Chicago’s Red Wave A conversation with Chicago DSA organizer Lillian Osborne on how socialist campaigns can build lasting power.

Chicago occupies a special place in socialist and working-class history. International Workers’ Day commemorates the infamous Haymarket affair of 1886, which occurred during the titanic struggle for the eight hour day. It is the city where the Industrial Workers of the World held its founding convention in 1905; it’s where the split between U.S. Socialists and Communists occurred in 1919; and it’s where the roiling conflicts over Vietnam, civil rights, and black power came to a head at the 1968 Democratic National Convention. Chicago occupies a central location not just geographically, but in the country’s industrial, political, and social history as well. When it comes to the history of our movement, all roads eventually lead to Chicago.

In recent years, Chicago has lived up to its historic role as one of the central hubs of labor militancy and political radicalism. The 2012 Chicago Teachers’ Union (CTU) strike was a milestone in contemporary labor history, and prefigured the wave of public education strikes that began in 2018 and continues to sweep across the country. That strike helped to stimulate a movement against the city’s deeply entrenched political establishment, which began to bear fruit with the election of Carlos Ramirez-Rosa, an outspoken socialist and community activist, to city council in 2015. Earlier this year, a new wave of self-identified socialists were elected to city council, a historic development that made international headlines.

DSA members have played an important role in building the city’s rising new left, and in taking on the infamous Chicago Democratic machine. Here, Chicago DSA (CDSA) activist Lillian Osborne talks to fellow CDSAer and National Political Committee (NPC) member Marianela D’Aprile about the political situation in Chicago and the prospects for taking the movement even further.

Marianela D’Aprile: Give me some context for how CDSA decided to get involved in electoral work and why the chapter chose their specific campaigns. What was the process that the chapter went through, and what were the outcomes?

Lillian Osborne: All DSA chapters have an interest in seizing on the Bernie Sanders and AOC moment, to use electoral politics to gain a larger platform and inject socialist politics into the mainstream. In Chicago, there had been ongoing conversations around backing candidacies for a while before the city council races; there was interest in backing Carlos’s (Ramirez-Rosa) potential runs for Congress and Lieutenant Governor. Even though those races didn’t materialize (Carlos decided not to run for Congress and was kicked off his gubernatorial candidate by his running mate for refusing to renounce the boycott, divestment, and sanctions movement against Israel – eds), members continued to discuss what DSA’s role in upcoming city council elections might look like. They were interested in building our organization and using the campaign to move working-class issues forward and using a socialist message to frame them.

My sense is that the chapter started to see these candidates coming forward out of their own ward organizations to run, and that was really exciting. A number of the candidates were both members of DSA and their own ward organizations. There was Byron Sigcho Lopez, running again after his first attempt in 2015 with a strong backing from his community organization on the southwest side, Pilsen Alliance, in the 25th ward. There was Rossana Rodriguez, a member of 33rd Ward Working Families. In 2015, that organization had run Tim Meegan, a CTU activist, socialist, and high school teacher, who barely lost the election. Later on, we endorsed Ugo Okere, a young activist in the 40th ward put forward bold socialist politics; after he didn’t make the runoff, we endorsed CDSA member Andre Vasquez in the 40th ward. And Jeannette Taylor, a long-time community organizer and member of the Kenwood Oakland Community Organization (KOCO) on the south side, sought our endorsement in the 20th.

Most of these candidates came out of movements of their own and out of the larger progressive movement in Chicago that’s been growing since 2010 or 2011. I think the turning point was socialists in the CTU organizing with communities against school closures, forming the Caucus of Rank-and-File Educators (CORE), taking office in the CTU, and waging a massive fight against austerity and neoliberalism in Chicago over the last ten years. So looking at this historical context, CDSA played an interesting role because so many of us are new to socialist politics and organizing.

MDA: It seems like the 2012 CTU strike, and perhaps to a lesser extent the union’s one-day strike in 2016, did a lot to lay the groundwork for the work that DSA and other progressive organizations in Chicago are doing now.

LO: Yes. Thirty-thousand members of the CTU went on strike in 2012, and I think that strike opened up a crack in Chicago politics. For a long time, the union’s leadership and working Chicagoans had accepted things like the decline of funding for cities and the advance of neoliberal politics. They had accepted on some level that this is just how things were done. Then Occupy Wall Street came to Chicago, then an increase in housing organizing, and these things channeled into the organizing that CTU was doing. So, CTU in a way galvanized the left and progressive movement, where resistance had maybe been more piecemeal previously, or on a smaller scale.

MDA: Another crack has opened up around housing. For a long time, Chicago was a holdout among big cities in the U.S. in terms of gentrification and affordable housing. It was the one big city in the U.S. where a young person just starting out could find an apartment that wouldn’t break the bank. That’s becoming less true. Did frustrations around that issue open up room as well?

