city remain targets, but the mayor is steadfast in her conviction that she made the best decision for Oakland. “I haven’t ever shared this with anyone, but I do sometimes say a prayer to make my heart big and strong,” Schaaf says. “I feel that leading with compassion and love is more important than ever in this day and age.”

 

Schaaf with writer Andrea Vasquez outside Oakland City Hall.

 

Heart of the City

Schaaf, who lives in Oakland’s Dimond District with her physicist husband and their two children, has spent most of her life in “the Town.” Born and raised in Montclair, she began serving the city as a child. She recalls volunteering with her mother, who once made young Schaaf wear a sandwich board and ask passersby for contributions to local school music programs. At age nine, Schaaf acted as a character at Children’s Fairyland and represented Oakland in parades and state fairs—instilling a sense of pride and ambassadorship of her city that ripened with time.

Schaaf attended Head-Royce, a private prep school, before transferring to the public Skyline High, where she was head cheerleader. The only years she lived outside Oakland were during university, first while studying political science at Rollins College in central Florida and then at Loyola Law School in Los Angeles.

“My college friends teased me that I was from the center of the universe because I would talk about Oakland so  much,” Schaaf says. “So, they thought it was hilarious when I became the mayor.”

Her postcollege aspirations were more professional than political, with the hope of becoming CEO of a multi-national corporation so she could travel the world, or a State Department worker specializing in arts and cultural affairs. (Schaaf’s father, a traveling salesman, wanted her to follow in her mother’s footsteps and become a flight attendant.)

Instead, Schaaf returned from law school to start her career at one of the largest law firms in Oakland at the time: Crosby, Heafey, Roach, and May (which has since merged with Reed Smith). During Schaaf’s time there, she and her mother founded Oakland Cares, a nonprofit that orchestrated hundreds of volunteer projects around the city.

The young attorney quit practicing law after only three years, later saying the work was boring. After leaving the firm, Schaaf spent her early thirties as a program director for the nonprofit Marcus Foster Education Institute, where she launched the first centralized volunteer program for Oakland’s public schools.

In the late 1990s and early 2000s, Schaaf cut her teeth in city politics as a top legislative aide for some of the city’s most iconic elected officials, including longtime City Councilman Ignacio De La Fuente and then-Mayor Jerry Brown. She ascended through high-ranking city jobs for more than a decade before serving on the city council from 2011 to 2015, where she earned a reputation as a policy wonk and a tireless booster for Oakland.

Schaaf has been described as enthusiastic and effervescent, and she often flashes a bright smile while rhapsodizing about her hometown. Fellow Oaklander Tomiquia Moss says she always saw the breadth of Schaaf’s love for the city, but it was not until Schaaf became mayor, and Moss her then–chief of staff, that Moss understood the depth of that love.

“Because the mayor is a white woman from the [Oakland] Hills and was an actual cheerleader and has an effusive personality, I think people misunderstand her projection of enthusiasm for a superficial commitment to our city,” says Moss, who served under Schaaf for two years. “It’s really important to know that it’s in this lady’s bones.”

 

“How Dare You?”

During a speech in Sacramento about a week after the ICE raids, Sessions blamed Schaaf for foiling the arrests of “800 wanted criminals that are now at large in that community,” citing the figure floated by ICE’s Homan. (Former ICE spokesman James Schwab, who resigned in March, later called Sessions’ statement “a flat-out lie.”) “So, here’s my message to Mayor Schaaf: How dare you?” Sessions implored. “How dare you needlessly endanger the lives of our law enforcement officers to promote a radical open-borders agenda?”

Schaaf shot back: “How dare you vilify members of our community by trying to frighten the American public into thinking that all undocumented residents are dangerous criminals?” she said. “How dare you distract the American people from a failed immigration system?”

Sessions denounced California’s sanctuary laws and warned that the White House was suing the state to block the policies, which limit employers’ and local law enforcement’s ability to cooperate with ICE and empower the state attorney general to oversee public and private immigration detention centers. (At press time, the lawsuit was still ongoing.)

Governor Jerry Brown called the lawsuit “a political stunt” that is “not about the truth” but “about dividing America.”

Brown, like many other politicians, condemned the White House’s directives without commenting on Schaaf. But a few political figures, including California Lieutenant Governor Gavin Newsom and U.S. Senator Kamala Harris, commended Schaaf for speaking out.

“I think Mayor Schaaf is doing exactly what she believes is in the best interest of her community, and I support that 100 percent,” Harris told reporters.

Another of Schaaf’s local advocates is Brian Stanley, former executive director of the Oakland Public Education Fund, who now works for the homelessness charity Hamilton Families. “It says something that she’s the one that said, ‘I’m going to stand up because this is what I believe, and this is what I believe this community believes,’ ” Stanley says.

