Sixty days on the trail: an inside look at Oakland’s mayoral race

September

Braids pulled back, arm tattoo covered by the long sleeve of her light gray suit, organizer Cat Brooks stares straight ahead. Her brows are furrowed, her lips pursed. She’s on stage ready to fight to be the next mayor of Oakland.

Two seats to Brooks’ right, Mayor Libby Schaaf takes her place at a folding table draped in wrinkled black cloth. Arriving a minute late, carrying a few sheets of paper, she looks out at the crowd, giving the audience a smile, bunching her cheeks and squinting her eyes.

There are just enough folding chairs to seat the crowd of about 200 gathered in Allen Temple Baptist Church’s auditorium for one of the first mayoral forums of the election season. The mayor is the first to speak. She swings the mic cord across the table and begins. “I’m hella proud to be born and raised in Oakland and have lived here my whole life,” Schaaf says, then gives a shout out to her alma mater, Skyline High School, before asking for Oakland’s vote on November 6. The audience applauds.

Taking the mic, Brooks stands, pushing back her chair, straightening her back and lifting her chin. “These are perilous times we find ourselves in,” says Brooks in a booming voice that could carry even without a speaker. “I’m running because I believe progress and development are good things, but they must happen in an equitable way that serves everybody, not just a chosen few.” Cheers erupt—a few stand to give her an ovation. Brooks sits down, preparing for the next question.

For the next two hours, Brooks, Schaaf, and the other seven mayoral candidates field questions from a moderator on illegal dumping, affordable housing and homelessness. As the night wears on, the challengers gradually amp up their attacks on the incumbent. Candidate Ken Houston calls Schaaf a “career politician,” while opponent Saied Karamooz compares her statements on homelessness to “Kellyanne Conway’s alternative facts.” At several points, the audience boos and yells indiscernible comments when Schaaf speaks. At one point, they become so loud the moderator is forced to intervene.

The mayor’s race has been a tempestuous one, full of anger and frustration at the current state of the city and desperation for change. For a group of liberal organizers, it’s been driven by a hope that Brooks, a progressive black woman, could defy expectations and unseat Schaaf, a popular white, moderate incumbent.

Brooks and her base believe they are part of a national movement of minority progressives challenging the Democratic establishment this election cycle, engineering stunning wins in the primaries. From Ayanna Pressley’s upset of a 10-term incumbent in Massachusetts to Alexandra Ocasio-Cortez’s similar victory in New York in her run for longtime fellow Democrat Joe Crowley’s seat, women of color are winning, and Brooks believes she could be next.

A lifelong organizer, Brooks’ activism took a turn in 2009. She had just moved from Los Angeles to Oakland as a single mother with her infant daughter when 22-year-old Oscar Grant, an unarmed black man, was shot and killed by a BART police officer. It changed her. She went from advocating for education equality to protesting the police and organizing demonstrations. In 2014, Brooks co-founded the Anti-Police Terrorism Project (APTP) to end what the organization’s website calls “state-sanctioned violence against Black, Brown, and poor people.”

That year, Schaaf was elected mayor at the height of Black Lives Matter movement, finding herself at odds with a vocal member: Cat Brooks. After May Day, 2015, when raucous protesters smashed windows and set cars on fire, Schaaf tightened city regulations, banning marches after sunset. Brooks camped out on the front lawn of Schaaf’s Dimond District home in protest. Eventually, the mayor abandoned enforcing the policy. The next year, Brooks led a failed effort to recall the mayor, criticizing Schaaf for her response to police officers involved in a sexual exploitation scandal, her support for increased police funding, and for what Brooks saw as a disinterest in discussing police brutality in minority communities.

Brooks says she decided to run for mayor on a March day in early 2018. On her way home, Brooks drove past a number of homeless encampments. She’d done this many times before, but this time when she parked in her driveway, she couldn’t get out of her car. “I was just so tired,” says Brooks. “I was so tired of fighting with Libby and tweeting at Libby and Facebooking Libby and doing interviews about Libby. And then I was like, ‘What if there was just no Libby?’”

She announced her campaign on May Day on her KPFA radio show, UpFront, and later posted her campaign video on social media. It showcased the tool she had used in dozens of protests: a green and white bullhorn. “Some people say there’s no place for these at city hall,” she says in the video, referring to the megaphone. “I’m not ready to put this down. I’m ready for you to pick it up.”

Her platform as a candidate: to shelter the unsheltered, create what she calls “truly affordable housing” and to “save Oakland.” Throughout her campaign, she has promised to open all city buildings to offer the homeless an indoor place to stay and use “public lands for public good.” She plans to require developers building new homes to set aside units for “low, low-income residents.” She refers to her run for office as “the people’s campaign.”