Over the last decade or so, there have been really strong housing-focused organizations across the city, especially in response to foreclosures and evictions following the 2008 financial crisis. About two years ago the Lift the Ban (LTB) Coalition emerged, which includes a number of community organizations from all over the city — many of the same ones running progressive and socialist candidates in the city council elections — and is leading the fight for rent control and against gentrification and displacement in the city.

Logan Square, on the northwest side, has been one of the most rapidly gentrifying neighborhoods in the city. It was gentrified in less than a decade. That has to do with the increasing power of real estate developers in the city.

One of the main ways that capitalists make money in this city is through real estate. So we’re seeing across the city, in working-class areas, the increasing of property taxes and rents — the effects of really big development and a broken tax system that favors the wealthy.

MDA: So how did you target that issue in Chicago DSA?

LO: A lot of people with backgrounds in housing organizing got involved in DSA with the surge in membership in 2016 and 2017. Those people had an interest in continuing to do housing work and in getting involved in the rent control campaign. So DSA started to get heavily active in the rent control campaign in late 2017. The initial strategy of the LTB coalition was to run non-binding referenda across the city on lifting the state-wide ban on rent control, to publicly raise the issue of rent control around the city.

In 2017, we took two precincts in the 5th ward on the South Side, near where Jeanette Taylor ran for city council and won. We pushed to canvass and talk to people; we ended up getting the referenda on the ballots, and they passed overwhelmingly. That’s what really started the campaign in DSA, and I think a lot of people were really excited about it because LTB is a working-class coalition fighting for a demand that could really empower working-class people and limit the power of big developers.

We don’t think rent control is going to solve all of working-class people’s problems. It’s not a panacea. But it’s a way for us to build stronger relationships with working-class organizations that are pushing an important agenda, and we see housing affordability as a real crisis in Chicago. The campaign is also an opportunity to deepen our understanding of Chicago politics, from capital to politicians to other progressive organizations. We’ve learned so much through doing this work.

After all that work, we got a seat on the leadership committee of the coalition, which was really exciting and a big accomplishment for CDSA.

One of the problems that emerged internally is that we were involved in this big, exciting campaign and coalition, but it had dwindling capacity within our organization because our chapter’s work was so spread out. At the time I think we had something like 18 working groups, all working on different issues and projects. So CDSA as a chapter restructured how we do campaigns, opening up the possibility of prioritizing campaigns that do three things: develop our organization, make more socialists, and increase working-class power. And CDSA voted to make LTB the first campaign that our chapter would put its full weight behind in that way, which also meant that we really had to make an effort as leadership to reach members to work on the campaign, which has been very successful.

Where the campaign started with members who had been involved in organizing previously, it’s now led by a group of new leaders in the organization, many of whom had never organized before joining CDSA, who were brand new to socialist politics a year or two ago. And now they are playing a central role in steering one of the most important movements in the city. It’s incredible.

MDA: Can you talk about the link between the LTB campaign and Carlos’s campaign?

The coalition is made up of some of the main organizations in the progressive and left movement in Chicago. A lot of the aldermen who ran in the city council election had a background in organizing around LTB and running their own referenda. Byron’s organization Pilsen Alliance ran one of the first referenda and really pushed forward the coalition. Rossana’s organization 33rd Ward Working Families ran one; Jeanette’s organization, KOCO, has been leading the coalition.

Interestingly her deputy campaign manager and Chicago DSA’s new co-chair, Robin Peterson — who I think is due a lot of respect and admiration for all of her work on LTB — and I both met our respective candidates through LTB, and later got involved in their campaigns and took staff positions.

Leading up to the November 2018 elections, the LTB coalition planned a number of ward-wide referenda across the north side of the city, including in Carlos’s ward, which was an escalation from previous smaller, precinct-level referenda. So DSA weighed our options and chose a couple of precincts in the far north side, where we have a pocket of members. We also saw that the 35th ward was an important place to put our weight because Logan Square is a battleground for gentrification. We knew Carlos was going to run for city council again, so this was a good opportunity for us to be part of the process of getting him re-elected while also talking with people about the issue of rent control and housing affordability.

I don’t think it’s a coincidence that socialist city councilors are emerging as leaders in the areas of the city where communities are fighting back against big developers, corrupt politicians, and austerity. What the CTU has taught so many of us, what Bernie Sanders has taught so many of us, is if we want change, we have to fight. These problems will not be solved in backroom deals.

We knew this was going to be a huge effort, maybe one of our organization’s biggest undertakings yet. I remember Robin saying, “If we do this, we’ll come out a totally different organization.” I think that’s something we need to hold onto as socialists: the willingness to enter important, difficult fights and being open to changing in the process.

MDA: It also seems like it was one of those working-class issues that you were talking about earlier that could start to draw some lines between working-class people and big capitalists.

