Chicago: the biggest city in the Midwest, hub for industrial unionism and also nursery for neoliberalism (through the Chicago school of economics). From this contradiction has emerged — most recently, in the dozen years since the landmark Chicago teacher’s strike — a rising tide of movement power. In 2023, Brandon Johnson, a former teachers union organizer backed by United Working Families (UFW), unexpectedly beat former Chicago Public Schools CEO Paul Vallas to take the mayor’s office.

Now, Chicago movements find themselves treading new ground as they work with a mayor they helped elect . They’ve pushed alongside him, as with the Treatment Not Trauma campaign to create non-police responses to mental health crises and reopen shuttered mental health clinics. But they’ve also found themselves at odds, as when an unprecedented number of migrants were bused in from red states and Johnson nearly hired a global security contractor to house them.

In March, Bring Chicago Home — a ballot initiative to tax the real estate industry and pay for the homelessness crisis — failed at the polls, serving as a continued reminder that, despite large progressive gains, change is often found on a razor’s edge. In mid-July, In These Times convened a group of longtime Chicago organizers to discuss where Chicago finds itself, including Katelyn Johnson (BlackRoots Alliance executive director); Asha Ransby-Sporn (a community organizer who helped lead Bring Chicago Home); Alex Han ( In.