Meanwhile, Schaaf has been running on a promise that a victory would grant the city stability and a continuation of the progress she says her administration is making. She touts the city’s Ceasefire program, which a recent study showed led to a 30 percent drop in gun-related homicides since the program began in 2013. As she tells the Allen Temple crowd, she’s proud to have created Oakland’s first Department of Transportation to “pave the damn roads.” Her proudest accomplishment, she says, is the Oakland Promise, which offers financial assistance public school students who hope to go to college.

She also lauds her experience as an elected official. With endorsements from nearly every regional leader—including California’s outgoing Governor Jerry Brown and Senators Dianne Feinstein and Kamala Harris—Schaaf argues that she is the candidate who’s worked in government and has connections to the major players who can help bring money and resources back to Oakland. Running with the slogan “Oakland Tough,” Schaaf is embracing her fighting side, defending her record and promising in her campaign ad to “protect Oakland’s values.”

So far, popular opinion favors Schaaf. An online survey done in June by EMC Research, a market research company with an office in Oakland, shows 49 percent of likely voters would pick the mayor, while only 11 percent would choose Brooks.

Schaaf also holds the advantage financially. By September, Brooks has raised a respectable amount of money in a short time: $108,000 in six months. But as quickly as the money has come in, it’s been spent. At the end of September, Schaaf’s campaign bank account has seven times what’s left in Brooks coffer: $322,308 compared to Brooks $44,594.

At Allen Temple, the debate is nearing its third hour, over its scheduled end time. Brooks stands and makes her final plea for votes. The room is silent. “I want to close with some very recent realities that are a direct result of the failure of this administration,” she says, as she tells the audience about the 37 people displaced after a fire at a Fruitvale homeless encampment known as The Village. Her speech gets louder and faster as she builds to her point, referring to the mayor but never calling her out by name. “Progressive in name only, Democrat in name only, in these times—in these dire and crucial times—it is no longer acceptable,” says Brooks.

“We have an opportunity on November 6th to change the game, to say ‘No, we want leadership that has been in the trenches with the people,’” exclaims Brooks. As she sits and passes the mic, applause and shouts emanate from the crowd. A person in the back yells, “Hell, yes!”

Schaaf is last to speak. She’s visibly agitated, raising her voice and repeating phrases like “I am proud.” Tightly clutching the microphone, she tells the audience she is “disappointed we heard so much misinformation tonight.” Someone in the crowd snickers, “Coming from you,” insinuating that it’s Schaaf who has spread inaccuracies.

Then she plays her Trump card, something she’s frequently been using on the campaign trail. In February, Schaaf had publicly warned Oaklanders about impending raids by federal immigration officials. Her announcement drew praise from many in the city’s progressive political community and communities of color. The president had threatened to prosecute her for obstruction of justice. In response, Schaaf appeared on CNN telling him, “I am not obstructing justice. I am seeking it.”

Schaaf reminds the audience about her appearance. “There is no one else up here who has gone on national TV and called our president what he is—and that’s a racist,” says Schaaf, briefing pointing one finger at the rest of the candidates. As her time runs out, some members of the audience start to yell at her, saying things like, “Enough, already!”

She speaks louder over the crowd. “That is why you can count on me to stand up for our community,” Schaaf says. As she sits with her head down, a handful of people clap, others continue to yell.

October

Packed in the back of a Lake Merritt coffee shop, people pull up stools and benches facing Schaaf. Straight from city hall, she’s in her work clothes: a purple collared shirt, black skirt suit and heeled riding boots. “You’ve probably seen me on TV,” says Schaaf as she paces from one side of the room to the other. “Tonight, you’re going to see a real person.”

At a meet and greet organized by Schaaf’s aesthetician, about 30 people, including the mayor’s mother, sit listening to her speak for an hour. “I’m totally embarrassed my mother is here,” says Schaaf looking wryly at a woman with a blond bob and acrylic glasses. “Clearly, I have not told a lie, because—believe me—she would correct me.”

Her mother, Barbara, nods in agreement.

Schaaf starts by delivering a version of her stump speech. She talks about her decision during law school at Loyola to join every student group—including the African American law student association and the La Raza Association—“because being from Oakland I needed to be around diverse people.”