LO: Absolutely. There’s this real-estate developer, Mark Fishman, who’s pretty notorious in Logan Square. He’s been pushing forward an agenda of gentrifying Logan Square and the surrounding neighborhoods. He’s a pretty ruthless guy. I’ve heard stories of people who have lived here for a long time being pushed out of their restaurant business by him, or being harassed by him. Carlos himself was pushed out of his ward office by Fishman.

The thing is, he basically wrote blank checks to previous aldermen. Rey Colón, the alderman that Carlos unseated in 2015, ran on an affordable housing platform and promised that no new condo buildings would be built beyond a certain point in the neighborhood — an area that’s since been gentrified. He won on that platform because working people know gentrification when they see it, and on some level know that it’s not a foregone conclusion. It’s something we can challenge politically. But as soon as Rey Colón took office, he had a meeting with big developers and real estate interests and immediately flipped. After that, Fishman had him in his pocket.

So when Carlos took office in 2015, Fishman expected that Carlos would also be up for sale. And Carlos made it clear to him that he was there for the community and to fight for working-class Chicagoans. Since then Fishman and other developers have had an investment in unseating Carlos.

Our campaign to re-elect Carlos was a direct fight against developer interests. Fishman recruited our opponent, Amanda Yu Dieterich, to run and he bankrolled her campaign, contributing more than $100,000 dollars, a third of her campaign donations. And he hid those donations through numerous LLCs (he has a separate one for each building he owns) and writing hundreds of checks under $1,000 dollars. In Chicago, donations over one thousand dollars must be immediately reported, and show up publicly in the campaign’s finances, whereas his smaller donations didn’t appear until the election was already over.

During the campaign, he also pushed Carlos out of his ward office and sued him for one hundred thousand dollars in back rent. Dieterich’s campaign sent out dozens of mailers, funded by real estate lobbying groups — so many that they were piled high in residents’ front hallways and on their front steps — calling Carlos a “deadbeat” and a bad worker who deserved to be fired. And in the two weeks leading up to the election, Fishman hung banners that said “Vote Amanda Yu Dieterich” on all of the apartment buildings he owned, in empty storefronts where he had evicted local businesses, and in Carlos’s old ward office.

From the very start of the election campaign, DSAers were knocking doors connecting the fight for rent control to the fight against corporate interests in our city. As we started to talk to people and hear their stories, the narrative became really clear: Carlos had been using his office to fight for working people’s interests, and for that reason, big developers, Rahm Emanuel allies, and the one percent were fighting back. To us, this election wasn’t just about securing Carlos’s seat, it was about winning a mandate for our movement. We saw the rent control referendum in the ward and the election as a way to increase the confidence and expectations of the working class. We saw our role as saying that rent control and other lofty reforms aren’t just desirable, they’re achievable when we fight together.

MDA: Right, we’re highlighting the interests of working-class people and giving them a way to articulate those themselves. It seems like the needle has shifted a little bit; even newly elected mayor Lori Lightfoot has been calling out big developers. That’s an issue that we know people are attuned to now, otherwise she wouldn’t be calling it out. What do you think these campaigns have done to raise expectations across the city?

LO: I think that if you were sitting in a room talking about great policies that would improve people’s lives, rent control would come up, but people would talk about how that’s a crazy idea and about how hard we will have to fight to get people on board. But having these conversations with people made it clear that people are widely supportive. The referendum in the 35th ward had a 71% support rate. And the two other wards that had ward-wide referenda had over 70% support rate. It polarized the election between working people and capitalists, and it raised our confidence: so many people support this, why is this even a question?

In terms of our own activists and members, we raised our own confidence as organizers because we went out and had those conversations and recognized that this isn’t as controversial as we might have thought. To be honest, I think many of us started out thinking of the working class as somebody else, but through the campaign realized our own stake in the fight and our power when we fight together.

MDA: Can you talk a bit about Chicago for All?

Chicago for All was a platform that CDSA created a couple of months into the election. It said we want education for all, housing for all, sanctuary for all, and the way we’re going to win these things is by taxing the rich, because we think that’s an important aspect of the politics we’re putting forward: fighting capitalists. So, we came together with all of the election campaigns in December and sat down to discuss the things we value, the things we have a base around, what we want to grow around, and how we communicate all of that across the city council campaigns. The organic development of the city council races was pretty decentralized. CDSA could not have done this work without the local organizations in various wards and city-wide organizations. Our attempt at connecting the issues that we were seeing across all these campaigns was the Chicago for All platform.

MDA: That also came up at the beginning of our conversation: working with these ward-level organizations. Can you expand on what that looked like and what the role of those relationships were during the campaign and moving forward?

