When it came to fundraising, Paul Vallas had Brandon Johnson beat. Days before the April 4 mayoral runoff, Vallas reported contributions of over $19 million, more than half of that coming from 44 individuals or organizations. Johnson clocked in at just over $11 million, largely from unions. But where Johnson had the upper hand, and what ultimately propelled him to an upset victory, was his community outreach — appealing to supportive voters to turn out to the polls.

The person leading that charge was Emma Tai, executive director of United Working Families, a political advocacy organization started in 2014 by social-welfare and labor groups, including the Chicago Teachers Union. Tai spoke to Chicago about the decade-long effort to elect a progressive mayor, how she abandoned a community organizer’s mindset of only going after winnable targets, and why she identifies with a certain rebel in the Star Wars universe.

How did you overcome Vallas’s financial advantage?

In the runoff, we were outspent two to one. I knew that if we won, it would only be because of organizing and our field operation, or what’s called our ground game. And our ground game was good. In the last five weeks, we were knocking on tens of thousands of doors every weekend. The number of people coming out to canvass was a very good sign. My lead organizer, Ryan Kelleher, ran a grassroots house-party fundraising program that originally had a goal of raising $100,000. And by the end, it raised $400,000. We ran out of numbers to text. We had to buy 100,000 new numbers. Our people were on the doors, and the Vallas people weren’t on the doors. We had a door-knocking program across all 50 of Chicago’s wards. I didn’t know what was going to happen, but I knew it was going to be close. And I felt confident that we left it all on the field.

The Johnson campaign was often portrayed as “big labor” or “the CTU machine.” Do you agree with that characterization?

Whenever people talk about big labor, it’s important to unpack what are you really talking about, because all a labor union is, is thousands of working-class people paying dues and voting on how those dues are allocated. I’m not sorry that United Working Families receives membership dues from labor, because those dues don’t come from one individual’s checkbook. When you look at the unions that backed Brandon, they came from organizations of Black women, health care workers, childcare workers, city employees, teachers, school aides, bus aides. I would love for those people to run the city of Chicago, because I’m frankly tired of it being run by white billionaires who have closed our schools, who have closed our clinics, who have given tax breaks to wealthy developers, to companies to increase their profits while children are literally being shot in the streets.

Your organization has campaigned for other CTU-backed candidates in various elections. What drives your approach?

We can’t win elections without organized people. Our opponents can win elections with just money, because they have a lot of money, and money will get you pretty far in electoral politics. I think our job is to raise enough money to be competitive. But we’re always going to hit a ceiling with that. And so we have to figure out the other things: the year-round organizing, the field operation, the terms of the issue fights, and the terms of the debate — those things are going to tilt the election results in our favor.

Electoral campaigns last maybe three to six months. But in terms of fundamentally changing the political terrain of our city or our country, you can’t do that in three months. That is a project of many, many years. I got my start in electoral politics because I had been working in community organizing. At the time, there was a very widely held belief that community organizers should only ask for what’s winnable. What was actually winnable was becoming smaller and completely insufficient because of a generational project by business interests, social conservatives, and the right to increase their profits and constrain the lives of poor and working-class and Black and brown people. Elections are part of the tool set, but they aren’t the only tool.

What are some of the other tools you use to effect change?

If you’re only operating in the three-month window of electability, you’re not going to move the needle in the way it needs to be moved. Brandon Johnson’s victory is not possible without the 2012 teachers’ strike. It’s not possible without the [2015] Dyett hunger strike. It’s not possible without the 2020 uprisings. It’s not possible without the 2012 occupation of the mental health clinics. Those weren’t, by community organizing standards, “winnable” fights. We needed all sorts of things: strikes, occupations, candidates taking on incumbents — sometimes they won and sometimes they lost. We needed to introduce legislation, sometimes knowing it was never going to pass. When you have a moment come around, like an election, that’s when you can really litigate.

[Former CTU president] Karen Lewis said in 2012 that you can’t close schools and not be held accountable. She said what the plan was 11 years ago. They just didn’t believe we could do it. But we have been right. We’ve increasingly won elections, we’ve learned and adapted our organizing, we’ve been responsive to movement moments, we’ve taken seriously the project of contesting for political power.

In [the Disney+ series] Andor, Diego Luna’s character, a thief, steals something from the Empire that deems him worthy of recruitment by the rebellion. He is questioned on how he accomplished the feat. He says he walked in, put on a worker’s uniform, and took it. He’s like, “It’s not hard to steal from the Empire. They’re so fat and satisfied, they can’t even imagine that someone like me could steal from them.” I just love that line, because if you’ve been a close observer of what’s been happening in Chicago politics the last 10 years, it is not hard to see that this was coming.