In the Mayor’s Race, Will Oakland Become the Next Boston?

In the eyes of the nation, Libby Schaaf is considered the “the resistance,” but in Oakland, she might be the establishment Democrat voters don’t want this season.


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Photo of Libby Schaaf by Chris Duffey

By many accounts, Oakland Mayor Libby Schaaf is more popular than ever. In February, she took a very public stand against the Trump administration’s xenophobia, warning the public about an impending ICE raid. That led to verbal sparring with the president and Attorney General Jeff Sessions, transforming her into a spokesperson of “the resistance” and giving her a level of national recognition that few Oakland politicians achieve.

But while Schaaf may have a radical edge in the eyes of the rest of the country, locally, she’s seen by many as an establishment Democrat who hasn’t done enough to address issues of gentrification, displacement, and homelessness. Schaaf’s administration also was has been rocked by several catastrophic examples of the failures of city government, including a police sex trafficking scandal and the deadly Ghost Ship and San Pablo Avenue fires. While these calamities weren’t the mayor’s fault, her administration’s responses were far from transparent.

So as she faces re-election, Schaaf runs the risk that she may no longer be progressive enough for Oakland voters.

“Even though Libby is a decent person, I think many activists have viewed her as not helping stop the process of displacement, and not helping poor people in Oakland during a building boom and housing crisis,” said Jack Kurzweil of the Wellstone Democratic Renewal Club, a progressive political organization active in Oakland politics. “I think what Cat Brooks represents, and to an extent Pamela Price, is a challenge to the status quo.”

These challenges would vex any mayor in a normal election, but Schaaf is seeking a second term during a year when Democratic voters, especially in liberal regions, appear to be gravitating toward radical candidates. A few challengers running far to the left have toppled establishment favorites indicating a desire for dramatic change.

When Schaaf first ran for Oakland mayor in 2014, she promised to modernize and fix the city’s dysfunctional departments. “Oakland government can be transparent, innovative, and efficient,” she said during the campaign.

She also pledged to “make Oakland safe again” by speeding up the recruitment of new cops to achieve a force of 800 officers, a level not seen since 2009. More officers would lead to less crime, she asserted.

And Schaaf said that the city’s real estate boom could be equitable. “We can revitalize our city, have progress and development, invite new people to be here, have new businesses open up, and we must do it in a way that the people who have always been here don’t get displaced and directly benefit from that new prosperity,” she said at the time.

Since then, the boom has accelerated and Oakland is adding thousands of new housing units. The police are staffing up. Crime has dropped. Streets are being re-paved. And Schaaf has overseen several successful public-private partnerships, most notably the Oakland Promise, which sets up college funds for high school students. Her list of achievements is long. But by other measures, it can be argued that she hasn’t convincingly delivered on some of those promises from four years ago.

She promised to reduce police misconduct settlements by about $4 million per year. “Payments in 2012-13 were $7.8 million. Cutting that number by half will free up $3.9 million,” Schaaf explained in her 2014 public safety plan. But just one settlement this year resulted in a $12 million payout to a motorcyclist struck by a police officer who illegally ran a red light.

Looming over everything is potential liability in the Ghost Ship case. The city may even be forced to issue bonds to pay off its gargantuan cost, depending how the case goes.

Oakland’s infrastructure is still crumbling. The sewers, in particular, have been leaking toxic sewage into creeks and Lake Merritt, and the department of public works has been accused of covering up these violations.

So has Schaaf created a more accountable and transparent city government?

“I feel like I have delivered on that promise,” said Schaaf in an interview. “When each of those crises hit, I was honest and transparent with the public about what our shortcomings are and how we will fix them. Particularly with the sex scandal, I was just as angry and horrified as the public.”

The mayor also has streamlined the development of new housing, and she supported several key tenant protections and campaigned successfully in 2016 to raise hundreds of million for affordable housing though Measure KK.

“We now have just under 7,000 housing units under construction about to come on the market,” said Schaaf.

But the mayor still hasn’t been able to shift the narrative around gentrification, displacement, and homelessness, as the city’s housing market remains unaffordable for all but the most affluent.

Schaaf’s response to the homelessness crisis has been innovative, but critics charge that it’s not enough. Her Tuff Shed program to provide immediate emergency shelter with access to electricity, bathrooms, secure storage, and social services is unlike anything else in California. But it hasn’t noticeably reduced the number of unsheltered people on the streets, and homeless advocates and activists have blasted the mayor for not spending more on the homeless.

John Kirkmire, an Oakland resident and activist working to address the homeless crisis around Lake Merritt, called the Tuff Shed camp on Northgate Avenue an “inhumane, undignified and a terrible way to treat the disenfranchised.”

