Two Years After Electing a Mayor, Chicago’s Left Keeps Contesting for Power

Middle-school-teacher-turned-union-organizer Brandon Johnson was sworn in as mayor, alongside the largest progressive caucus ever on the Chicago City Council. Very much in the spirit of the campaign that got him there, the newly inaugurated mayor closed out his speech with the same momentous rhetoric and energy that bottom-up movements rely on to inspire people against all odds: ​“I’m talking about a revival in the City of Chicago, where the soul of Chicago comes alive. A brand new Chicago is in front of us.”

It’s true there have been big wins since then. But while some things are markedly different about the Chicago we are in now and the left’s position in it, what’s not new is that everything is about power.

Over the past month, I talked to 15 longtime Chicago organizers about the political moment. Some are now in elected office, some lead big labor unions, and others are at community groups or neighborhood-based independent political organizations, but all see themselves as part of Chicago’s left movement. What was clear as I approached these conversations and organizers approached the moment was: It’s all about so much more than Brandon. Most of our conversations circled back to power — what kind we need, how much is enough and the difficulties of wielding it to deliver for Black, Brown and working-class people.

For many organizers, at times even myself included, it may have felt like winning the mayor’s office would mean more power to transform the city more quickly than it has, that having a third of City Council being progressive would make for a stronger bloc than it has (because at the end of the day, it’s not a majority), that outside movement forces would be more coordinated than we are, that the opposition might be less multipronged, more afraid of us or less effective at battling the Left than it has been.

When I sat down last week with Chicago Teachers Union (CTU) President Stacy Davis Gates — who has been a key leader in the coalitional efforts to win political power and just delivered a teachers’ contract with historic measures for the common good — she rightfully pointed out that Chicago does not quite have a model for what we are doing. And why would we? Because, as she reminded me, ​“Society is not set up for people like us to win.” Chicago organizers, she said, should own our power, take stock of our impact and still be able to hold the complexity that what we’ve achieved is still not nearly what our people deserve.

Chicago is still, structurally, a deeply segregated city along lines of race, class and disinvestment, with more tax breaks for corporations and the wealthy than mechanisms to make them pay their fair share. We still have a gutted public sector, visible in the form of closed schools sitting empty in Black neighborhoods and former mental health clinics turned into hipster wine bars in gentrified ones. We have an enormous wealth gap and a 30-year difference in life expectancy between Streeterville and Englewood.

And yet there have also been some big accomplishments for the Left in partnership with a more progressive City Hall, even if all were contested, and interpreted differently by different players, and none are nearly ​“enough.”

A mayor who was elected with strong labor support, especially from the CTU and SEIU Healthcare, has delivered for workers. Chicago abolished the subminimum wage for tipped workers and expanded paid time off for all city workers. It also passed a historic teachers’ contract that places a nurse or social worker in each school, doubles the number of libraries and librarians, shrinks class sizes, and includes specific protections for Black, LGBTQ, and immigrant students.

And just this week, the mayor announced a city investment that would increase pay for educators at early childcare centers across the city, a step toward fulfilling SEIU Healthcare’s vision of childcare for all. SEIU Healthcare Executive Vice President Erica Bland, one of the most powerful labor leaders in progressive state politics, explains that the union’s involvement in politics is about ​“delivering a better quality of life” for both members and their communities. Bland emphasizes that childcare workers are the ​“workforce behind the workforce”: improving their pay and working conditions benefits not only workers but the working families they serve.

Chicago also invested in the Treatment Not Trauma program, which is now starting to send mental health professionals (instead of armed police) to respond to some mental health crises, and reopened two of the many free public mental health centers that previous administrations had closed down. Thousands of youth jobs have been created, including funding for a program envisioned by young people which involves hiring youth as peacekeepers to lead violence prevention efforts with their peers. Data shows youth jobs are one of the most effective ways to address community violence, whose decline Johnson’s administration touts.