She mentions her feud with the president. “He’s threatened me many times with jail and ‘Lock her up.’ But I have a good attorney,” says the mayor with a grin. Schaaf also touches on another fight, a “Twitter war” with the mayor of Cupertino, because during the same year Apple opened its headquarters there, bringing in 12,000 new workers, the city approved just 27 new units of housing, forcing many to live in Oakland, as Apple’s CEO would later complain.

After 15 minutes she opens the discussion up for questions. Drifting easily around Perch Coffee House, she responds to a few comments about the quality of Oakland schools while passing the mic to an audience member, who asks the most popular question this campaign season: “What are we doing to address the homeless crisis?”

The most recent survey—done in 2017 by the nonprofit EveryOne Home—estimated there are roughly 6,000 homeless people in Alameda County, and half of them are in Oakland. To address the issue, Schaaf’s administration has purchased and transformed two buildings into “rapid re-housing facilities” that offer social services and financial support to get residents into permanent housing. She and staff in the City Administrator’s Office are also working to open temporary Tuff Shed cabin communities, tiny homes behind locked gates meant to serve as transitional housing.

Access to the Tuff Sheds is offered geographically, meaning those who live in camps near the site are offered a spot first. People are allowed to decline the offer, but if they refuse, they will likely have to move their tents. It is the city’s policy that the area near the Tuff Shed site is cleared within a month of the shelter opening. Schaaf tells her audience that not everyone is “crazy about this. Nothing I do in Oakland is without controversy.”

“I’ve got everyone yelling at me on every side of the issue,” says Schaaf with a sigh, adding that she feels her approach is a compassionate one. If the Tuff Shed site is full—and the city does not have a spot to offer an unsheltered person—they will not clear their encampment. “We believe unless we have a place to offer someone, we shouldn’t force people to move,” she says.

Resident Phillip Johnson, who says he intends to vote for the mayor, raises his hand to disagree. “I think they should be told to leave,” says Johnson of the thousands of people living on the sidewalks and in RVs. As he waves his arms back and forth, his voice gets louder as he lists the issues he ascribes to homeless people, like RV’s taking up parking on the streets. After three minutes, a friend in the back stands up. “Brother, I love you, but some of us have questions, too,” he says.

Playing referee, Schaaf steps in, “I do really respect your point of view and your anger,” she says.

After a few more back and forths about illegal dumping, housing and affordable pre-school for all, it’s time for the last question. A woman in the back asks: “What’s possible for Oakland five years from now?” The mayor pauses. “Revitalization,” Schaaf says. “My hope is that we can prosper and revitalize but do it in a way that lifts up out long-time residents, that lifts up our most vulnerable residents.” She adds that a mayor going in the right direction needs a second term to offer stability and momentum.

The crowd gives her a warm round of applause. “If you have any more questions, you can ask my mother,” says Schaaf with a laugh as she grabs her purse, hugs a few goodbyes, and rushes out the door.

Wiping down the wood tables, Perch co-owner Kedar Karde says that tonight, he changed his vote from Brooks to Schaaf. “I blamed a lot of failures on her,” says Karde, referring the mayor. Now he feels it was an unfair view—that the city’s issues are bigger than Libby Schaaf.

But, he points out, that’s just his personal vote; the coffee shop is not endorsing Schaaf. If it did, he worries it would be bad for business. “It’s a heated race,” says Karde, noting that just agreeing to hold this meet and greet with the mayor “turned into a really big deal with our customers.” Some suggested they might stop coming to his shop if Schaaf was allowed to campaign in the space.

Community activist David Wofford, who ran for the District 5 city council seat in 2008, is also in the audience. He says he’s voting for Schaaf. To him, the race is already decided. “You’re probably too young to know this, but MC Hammer challenged Michael Jackson to a dance-off,” says Wofford, implying that Schaaf is Jackson and Brooks is MC Hammer. “MC was never on Michael’s level. It’s a different level.”

Schaaf’s work in city government began in 1999, when she became a legislative aide for then-council president Ignacio De La Fuente (District 5). After that, she transitioned into the mayor’s office, serving as special assistant to then-mayor, now California governor, Jerry Brown. In 2010, Schaaf became a politician herself, winning Oakland’s District 4 city council seat, representing wealthy North Oakland neighborhoods including Montclair and Dimond. Three years into her term, Schaaf decided to run for a promotion, filing paperwork to launch her campaign for mayor.

In a flooded candidate field that included then-incumbent mayor Jean Quan and City Councilmember At-Large Rebecca Kaplan, Schaaf was the underdog. An Oakland Metropolitan Chamber of Commerce poll released a few weeks before the 2014 election showed her coming in third behind Quan and Kaplan.

