Harold Washington’s Legacy Still Hangs Over Chicago

A new documentary shows how Mayor Harold Washington upended politics as usual in 1980s Chicago. What goes unsaid is how quickly Washington’s legacy was undone after his untimely death.

Chicago mayor Harold Washington at his second inaugural party at the Bismarck Theater, Chicago, Illinois, December 14, 1986. (Paul Natkin / Getty Images)

On November 13, 1979, Birmingham, Alabama elected its first black mayor: Richard Arrington, Jr. He would serve five terms over twenty years, presiding over an expansion and modernization of the city that won over even many white voters in the deeply racist city. To my grandmother and many members of my family who lived in Birmingham, though, his ascension to the leadership of the city signaled the Apocalypse. To my family — white, working-class, and for the most part, deeply immersed in Southern-style white supremacy — it meant only one thing: whites had lost power in Birmingham forever. Blacks would run riot and exact a terrible revenge on whites for their perceived mistreatment. It wasn’t just a new political era — it was the end of the world.

Four years later, a similar scenario would play out in Chicago, the city I later called home. But the unlikely, almost miraculous election of Harold Washington to the mayor’s office of what was then the second-largest city in America was even more shocking to the white establishment. Washington, the most remarkable figure in the already remarkable history of Chicago politics, reluctantly volunteered to fill the void left by another mayor who had served for twenty years and multiple terms: the notorious Richard J. Daley. Daley was the head of a machine that ruled every aspect of the city, and under that rule, Chicago somehow managed to be even more segregated than Birmingham. Daley’s participation in the 1919 race riot set the tone for how he would govern the city as mayor, and the idea that a black man would take his seat was unthinkable to the establishment he built.

This is the story told to mixed effect by a new documentary, Punch 9 for Harold Washington. Directed by Joe Winston (who also helmed the film version of Thomas Frank’s What’s the Matter With Kansas?) and produced by a diverse group that includes comic and actor Craig Robinson, NBA star Derrick Rose, and Josh Braun (a producer of Peggy Guggenheim: Art Addict and Wild Wild Country, among many others), the film largely succeeds in its own aspirations. It uses a broad range of archival footage combined with interviews and historical context to tell the story of Washington’s gripping and often astonishing win over an entrenched political machine, an electorate galvanized along racial lines, and various interest groups paralyzed by infighting over who would get how much of Chicago’s power structure.

It’s difficult to explain the importance of Washington’s election, both for nonlocals and for those too young to remember him; he accomplished a great deal of progressive reforms in a notoriously corrupt city. Washington advocated for more popular control of government and access to municipal power for groups that had always been kept out. He not only broke the stranglehold of the Daley machine but replaced it with a multiracial coalition that created countless new opportunities for people of color to take part in city government, for good city jobs and constituent services for Chicagoans who lacked connections to the machine, and for community organizations to have a voice at city hall. He wanted to see constituent services become universally available instead of a reward for party loyalty, and he was a foe of Ronald Reagan’s austerity politics and pro–small government ideas.

But, also like other reformers, Washington underestimated the tenacity of his opponents, failed to anticipate the effect an economic downturn and the cutting off of federal money would have on his plans, and lost opportunities to instill the kind of discipline that would ensure his coalition would survive his death. Within a short time of his untimely death in office on November 25, 1987, business as usual largely returned to the Chicago mayor’s office.

Washington the Man vs. Washington the Legend

The documentary has a quick pace and a well-constructed narrative, managing to build incredible suspense out of a story everyone already knows the ending to. It begins with the unexpected death of Daley, which threw Chicago’s political future into doubt for the first time in decades, and ends with the even more unexpected death of Washington.

Some of the archival footage is astonishing: machine mayoral candidate Jane Byrne decked out in furs and chain-smoking in the back of a limo; Washington offering a tour of his small apartment, littered in every room with piles of books; an impossibly young-looking Barack Obama, his face bearing an enigmatic expression, staring at the newly elected Mayor Washington from across the room.

Other choices by the filmmakers aren’t so welcome. Progressives and socialists will recoil at the sight of Rahm Emanuel, the future mayor and a key architect and overseer of the neoliberal policies that have kept democracy in Chicago bogged down in the swamps of money and connections. (At the screening I attended, more than a few audience members had voted for Harold Washington, and one next to me audibly hissed when Emanuel appeared.)

Obama, in keeping with the politics of the kinds of people who can afford to finance a film like this, is portrayed as a direct successor of Washington, both tactically and strategically — a portrayal that requires ignoring the numerous missed opportunities of the Obama years in tangibly improving the lives of black people in the United States. And while the appearances of the likes of future Obama aide Valerie Jarrett and longtime local machine politico Dick Mell might cause bile to rise, nothing will rankle like then mayor-elect Lori Lightfoot positioning herself as the natural heir to the Washington legacy.

