“Is this for Rahm or Chuy?” a woman garrisoned in front of her West Side of Chicago home says, more as a warning than a question, her hands extended into stop signs. She’s got no love for Mayor Rahm Emanuel, but she also doesn’t want to hear about his challenger in the city’s first-ever mayoral run-off, a Cook County commissioner named Jesus “Chuy” Garcia.

“It’s for me,” Tara Stamps sings playfully, proffering a palm card with her smiling face on it. She quickly explains that she’s a veteran Chicago public schools teacher and she’s running for alderman. “I’m asking for your support if you’re open to electing a new representative.”

The afternoon is spirit-pummeling cold for late March, and Stamps, 46, is bundled in a red beret and red plaid peacoat with a Chicago Teachers Union button pinned to her lapel. A first-time candidate, she’s a natural at retail politics. She possesses a commanding voice that shifts seamlessly between colloquial rapport and tirade, and the generous gap between her two front teeth seems, if anything, inviting. At another house on the same block of cramped brick bungalows in the largely African American ward, she repeats the name of the young mother who answers the door, drawing it out like they're longtime friends—“Okay, Sha-von-dah!” Then she launches into her plans to hold civics classes in the ward, so people there understand the benefits of an elected school board (in Chicago, it’s appointed by the mayor), and the ways that Mayor Emanuel is starving neighborhood schools. “It’s a mess. We the only people that can stand in the gap between them and us.” The thirty-seventh ward, on Chicago’s western edge, is a distant ten miles from City Hall, but Stamps is talking about a “gap” that isn’t only one of space but also of race, resources, and safety. “We need to advocate for our neighborhoods and our schools. That’s what’s at stake in this election.”

Stamps is running against an incumbent named Emma Mitts, but in many respects her opponent is the mayor himself. “It’s a referendum on Rahm. He’s not invested in black communities,” she told me as I tagged along over several hours of afternoon campaigning. “Mitts is in lockstep with Rahm. She’s voted 97 percent of the time with him on policies that devastate her own community.” For the vote in February, Emanuel raised tens of tens of millions of dollars, of which $7 million alone went to TV ads; he faced off against relative unknowns; and he enlisted the support of Barack Obama, who stumped for his former chief of staff in spots on black radio (“Let’s be honest, at times the guy can be a little hardheaded”) and joined the mayor in Chicago in the days before the vote. And still Emanuel was unable to secure the 50.1 percent of the vote needed to win outright.

Stamps’s rise from self-proclaimed “activist teacher” to one of an actual political candidate is also the story of Emanuel’s plummeting popularity and of the emergence of a formidable anti-Rahm opposition from the left. She is representative of the city’s broadly drawn battle lines in this election. Downtown versus the neighborhoods. Teachers and unions versus private interests. Blacks, Latinos, and the progressive left versus the man they’ve dubbed “Mayor 1%.”

Back in 2011, Emanuel’s first run for mayor was a ho-hum affair, in which he easily won 55 percent of the vote against five candidates. The only real drama came when he had to prove in court that he was a resident of Chicago, since he’d rented out his North Side home during his Washington sojourn. The bellicose Emanuel wasn’t beloved by Chicagoans, but that was part of his appeal. After Richard M. Daley’s 22 years in office (and a Daley as mayor for 43 of the previous 56 years), he represented both a break from and a continuation of the past. He was chummy with the city’s business elite: Between his time in the Clinton White House and his run for U.S. Congress, he worked for the Chicago branch of a major investment-banking firm, raking in $18 million for himself in a little more than two years. But as well, his ties to Obama helped him with black voters.

I remember sitting down in 2011 with the tenant representative of what remained of the legendary Cabrini-Green public housing complex, on the city’s Near North Side. She is as hard-bitten a cynic when it comes to politicians as anyone I’ve met and with good reason—she’d seen every public housing high-rise in the city demolished over the previous decade and a half, with most residents left to rent in the private sector with government-issued vouchers. But she went all soft thinking about the possibilities of the new mayor. “I don’t know if you know about Saul going to Paul in the Bible,” she said, referring to Saul’s conversion from a persecutor of Christians to one of Jesus’s apostles. “I think Rahm might be Saul going to Paul. I hope that’s the case.”

The first real jolt of disaffection occurred just before the start of the school year in 2012, when Chicago's teachers went on strike. Teacher strikes seemed almost a seasonal rite when I was a Chicago public schools student, but there hadn’t been one for 25 years. Emanuel was demanding a longer school day and greater reliance on student testing to evaluate teachers. Teachers wanted more pay, especially if they were expected to work longer hours. Underlying the standoff, though, were issues that were fueling education fights all over the country. Karen Lewis, the president of the Chicago Teachers Union, assailed the “teach and punish” strategies being pushed by both Emanuel and Secretary of Education Arne Duncan, whom she heaped scorn upon when he ran Chicago’s school system. (At a rally she once mocked Duncan for having a lisp.) She regularly denounced charters for benefiting private management companies and draining resources from neighborhood schools. During one of their contract negotiations, Emanuel shouted, “Fuck you, Lewis.” The rough-and-tumble politicking that served Emanuel in Washington suddenly looked different when he was cursing out a 59-year-old black woman in Chicago. The strike dragged into the school year, lasting ten days.