Former Oakland Mayor Jean Quan said Schaaf faces a potential scenario similar to what happened in Boston. Earlier this month, Boston City Councilmember Ayanna Pressley, a progressive black woman, crushed 10-term Congressmember Michael Capuano, who is white, in the Democratic Primary. Capuano was seen as safe because of his strong progressive record and endorsements from Democratic Party bigwigs.

Schaaf’s secret weapon in the 2014 election was Gov. Jerry Brown’s endorsement, and this time around she has been endorsed by Sens. Dianne Feinstein and Kamala Harris, and former San Francisco mayor and gubernatorial candidate Gavin Newsom, in addition to Brown. It’s not clear this will mean anything come November, however.

“Voters there [in Boston] thought maybe it was time to have more people in Congress who grew up poor and had to struggle with the kinds of problems we’re trying to solve,” Quan said. While Schaaf is also considered a strong progressive candidate, she may not be viewed as the agent of real progressive change this time, added Quan.

Following the surprising victory of Alexandria Ocasio-Cortez in a New York congressional primary race in June, some are saying this is also the year for women of color in politics, and Schaaf happens to be facing two very strong black women.

Cat Brooks has never held elected office, and until recently, it seemed inconceivable that she would. Even Brooks describes her campaign as something she was “pulled” into. But in her stump speeches, Brooks positions herself as the “rational” candidate when Democratic Party voters appear to be moving to the left. Her critique of Schaaf is that the mayor simply isn’t doing enough to address the major crises that are impacting Oakland’s working-class communities.

“Our babies are dying in the streets. Thousands more are sleeping in them,” she said at a debate held by the Alameda County Democratic Party in August, referring to gun violence and homelessness. “And thousands more are being pushed out of their city.”

Schaaf has, in fact, presided over a dramatic decline in gun violence, but it’s not due to her initiative to hire more police. Rather, it appears to be the fruit of Operation Ceasefire, a crime reduction strategy initiated under Quan that Schaaf supported. As a result, over the past seven years, shootings and homicides have steadily dropped.

But Schaaf’s push to hire more cops hasn’t worked out well. An audit by OPD’s inspector general revealed in 2017 that numerous officers were hired even though they had various red flags on their records. It gave credence to the theory that recent explosive police misconduct episodes were an outgrowth of the hiring blitz.

Before running for mayor, Brooks would advocate for abolishing the police. Now, she’s proposing to redirect the $30 million spent annually by the Oakland police on overtime to job training, mental health services, low-income housing, and other “preventative” measures. It’s just one way Brooks has shifted subtly toward the center, toning down her image as a firebrand revolutionary.

But while voters might be moving to the left, it’s not clear that enough people are willing to embrace a candidate like Brooks who has a long record of radical activism. Brooks’ engagement in politics in recent years has typically involved direct action and disruptive marches in which she has led coalitions making non-negotiable demands. To be a successful mayor, she’ll have to shift to a consensus-building mode instead.

Pamela Price, considered another frontrunner against Schaaf, is just as critical of the mayor’s public safety record. She’s especially focused on what she claims is Schaaf’s failure to hold the police accountable for misconduct.

At the Wellstone Democratic Renewal Club’s candidate forum in August, Schaaf claimed that she took the extraordinary step of firing three police chiefs in a row to clean house during the sex trafficking scandal. Price countered that Schaaf had previously described Sean Whent’s sudden departure as being due to “personal reasons,” not because she fired him. And Schaaf didn’t fire Whent; he was allowed to resign.

More recently, Schaaf’s new police chief, Anne Kirkpatrick, actually promoted other police brass who were implicated in covering up the sex trafficking scandal. These and other actions underscored that Schaaf hasn’t delivered on her promise of cleaning up and modernizing OPD.

Price points to the election results from June’s primary in which she ran against Alameda District Attorney Nancy O’Malley as evidence that she can win in this new political atmosphere informed by the success of Black Lives Matter. Price carried Oakland’s flatlands neighborhoods thanks to a strong turnout by black and Latinx voters. She thinks it’s a sign that Oaklanders want a mayor who will take radical steps to hold the police accountable, and tackle other issues with similar energy.

Schaaf thinks Oakland is different and if voters here are shifting further to the left, they’ll still pick her to lead. “On a national stage I’ve taken a pretty radical position around sanctuary cities, around protecting our immigrant communities,” she said. “I’m very clear and have a very unapologetic moral compass that has certainly been tested and shown.”

Whether Schaaf’s new reputation as a spokesperson of “the resistance” will burnish her progressive image with Oaklanders enough to overcome the pitfalls of her first term remains unknown — until November.

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