But this, according to Oakland political consultant Jim Ross, was one of the reasons Schaaf eventually won. “You don’t want to run as the frontrunner, because everyone gangs up on you,” said Ross, who among other things, lead the successful campaign to pass Oakland’s Measure JJ in 2016, strengthening the city’s rent control laws. To Ross, Schaaf ran as a competent “good government” candidate who appeared neutral, a benefit in a ranked-choice election.

Ranked-choice voting allows voters to pick their top three candidates. If no one wins more than 51 percent of the vote in the first round of vote tallies, the race will go to “rounds.” The candidate in the last place is eliminated, and their votes now go the voters’ second choice. This continues until a candidate receives more than 51 percent of the vote.

Schaaf also had a strong base in city council Districts 1 and 4— the hills and North Oakland—the part of Oakland with the largest base of consistent voters. These politically-moderate home-owners helped propel Schaaf to victory, according to Ross. “If you look at a map of Oakland where people vote, the vast majority of voters are east of the 580,” said Ross.

She also had top political advisors, hiring the powerhouse consulting firm SCN Strategies. The firm, led by Ace Smith, has an impressive reputation that includes helping get the last two California governors elected, running Kamala Harris’s successful bid for a US Senate seat, as well as the Ed Lee’s final election as San Francisco’s mayor. One of their clients—Schaaf’s former boss Jerry Brown—endorsed her during the last weeks of the campaign. By the next poll, Schaaf had pulled into second place.

To Greg McConnell, the executive director of the Oakland Jobs political action committee, Schaaf was destined to win in 2014. “I think the city was looking for something new,” said McConnell. “Libby was the new excitement and new energy.”

On November 4, 2014 ranked-choice worked in Schaaf’s favor. While she may not have been every voter’s first choice, she picked up enough second and third choice votes that when neither Quan nor Kaplan won outright on the first round of balloting, she was able to pull ahead. Schaaf celebrated her victory by riding through the streets of Oakland with MC Hammer in a fire-breathing art car shaped like a snail.

During her first term, Schaaf, for the most part, has remained well liked. McConnell notes that his consulting firm, which polls Oakland voters every six months, shows that Schaaf’s approval rating has never fallen below 61 percent.

But despite her popularity, throughout her campaign Schaaf has been insisting that a 2018 reelection “is not a lock.” “This is a city that does not like authority or power,” she says to a small group at a house party in Grand Lake, as supporters peck at a cheese plate and a loaf of banana bread. “As an incumbent, you are always at risk of being subject to this hunger for change.”

A woman sitting in front of her on the flowered couch asks, “So how can we help?”

“Tell your friends,” replies the mayor.

Late October

The race is tightening as November approaches. In West Oakland, Cat Brooks is working hard to catch up. In the last few weeks, her schedule has been packed with door knocking on the weekends and speaking engagements during the week. She says she’s sleeping very little, working 15 hours a day. “People say Libby has a slam dunk,” says Brooks. “Y’all ain’t seen nothing yet.”

On a Wednesday night after speaking before a Neighborhood Crime Prevention Council meeting in North Oakland, Brooks pulls up to an “arts fundraiser” intended to bring in some last-minute campaign contributions. Outside alaMar Kitchen & Bar in the Lake Merritt neighborhood, five kids scribble colors on black and white campaign posters. Inside, a trio of jazz musicians can be heard but not seen. Brooks supporters in t-shirts and pins are squeezed shoulder to shoulder to hear the candidate speak. The campaign staff taps the crowd for donations, time or money—they need all of them. “We’re trying to get some TV commercials on the air next week and they cost a lot,” yells a Brooks campaign volunteer.

Brooks steps up to seal the deal. “Where do I begin?” she asks, looking across the room, a giant grin on her face and tears in her eyes. The group, drinks in hand, yells in support. “We’re up in the polls,” hollers Brooks.

Days before, a poll released by the Oakland Chamber of Commerce showed Schaaf with 37 percent of the vote. Brooks and another mayoral challenger—civil rights attorney Pamela Price—each claimed 17 percent. Another 17 percent of voters were undecided.

Campaign manager Aisha Dew says this poll is exactly what they are hoping for. The campaign never expected to be ahead. She notes their goal is to prevent Schaaf from getting a majority in the first round of vote counting, thereby triggering multiple rounds. Picking up second and third choice votes is their best shot at winning, Dew says.

Dew is no stranger to running campaigns from behind. In 2017, she led progressive candidate Vi Lyles to become the first black female mayor of Charlotte, North Carolina. If Brooks wins, she’d likewise be the first black female mayor of Oakland.Dew joined the Brooks’ campaign late, coming on just two months before Election Day.