And when Texas Gov. Greg Abbott started busing asylum seekers to Chicago, the Johnson administration passed an emergency spending package in its first City Council meeting (after unmet calls for federal funds) and set up a whole new set of systems to receive the tens of thousands of new arrivals. While this process was more than imperfect and left many frustrated or at odds with the administration, at its height the city was offering shelter to thousands while other cities turned people away. And the city defended its sanctuary status in the face of Trump administration lawsuits and hostile Republican lawmakers calling the mayor to testify. 

Chicago was the first major city to pass a resolution calling for a ceasefire in Gaza. We also just became the largest city in the country to pass legislation investing in green social housing: permanent, affordable housing in city-owned, environmentally friendly, mixed-income developments. Financed by a revolving city loan fund, projects are expecting to break ground in 2026.

Though achieved in collaboration with a more progressive City Hall, many of these victories still involved considerable outside agitation and protest. In the run-up to January’s ceasefire vote, for example, community members packed council meetings for months. 

Making progress on policy demands has also involved contestation between forces on the Left about what tradeoffs are acceptable. Initial proposals for Treatment Not Trauma, for example, involved redirecting money to follow the shift from policing to public health. Ultimately, a desire to foreground the affirmative and avoid being dismissed as ​“defund” won; in other words, the ​“invest” demand was delivered, but the ​“divest” demand was not.

And of course, there is a long list of city decisions that many are rightfully unhappy about or disagreed with, such as who would staff the mayor’s office and lead city departments, or the speedy contract with the Fraternal Order of Police that included big raises without more reforms (which Johnson defends as pro-worker). Some organizers who supported Johnson saw him making other decisions they didn’t understand or see coming, even as those decisions impacted their communities.

When I spoke with Johnson about this, he offered a carefully crafted reflection. ​“I regret that I did not put forth that same amount of energy to make sure that the coalition was firm and ready to help lead, to effectively govern, and [break] through all of the noise — some of it was accurate, but a lot of distortion,” he said. ​“It’s been really hard to run government while also effectively communicating the ​‘what’ and the ​‘why’ of what we’re doing.”

Communication is important, but we shouldn’t let our focus here obscure inevitable relational dynamics between movement and mayor, or the larger set of lessons about how real change is made. 

In the politically challenging times we are in, with the structural reality we have, one of the best measures of strong political leadership is showing that you are someone who will fight for everyday people in the face of the rich and powerful. The Left and Chicago more broadly would benefit from seeing even more of the honest grappling we got a taste of in the mayor’s two-year press interviews and the kind of bold progressive leadership willing to be one vocal part of a royal ​“we” taking on the billionaire right, racist police organizations and the local political class doing the bidding of corporations.

The victories of the past two years involved a confluence of forces and a diversity of strategies: outside organizing campaigns; media efforts to shift public narratives; elections that reshaped who the decision-makers were; strategic coalition building; the politics of landing policy. Most were the result of years-long organizing campaigns, forged long before the 2023 election, uniquely able to advance in the new terrain. It took all this to get to a place where we now have a mayor who won’t shut down schools, who won’t privatize major city services, and who will use the remaining federal Covid relief dollars to reopen clinics instead of squandering it on banks and police overtime (although excess money for abused police overtime is still a problem).

And, in addition to strong left political leadership inside and outside of both City Hall and union halls, it’s going to take building, winning and wielding so much more to win on more fronts at once in order to achieve the more egalitarian city we deserve.

More than a decade of watching elected officials close down schools and clinics, divest from neighborhoods and cover up police murders — despite massive protests, clear public opinion on our side and powerful organizing — is what drove many organizers across communities to want to take power away from political decision-makers who could so easily tune out our voices and constituencies. 

