Every city in America has Chicago’s problems, but Chicago is the only city in America that is leading the way in advancing a real political alternative that is seriously contesting for political power to expand the public good.

That’s shaped by a couple different forces. Chicago was for a long time run by the Daley family and a set of local fiefdoms and political organizations that all had various arrangements with the central political operation coming out of the mayor’s office. That political patronage system declined and transformed into finance-based systems of political patronage, which was what Rahm Emanuel orchestrated — he was able to command political loyalty through the disbursement of campaign contributions and other political favors. When he stepped down, Lori Lightfoot was mayor for four years. In many ways, she inherited very difficult conditions, but she also made very bad political decisions, so it left her vulnerable.

Those are some of the conditions we’re operating in. But the best opportunities are not the ones that you luck into, but the ones that you make for yourself.  Chicago has seen a protracted struggle for racial and economic justice. When you look at things like the 2012 teacher’s strike; the 2012 occupation of the public mental health clinics, which were closed under Rahm Emanuel’s first budget; the protests over school closings led by the Kenwood-Oakland Community Organization and what was then the Caucus of Rank-and-File Educators (CORE), which would go on to win control of the CTU — these were all struggles that didn’t constrain themselves to the widely held theory in community organizing that you only go for what’s winnable. These struggles self-consciously situated themselves in the idea that if you only go for what’s winnable, you’re playing on an increasingly smaller strip of the possible.

These were fights that weren’t winnable in a one-, two-, or six-month time horizons, but it was only through waging them that we collectively were able to expand the sense of political possibility.

That was true for me personally in my trajectory as an organizer; I was trained in the school of you go for what’s immediately winnable. I was working on public education issues when the teacher’s strike happened in 2012. The entire city shut down for seven days, and it completely exploded my own personal sense of what organizing could be and what contesting for power could look like.

The 2013 school closings put my life on a totally different track. When the 2012 strike happened, I felt this tremendous sense of power, of political possibility, of solidarity; that was immediately snatched away by a power structure that closed the most number of public schools in history — the majority of them black. To be in those school board meetings with parents crying and security guards hauling them away from the podium because they had exceeded their time limit — a lot of our bonds were forged in that moment. I went from feeling so powerful and having so much hope and possibility to feeling so powerless.

As a result of that experience, I started working in electoral politics, because I didn’t want the people who had stood by while Rahm Emanuel closed those schools to hold onto that power. I worked for Jay Travis, the first candidate who [then CTU president] Karen Lewis recruited to run for office, when she challenged an incumbent state representative in 2014. After that, Brandon and [CTU leader and now president] Stacy Davis Gates kept asking me to work on other campaigns, including Karen Lewis’s brief campaign for mayor in 2015 and then Tara Stamps’s, who ran for city council in 2015.

I saw as campaign manager that it was very, very hard to win elections. Every election I had worked on in Chicago at that point, I had lost. But I did believe that we could and should be able to win — that if we truly believe what we say we believe, that we are the many, not the few, that this is organized people versus organized money, we should be able to at minimum win some elections.

Elections are structure tests. They’re the snapshot in time that can tell you if we’ve won the majority of people to our politics. The goal of our organizing should be to win majorities and build a multiracial working-class political majority. Elections are indicators of how far along we are toward that. Electoral politics are one tool in the tool kit for class struggle.

UWF’s most important intervention was understanding that if you want to change the outcome of an election, it’s going to take more than an electoral campaign — it’s going to require changing the broader terrain in which we were organizing. Even if in the short term, you might not pass that piece of legislation or keep that mental health clinic open. We have to wage fights that show that we have an alternative, that the political establishment as currently structured cannot deliver, so that then we have a basis to make a case for something better.

People have a well-founded skepticism of politics, because political operatives and organizers often don’t tell the truth. We say, “Oh, just elect the right person, and it’s all fixed.” That’s not true. There’s a much broader set of work that is incumbent not just upon the candidate or the elected official to do, but upon all of us to do.

You think about, for example, the story of the 33rd ward on the Northwest Side of Chicago. They ran a CTU member, Tim Meegan, in 2015. He didn’t win, but some of the volunteers from his campaign stayed together and built a ward-based independent political organization called 33rd Ward Working Families. That organization elected one of their own, Rossana Rodriguez-Sanchez, as alderwoman in 2019.

The 33rd Ward Working Families have been constantly in conversation both with each other and with a wider side of ward constituents to think about how to continue to raise people’s expectations, showing that there’s a different way to do things. That was the basis for continuing to reelect Rossana, to elect more people like her, and to build more organizations like that. It’s a project of imagination, but it’s incumbent upon all of us to make it real.

The work that’s required is not possible to win over the course of an election cycle. The scope of our organization has expanded. Shortly after I became executive director, UWF built an individual membership program, a way for individuals to become dues-paying members of UWF, whereas previously it had been made up only by organizational members — more like an organizational coalition or collaborative.

Mike Parker wrote an interesting article about democracy in organizations and how one of the key measures is whether people really believe and see for themselves that there’s a way by which the minority viewpoint can become a majority viewpoint. Building an individual membership program was a really important example of this. A number of the organizational members of UWF at the time had reasonable and serious concerns about creating an individual membership program. As an example: you’re not an individual member of the Chicago Federation of Labor [CFL] — you’re a member of a union that is a member of the CFL.