While the campaign is door knocking in every Oakland neighborhood, Brooks prioritizes voters in the flats, spending hours drumming up votes from those who’ve never cast a ballot before, starting at the San Leandro border and working their way west.

It’s this energy that Erin Armstrong, the chair of the political action committee of East Bay Women’s Political Alliance, says is capturing voters’ imaginations. “She helped put East Oakland and the flatlands on the map in a way that we haven’t seen a lot of mayoral candidates do,” says Armstrong.

That push brought together progressive organizations from across Oakland, says Carroll Fife, a grassroots organizer in Oakland for nearly 20 years. A self-described “Cat fan” who’s known Brooks since she moved to Oakland in 2008, “Cat’s voice and the issues that we are all fighting for are all coming together in one place,” said Fife. She lists groups like the California Nurses Association, the Harvey Milk Democratic Club, Oakland Justice Coalition and the East Side Arts Alliance as groups that have historically advocated for individual agendas but this election all endorsed Brooks.

Progressive political watchers say that Brooks’ campaign helped bring out first-time voters and political skeptics who are critical of the direction Oakland is heading under Schaaf’s watch. “It’s not just people who knew Cat. It’s people who were like, ‘Oh, wow. This shit is fucked up, and this agenda would benefit me,” says Isaiah Toney, a progressive Oakland activist who this year ran Clarissa Doutherd’s race for Oakland’s District 4 school board seat. Doutherd, like Brooks, is a progressive black women and first-time candidate challenging a longtime Oakland politician, former school board president Gary Yee.

And political watchers agree that Schaaf had lost some of the support she had in 2014, particularly amongst Oakland’s second biggest voting block, African Americans. According to McConnell, many did not “think they were benefitting from the change and growth that were happening in the city, which is why a candidate like Cat Brooks was able to start making some noise and attracting attention.”

Ross agrees, saying that the second time around, Schaaf has to face a new challenge: blame for the state of the city. “There’s no doubt there are a lot of people who are fundamentally disappointed in the direction the city,” says Ross.

At her fundraiser, Brooks, too, reminds voters that Schaaf’s reelection bid isn’t a lock. “We’re not ahead of her yet. But we’re inching up there because the people’s message is spreading like wildfire, and it’s spreading because of all of you,” declares Brooks.

Gina Tomlinson, an information technology executive, stands at a nearby cocktail table clapping along with the crowd. She’s voting for Brooks. “I was on her immediately,” says the Ohio native. “I never wanted to vote for anyone else.” She’s not sure Brooks will win, but she’s hopeful. “We’ve seen these other dark horses across the country and win,” said Tomlinson, referring to Ocasio-Cortez’s June primary victory. “It can happen.”

To Tomlinson, a Schaaf victory¬ would be a “horrible thing. Two years from now—certainly four years from now—Oakland will be unattainable for the masses.”

“Let’s take our city back y’all,” Brooks yells to a revved-up crowd. “We have an opportunity to make a real change. We’re not talking about the blue wave. We’re talking about the progressive wave.”

November

Mug in hand and purse slung on her forearm, Brooks walks into her campaign headquarters, a building behind a West Oakland church. It’s the last Saturday before Election Day. The room is covered in posters and whiteboards, including an Election Day countdown. On the front table, Brooks’ distinctive green and white bullhorn is on display.

“I got my own mailer in my mailbox,” she tells a campaign volunteer coordinator, giggling.

It’s 9:30 a.m. and the headquarters is already full of people. Volunteers sit sipping Folgers and snacking on donated donuts, cut in half so they can be shared with the large group. It’s their last push to get out the vote.

Circling the room, each person introduces themselves. Some are first-time volunteers, but many have been coming since the office opened in July. “I’m so excited with what we’ve built,” Brooks tells them. To any doubters in the room, Brooks delivers this message: “We are in spitting distance right now. Don’t let anyone tell you we can’t do this. Don’t let anyone tell you she’s got it in the bag. No one in this race has it in the bag.”

Brooks’ campaign field director Katie Tertocha works to fire up the crowd even more, asking the volunteers why they decided to come. A woman clears her throat and says with a quiet voice, “In these political times that are terrifying, you give me hope, like you’ve always given me hope. Right now you are really a unique, powerful source of hope for me. So, thank you.”

Another woman says she was in West Germany when the Berlin Wall came down. “That was people power, and I believe this is our people power,” she says.

After the volunteers are dispatched to door knock in East Oakland, someone asks Brooks if she thinks they can win. “That’s the plan,” she responds.