Out of that dissonance, between seeing racist divestment in the form of school closures and the continuing reality of violent policing, came my early organizing efforts of the 2010s, which sought to call out the outsize investment in policing and need for investments in communities instead. This organizing continued into 2020 when, under Mayor Lori Lightfoot (2019 – 2023), the city disregarded the roughly 32,000 people (87% of respondents to a question on the city budget survey) who wanted to see a reduction in police spending, as well as the thousands who applied direct pressure on City Hall as a result of a massive citywide organizing campaign. As an international protest movement unfolded, this moment underscored the limits of our power.

Organizer Matt Ginsberg-Jaeckle points out that the old school methods of community organizing had been particularly effective under former Mayor Richard M. Daley (1989−2011) because the longstanding Daley machine’s power was kept in place via an interconnected set of political relationships and patronage at the ward level, with ​“actual rootedness in different neighborhoods.” Ginsberg-Jaeckle organized community-led campaigns that were successful at preventing mental health clinic closures under Daley not once, but twice.

Organizing under Daley’s successor, Rahm Emanuel, who came in with Wall Street money, the support of Chicago’s business community and a determination to control the media narrative, was a different story. ​“It didn’t matter what we did to Rahm, he wouldn’t budge on stuff,” Ginsberg-Jaeckle recalls. ​“We came face to face with the limitations of an approach that had been premised on, ​‘You don’t really touch electoral politics.’ ”

So, anchored in large part by United Working Families (the local political party founded in 2014 by a coalition of progressive labor organizations) the Left began electing progressives to city, county and state offices, building up to the coordinated campaign and slate that got us the current makeup of Chicago’s City Hall and sent Delia Ramirez to Congress.

Former UWF Executive Director Emma Tai recalls the reaction from the opponents when working-class movement began running political campaigns against incumbents. It was ​“really different than protests and press conferences and letter writing campaigns and all that other stuff I had done,” she says. ​“It was really in the lane of electoral contestation that I saw how much they didn’t want us to win.”

Many of those elected officials are former organizers themselves who became convinced of the need for political power. Second-term Ald. Jeanette Taylor participated in the hunger strike that reversed the closure of just one of the 50 schools closed under Emanuel. She recalls the feeling that drove her to run for City Council in 2019: that ​“no matter how much we protest, no matter how much hell we raise,” local decision-makers were ​“dead set on not understanding.” 

I personally could see the possibilities that had already begun to open up by having just a few leftists in office to collaborate with over time. Already, Ald. Rossana Rodriguez-Sanchez, also elected in 2019, had introduced the Treatment Not Trauma proposal to City Council after what she described to me as the ​“prophetic” feeling of being given marching orders by the resurgent racial justice movement when the George Floyd protests and the police budget organizing unfolded in the summer of 2020. 

With this movement context, many of us from the racial justice movement leaned in behind the coordinated campaign that elected both the mayor and a big freshman class of progressive alders.

In 2023, the movement went for the most and won the most. It was the message about ending the tale of two cities, the idea of sending people to City Hall who’d been arrested blocking elevators there in protest of closing clinics and schools, and the process of unifying the city’s grassroots movements around policing, education, housing, mental health and labor from the South Side to the Northwest Side that created enough momentum, tapped into enough hope for what was possible and mobilized enough people to knock doors and energize their communities to elect a mayor who was outspent by nearly 2-1. ​“It was extremely important for us to be able to win in numbers,” emphasizes former organizer and first-term 26^th Ward Ald. Jessie Fuentes, ​“because it was in that way we were going to be able to move the agenda that we all had fought so hard for.”

Longtime education organizer Jitu Brown — who now sits on the Chicago Board of Education he fought to reshape for decades (I ran his campaign) — stresses that elections and politics are one important part of our work but should never be the only part. Brown likes to remind many of us that, in his decades of organizing in Chicago (which involved wiping the tears of mothers whose babies’ school were being closed at school board meetings, then getting arrested), there was a time when the movement’s power was much smaller than it is now. Seeing a coalition of forces he helped build culminate in real political power means ​“it’s not David versus Goliath anymore; it’s a fight.” 