Meanwhile, you had others who argued that we needed individual members in order to make this an organization that felt real to large numbers of people and had the people power you need to move a political agenda. We had a principled debate about the issue, took a vote, and started organizing individual members.

The idea that UWF should have individual members who can hold seats on our decision-making body and vote on endorsements — that was a minority viewpoint that became a majority viewpoint. Now, six years later, our ability to organize individual members has turned out to be key for UWF and its success. We have member committees working on endorsements, policy research, reading groups, and political education.

There are so many unorganized people in Chicago, despite how many organizations we have. There are so many people who don’t have a political home, who aren’t connected to an organization. Why would we leave that on the table?

As we’ve done this work, we’ve learned that we can’t just “do elections,” but that we also have to be involved in the issue work that happens before and after an election. This has meant not only organizing individual members, but convening more and more issue campaigns that bring together our elected officials and our grassroots members.

For example, in 2021, one of our city council members shared with us this slide deck from a mayoral briefing that showed that the Lightfoot administration had spent an astonishing $280 million in COVID relief money on the Chicago Police Department, specifically on the overtime that was spent suppressing the 2020 uprisings.

Out of that revelation, we were able a wage a citywide campaign around the American Rescue Plan funds, writing a whole package of $1.9 billion legislation that didn’t pass, but fortified our ability to move as a legislative caucus, to extract concessions from the budget process, and for grassroots members and elected officials to practice being in a different kind of relationship with each other about how we govern and exercise power on that stage.

It is a political decision to have a city where half of its people can’t have their kids playing outside without fear of getting shot. It’s not a fact of nature, it’s a political decision that is being made by a certain set of people, because those conditions benefit them or their donors. We have to be laser-focused on what we think is actually going to work.

That is what is right about Brandon and his approach. It’s not just a talking point: safe communities are communities that have good jobs and good schools and places for young people to go and places for families to live. There’s twenty thousand students in Chicago public schools who are homeless right now. We are offering the opportunity to actually invest in people, such that communities are able to live safer, more peaceful, and more stable lives.

If public safety were just a policing issue, if more police made people safer, Chicago would be the safest city in the United States. It has more cops than any other major city except for Washington, DC. But it’s very clear that is not working. The question is, where is the political will to try something different? I think we have an opportunity to do that. We can’t address it without addressing the fact that brutal inequality is making those conditions a reality in the first place.

Public safety is not just a policing issue. We have to push for all of the systems of care that prevent violence in the first place — things like jobs, mental health clinics, fully funded schools, social workers in schools, affordable housing.

In terms of Catanzara, it’s important to be clear about our analysis.

The coalition field program that UWF helmed did a lot, but it was made up of others as well — community organizations, labor organizations, IPOs. We knocked on over half a million doors. When you knock on that many doors, you’re going to talk to rank-and-file police officers, many of whom would agree with us that they were being asked to do too much — that by the time they get to the crime scene, it’s already too late; that the homicide clearance rate is too low. There are issues that rank-and-file members of the Chicago Police Department share parts of our analysis on that Catanzara and the Fraternal Order of Police do not.

The FOP is an extremist right-wing organization. The “blood on the streets” comment underscored that. Catanzara’s public support for the January 6 capitol attacks underscored that. There is a set of people in the Democratic Party who knew Vallas drew this kind of support, who knew that Vallas’s campaign was emboldening and legitimizing people like Catanzara, and who decided not only was that not disqualifying, but that Vallas was nonetheless still a better candidate for mayor than the black labor leader who had dedicated his life to serving poor and working-class children.

I think we should be really clear about what that tells us about class alignment and the political system as it exists today.

For me, those endorsements were usefully clarifying. You have [Donald] Trump’s secretary of education and [Barack] Obama’s secretary of education both endorsing Paul Vallas, who has decimated every public school system he’s ever been put in charge of. That is something that we should all keep in mind for a long time.

When we say “unions,” who are we actually talking about? We’re talking about thousands, tens of thousands of working-class people who put aside part of their paycheck to give to an organization that they then elect the leaders of, to make decisions about how to spend those funds in order to advance their interests as the working class.

Where is that question really coming from? It’s usually coming from very wealthy people who are concerned that their money will be no match for the power of many working-class people. They’re afraid of that collective political power, in this case coming from many black women.

It’s a question that I don’t take very seriously. I would love for more working-class black women to be in charge of the city departments and agencies that have left them behind for years.

The council has become a more serious deliberative legislative body. It has taken strikes, occupations, pressured elected officials, and introduced legislation that you know is not going to pass or voting no on legislation that you know is going to pass anyway, for us to get to this point.

Usually voting no on something that’s going to pass anyway has a political costs to it; UWF-backed city council members over the past four years have shown that it doesn’t have to be a rubber-stamp council — that you can stick together, you can negotiate as a block. In so doing, even if you don’t get everything you want, even if it’s in the immediate sense a loss, you’re helping create the conditions to elect more people next time.