Meanwhile, the mayor is firing up her own volunteers for a final round of door-knocking at a last-minute get-out-the-vote event in Rockridge. “We’re down to the last three days,” shouts Miles Gordon, Schaaf’s campaign manager, to volunteers packed into the upper level of Oliveto restaurant.

The mayor stands next to longtime supporter MC Hammer, who is sporting all black and wearing sunglasses indoors. “It’s so incredible to see people willing to spend a Sunday working for democracy—so don’t think you can just take a selfie with Hammer and then go home,” Schaaf says to a round of laughs.

Hammer supported Schaaf during her first run for mayor, and four years later, he’s still on “Team Libby.” “This is the perfect person in this time, in this era, for the city of Oakland,” exclaims the recording artist, inspiring a spontaneous chant—“Libby! Libby! Libby!”—that ends in a group picture.

After a few more photos for Facebook, groups of two are sent off with a list of addresses to visit and instructions to hang “Libby for Oakland” door hangers on a couple hundred knobs.

“We love you, Mayor Schaaf,” two men say in unison on their way out to volunteer.

Election Day

At 8 a.m., Schaaf arrives at the Rene C. Davidson Courthouse to vote for herself. A crowd of reporters is waiting to capture a few shots of the moment.

Shaking a few hands, Schaaf smiles as she walks up to the ballot drop box. “All right, I voted,” says Schaaf looking out at the crowd to as she places her mail-in ballot into the slot.

Meanwhile, at her Grand Lake campaign headquarters, a half-dozen interns—primarily UC Berkeley students—are taping blue and orange streamers on the back wall, creating temporary striped wallpaper. They’re preparing for tonight’s campaign watch party. While they aren’t Oakland residents and therefore cannot vote for Schaaf, they’re hopeful victory is close.

“I’m not from here, but I’m a Libby supporter,” says 20-year-old student Tausif Khan. Khan says that his parents are immigrants from Bangladesh and what Schaaf did to warn residents about impending immigration raids “resonated” with him.

In the front of the headquarters, old pizza boxes are stacked on the counter where Becky Taylor works the front desk. A longtime friend of the mayor, Taylor says she was initially skeptical that Schaaf should run. “I think subconsciously I didn’t think she was really that tough. But now she’s proved she’s tough as nails. Her campaign slogan is ‘Oakland Tough,’” says Taylor.

Across town at Cat Brooks’ West Oakland headquarters, more than a dozen volunteers sit at plastic folding tables, a printed call list in front of them, working the phones to turn voters out. “I’m calling to see if you voted for Oakland mayor,” says Cherri Murphy, who has been with the campaign since it started.

“I’m feeling really good about it,” says Murphy when she’s not on the line with a voter. The Lyft driver says she’s optimistic because every Oakland passenger she talks to is voting for Brooks. When asked why she is not supporting the current mayor, she chuckles. “That’s my response. I laugh,” says Murphy.

Across the table, another volunteer chimes in. “The state of the city tells you why not Libby,” says Cheri Lynn. “All the homeless people tell you why not Libby. The trash on the streets tells you why not Libby.”

Brooks isn’t in the office—she’s at her longtime polling place, the North Oakland Missionary Baptist Church, waiting for her husband so the two can vote together. “I’m hopeful,” Brooks tells the reporters who are waiting to capture a picture of her vote. “You never know, but we have a shot.”

Finally, her husband, Terrance Franklin, arrives to cast his ballot. Originally from in Trinadad and Tobago, this is the first American election he’s participated in. The swarm of media follows Brooks into the building as she sits down with her husband to fill out their ballots. “Can you see who I’m voting for?” Brooks asks the crowd, laughing at the spectacle.

Election Night

At 8 p.m. the polls close, but results have yet to post to the Alameda County Registrar of Voters website.

At Red Bay Coffee in Fruitvale, at Brooks’ campaign watch party, it’s standing room only, although the candidate has yet to arrive. Sporting blue and white “Cat Brooks For Mayor” t-shirts, supporters swig coffee and wine in a room lit only by blue and red stage lights. A projector screens ABC7’s election coverage on the screen above the dance floor. Despite the news channels on the screen, the roastery feel more like a club than a campaign party, as DJ Bryson Wallace spins funk and dance records. Outside, a food truck serves jerk chicken burritos and Jamaican beef patties, while a trailer booth offers instant photos.

