In 2012, Chicago’s school year began with the city’s first teachers’ strike in a quarter century and ended with the largest mass closure of public schools in recent U.S. history. On one side, a union leader and veteran Black woman educator drew upon organizing strategies from Black and Latinx communities to demand increased school resources. On the other side, the mayor, backed by the Obama administration, argued that only corporate-style education reform could set the struggling school system aright. The stark differences in positions resonated nationally, challenging the long-standing alliance between teachers’ unions and the Democratic Party. This book recovers the hidden history underlying this battle. It tells the story of Black education reformers’ community-based strategies to improve education beginning during the 1960s, as support for desegregation transformed into community control, experimental schooling models that pre-dated charter schools, and black teachers’ challenges to a newly assertive teachers’ union. This book reveals how these strategies collided with the corporate reorganization of the public sphere during the late twentieth century, laying bare ruptures and enduring tensions between the politics of Black achievement, urban inequality, and U.S. democracy.