Washington, as can be seen in almost every frame of the documentary, was a remarkable figure, simultaneously a validation of and a refutation of the “Great Man” theory of history. He was brilliant, incredibly well-spoken and charismatic, unsentimental about politics but with a genuine desire to make politics work for the most people in the most ways. While flawed (Punch 9 for Harold Washington tends to gloss over the compromises he was forced to make, particularly with business, to achieve his extraordinary victory), he was a once-in-a-generation figure, and likely no one else could have accomplished what he did.

By encouraging transparency in government and community empowerment, making city services more widely available, and developing the Political Education Project (PEP), which organized and instructed people of color once denied access to municipal politics, Washington didn’t establish a dictatorship of the proletariat in Chicago. But he did institute desperately needed reforms in the city.

But Washington was also a man who understood the unique power of the people, who knew that it would take a mass movement to breach the fortress around city hall built by the Daley machine. He knew it would take a collective effort to unify the warring factions of Chicago’s multiple power bases, and was unafraid to speak to all of them on their own terms, going out into communities not just to glad-hand, but to make his case to the ordinary men and women who would sweep him into office. The PEP offered hands-on instruction to black and Latino candidates and provided them with information about poll monitoring, field operations, fundraising, and volunteer coordination. Washington spoke directly to cab drivers, hairdressers, and even sex workers — black Chicagoans written off by everyone, including themselves, as viable participants in electoral politics — and plainly described the power of their votes as part of a mass movement.

Washington’s attempt to build a new system based on opportunity and equal access to government posed such a threat to the Daley machine’s old-school system of favor and patronage — which built itself on the back of the working class, but the white working class exclusively — that, as we come to see, tens of thousands of Democrats turned into Republicans overnight. These voters threw their loyalty to Chicago GOP gadfly Bernard Upton, a former state representative and onetime civil rights activist, and gave the moribund Republican Party its best chance at a toehold in the city since the turn of the century.

Upton ran a nakedly racist campaign, but Washington’s ability to create solidarity among the non-white working class was a powerful counter. But after Washington’s death in 1987, that sense of solidarity evaporated. As the remnants of the coalition that unseated the Daley machine fell apart during a scramble to secure power of their own, a void was created that was filled by none other than Daley’s son, who stepped into it for an even longer tenure than his father’s and guided the city into the neoliberal era.

Ultimately, what is so striking about the story told by this documentary — which so effectively shows how one man and the coalition he built were able to transform a city seemingly immune to change — is how quickly that change disappeared. So many of the major players of the events of forty years ago are still with us in Chicago: Ed Vrdolyak, the alderman who headed the “Vrdolyak 29” that paralyzed Washington’s ability to govern by staffing key committee positions with their loyalists and consistently voting against his proposals, is still around and rolling in wealth as the head of a successful law firm managed by his sons. Ed Burke, one of Washington’s most tenacious foes, is still a sitting alderman despite his advanced age and a list of scandals a mile long. Many of the interviewees and “historical” sources shown in the archival footage have moved on to become local power brokers in their own right.

And, most tellingly, there is another void left open by the collapse of the Daley machine following the end of the mayoralty of Rahm Emanuel, who left under a dark cloud following his participation in the police murder of Laquan McDonald and its subsequent cover-up by his administration. The candidate who tried to fill that void and build her own coalition was Lori Lightfoot, who in Punch 9 for Harold Washington calls him an inspiration and a motivation. But her administration has been as bad as or worse than Emanuel’s, marked especially by police corruption and violence no different than that openly endorsed by Richard J. Daley. Police brutality is today as bad as or worse than it was before Washington’s victory, black poverty has resurged after decades of slow progress, and the city is segregated as it ever was as it also rapidly gentrifies.

In the final irony, attempts to forge a progressive coalition that can change these conditions are well underway but undermined by players from the Washington era itself. Chicago is facing a new mayoral race in February 2023 that is crowded with challengers to the incumbent, Lightfoot. One of them, Cook County Commissioner and former rank-and-file Chicago Teachers Union member Brandon Johnson, has spoken of himself as the new Harold Washington, but another recently announced candidate, Congressman Chuy Garcia, was a stalwart ally and key aide to Washington. And as progressives forsake backing a unity candidate in favor of building their own small fiefdoms, the elements of the old Chicago political machine wait patiently for their chance to come again, a chance that grows more likely with every instance of infighting on the city’s broader left.

Punch 9 for Harold Washington is an excellent documentary that has arrived at the right time but with the wrong message. Chicago was torn to pieces on the occasion of his death, first with grief and then with political division, as backroom deals and an unwillingness to back Washington’s successor allowed a new Daley to take power.

The film convincingly argues that everything that has happened in this city since then is haunted by the spirit of Harold Washington. While this is undoubtedly true, Punch 9 seems to believe that his ghost is a source of inspiration, of wisdom, and of hope for the future. As Chicago struggles to find its way to a better future, it seems far more likely that Washington’s specter is a cautionary tale, a story of lost opportunities to build a government that brings power to the people instead of enrichment to the connected — and that he looks down at the city not with pride and accomplishment, but with a fear and apprehension of being misunderstood. His legacy belongs to all of us, but his triumph may never be repeated.