Inside, Asantewaa Boykin, co-founder of the Anti-Police Terrorism Project, sits in the back of the room feeding chicken to her young son. “I believe in her,” says Boykin of her friend. She says she’s proud of what Brooks has accomplished, running a race against a strong incumbent. “She was born a black woman in America. It’s always been an uphill battle.”

Meanwhile, at Schaaf’s campaign headquarters, supporters and volunteers are nibbling on quesadillas while simultaneously monitoring CNN for results and the front door for Schaaf to arrive. The former restaurant is packed to the doors with members of “Team Libby,” including the man who designed the snail car she rode to claim her 2014 mayoral victory.

A little after 8 p.m., the first wave of results appears online, just as Schaaf arrives. “The mayor is here!” shouts a supporter, followed by an eruption of camera flashes and clicks. After a quick interview in front of a swarm of TV cameras, Schaaf refreshes the voting results page. “We are in the lead at 65 percent!” she yells as excitement erupts all around her. “And Cat Brooks has 15 percent!”

When Brooks and her campaign entourage arrive at their party a few minutes after that, the room explodes with deafening cheers. The candidate is immediately surrounded by friends and supporters looking for a hug. Brooks soaks it all in, dancing and laughing as she makes her way to the microphone. “We decided to run together. We knocked on doors together. And now we’re going to win together,” Brooks tells the crowd, smiling at all the familiar faces. “We didn’t build a campaign. We built a movement of thousands of people that are committed to build a truly progressive Oakland.”

Dew, the campaign manager, tells the crowd to sit tight. They’re not expecting final results for a while. Maybe not even for two days—they’re anticipating that a large number of mail-in ballots will take the registrar more time to count. For now, Brooks encourages the crowd to “eat, drink and love on each other.”

By 9 p.m. at Schaaf’s party, there are no new results, but the mayor is all smiles as she attempts to learn a dance from Chicago rapper B.Bandz. Wearing red shoes and a black sequined jacket, he two steps back and forth. The mayor, wearing an orange suede dress, mimics his moves, a second behind. “It’s the victory dance. Come on now!” says someone from the crowd.

At Brooks’ gathering, half the crowd is now enjoying a raucous dance party. Sweating and spinning, few see Schaaf’s name pop up overhead on the projector playing ABC7’s Election Night coverage. There’s a check mark by her name, indicating Schaaf’s early lead. But with only a fraction of the precincts counted, the race still hasn’t been called.

Outside, campaign staff cool off as Brooks makes the rounds, speaking with reporters camped out at her watch party. “Only 17 percent of the votes are in,” says campaign volunteer Ari Trujillo-Wesler. She’s predicting that Schaaf will get less than 51 percent of the first-choice votes, forcing a new round of ballot counting. “I’d be really surprised” if the mayor wins outright, says Trujillo-Wesler.

Just after 10 p.m., Schaaf supporters are toasting with tequila. “It’s from Oakland!” a volunteer says while pouring drinks. Schaaf continues to mill, talking with supporter after supporter, hugging and smiling as she waits for the results to update. Pulled aside by an Oakland North reporter to talk how her second campaign went, Schaaf loses her smile, saying that this time around, “when you’re the mayor, it’s harder to campaign. I really had to put my job before the campaign.”

“Certainly, the debates were a little more raucous than four years ago, as far as people booing,” she says, recalling the debate at Allen Temple.

By 11 p.m. there are still no new results, and both watch parties are starting to fizzle. Schaaf’s early lead has some supporters declaring victory. “Ha! Look, John Madden texted me ‘Congratulations!’” Schaaf says, laughing out loud and showing her phone to her campaign manager. But the registrar’s office still has the majority of the ballots to count, and Schaaf decides to head home without waiting for the final results. “I’m feeling like it’s still not over,” Schaaf says. “Four years ago, I stayed up until 3 a.m. I don’t know how long I’ll last tonight, though.”

At Brooks’ watch party, the crowd has also thinned out. Cleanup begins and Brooks leaves quietly without conceding or making a public speech. “No matter what, we won,” she says, walking away with her husband and a few close friends.

A few stragglers remain, helping to put the roastery back together. The DJ starts to tear down his lights and volunteers shift tables and chairs back to the dance floor. Brooks’ supporters are hopeful that more ballot counting will tighten the race. “I’m not seeing check marks on any person,” said Trujillo-Wesler, referring to how TV news broadcasts declare a projected winner. “It might be Thanksgiving before we know who the mayor is.”

The next day

At 3 a.m. more results are posted on the registrar’s site. With 100 percent of the precincts reporting—but without the registrar completing the count of the mail-in ballots—Schaaf has won 56 percent of the first-choice votes. Brooks has 22.8 percent.