And it has definitely been a fight. 

For Jay Travis, who served on Johnson’s transition team where she saw herself representing the Black working-class base she organized on the city’s Southeast side for decades, the 2023 election marked ​“possibility, not a panacea.” She puts it like this: ​“It hasn’t changed the fact that very wealthy people are wanting to control what happens in Chicago. There was a coalition that was able to strategically secure a win in spite of that, but those factors that we were up against in that battle — that opposition is still very real.” The alliance of neoliberal forces that the movement has worked to challenge are still very much actively working and spending money to benefit their interests. 

When Bring Chicago Home — a community-driven proposal to fund affordable housing and address homelessness with a progressive tax on multi-million-dollar real estate sales — was put to a ballot referendum in March of 2024, the real estate industry spent millions to oppose the measure. TV ads playing into general anti-government sentiment, mailers spewing misinformation about who would benefit and who would pay, and a lawsuit that temporarily invalidated the ballot question altogether (and had to be fought in the courts) all confused voters. 

Despite a massive organizing push on our end (I was deputy director on the ballot campaign) — which included knocking more than 300,000 doors and contacting more than a million voters by phone or text; securing endorsements from hundreds of community organizations, faith leaders, and elected officials; producing powerful testimonial ads featuring campaign leaders who had experienced homelessness, and so much more — the well-funded opposition campaign still sunk support. Not only did the business-aligned political establishment see the progressive measure as a threat to the bottom line of corporate developers (who profit from the unaffordability of housing), but the measure was also used as an early opportunity for capitalists to undercut Johnson and the progressive movement he represents in Chicago politics. Anti-incumbency bias, anti-institutional sentiment and fear of higher taxes were all on their side, and the headwinds were strong enough to defeat a fighting coalitional effort that involved the collaboration of an enormous set of actors.

An aligned set of forces, this time anchored by Walmart family-funded school privatization organizations, used a similar approach in the school board races in the fall of 2024. Privatizers and progressive movement similarly fought it out. Some, but not all, of the community-labor coalition’s slate made it on to the new Board of Education.

Also in 2024, we saw newly formed political organizations — anchored by the city’s business class, real estate industry, finance sector and corporate Democratic insiders — borrowing from the movement’s playbook by running a pressure campaign to try to undercut the mayor’s budget. Chaired by former Emanuel campaign manager and advisor Michael Ruemmler, the new One Future Illinois political formation made its first big attempt at sowing division among a loose progressive coalition with a series of mailers and digital ads encouraging alders to vote no on Johnson’s second budget. 

Another new entity, the Common Ground Collective, boasts having already raised $10 million aimed at ​“defeating extremism” in City Hall with its sights set on challenging the mayor and progressives in City Council who supported the ceasefire resolution. Sending opposition mailers not so subtly aimed at incentivizing progressive alders to distance themselves from the mayor — a full two years before re-election — signals an early and aggressive approach. 

The Left’s advantage in the face of these attacks at the ward-level is that we are anchored by what is an expansive (but by no means comprehensive) network of organized bases of people who knock doors, have real conversations, are part of shared communities and create some resilience against the power of cold, paid-for political comms. This is instructive for what it looks like to fortify our power and our unique ability to organize.

“We’ve always been able to prove that people can beat money,” says Erica Bland of SEIU Healthcare, which represents more than 35,000 majority Black and brown workers in the City of Chicago, and was created in part via the bottom-up organizing of some of the state’s most precarious Black workers in the 1990s and 2000s (via the local’s ACORN-founded predecessor Local 880). ​“It’s really about our members understanding what’s at stake.”

For Chicago Teachers Union President Stacy Davis Gates, the gap between what working-class communities in our city truly deserve and what we have built the power to deliver is still wide. She put it like this:

We saved six schools from closure. And, in a city that closed schools every single year until we got a moratorium on it, it is big and visionary when you can stop the closure of six schools. 