In May, a Republican congressman introduced the Mayor Libby Schaaf Act of 2018. Iowa Rep. Steve King’s bill would punish officials who stand in the way of federal law enforcement with up to five years in prison.

While people on both sides of the issue either exalt or crucify Schaaf as a defender of immigrants’ rights, she is trying to get back to work as Oakland’s mayor, turning down numerous invitations to give keynote speeches and national interviews.

“My job is not to be a national spokesperson on immigration policy,” says Schaaf. “My job is to fix the potholes, to solve homelessness, to address the housing crisis in my city; it’s to continue to drive down crime. It’s to make sure we have a flourishing economy and full employment. That’s the job of the mayor.”

 

Fighting for the Future

Back at Oakland City Hall, the mayor has plenty on her plate—from an experimental and controversial initiative to clean up sprawling homeless encampments by offering temporary lodging in converted Tuff Sheds, to a shifting economy that continues to push out many middle- and low-income Oakland natives, to 3,600 housing units going up by the end of the year in an effort to increase housing stock and create jobs. At the same time, Oaklanders are grappling with dramatic changes in their city that bring improvements as well as growing pains.

“It is absolutely multidimensional chess that they have to play every day in order to try to move this work forward,” says Stanley, who worked with Schaaf on Oakland Promise, a multifaceted cradle-to-career program aimed at getting more Oakland-​born children and local public school students to graduate college.

Throughout the tragedies and challenges Schaaf has faced in office, Oakland Promise has been a labor of love that keeps her going. “You hold the grief and the suffering and the anger of a whole city, and that’s your job,” she says. “I think every politician needs a passion that gives them the energy to deal with all of the other things that come with the office.”

Schaaf also hopes Oakland Promise will help carry her into a second term; the program is a pillar of her reelection campaign, along with tackling public safety, infrastructure improvements, affordable housing, and homelessness.

“She is someone who believes very strongly that the best days of Oakland are ahead of us, and she’s trying to ensure that that future comes true,” Stanley says. “She is effusive in her enthusiasm about Oakland. And the hard stuff pisses her off just like it pisses everyone else off.”

If Schaaf is reelected this November, next year will mark her 20th anniversary as a city of Oakland employee. Constituents may have mixed feelings about her Tuff Shed program, or her alert about ICE, or losing the Raiders, but Schaaf says that among her mayoral opponents—who include community organizers Cat Brooks and Ken Houston—she can point to “real results.”

“Whether people always agree with me or not, they know that my heart is in the right place,” she says, “and that I come from an absolute dedication to the people of Oakland.”

 

The Mayor in Action: Memorable Moments

JANUARY 2015: INAUGURATION
A one-term council- member challenging an incumbent mayor, Libby Schaaf surprises many when she sails past 15 candidates to win Oakland’s 2014 mayoral election. She rides to her inauguration in a huge, mechanical, fire-breathing snail built by local artists for Burning Man—a nod to her commitment to the city’s creative community.

JUNE 2015: THE WARRIORS’ BIG WIN
For the first time in 40 years, the Dubs take the NBA championship title. An estimated half million revelers line the victory-parade route, which Schaaf and rapper MC Hammer roll through on her now-famous snail car. By fall, however, the team buys land for a new arena in San Francisco.

SEPTEMBER 2015: A LETTER TO UBER
After ride-sharing giant Uber spends more than $120 million on a site for its new Oakland headquarters, Schaaf sends company leaders a letter urging Uber to promote “techquity,” Schaaf’s term for balancing business goals with residents’ interests. Uber never writes back and abandons plans for the East Bay headquarters.

DECEMBER 2016: MOURNING FIRE VICTIMS
Schaaf is booed as she addresses the grieving city at a vigil for victims of the deadly Ghost Ship warehouse fire. Many blame the tragedy on the dearth of affordable housing options that drives some artists into makeshift homes and studios.

MARCH 2017: GOOD-BYE TO THE RAIDERS
When the Raiders announce they are leaving Oakland for Las Vegas, Schaaf lobbies the team to stay but draws the line at subsidizing a new stadium with taxpayers’ dollars. She insists that freeing the stadium property for redevelopment is better economically for Oakland.

JANUARY 2018: PROTESTERS AT HER HOME
About 50 activists pitch tents in front of Schaaf’s house to underscore the city’s worsening homeless crisis. She responds by saying she is “proud to live in a city where freedom of speech is fiercely practiced.”

FEBRUARY 2018: ANNOUNCING ICE RAIDS
Schaaf posts an alert on social media that ICE will sweep the Bay Area in the following days. As President Trump calls her actions a disgrace, the mayor says, “I did what I believe was right for my community … to protect public safety.”

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