Later that morning, Brooks concedes on Twitter, thanking her supporters. “You who showed up and showed out. We have built a base of united Oakland, committed to building a progressive Oakland,” she writes. And then, referring to the mayor, she writes: “let’s hold her feet to the fire and build the town we want to see and deserve.”

Brooks has yet to call the mayor. After a long night and a tough campaign, she naps Wednesday.

Meanwhile, in the cafeteria at St. Vincent De Paul Community Center in Oakland, a few dozen top volunteers and campaign staff wait for Schaaf to declare victory at a press conference. “You’re going to have four more years of me,” Schaaf says as she walks in to a round of applause. Schaaf immediately takes her place at podium, telling the group of reporters, “I am so grateful and humbled to have been reelected for another four years as Oakland’s mayor.”

But at the Alameda County Registrar of Voters office, staff continue to count ballots. An estimated 250,000 still needed to be tallied, including thousands from Oakland.

By 5 p.m. Brooks removes her Twitter concession, telling Oakland North by telephone, “Not all the votes have been counted.”

What’s next?

A week later, Brooks is sitting in a Dimond district coffee shop. Her campaign attire is gone. She sports her natural hair, yellow pants, and a flowered blouse that allows her tattoos be on display again. Brooks has yet to concede, but the result is clear. In total, now that the mail-in ballots have been tabulated Schaaf earned more than 84,000 votes—53 percent—while Brooks secured more than 40,000, for 26 percent.

“I am shocked,” Brooks says, her eyes welling up. “I want this to be my daughter’s home,” she continues with a crackle in her voice, as a few tears run down her cheek. “It scares me that 80,000 people think that what has happened in the city is okay.”

In the middle of the interview, Brooks’ phone rings. A few texts ding. It’s been like that since the election, says Brooks. “Someone asked me on the campaign, ‘Do I think we’re building a movement?’” Brooks says she answered, “Yes,” and that she believes she’s part of a nationwide progressive push to elect women of color. She believes that push is not over. “We’ll keep working and we’ll keep fighting,” says Brooks. “This what we do.”

Will she run again for Oakland mayor? Hesitating a few seconds, Brooks then looks up and answers, “Yes. I’m 94 percent sure.” She laughs a little at the margin of error she’s giving herself. “I like the 6 percent wiggle room,” she says.

Schaaf did not grant Oakland North’s request for a post-election interview, and her spokesperson did not say what’s next for her. It won’t be another run for mayor. Oakland only allows mayors to serve two terms.

But many political observers give good odds that Schaaf will run again for something. “If everything keeps going, she could be a frontrunner to run for statewide office if she wanted,” says Ross. He tosses out the idea of a race for lieutenant governor or state attorney general. Armstrong adds that a state assemblymember or senator position are also options. “Oakland’s a great proving ground for politics. We don’t hold our punches,” says Armstrong.

That said, Ross cautions that a second term for mayors is often the most challenging. “Four years is a long way away in politics,” says Ross.

Brooks’ name is now firmly in the mix for Oakland’s 2022 mayoral race. “She’s the front-runner in four years,” says Toney. He believes with her 40,000 votes, the organizer has built a base. “That’s remarkable for such green new folks,” he says, referring to Brooks’ campaign volunteers.

He believes she’s mobilized a voting bloc of progressives who should be courted in the next election cycle. “That’s a group of people that should not be abandoned. They should be organized, and they should show up right with a quarter of the votes to the next election,” Toney says.

McConnell isn’t sure this is a base, but he is impressed by Brooks’ showing. “Cat Brooks should have got like 3 percent of the vote—just her immediate circle,” says McConnell, who compared the mayoral race to the battle between David and Goliath. “The fact that she got the number of votes that she did suggests her argument resonated with some folks.”

Ross agrees, calling the final vote total “really respectable,” and arguing that Brooks “went from basically zero name ID or very limited name ID” to 26 percent of the vote. If she’d been marketing a product, rather than running a mayoral campaign, getting 26 percent market share in three months would have made her a “hero,” says Ross.

Sitting in the coffee shop, Brooks says her plan from the jump was to connect Oakland progressives, and that won’t stop just because she lost this election. “Now we have to take this thing and move mountains,” she says.

Right now, she’s going to rest. She’s ready to spend time with her husband and 13-year-old daughter. But she also has a message about the future: She’s an organizer who’s not going away.

“We’re going to continue to fight for the Oakland we want to live in,” she says. “But this time”—she pauses midsentence to smile—“with more people.”

Reporter Ali DeFazio contributed reporting. for this story.