Mental healthcare, clinics, the funding and sustenance of our public schools, eliminating a sub-minimum wage, giving workers paid time off: All that is transformational for somebody who never had it. Now, do they deserve more? Sure. Both things are true. Yes, it’s transformational that they had something that they’ve never had before and didn’t have a vehicle to getting. And yes, they need so much more.

And there is a long list of demands yet to be realized that would protect communities at the margins: Seemingly on the horizon (listed as one of the mayor’s 2025 priorities) is the Hazel Johnson Cumulative Impacts Ordinance, which would put in place important protections against toxic developments that have tended to negatively impact the environment and health of poor and working-class Black and Brown communities the most. It would require the city to integrate assessment of the health and environmental impacts in zoning, land use and permitting decisions. 

Also yet to be realized are demands from tenant and housing justice organizers working for affordable housing protections in the predominantly Black South Shore neighborhood, impacted by the development surrounding the Obama Presidential Center on the lakefront. And public health and safety organizers (myself included) are still pushing for redirecting funds from a police ​“slush fund” — hundreds of millions of dollars reserved for longstanding vacant officer positions and widely abused overtime pay — toward community programs that might otherwise face cuts in the budgeting process.

The city’s challenging budget situation — a result of decades of neoliberal reforms and quick-fix privatization deals that hurt the public — also doesn’t help with the ability to deliver solutions in the immediate future. With federal Covid dollars expiring and a structural budget deficit with a $1.25 billion budget gap forecasted for next year, charting a new path that doesn’t rely on austerity cuts is the city’s important task at hand. Chicago is not unique in this situation. For decades, the prioritization of free-market corporate profit has been the consensus policy in American politics, with cities suffering community disinvestment and budget cuts to social services and public good institutions. Progressives looking to win robust and equitable investment in hard-hit communities and the public good must now work toward solutions of how we get from the economy we have to the one we want.

Generally, the consensus among Chicago progressives is that the City needs to find the money to avoid budget cuts and protect important new investments. Regardless, there will be contestation around the choices made to get there and the power analysis around what can be conceded. Some emphasize the need to trim down the police department budget; others emphasize the need for state-level collaboration and billionaire Gov. JB Pritzker’s responsibility to deliver more progressive revenue where the municipalities don’t have the power to. Others see the politically unpopular option of raising property taxes as the inevitable and fiscally responsible way to balance the city budget.

Facing opposition with lots of money and power (whether from the real estate industry, the neoliberal donor class, pro-Israel forces, or hostile media institutions), many local leaders on the Left acknowledge there’s been both some relational strain and burnout over the intensity of past two years — as we face that our power still is not enough to transform what we’d like and try to work together across difference in a deeply segregated city anyway. What is clear to most, however, is that the moment calls for us to fortify our wins, come together, fight the far Right and build on our power. 

As the billionaire Right takes over at the federal level and steamrolls ahead with their agenda, the stakes of coming together and continuing to fight are high.

Emphasizing the work it has taken to win even what we have so far — even though it’s not enough — Rodriguez-Sanchez said, ​“This is not luck. We have organized to the point of pain, you know, like we have knocked so many doors, we have held so many teach-ins, we have been in so many picket lines, you know, and that is not just luck. That is a lot of energy and labor put into organizing ourselves to get these wins.” 

It’s something we know how to do.

Also calling on the movement to unify to protect and build on our wins, longtime community leader and respected elder Frank Chapman penned an open letter calling the Left to meet the moment and affirming that we should do so ​“based on maximum demands,” rather than succumbing to fear or division. ​“We need unity based on pushing our progressive agenda forward — not the politics of compromise or groveling to the powers that be.”

Delivering on maximum demands might be hard to do in a progressive city under a Trump administration with a powerful resurgent neoliberal opposition, but our dynamic here in Chicago sums up both so much of what is wrong in American politics and what challenge the Left must surmount — if we are serious about grabbing onto the power it takes to build a different type of world.