Tara Stamps, a rank-and-file member of the teachers union at the time, proved to be a fiery orator on the picket line and at huge demonstrations downtown. Her mother, the late Marion Stamps, was a bullhorn of a woman who operated a community center at Cabrini-Green, started an Afro-centric alternative school, and dragged her five daughters to every protest and meeting that she ended up throwing into chaos. Tara recalls standing atop the Illinois governor’s desk as a young girl, stomping on crackers. “We were direct action,” she laughed. At her middle school, she led other students on a boycott of the lousy cafeteria food. “I get my leadership philosophy from my mother," she said. "You sometimes have to say inflammatory things to shock people into paying attention to racist practices.” She saw the teachers’ fight as one of civil rights, involving access and Americanness. “If charter schools are our best hope, why aren’t they in white neighborhoods? I’m so tired of black folks being part of the white man’s experiment, I can’t see straight.”

When the strike ended, both sides claimed victory. The mayor got his longer school day. I happened to interview him a few months later, and in his typical sparring style he dismissed a question I asked because I’d referred to the strike as “controversial:” “I don’t buy your characterization,” he said. “You couldn’t take the longer school day away now. Try to take it away. Try. Try, Ben.” As for the teachers, they got a bump in pay. And while parents weren't happy to see their children out of school, the union had also demonstrated a strength and discipline that had long been absent from the labor movement. Many Chicagoans admired the union for standing up to the mayor. For sure the ire directed at Emanuel carried with it the accumulated frustration of the Daley years, during which the city center was polished into a gleaming gem and numerous public assets—parking meters, roadways, schools, public housing—were transferred into private hands. As approval for Emanuel declined, Lewis emerged as his foil. “Through the teachers strike,” Stamps said, “we saw that Karen wasn’t only intelligent, but had the chutzpah to advocate for poor and oppressed communities and to fight for the neighborhoods and the city that we deserve.”

Opposition to Emanuel coalesced the following spring. In May 2013, the mayor shuttered 50 public schools. Most of the schools had low enrollment and a history of lousy test scores. They were almost entirely in black and Latino neighborhoods: poor communities that had experienced huge population losses slowly over two or three decades as industry and jobs disappeared from the inner city, then with a rush after 2007 with the mortgage crisis erasing much of those areas' remaining wealth. From 2000 to 2010, Chicago’s black population plummeted by 181,000, a staggering 17 percent decline. These were also the neighborhoods being terrorized by a recent spike in homicides and shootings. (Stamps helped fight to keep open a targeted school near Cabrini-Green. People who actually knew the area warned that students from the shuttered school would have to travel across long-standing gang lines to attend their new “receiving” school. The school was among the few to win a reprieve.) If the mayor had announced a long-term strategy for how to redevelop, or maybe even how to sensibly shrink these battered areas, then that might have been acceptable. But the closures came from on high in one fell swoop, the largest mass shutdown of schools in the country’s history. For many of these communities, the schools felt like a last remaining anchor, and their closing was viewed as either an act of cruel indifference or possibly something more sinister. “I’m not a conspiracy theorist, at least not all the way, but what’s going on is a form of ethnic cleansing,” Stamps said.

In response to the closures, the Chicago Teachers Union decided to field its own members as candidates in the election. As far as policy, labor groups couldn’t even rely on Democrats any longer to support their interests, and the unions were limited in what they could accomplish on the picket line or in the collective bargaining of contracts. So last summer Stamps and several of her colleagues sat through five weeks of union-led workshops. “How-to-be-an-alderman classes,” she called them. The union would provide her with advisors, foot soldiers, and money—she’d receive nearly $200,000 from labor groups. The teachers union hired someone to coordinate the messages of their candidates, and Stamps took on a campaign manager who’d steered other candidates backed by the union. In August, I attended a campaign kickoff at her house. Fellow teachers and several of the first students she ever taught—now men and women in their late 20s and early 30s—gathered to collect the signatures required to get her on the ballot. An organizer from the Chicago Teachers Union passed out tear sheets with data on every voter in the ward. He’d worked on a dozen campaigns, and he told the volunteers that to sell Stamps they needed to tie Mitts to Emanuel and his unpopular policies: first and foremost school closures, but also the spread of charter and turnaround schools, the shutting of mental health clinics, and the dissemination of ticket-issuing speed cameras that seemed like yet another scheme to siphon money from the people who could least afford fines.

