by MARK ENGLER & PAUL ENGLER

A new documentary explains how, 40 years ago, Chicago’s first Black mayor shattered status-quo politics in his city, offering insights that remain relevant for grassroots movements today.
Four decades ago, at the start of 1984, Harold Washington was finishing his historic opening year in office as Chicago’s first Black mayor. An outsider candidate who had been persuaded to run by the city’s social movements, Washington represented a major break from the past, and his 1983 victory served as an important milestone in the efforts of Civil Rights activists to gain footholds in electoral politics. Today, as social movements increasingly take interest in running insurgent candidates for office, Washington provides a vital model for how grassroots forces can bring new constituencies into the electoral realm and upend the established practices of insider politics.
Once in office, the mayor—widely known in the city simply as “Harold”—faced entrenched opposition. And yet he was able to take significant strides in dismantling the city machine. Run for decades by Richard J. Daley, this machine long maintained a racist and inequitable system of distributing municipal resources.
Tragically, Washington died of a heart attack just months into his second term, in 1987. His sudden passing created a lasting trauma for progressive forces in the city and raised questions about what more he might have been able to accomplish had he lived. More recently, the 2023 election of a new progressive mayor in Chicago, Brandon Johnson, has both generated fresh hope and created revived interest in the lessons that might be drawn from Washington’s example in taking on Chicago’s old guard some forty years ago.
As a filmmaker, Joe Winston has tackled topics ranging from conservative organizing in America’s heartland (as director of 2009’s What’s the Matter with Kansas) to the influence of the ultra-rich on our political system (as producer of 2013’s Citizen Koch). His latest film, Punch 9 For Harold Washington, is showing in coming months in cities including Denver, Atlanta, Nashville, and Chicago, and it has just been made available for both educational use and community screenings.
We spoke to Winston to discuss insights that Washington’ story can provide for social movements looking to bring new voices into electoral politics today. Our conversation has been edited for length and clarity.
Mark Engler: Tell us about your background and how you got involved in this story.
Joe Winston: My film, Punch 9 for Harold Washington, is about Chicago’s first African American mayor. When he was elected in 1983, I was a junior in a high school that was located just three or four blocks from Harold’s apartment. He was a huge figure in Chicago, and the turbulent times of his election, governance, and untimely death are something that no one who lived through it can ever forget.
As a documentary filmmaker, I realized years later that the story of Harold Washington has universal significance. As a trailblazing Black mayor in a city which was undergoing rapid demographic change, the kinds of coalitions that Harold had to build in order to win an election—and then subsequently to govern—had tremendous resonance. That was particularly true in the Obama era. Barack Obama came to Chicago as a community organizer partly because Harold Washington had taken office. And, subsequently, the white backlash to Obama’s presidency mirrored almost exactly what Harold Washington had to navigate as mayor of Chicago.
ME: Before he decided to run for mayor in 1983, Harold almost had to be drafted by social movements. He made a number of demands that local organizers had to meet in order for him to run, including the demand that they register 50,000 new voters—which seemed like an impossibly huge number.
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