LO: Each ward organization was important for the elections because they had these grassroots connections with people who had lived in the area for a long time, and they all had really progressive, independent politics. These ward-level community organizations came out of a strategy devised in the 1980s by Harold Washington to defeat machine politics by establishing independent political organizations. So that effort was renewed in recent years and was really important for building the kind of base necessary to fight corporate campaign funding. Every city council campaign CDSA was involved with in 2019 was outspent at least by 2-1. In Carlos’s race, our opponent doubled our fundraising. In Andre Vasquez’s race, Pat O’Connor spent a million and a half dollars. He outspent Vasquez by eight times. That’s the kind of funding you need for a congressional race, and it was just in one ward. There are very strong capitalist interests in these areas across the city, and they don’t want to cede this ground.

MDA: Right, so it was important for CDSA, which is a newer, city-wide organization to partner with these ward-level organizations who have been organizing for a long time and know the ground. Is it accurate to say that CDSA was providing the big-picture framing and the courage to really name the enemy and go after them?

LO: Yes, and I think the other aspect is that DSA as a broader phenomenon is doing a couple of things. We’re creating a national narrative that is affecting even Chicago city politics. We have 1,800 members in Chicago. That’s a big deal. We’re the biggest socialist organization in Chicago in a long time. We recognized that our strength was our socialist message, which is important for raising class-consciousness and activating working-class people.

We’re also activating brand-new organizers, people who were not in the movement milieu are suddenly getting extremely involved in left politics. That’s incredible. That’s what allowed us to get 300 – 400 of our members involved in these various city council races. DSA supplied the vast majority of our base of volunteers in Carlos’s election. And any race that got a DSA endorsement saw a huge difference in their turnout. That’s because people are excited about the ideas we’re putting forward — and they’re excited about socialist politics. DSA is doing this, but it’s also coming in the wave of Bernie Sanders. He’s speaking to people’s real material needs and calling out the problem. We’ve been seeing these issues but finally have someone like Bernie Sanders giving voice to that nationally.

On some level, that also happened during the CTU strikes in 2012 and 2016. So there’s renewed interest in progressive issues, but also it’s specifically about socialist politics, and that’s really exciting.

We’re also continuing to build relationships with those ward organizations and building up DSA as a strong, unified organization. We see ourselves continuing to build these relationships with aldermen through our combined organizing efforts. So there are other organizations in the city with lots of resources and paid staff who have the capacity to be in city council every day, talking about policy and lobbying elected officials. DSA doesn’t have those resources, but our real strength is that we have a truly democratic and membership-driven organization focused on moving the needle on various issues and pushing a socialist message. So we’ve begun to emphasize that strength and are continuing to develop our organization through our chapter’s major campaigns: Medicare for All, Lift the Ban, and a campaign to democratize ComEd, our municipal power provider.

MDA: In a way, you’re looking to use the electoral gains not just to have people in office but also to engage those 300-400 people that have been showing up and channel their energy beyond electoral work.

LO: Absolutely, and also engaging our city councilors around building that campaign work going forward, and using their platform to do that. At this point, DSA doesn’t have the ability to discipline the officials that we just elected in a meaningful sense. We’re not a party. But the people we’ve endorsed, who we’ve vetted and interviewed and democratically decided to endorse, the reason they might change their tune and go in a different political direction than our organization is not because they’re looking to sell us out, but because they may make different strategic and political calculations than us when faced with the pressures of elected office. So for us it’s important to build strong organizing relationships with the aldermen, creating the mechanisms to do that democratically in CDSA, and focusing on developing our organization and our continued campaign work, rather than assuming that the endorsement is going to last forever.

During the election campaign, the idea of building a socialist caucus in city council garnered a lot of excitement in DSA and the press picked it up. But because we were a part of a mostly informal coalition effort that was fairly decentralized, there were competing conceptions about how our movements and organizations should approach electoral politics and the new gains in city council. The progressive organizations that are focused on running and winning elections see their role as primarily legislating and building coalitions on city council. For them, a socialist caucus looks a lot like a litmus test that would prevent a large progressive coalition from coming together. They, understandably, want to “get things done.”

For us, the socialist caucus represents an opportunity to create a strong left pole on city council and a space for socialists to organize, not simply in order to pass legislation, but to use their seats to advance grassroots movements together. We don’t believe that building a strong left vision limits what’s politically possible — we believe it expands it. And we have to continue making that case to the aldermen we elected and continue building organizing relationships with them in order to form a meaningful organizing body like a caucus.

I think this is an extremely important lesson for socialists engaging in electoral work. We need to be very clear about our goals and purpose.

CDSA sees electoral politics not just as legislating, though of course we advocate for reforms that can improve working people’s lives. We see our role as raising class-consciousness and activating working-class people to organize, whether that’s in their workplace or in their community, and not just for a candidate. We want working people to know that when we fight, we can win. And I think this election is a perfect example of that.