Karen Lewis was poised to run for mayor against Emanuel. As a potential mayoral candidate, she was intriguingly complex. Black, Jewish, and an Ivy Leaguer fluent in Italian, she became a chemistry teacher after discovering she detested medical school. She also hails from the same racially and economically diverse South Side neighborhood that launched the political careers of Harold Washington, Carol Moseley Braun, and Obama. It was possible that her incendiary rhetoric would alienate many voters, but she’d been toning it down of late, and it seemed just as likely that people would come to find her intelligent and charming. Because Lewis was a newcomer to politics, she also offered enough of a blank slate that progressives could imagine her embodying most of their hopes (see Obama and Bill de Blasio). Two early polls showed her with a significant lead over the mayor. She held fundraisers, lost weight, underwent a makeover, updated her Twitter page. Then, days before announcing her bid, she was diagnosed with a cancerous brain tumor. The teachers union drafted Garcia to run in her stead.

As I drive with Stamps through her ward, she points to roadwork in progress and a giant brush pile along a curb. “Rahm hasn’t been in the black community until he got into runoff,” Stamps said, with little surprise. A few days after the February vote, the mayor announced he would remove 50 red-light traffic cameras from 25 different intersections around the city.

Stamps told me that life in the thirty-seventh ward has gotten worse under Emanuel: 31 homicides in 2013 and 36 in 2014; an unemployment rate between 20 and 30 percent for the three zip codes comprising the ward; upwards of 30 percent of residents living in poverty. Even on a relatively well-to-do block, with a large number of reliable voters identified on her walk-sheets, Stamps showed me the campaign literature that had accumulated in front of a couple of the bungalows—a tell-tale sign of abandonment. The brick front of another home was splitting in two. Stamps teaches fifth grade at a school in the Cabrini-Green area, but three years ago she moved to the West Side neighborhood because property values were lower and she could afford a house there. There are vacant homes on her block, and last summer someone stole the copper from her central air unit.

“People are waking up and seeing this relationship between Mitts and Rahm,” she told me. “It’s taken a while for families to connect the dots—from school closings, to jobs, to viable communities. There are people in power who benefit from those dots not being connected. People here know something is wrong, they feel the effects of it. They see it when they go to the store. Now they’re able to start pointing to the cause.”

The most recent poll has Emanuel with a 28-point lead on Garcia. “If Karen hadn’t gotten sick, she would have kicked Rahm’s butt,” Stamps said. Stamps is an ardent supporter of Garcia, who, as an alderman, was closely aligned with Harold Washington and later became the first Mexican American elected to the Illinois senate. But she’s come across numerous people in the ward who back her, despise Rahm, and yet don’t trust that Garcia would look out for the interests of black Chicagoans. “It’s about race, prejudice. It breaks my heart they don’t support Chuy. They can’t see the big picture.”

Chicago is buried in a fiscal crisis, with a $20 billion shortfall in its obligations to public-employee retirement funds. Like many union-backed candidates, Garcia has had to answer the charge that wouldn’t take a hard line in negotiations with the same groups supporting him. The polls suggest his answers haven’t been convincing enough. But Stamps believes teachers and other city workers shouldn’t be expected to sacrifice more than others, especially in a city already riven with inequity. It’s a stance that plays better in the neighborhoods than citywide. “The city wants to keep taking money out of the pot of people who already put in, for a defined benefit for the good service that they put in for this city,” she said. “It’s always the workers they want to balance the budget on. But the rich people in this city are the richest they’ve ever been. You keep crying broke and foul, but then you jockey to get the Obama library? That money doesn’t fall from heaven. Then you try to build a DePaul basketball stadium, for a private university, and a losing team at that, that doesn’t need a stadium? And our babies here don’t have a facility that they can go to and play basketball and be safe.”

In February voting, Stamps received 2,593 of the ballots cast to Mitts’s 3,910, with barely a quarter of registered voters going to the polls. Stamps is confident she would have won outright if Lewis had been able to run. But she still feels good about her chances on April 7. She’s been performing well in debates and in public forums. She’s been stumping non-stop, heading out to senior centers and block parties, revisiting supporters at their homes and spending time at train stops and schools. Her mother, Marion Stamps, ran unsuccessfully for alderman twice in their Near North Side ward. But Tara said her mother was a community organizer trying to take on the Democratic machine without the resources needed for the fight. By contrast, she now has the backing of a powerful organization with an aggressive field operation that will be out in full force with reminders and rides come Election Day. And she’s helped as well by a sense that she’s part of a much bigger fight, one that involves the future of progressive politics in the city. At an event at her campaign office over the winter, I heard her say in a speech how her local contest was part of this wider movement that might still be taking its first steps. “Take a ward, start a revolution,” she proclaimed.